#METABOLOMICS WORKBENCH boryana_ptrva_20240116_222612 DATATRACK_ID:4583 STUDY_ID:ST003087 ANALYSIS_ID:AN005049 PROJECT_ID:PR001918 VERSION 1 CREATED_ON February 16, 2024, 11:26 am #PROJECT PR:PROJECT_TITLE Metabolomics of Mouse Embryonic CSF Following Maternal Immune Activation PR:PROJECT_SUMMARY The embryonic cerebrospinal fluid (eCSF) is critical for the developing central PR:PROJECT_SUMMARY nervous system (CNS), from neurogenesis to lifelong cognitive functions. Changes PR:PROJECT_SUMMARY in eCSF composition due to inflammation can impact brain function. We recently PR:PROJECT_SUMMARY identified an abnormal cytokine signature in eCSF following maternal immune PR:PROJECT_SUMMARY activation (MIA), a mouse model of autism spectrum disorder (ASD). We PR:PROJECT_SUMMARY hypothesized that MIA leads to other alterations in eCSF composition and PR:PROJECT_SUMMARY employed untargeted metabolomics to profile changes in the eCSF metabolome in PR:PROJECT_SUMMARY mice after inducing MIA with polyI:C. We report these data here as a resource, PR:PROJECT_SUMMARY including a comprehensive MS1 and MS2 reference dataset, and present additional PR:PROJECT_SUMMARY datasets comparing two mouse strains (CD-1 and C57Bl/6) and two developmental PR:PROJECT_SUMMARY time points (E12.5 and E14.5). Targeted metabolomics further validated changes PR:PROJECT_SUMMARY in eCSF upon MIA. We show a significant elevation of glucocorticoids and PR:PROJECT_SUMMARY kynurenine pathway related metabolites. Both pathways are relevant for PR:PROJECT_SUMMARY suppressing inflammation or could be informative as disease biomarkers. Our PR:PROJECT_SUMMARY resource should inform future mechanistic studies regarding the etiology of MIA PR:PROJECT_SUMMARY neuropathology and roles and contributions of eCSF metabolites to brain PR:PROJECT_SUMMARY development. PR:INSTITUTE Boston Childrens Hospital PR:LAST_NAME Petrova PR:FIRST_NAME Boryana PR:ADDRESS 300 Longwood Av, Boston, MA, 2115, USA PR:EMAIL boryana.petrova@childrens.harvard.edu PR:PHONE 6173557433 #STUDY ST:STUDY_TITLE Metabolome changes in embryonic CSF (Part 9) ST:STUDY_SUMMARY Untargeted MS analysis of embryonic CSF at E14.5, 48 hours post PolyI:C or ST:STUDY_SUMMARY saline injection into mother. ST:INSTITUTE Boston Children's Hospital, Harvard Medical School ST:LABORATORY Kanarek Lab ST:LAST_NAME Petrova ST:FIRST_NAME Boryana ST:ADDRESS Enders 1116.2 300 Longwood Ave ST:EMAIL Boryana.Petrova@childrens.harvard.edu ST:PHONE 6179197352 #SUBJECT SU:SUBJECT_TYPE Mammal SU:SUBJECT_SPECIES Mus musculus SU:TAXONOMY_ID 10090 #SUBJECT_SAMPLE_FACTORS: SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data SUBJECT_SAMPLE_FACTORS - 1 Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP381_mock SUBJECT_SAMPLE_FACTORS - 2 Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- RAW_FILE_NAME=20200923_QEF1_HILIC_CSF_Jin_BP373_mock SUBJECT_SAMPLE_FACTORS - 3 Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP374_mock_1 SUBJECT_SAMPLE_FACTORS - 4 Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP377_mock_2 SUBJECT_SAMPLE_FACTORS - 5 Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP378_mock_3 SUBJECT_SAMPLE_FACTORS - 6 Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP375_treated_1 SUBJECT_SAMPLE_FACTORS - 7 Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP376_treated_2 SUBJECT_SAMPLE_FACTORS - 8 Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP379_treated_3 SUBJECT_SAMPLE_FACTORS - 9 Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours RAW_FILE_NAME=20200924_QEF1_HILIC_CSFJinNew_BP380_treated_4 #COLLECTION CO:COLLECTION_SUMMARY All animal studies were performed under the protocol approved by the CO:COLLECTION_SUMMARY Institutional Animal Care and Use Committee (IACUC) of Boston Children’s CO:COLLECTION_SUMMARY Hospital (BCH). All mice were housed in a 12h light-dark cycle with ad libitum CO:COLLECTION_SUMMARY access to food and water. CSF, eCSF, was collected from the cisterna magna of CO:COLLECTION_SUMMARY the pup embryos and mother, and centrifuged at 5,000g for 10 min. at 4 °C to CO:COLLECTION_SUMMARY remove any tissue debris. CSF samples were kept on ice and analyzed the same day CO:COLLECTION_SUMMARY as collection. CO:SAMPLE_TYPE Cerebrospinal fluid #TREATMENT TR:TREATMENT_SUMMARY For polyI:C experiments: Pregnant female mice were injected intraperitoneally TR:TREATMENT_SUMMARY (route of administration) with a single dose of 20 mg/kg polyI:C (sigma aldrich) TR:TREATMENT_SUMMARY and controls will receive an injection of 0.9% saline embryonic day 12.5-14.5. TR:TREATMENT_SUMMARY Samples were collected either 3hrs or 48hrs post injection. #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Per condition, 5uL of maternal serum, CSF, were extracted by brief sonication in SP:SAMPLEPREP_SUMMARY 200/100μl (serum/csf) 80% methanol, supplemented with isotopically labeled SP:SAMPLEPREP_SUMMARY internal standards (17 amino acids and reduced glutathione, Cambridge Isotope SP:SAMPLEPREP_SUMMARY Laboratories, MSK-A2-1.2 and CNLM-6245-10). 10uL Embryonic CSF (eCSF) was SP:SAMPLEPREP_SUMMARY extracted per condition using the previously described buffer quantity, and the SP:SAMPLEPREP_SUMMARY flash frozen liver chunks were extracted in 300uL of the previously described SP:SAMPLEPREP_SUMMARY buffer. After centrifugation for 10min. at maximum speed on a benchtop SP:SAMPLEPREP_SUMMARY centrifuge (Eppendorf) the cleared supernatant from CSF and eCSF was dried using SP:SAMPLEPREP_SUMMARY a nitrogen dryer. Samples were reconstituted in LCMS water by brief sonication. SP:SAMPLEPREP_SUMMARY Extracted metabolites were spun again and cleared supernatant was transferred in SP:SAMPLEPREP_SUMMARY LC-MS microvials. Serum followed the same protocol, except that an additional SP:SAMPLEPREP_SUMMARY 20-minute centrifugation was administered, and homogenization for 5 minutes. SP:SAMPLEPREP_SUMMARY Final LCMS water reconstitution values for tissue type were 50uL (maternal and SP:SAMPLEPREP_SUMMARY embryonic serum), 15uL (maternal CSF and eCSF),. A small amount of each sample SP:SAMPLEPREP_SUMMARY was pooled and serially diluted 3 and 10-fold to be used as quality controls SP:SAMPLEPREP_SUMMARY throughout the batch run. Two microliters (equivalent to 0.2 ul of CSF) of SP:SAMPLEPREP_SUMMARY reconstituted sample were injected into a ZIC-pHILIC 150 × 2.1 mm SP:SAMPLEPREP_SUMMARY (5 µm particle size) column (EMD Millipore) operated on a Dionex UltiMate SP:SAMPLEPREP_SUMMARY 3000 UPLC system (Thermo Fisher Scientific). Chromatographic separation was SP:SAMPLEPREP_SUMMARY achieved using the following conditions: buffer A was acetonitrile; buffer B was SP:SAMPLEPREP_SUMMARY 20 mM ammonium carbonate, 0.1% ammonium hydroxide. Gradient conditions were: SP:SAMPLEPREP_SUMMARY linear gradient from 20% to 80% B; 20–20.5 min: from 80% to 20% B; 20.5–28 SP:SAMPLEPREP_SUMMARY min: hold at 20% B. The column oven and autosampler tray were held at 25 °C SP:SAMPLEPREP_SUMMARY and 4 °C, respectively. The MS data acquisition was on a QExactive benchtop SP:SAMPLEPREP_SUMMARY orbitrap mass spectrometer equipped with an Ion Max source and a HESI II probe SP:SAMPLEPREP_SUMMARY and was performed in a range of m/z= 70–1000, with the resolution set at SP:SAMPLEPREP_SUMMARY 70,000, the AGC target at 1x106, and the maximum injection time (Max IT) at 20 SP:SAMPLEPREP_SUMMARY msec. For tSIM scans, the resolution was set at 70,000, the AGC target was SP:SAMPLEPREP_SUMMARY 1x105, and the max IT was 100 msec. Relative quantitation of polar metabolites SP:SAMPLEPREP_SUMMARY was performed with TraceFinder 4.1 (Thermo Fisher Scientific) using a 5 ppm mass SP:SAMPLEPREP_SUMMARY tolerance and referencing an in-house library of chemical standards. Pooled SP:SAMPLEPREP_SUMMARY samples and fractional dilutions were prepared as quality controls and only SP:SAMPLEPREP_SUMMARY those metabolites were taken for further analysis, for which the correlation SP:SAMPLEPREP_SUMMARY between the dilution factor and the peak area was >0.95 (high confidence SP:SAMPLEPREP_SUMMARY metabolites). #CHROMATOGRAPHY CH:CHROMATOGRAPHY_SUMMARY ZIC-pHILIC CH:CHROMATOGRAPHY_TYPE HILIC CH:INSTRUMENT_NAME Thermo Vanquish CH:COLUMN_NAME SeQuant ZIC- pHILIC (150 x 2.1mm, 5um) CH:SOLVENT_A 100% acetonitrile CH:SOLVENT_B 100% water; 20mM ammonium carbonate, 0.1% ammonium hydroxide CH:FLOW_GRADIENT 0-20 min: linear gradient from 20% to 80% B; 20–20.5 min: from 80% to 20% B; CH:FLOW_GRADIENT 20.5–28 min: hold at 20% B. CH:FLOW_RATE 0.150mL/minute CH:COLUMN_TEMPERATURE 25 #ANALYSIS AN:ANALYSIS_TYPE MS AN:ANALYSIS_PROTOCOL_FILE BCH_Kanarek_Lab_protocol.pdf #MS MS:INSTRUMENT_NAME Thermo Q Exactive Plus Orbitrap MS:INSTRUMENT_TYPE Orbitrap MS:MS_TYPE ESI MS:ION_MODE NEGATIVE MS:MS_COMMENTS HESI, See uploaded protocol.docx for metabolite metadata "Tags" key and MS:MS_COMMENTS explanation #MS_METABOLITE_DATA MS_METABOLITE_DATA:UNITS a.u. MS_METABOLITE_DATA_START Samples 1 2 3 4 5 6 7 8 9 Factors Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- Sample source:mock | Developmental Timepoint:- | Maternal Treatment (injection):- | Collection Time:- Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours Sample source:embryonic CSF | Developmental Timepoint:E14.5 | Maternal Treatment (injection):polyIC | Collection Time:48 hours XYLOSE/ARABINOSE/LYXOSE 197350.967 193150.4199 6248523.952 7103032.567 5595954.125 6434460.04 4509174.836 6141065.237 5863922.129 Veronal 72570.86119 62624.68944 1016321.36 1355990.667 1246987.724 1099100.058 1083940.997 1235511.974 626675.6153 valine 252487.9566 85861.72048 290889820.4 219990052.5 240188429.5 213331829.8 244694740.9 251215178.9 179565660.7 uridine 103519.2961 182438.989 121217464.2 103047028.5 89399646.69 92874474.71 124431959.6 134626588.2 113289099.8 URATE 1600777.324 2373711.606 33572337.78 31949340.47 26666045.4 40610822.47 36303402.13 34461195.05 34654645.29 Uracil degenerate 235194.6053 453834.2348 6956392.446 7597754.823 6701310.961 6236175.258 6178223.448 6885810.897 6737949.494 Uracil degenerate (2) 836009.3676 1149897.957 7990165.067 7081499.798 5846198.749 6413296.344 7652130.932 8522173.672 7011195.133 uracil 1668623.753 862177.8543 17533195.43 12270848.55 11115615.77 13159490.07 13498316.54 17389626.74 14898021.03 tyrosine 255982.4164 352868.7956 69129739.38 53198072.41 58908801.39 40679443.1 72586845.95 63067301.21 39565070.76 tryptophan 199063.3483 121920.9089 96625443.95 88180231.35 92851777.3 104802163.6 76545090.51 93900614.93 77365827.38 TI0889000 34299.27458 33118.3245 169002.5869 377779.1803 396471.5869 294240.4687 526076.5279 265639.095 358852.6047 Thymine 3537919.747 4998102.55 29880147.59 33736136.17 32022012.29 45848072.64 22666235.9 25054468.15 23992059.43 thymidine 76094.77715 75031.09766 10771007.71 12261221.59 15362244.17 6365026.144 10525367.81 9132120.568 11034093.46 threonine 528042.2261 570315.3488 78577281.64 71457658.15 117707588.6 54682118.77 57339212 70895554.56 31724088.69 Tauropine 108604.8311 91499.06387 26528343.7 24886461.03 21762877.58 25183451.88 20925735.57 28501992.64 33396474.08 taurine 637496.5737 476594.3099 87474849.65 80579006.39 96670995.6 76696690.16 112760088.2 88966433.38 47476272.06 Sulfuric acid 14776854.11 16212530.61 295682398 315718046.7 327731120.2 241686669 256617723 264566128.9 265046238.3 Stearic acid 10866883.87 12414184.23 32513277.42 65175178.74 66970727.52 31528238.53 40657691.97 38049051.42 84370499.73 Spaglumic acid 93587.92471 164936.2681 2279113.326 1850765.982 1461032.752 1757921.501 2024129.671 2342497.635 1926899.603 sorbitol 76711.24267 76527.55364 7276213.057 8905495.664 8012005.479 8802398.821 6641016.992 8241100.064 10207337.66 Serine degenerate 974456.1739 700225.5152 8083898.598 15950606.92 15428614.87 5707082.709 16611837.58 15435935.86 5311604.644 serine 146689.1988 643612.4408 17349655.44 17026433.65 20790642.44 14914226.34 20273744.49 18971941.03 11032667.89 Sebacic acid 1577318.997 1354799.922 4400094.131 4089321.117 4850637.459 5491703.883 3952332.109 5897906.569 6064611.178 Rivastigmine 31658.72378 32001.06901 768769.7253 821843.8932 866144.396 737984.7256 461450.8873 612902.3558 577706.1229 Retinyl acetate 60504.48694 57482.50247 369270.2462 20171371.37 12372138.35 947277.5303 2923577.633 1066355.605 8626664.957 Quinolinic acid 86662.51086 77875.02237 8980852.128 10437648.79 10268989.73 9991941.625 9353823.384 13207484.69 11660406.3 Pyridoxal 1314460.217 126050.3047 10293814.9 9364422.376 10586715.01 10236193.48 6873768.21 12644770.2 10579942.04 pseudouridine 141470.8158 117794.7653 40445965.21 49173995.78 43666251.75 37660196.44 32271124.37 41451727.48 41224422.14 Protocatechuic acid 163401.1748 56532.47096 6613407.724 6931362.652 5552499.856 8381217.322 5583212.862 7986110.054 8367245.151 proline 83775.65227 147157.005 76273337.74 54784279.44 73516291.86 57264336.69 75080904.48 79902920.71 37237991.56 Portulacaxanthin I 106342.2266 111694.1199 39680524.23 32007289.49 32358490.9 21046513.05 16425238.75 28738881.62 31891218.1 Pivagabine 322545.7586 200264.3233 1119398.94 1144289.332 1235960.176 1340586.854 777059.3231 1531316.026 1403638.327 Piracetam 138998.0669 392085.7031 9855825.502 11191769.35 10542331.22 11910350.27 7549026.766 8682931.859 8249052.284 Pipecolate 106334.3586 85981.93127 2729004.542 2629070.636 2858953.975 3143971.906 1654732.897 4887266.907 2629325.641 Picein 121803.1871 135489.9488 13612530.79 15320712.24 12487948.93 14946417.13 10764865.35 15828342.25 12654319.31 Phosphoric acid 1935416.961 992977.1075 74214414.27 131126695.8 116298994.1 98744676.89 111294198.2 127201274.4 140503659 phenylalanine 127690.8281 135480.1328 185198801.2 153184962.6 175337253.1 133924419 178986323.9 163789882 115661432 Paraldehyde 1427167.29 372123.805 18468784.06 16828568.19 16923284.17 13989084.98 10773058.68 14226038.75 9423719.672 PANTOTHENATE 198840.221 222546.4654 1190896469 1281561333 1095837022 583376074.9 1136020218 733058295.6 610058896.4 Palustrine 37007.19219 36579.68641 5422386.672 6570937.93 6560006.307 6180916.372 4341292.833 4693746.932 5086814.047 OXOPROLINE/PYROGLUTAMATE 8968567.912 4986485.575 35860852.98 36312168.59 37845298.55 33578080.38 39618154.6 41159712.88 33584004.5 Oxalosuccinic acid 10172655.37 1065043.164 18217267.94 17424156.13 21798704.43 14359676.78 23444342.23 21811531.5 23994654.5 Orotic acid 183127.4928 1948457.965 39186765.9 35156335.42 34469247.58 31371083.63 30377096.67 39373474.55 34136677.53 Ornithine degenerate (RT = 9.874) 138004.033 106467.1596 8563467.312 7964523.489 10770866.9 10120341.22 9437737.331 11890330.27 8641980.148 Ornithine degenerate (RT = 14.706) 114844.404 109238.9881 31733993.87 23950370.03 26847182.85 25789654.23 39770733.21 36720714.29 21431377.22 ornithine 133205.3595 158425.3992 3878973.855 4184411.762 4747324.847 3619446.725 6781425.698 5777566.829 3461615.6 O-Acetyl-L-serine 182898.6018 179356.8605 7976297.067 8909007.649 9388973.056 7106964.145 6801299.594 8917179.475 7273912.734 N~2~-Acetyl-L-ornithine 108341.5096 106866.0282 16517802.46 13992282 17629043.68 12215292.33 10300367.51 16084326.97 11256198.06 Nitrosoguvacoline (RT = 2.163) 25110.85335 43159.72916 1838086.906 3722622.766 3884433.475 1257579.784 3803907.723 3250287.574 861377.6878 Nitrosoguvacoline (RT = 2.163) (2) 174066.1768 196287.9689 4544854.221 7695025.703 7835687.602 5041217.476 7452115.321 7007218.582 2429377.122 Niacin 1702836.536 1299069.351 7367369.238 8809343.336 8255763.059 9676699.26 8284177.27 10750988.01 9807797.51 N6-METHYLLYSINE 125832.1956 149934.5544 7225589.747 7620528.972 11200364.18 4564970.778 4996848.84 6690241.382 4618414.702 N-ACETYLSERINE 60245.30491 194043.0124 9541125.007 10738625.85 9872054.428 8862177.893 8980193.466 9028847.572 8322913.277 N-Acetylnorvaline 267122.5261 148647.7367 3004945.492 2321342.245 2347883.556 2855559.67 2163276.3 3985536.518 3395464.603 N-acetylmethionine 103017.1163 114592.9276 4662887.985 3989028.809 3603812.653 3523271.859 4077658.066 5730582.005 4425883.125 N-Acetylgalactosamine 6-sulfate 338185.5707 857850.4417 50891607.44 25556884.2 18625225.01 42460981.09 31455159 48695945.3 87490506.54 N-Acetylaspartic acid 13358223.73 12393988.33 83976982.44 75072554.39 72295595.55 69180652.8 73017989.93 84904390.74 80305038.18 N-ACETYLALANINE 1383631.452 1519575.463 10493690.08 11435230.86 11579597.84 17225249.09 9482471.254 13434400.59 10412464.73 N-Acetyl-L-leucine 303237.1218 192345.6219 3877146.021 4368073.033 3111084.026 3424249.188 3077912.281 4754382.667 3840578.892 N-Acetyl-L-aspartic acid 24669502.83 6764481.038 70426160.9 82549323.43 99109817.14 56790143.43 84014822.94 88198938.44 72859755.68 "N(3)-(4-Methoxyfumaroyl)-2,3-diaminopropionic acid" 80287.93499 79256.90543 3007465.467 4420296.754 4383016.163 3338877.657 4120458.678 3725729.72 1848011.964 N(2)-succinyl-L-citrulline 171928.6141 209565.8482 12595087.86 13279300.59 16485936.39 11108269.82 16951325.95 15644179.05 9815861.528 myo-inositol 303327.5525 705883.9523 124830213.8 167567845.2 146913312.1 113076745.5 89872022.96 128841289.6 131960667.8 MW_946.36560@RT_1.650 33773.50343 32534.96814 35506.56993 808401.5839 694793.5834 560319.1572 822799.8561 392724.8514 791357.9785 MW_886.56034@RT_1.647 46160.74008 42486.92249 594547.8231 5410591.984 4138914.943 1025801.83 1911539.599 970842.7352 3753036.377 MW_884.54470@RT_1.649 44101.76211 40591.81342 69713.26553 1021071.44 633946.2817 152363.1872 289101.289 84131.01015 565234.3661 MW_867.56624@RT_1.697 49924.71828 45070.738 106599.318 1129143.438 887281.4998 541597.4505 580312.982 231541.3017 925676.4538 MW_858.53001@RT_1.652 42162.63828 38807.01959 320002.5757 2624728.468 2138758.747 502484.7662 944530.4344 398236.2545 1638279.223 MW_843.56688@RT_1.705 48745.47683 44006.14947 286795.9962 1791948.336 1622289.931 801928.8457 807987.5893 487209.3166 1553068.763 MW_819.56496@RT_1.710 66216.87031 62909.57255 741181.5534 4901970.622 3093600.189 1882898.165 1285284.788 637097.3405 3245313.241 MW_793.54972@RT_1.717 62357.80401 59243.25293 444814.6515 1882133.356 1142836.721 892166.0848 632644.812 343051.2845 1475926.732 MW_750.50849@RT_1.757 43191.37743 41034.12136 969884.6074 1118392.783 1111726.225 265273.7288 645694.1679 614043.1483 947215.5237 MW_747.52194@RT_1.684 49377.11951 46155.90699 550205.5865 2888413.021 2334798.783 789243.1228 953285.9031 589590.1155 1941516.185 MW_701.44562@RT_1.745 40143.20439 38138.19374 391033.3863 871966.3159 349243.0479 42340.63141 324477.9511 255432.5118 164789.891 MW_687.43064@RT_1.751 46715.40653 44382.13771 519957.8337 923630.101 452049.3389 49380.4379 467546.5615 241902.7092 447747.4891 MW_641.40835@RT_1.745 47259.23262 44898.80161 6268058.549 931333.1342 951304.5689 81288.59949 796374.6474 1285081.319 571323.7523 MW_585.36445@RT_1.872 61895.56615 57556.76067 105932.376 1188275.816 1134359.448 399919.4644 355073.0823 75662.23855 563936.3562 MW_557.33318@RT_1.931 81410.53602 75827.65695 359696.3913 4375769.988 2886925.199 978775.8627 917596.1862 415465.9141 1702986.102 MW_473.09572@RT_4.840 63344.86347 111636.8956 635270.1395 588664.6384 550299.5616 388232.7892 585237.366 728070.2163 564935.8797 MW_466.10637@RT_4.823 82595.73376 145563.9937 1378312.225 1309123.045 999565.3452 798796.4328 1381180.875 1343640.89 1389920.774 MW_448.14117@RT_1.779 62140.69387 59036.98667 924265.4189 974003.3825 1141768.405 569765.0382 1250027.976 913680.1786 987804.3002 MW_438.24739@RT_1.771 186010.5337 99142.28319 6235381.214 11534139.75 12186964.27 8593734.504 8331508.084 6040301.485 10885777.64 MW_412.13438@RT_6.720 124818.3259 92503.35816 1818103.259 2824385.537 2121537.971 2294784.161 1862466.631 2201655.671 2651907.071 MW_411.22806@RT_1.761 59281.84715 56320.9292 935204.0278 1872328.139 2538371.353 65506.16386 1355408.998 1022450.36 2006587.574 MW_391.24662@RT_1.765 63224.21222 60066.38712 4133679.396 7638344.505 6344779.88 2328707.534 4547370.626 3414805.054 6135887.25 MW_375.25184@RT_1.754 7789278.468 7576670.284 122282642.7 219182440.1 211410611.3 78935768.19 120210647.5 99513302.86 172540836.9 MW_370.20516@RT_14.713 80865.06216 76918.13663 3182286.035 1751970.316 2387459.99 2597960.501 4925950.31 4023812.476 1446908.145 MW_344.21960@RT_2.034 30972.35756 29049.4371 1249891.36 309354.5186 374451.8332 186546.7458 240794.2461 245155.8873 278351.1826 MW_344.19851@RT_1.985 50572.66999 48766.79259 775388.046 1196159.677 1905830.107 1026402.648 736997.7642 870984.6953 1262205.743 MW_332.27121@RT_1.719 60603.49441 57576.56487 105736.7249 2465958.544 1152003.365 93528.34853 307485.0198 71201.62246 1082143.283 MW_330.19806@RT_1.649 48899.84088 45008.02513 96416.05797 2248998.615 2422271.715 596081.5364 2788046.338 1086733.109 2588496.016 MW_323.22056@RT_1.961 66949.16245 63192.6018 718675.5022 1441188.311 1625682.614 651546.7651 1187994.773 972312.9125 709232.1111 MW_320.07046@RT_14.104 97109.6643 94774.19789 10587119.07 8001185.177 10583220.22 6527200.718 11876821.44 10104426.78 5676206.404 MW_314.19267@RT_14.110 113835.4219 111097.7046 6972759.954 5792396.236 7813198.661 6152007.795 8223659.273 7925203.64 4384137.723 MW_310.10822@RT_2.186 262392.2832 271978.3291 66768642.59 200068445.9 74326413.87 28545630.02 63228149.9 58462410.37 112177819.9 MW_303.15422@RT_11.640 74270.58235 73706.50921 3977849.159 3799480.732 3861557.332 3424026.812 5365574.938 4541582.18 3078308.343 MW_298.17749@RT_2.175 71406.68572 46697.3816 714566.6241 754410.1034 1127907.177 1223131.563 341668.2264 1283880.896 640418.7186 MW_294.08461@RT_2.769 75021.38013 77398.51645 2709893.437 2703087.288 2900629.439 1205510.565 1720263.557 2580524.657 1776180.19 MW_290.04391@RT_6.262 435725.8546 126415.6767 58916624.52 111710224.3 110703823.4 91329821.81 89133113.45 115122087.9 112245360.2 MW_282.14936@RT_1.796 75838.93587 43905.56407 351592.8657 449797.756 349305.8713 155048.5485 697888.7412 672518.187 636212.5996 MW_280.13409@RT_2.151 97294.0309 34793.51584 387561.6515 876168.1577 175741.0611 241882.4087 646029.9243 1303743.601 557789.9128 MW_275.14740@RT_11.657 77178.0698 72978.70719 8402489.053 9192203.841 10767513.27 7668884.283 10839586.16 10126091.07 6752136.067 MW_273.04782@RT_2.767 1117654.959 652307.0277 4697623.632 10535314.88 11225329.89 3625563.763 5612550.969 5855304.349 4948338.319 MW_271.21416@RT_1.957 328607.1779 42692.05001 1393455.826 1949338.841 1645327.824 1283763.368 2528388.42 1461225.981 1700616.266 MW_261.05277@RT_6.228 145940.2445 114909.7014 17929495.23 22401389.61 21230466.87 23108456.24 16100131.24 17516119.78 23202761.96 MW_246.08459@RT_4.999 922751.4131 1011379.258 14997118.38 18474680.74 18231158.56 13558347.94 11754291.06 15063616.05 16433982.52 MW_228.00319@RT_8.794 12231274.42 573073.4853 38525946.7 34419791.13 17279204.29 25621061.37 35084886.61 13206362.96 23860296.54 MW_224.08912@RT_6.649 156799.739 117686.9379 13881060.31 15707735.56 14914044.5 13298918.36 11218012.89 13887502.86 15212825.38 MW_219.03745@RT_3.495 934159.166 668266.901 4788264.237 6847214.279 6084925.642 3026638.799 6140361.965 5306514.566 2728000.195 MW_215.04261@RT_1.974 85973.41268 247709.6397 1698039.974 3430915.53 3589767.059 840359.5305 2005033.588 2298107.085 894884.4488 MW_202.02961@RT_2.007 45077.53509 43525.48131 81550823.47 112650781.7 105715389.8 38613691.25 65009156.36 75199474.39 67162519.84 MW_196.09328@RT_14.706 55202.6375 52508.26377 544476.5602 632297.8131 527044.4013 984241.3292 1307035.56 1077166.905 690866.1413 MW_184.04800@RT_2.285 87874.91993 66120.53881 2169605.084 3556856.411 5001232.433 2529624.03 3544775.52 4749442.414 778042.1948 MW_182.10569@RT_2.096 45278.65178 43719.6734 736890.5923 1338035.488 1301410.626 600564.2103 2351412.815 2003146.662 179124.4431 MW_168.12646@RT_2.542 75688.98201 76840.15761 3731790.315 4803777.15 4717038.294 3734774.477 6116421.677 5813155.425 1476775.301 MW_156.08958@RT_2.615 77312.04383 74125.20703 4167007.934 7598611.778 7352657.049 3035553.667 6610945.636 6265202.754 2253217.599 Mimosine (RT = 2.465) 276479.3748 563673.2878 1227811.076 1881429.814 2082184.959 1037657.505 2590399.492 1855411.646 941922.3698 mH 1100976.523 2664775.612 30337035.71 25516038.03 24542856.22 23282389.73 21539007.2 28218869.55 24300590.54 MFCD12546417 59536.73047 66226.74457 134461051.4 121092491.5 101956726.2 154168988.9 99556412.37 126292319.7 161716160.8 METHYL GALACTOSIDE 290681.2619 340747.0212 8642163.254 9992779.547 11391735.25 8584189.305 9264367.429 10610426.8 10495983.95 Methionine sulfoxide 189157.1333 545494.3535 14375634.78 11658704.05 13301076.74 10888328.84 11191055.36 14835219.58 11116488.4 methionine 154716.4812 98993.96325 47832319.7 42086283.38 40998219.06 37655804.97 39830436.16 45482625.81 36322260.15 Malonic acid 8707149.218 3922114.917 20365142.38 27316237 25578712.33 15996183.65 20109145.21 21640147.49 22840099.11 MALEATE 196843139.3 35432525.39 424652130.9 505346348.4 510779409.1 465155971.2 394388839.3 480908637.3 505353667.2 malate 7128489.377 8114966.416 119487890.8 79242480.84 75411777.62 83197112.09 83536034.02 112788796.7 76774620.2 lysine 101804.8323 99356.44808 224228489.7 188858054.8 275918792.8 175215674.8 247554969.4 268412112.7 129303806.5 leucine 321802.0027 377227.8719 405018774.1 355511893.2 387979719.3 305954191.3 424266165.8 430507828 277988438.1 lactide 5101559.655 6692847.248 24857862.11 35463507.54 35969664.7 24074689.95 11627369.12 25189835.78 31826380.86 Lactic Acid (tail) 26751800.67 30076516.27 382708428.8 249507436 327898670.6 367635356.4 332450122.7 259650726.6 266502442.1 lactic acid 44263616.74 12942226.56 3892620980 3141356731 2838363464 3720829088 3185904141 4107923886 3517490689 L-coprine 184496.775 131383.7869 3076709.138 3799662.78 3454765.43 3908989.413 3035545.667 3119927.994 1679499.902 Juniperic acid 91075.24045 117963.537 905543.0312 3887631.433 3074674.49 905639.0063 1230331.884 858416.6459 2496360.48 Itaconic acid 37345662.73 14386549.83 114479805.9 138406563.7 133527219.2 99262183.48 115096707.5 139562265.2 119523729.1 isoleucine 233450.6046 485623.1034 285201381.8 257603351.2 288758866.9 225931763.1 243151774.9 294022197.2 194986595.1 isocitrate 159997820.8 103366691.6 2828993120 3205342282 3246761851 3123191256 2107625267 2090528537 3635373145 Isethionic acid 203757.7747 225422.7926 81943010.64 96494458.98 99119694.28 86405477.41 54120665.4 82380254.97 96136598.44 Isethionic acid (2) 218027.7997 300548.7961 76117064.79 87830489.99 57818410.47 52688927.11 60887980.27 64165470.15 70646404.98 inosine 122296.0469 109032.782 8704107.433 7194945.733 5623413.117 8741585.306 8823357.048 8848505.915 8104491.557 Imidazolelactate 65316.76913 687541.8209 5388465.684 6147147.087 6652895.3 5505385.305 6025134.684 6076982.038 4028706.78 hypoxanthine 158055.2966 166421.5809 27378622.29 24511523.28 18288134.36 29510517.1 29432973.55 32734390.37 33039180.7 hydroxyprolie/5-aminolevulinic acid 190123.0607 152520.9812 21786806.73 20249334.08 26021443.04 22712103.23 15451916.69 23962882.45 19468914.01 hydroxyacetone phosphate 101885.2614 86116.11754 22524027.12 23734575.68 24588334.14 28242418.94 23391592 29840615.81 29154282.74 Hydroquinone 155805.8322 65679.55035 5816677.724 5428642.258 4924413.898 7077824.54 4822817.803 5985287.506 7580437.413 Hydrogen bromide 319437.6675 229199.511 30919416.07 32830593.75 32499024.51 29532396.1 27289818.91 34057442.77 31865946.29 Hopantenic acid 141335.463 170413.9231 6856934.877 7059965.64 5775644.752 3299385.272 4134355.84 4276207.866 4077341.138 Homovanillic acid 94225.7241 91564.5257 51403400.47 47231737.65 48478028.41 42901576.45 39748177.68 47122691.76 41372210.74 Homo-L-arginine 119838.4115 113949.7862 14022209.77 11625441.49 16944121.28 13173131.91 10838366.65 15755762.25 8776905.943 histidine (tail) 151551.1736 97608.63794 16071831.06 18790756.84 24129179.28 18800298.32 20940902.92 29209998.11 16002982.07 Hippuric acid 87143.32922 96935.43733 9301814.347 6738880.249 6148604.439 11570790.43 6511778.661 9994097.188 9821745.221 glutamine 1382626.848 366810.4638 138675955.1 177707784.1 204476929.2 125928773.9 149299445 183096235.4 122375979.1 GLUCURONATE 211993.7604 332904.0646 23307025.59 19466808.45 18900238.25 20925424.88 15923560.25 23884927.93 21859447.01 glucose 3891868.708 5105827.342 109021207.8 147621514.2 149744548.2 101508363.2 51826993.62 54925661.21 79547719.39 GLUCONATE 200926.7922 98070.02864 43789434.33 59534129.99 63396095.47 55660613.37 33690793.09 64478184.56 58192564.77 Formylisoglutamine 413742.1054 735559.08 1359000.221 2686077.323 2944849.986 1088842.728 2786461.374 2408451.281 904790.8909 Fomepizole 1146844.969 1211411.871 4273377.337 4606254.971 4302052.124 6637250.715 3304523.577 2797079.13 3127952.272 Ethylparaben 70369.18199 90501.51707 5111709.287 5529731.853 6685858.347 4301508.513 4129440.222 4727659.258 4385757.847 Ethopabate 128436.4605 133128.6634 3677817.759 2567697.357 2574705.836 2402766.509 2785040.698 3593198.981 2322574.016 Erythrose 1154907.32 905026.271 11982518.61 16065774.15 17902910.47 9440081.252 12166540.64 12959950.75 9621916.464 epsilon-(gamma-Glutamyl)-lysine 138223.0748 179672.6853 2214393.139 2726609.872 2763907.207 2033593.53 2458372.825 2533490.961 2023798.792 dihydroxyphenylalanine 1081227.13 656585.8098 3806158.394 5151687.411 5362290.527 3302417.175 4010393.636 4224585.021 4821295.759 Dihydrothymine 501005.7588 495386.6695 15282464.77 23946706.99 28518207.88 15740054 18662377.6 20164919.55 14298235.45 DEOXYURIDINE 81271.1281 91076.31517 11289596.8 12203965.4 15635422.87 8101850.001 10913270.05 8742674.912 9784006.999 D-Gluconic acid 1497758.238 102656.7524 28316209.81 29955822.14 28781601.31 31715391.83 19003909.69 30911517.24 33321663.08 D-(+)-Pyroglutamic Acid 1071133.804 16535097.43 34024195.37 53943628.61 79184399.46 45054388.58 46969852.83 65899817.48 40856241.02 cytidine 183975.2508 120245.3076 18266440.84 16113762.7 13352586.63 16985351.47 17336603.93 20729510.58 17484268.28 Cysteine-glutathione disulfide 93677.06066 230124.3683 2807766.593 2064420.309 2321257.888 2385003.555 2970156.863 2826190.688 2114732.147 Creatinine degenerate 443426.265 275639.8111 33189322.98 25102178.19 25700598.64 28225790.59 14520386.49 33421969.32 14925146.04 creatinine 2327542.049 2111202.814 16523490.18 19604891.19 20147812.62 20886055.69 15798978.18 20198599.32 19024805.27 creatine 107403.5505 119180.0689 20473392.89 18445311.56 20907364.93 19075706.42 15021305.67 20931265.53 16988313.89 citrulline 136803.5629 105541.0226 4982333.412 4787644.437 5944218.476 5952380.935 5110624.718 7230714.109 5212513.622 Cinnamic acid 125015.2227 132641.312 9454689.262 7570958.548 9677783.982 6504292.755 9177367.863 8393897.591 5575326.204 Chlorogenic acid 243635.4218 618012.0391 5365996.717 6519161.106 7176031.174 5930620.733 3489176.338 5870797.339 6059654.876 Beta-Hydroxybutyric acid 1655908.878 1429245.463 44115960.5 40318432.67 28714363.91 29408563.85 36527062.51 31021987.76 35377499.74 asymmetric dimethylarginine (ADMA) 120483.1935 115651.2251 2326840.772 2150032.008 2788609.388 1896439.576 2033509.485 2347588.069 1281934.878 Aspartame 213661.7947 133156.8182 2867438.99 1658620.601 2880539.174 2220578.92 3363316.37 2676644.448 2069460.815 ascorbic acid 2-sulfate 105925.1794 101066.0301 24242494.38 25671437.41 24696412.12 23875036.66 14412573.51 33097766.14 28523158.69 argininosuccinate 68214.7744 66818.03565 3337753.791 4088287.459 3716935.316 2761550.732 4100900.398 3853929.313 2952420.653 arginine 118711.6982 112917.5243 100236400.5 75652039.6 84279831.3 82796183.66 122936542.2 113204799.8 68630553.63 Arachidonic acid 64981.30899 61735.72315 113374.8287 5773869.429 2999258.874 248675.437 722887.8124 216633.6428 2625288.435 anthopleurine 96591.32963 93863.31991 2300460.171 1841824.06 2107210.965 2026734.025 2197289.095 2588893.503 1922222.281 AMPA 84621.56834 651413.6965 3298891.399 4439473.701 4494836.736 2928147.691 3861482.746 4022313.268 2129531.079 Aminolevulinic acid 2269641.12 1839657.429 8038555.18 7257822.532 6943158.834 7372916.582 7163606.747 7597135.494 7363154.392 alpha-Ketoglutaric acid 4207784638 160324679.7 9182480309 10980655885 11025819854 10074957778 8602656164 10410786732 11009397481 Aloin B 110595.1323 105695.4064 1224074.3 1552031.295 1200471.492 707422.5713 731125.3554 608120.2097 576226.131 allantoin 193158.3257 527260.8854 19540949.28 19646896.91 21203647.42 21353441.65 14728489.8 18513831.39 19966913.47 alanine 2535874.107 3760319.258 149398801.6 126351495 128323393.7 118717871.2 110003053 159956024.2 93860454.22 afegostat 195207.5873 186559.2531 14610664.56 15553996.32 12661909.32 6454799.64 13582731.47 8915960.896 7649593.242 afegostat (2) 117611.3469 87162.23728 5867761.26 5438531.598 6799762.219 5380850.212 3852599.765 6046521.806 3916610.088 Aceglutamide 55631.25821 52981.72982 2323281.574 2559840.853 2319478.334 2664947.615 2034615.341 2627534.133 2389525.165 7-Methylguanosine 147767.2538 260420.1286 2977713.579 3350150.605 2651408.441 3193478.485 2733767.804 3321890.434 3226076.021 6-Deoxy-D-arabino-hexos-2-ulose 2206915.146 226110.6056 10016066 20193078.16 11914681.81 10513365.45 10631983.95 10883299.31 11880829.92 5-Methoxy-3-indoleaceate 89629.21773 157959.5736 9070644.418 10354989.82 8706551.311 8944621.564 7025489.918 9162291.557 10112066.95 5'-O-[(3-Amino-6-hydroxy-6-imino-2-oxohexyl)(hydroxy)phosphoryl]adenosine 123102.2635 274495.1459 683852.9374 1317808.771 1624740.511 709697.2738 537261.0259 795974.0636 1251341.096 4-tert-Octylphenol monoethoxylate 45892.43398 45364.54912 465730.3231 1048603.084 1069371.839 517884.2959 356180.0884 269251.9789 916587.4833 4-phenolsulfonic acid 47015.52886 47400.92983 135818506.2 112847320.3 165678259.6 48579574.24 55776239.45 56689083 76158633.5 4-ACETAMIDOBUTANOATE 251264.0691 270056.7244 3745930.43 3554451.697 3545988.841 3368874.843 2626409.497 4060378.104 3420398.523 4-(Hydroxymethyl)benzenesulfonic acid 48552.69114 49297.79971 1850357.657 1954615.91 2500962.296 1686205.554 3269996.052 2664343.578 2174574.015 3-Sulfinoalanine 95692.31332 77543.76584 13922059.34 13356998.8 12939445.61 10900203.83 10224171.88 13250515.36 13687453.19 3-OH-isovaleric acid 1387594.366 1715239.392 32685436.81 39674476.14 37359652.59 29574122.6 21886248.56 33536042.27 31584289.12 3-O-feruloyl-D-quinic acid 135046.5098 213899.6274 142075299.2 236114167.5 279699502.3 112884101.3 86022449.9 139284364.5 182153567.2 3-methyl-2-oxopentanoic_acid 8155389.914 6745409.478 39266688.71 39729662.36 36103356.98 36292225.47 34245163.93 42338150.82 34781275.06 3-HYDROXYMETHYLGLUTARATE 2995554.655 3929933.41 48662899.79 65801854.26 80771958.91 55585350.12 44867032.37 49677350.41 72528350.54 3-hydroxyisobutyric_acid 717594.0448 648803.9064 15532820.35 7392179.753 17430789.08 12439755.44 8017825.824 9755732.716 7893245.522 3-hydroxybutyric_acid 1236128.496 1026538.928 18325094.83 13672577.24 24237191.28 15147677.5 11326016.63 16511784.02 12275263.25 "3'-Hydroxycotinine, Cis-" 117374.1618 96818.9813 14011541.18 18624417.49 22036888.42 9139864.172 11279416.84 20194618.84 15678894.35 2-O-Sulfo-L-idopyranuronic acid 92260.24171 92141.53397 3134734.25 3059969.074 2471205.845 1671006.501 1866434.503 1169410.854 2569549.811 2-Hydroxybenzyl 1-hydroxy-6-oxo-2-cyclohexene-1-carboxylate 170715.4696 172695.4943 1216388.932 1400141.479 2768993.007 937551.3629 975410.5733 1154529.195 476340.1878 2-Furoic acid 38947554.47 19492605.15 341630040.1 388536034 393031043.5 383296849 261468323.4 258896148.8 439338233 2-Descarboxy-betanidin 184740.9319 468618.7223 1596907.205 1050656.311 1813364.466 1241801.852 1316922.754 1559830.753 2026742.869 2-arachidonoylglycerol 24869.68641 24582.39268 296392.7834 606753.4147 1151245.622 334661.0162 501170.6752 214234.7878 773206.6649 "2,3,6-Pyridinetriol" 512096.9978 782477.3659 4156750.532 7378978.031 6995488.02 2634225.896 3276116.076 2574868.613 2297021.67 "2,3,-DIHYDROXYBENZOYLSERINE" 71563.50519 72741.04488 2427808.251 2232117.51 1715699.269 2107792.98 2586522.856 2485203.683 2340340.614 1-Stearoyl-2-hydroxy-sn-glycero-3-PE 75766.08394 74894.57279 129671.3446 2056376.669 1437575.661 422376.1848 428479.9391 167501.9105 588511.9586 1-(sn-glycero-3-phospho)-1D-myo-inositol 78811.66895 70820.24767 3876901.703 4491642.304 4444163.946 4422715.162 3582870.389 4484913.349 4203758.47 "1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid" 1411472.591 681819.1398 15578951.32 19002283.54 18727523.96 15957716.2 9826300.915 16510611.18 17100485.12 .alpha.-Aminoadipic acid 166563.0119 102015.3332 17320111.57 18258110.57 19128496.08 13354305.63 12869686.78 17535407.67 16035954.76 "(3S,4R)-3,4,5-Trihydroxy-4'-oxo-3',4,4',5-tetrahydro-2'H,3H-spiro[furan-2,1'-naphthalene]-6'-carboxylic acid" 176752.8713 377190.2395 245476893.2 351557362.1 377411054.9 229328684.4 184093207.4 234801143.8 310193788.9 "(2S,3R)-3-[(2-Nitro-1H-imidazol-1-yl)methoxy]-1,2,4-butanetriol" 66083.06669 75720.36292 2291447.679 1838534.005 2374815.478 1771187.495 2373098.96 2102487.849 1788655.204 (2-Pyridinyloxy)methanesulfonic acid 67924.70484 78215.35348 19876497.84 20249557.79 15653750.68 17640017.27 15180248.45 23084709.33 22835003.01 (2-butyl-1H-imidazol-4-yl)methanol 122933.7279 103718.9972 1613326.745 2174624.152 1974446.642 1766103.792 2313616.349 2199323.976 676532.2021 (+)-castanospermine 99704.75409 110908.3625 3300524.232 3110761.717 1839762.912 2699726.548 2573000.24 3390160.886 2605489.799 C15 H16 O8 237783.8013 365612.6879 261205614.1 387418148.9 438535570 254529554.9 198756922.9 273741071.6 333102981.5 C8 H12 N4 O5 P2 88432755.36 87173209.92 401309573.6 483884504.8 480461698.1 433391849.6 367071619.4 436965681.2 489088038.2 C11 H18 O11 P2 64584950.68 65062487.26 334426676 410589439.8 407155318.7 361353491.2 302234982.8 369767962.8 414891480.4 C6 H9 Cl O7 24086239.29 2842181.246 280858012.8 216332769.7 200451241.9 158150151.7 208127712.3 251131783.1 208981563.9 C4 H9 N O4 S 96572.52172 93845.04318 296376963.7 296127099.9 301047637.6 243939784.7 246827803.5 299067120.2 294029665.2 C7 H13 O4 P S 64666991.44 65093874.74 268888325.8 323759240.5 319981942.9 290394924.1 246240406.2 293256429.9 324815440.1 C5 H11 O3 P S 91688639.71 96021103.47 280272957.2 320211092.4 314377152.5 296749755.1 272534411.2 302656479.6 328211250.2 C4 H6 O P2 S2 95108.94033 63769.53773 130759413.6 144639699.8 155560478.9 104562625.9 106685680.8 116784382.6 114066930.5 C9 H16 O10 P2 43390114.78 47261946.75 223811238.5 272556396 268205790.8 249431431.8 211325861.1 259275572.1 270781148.3 C10 H20 N2 O15 P2 24836249.73 24985026.35 146861557.5 184486987.2 184060806.7 160283063.5 130725080.3 165189669.1 187459853.5 C7 H13 N4 O6 P3 S 13730842.73 10212791.72 169886155 183688483.3 180952851.5 165744043.2 94462341.53 86997631.22 195847431 C7 H14 N2 O14 P2 27032611.7 30088251.22 159491296.7 197064687.8 192272074.2 184467267.3 149146874.8 188046290.6 196530717.1 C5 H6 N4 O4 P2 38778289.38 46126482.48 153036646.6 120997613.4 171254704.8 165193649.6 146492194.6 176128430.6 174781383.2 C11 H14 N8 O16 P2 16344334.01 16996964.07 116508281.7 150112362.5 147988352.8 132306300.2 105999026.3 139186871 148701221.7 C10 H10 N10 O6 P2 20561391.32 21641630.52 121933046.7 151935736.2 146714246 136363516 110284723.9 139651731.8 147876458.9 C14 H7 N8 O11 P 17054858.12 17659722.92 113927091.9 144440442.7 139922372.8 130362255 103636874.5 134130136.5 142388149 C14 H30 N8 O8 99224.94468 104477.1831 78830865.05 82488933.88 63826041.99 18223243.93 70193205.77 32585693.61 21947481.98 C8 H12 O10 P2 24132888.17 28072140.72 121511927.5 143547419.3 139783224 136486899.4 115582428.9 54723849.67 137533513.8 C6 H9 Br O7 1043807.537 126234.6324 94266396.71 90040566.46 84142904.45 72756765.94 75130769.06 86456281.04 83755878.43 C4 H15 N2 O5 P3 28357889.95 30307318.97 121861960.4 142552198.4 138030732.5 133325841.9 113212575.1 137660822.8 142626372.5 C16 H17 N4 O16 P 10579475.86 10225956.2 67264349.39 84244115.34 83912823.23 71815583.44 58311721.55 73934130.52 86658875.86 C6 H9 Cl O7 (2) 5015655.139 237606.166 60961831.38 55441201.49 49847796.66 47605663.33 48652365.48 45772094.53 62774083.22 C17 H11 N10 O17 P 9307909.472 9228100.687 67118030.68 86238039.09 85009984.51 73282670.49 56252138.88 77608378.51 87976969.53 C14 H15 N4 O15 P 10998142.4 11694154.37 71251479.86 90878299.12 90024286.65 81694555.29 65329385.53 85079859.97 90775468.62 C5 H7 Br O5 611796.1501 99701.20094 40633786.09 49920321.57 50106712.51 46219585.38 39998087.51 49842782.95 47239996.43 C8 H16 O8 155428.8425 203029.4382 43410281.82 57992967.15 52299421.61 37846214.1 31287471.83 44485479.7 46249046.95 C4 H14 N2 O7 P2 S 10117883.52 7141635.423 105135182.8 117212717.1 117501478.2 106335828.6 102209348.1 48355020.65 210417490.6 C5 H7 Cl O5 3071174.978 191224.9673 34384419.06 42557236.24 41212787.22 37616129.23 32067563.83 39504868.75 41952805.7 C7 H10 O6 S 166538.9086 108849.0012 42529126.99 37474680.99 31972397.42 35788440.36 35762108.38 49970880.09 40948637.08 C6 H10 O12 S 89080.1889 1055117.281 34285087.63 36907116.63 20655766.91 30510413.33 29570834.03 28213694.46 37166706.14 C23 H37 N3 O5 1813597.104 1646869.074 27162461.31 40535662.85 40875388.47 17446988.21 25038134.66 21579708.41 33402216.34 C11 H7 N10 O14 P 5849785.664 6643082.758 42932218.56 55332737.25 54303723.31 49819962.95 40017529.87 54069828.43 54424893.78 C20 H19 N4 O18 P 4725064.645 4531228.405 31646132.45 41728562.74 41525136.58 35257252.4 27234719.87 37139876 42737139.76 C12 H5 N8 O10 P 6684439.245 7459001.735 43877075.92 54161724.75 53104441.71 49785036.72 41809712.02 53451701.38 52864377.39 C15 H9 N10 O16 P 4847071.616 5197856.198 38288472 49655958.25 48596497.69 44474807.88 34190370.46 46323984.18 50371021.18 C21 H23 N O10 199125.9129 202471.9734 33665351.65 35709669.54 30812468.62 17452237.27 30811339.87 21296286.64 18416555.03 C33 H9 N8 O12 P 3813712.757 3903791.012 28012438.02 37065001.7 37021768.72 32107401.14 24699945.1 33743355.45 37689904.2 C12 H22 O7 S 449240.1804 178701.3603 34020677.8 58423076.04 33341290.38 28744720.85 33728034.22 58462410.37 35222390.82 C2 H Cl N10 O 1749110.676 1445109.695 32659604.51 31910404.27 28314878.54 22819495.12 20643394.48 26772944.79 30777145.51 C6 H8 N6 O9 P2 7219206.029 8664537.963 43047245.88 35397942.21 48026183.7 46891094.16 39625037.46 18872604.52 48459134.71 C H4 O6 S2 143190.28 72435.70735 27202898.99 27990380.03 28056332.81 22094563.88 24734775.94 24943811.77 23864021.66 C4 H10 O5 S 352579.5735 94300.98411 22180214.04 23409019.21 39037559.32 15446140.73 17626851.57 38619583.67 24813146.25 C10 H14 O6 S 207888.5489 218892.6389 27095150.01 52317539.41 41947433.15 17672491.32 19288256.25 23669212.08 30969493.74 C12 H18 N8 O16 P2 3503483.096 3437009.504 25763806.96 32827713.18 30628664.49 27450616.41 22655054.42 29594471.35 33433218.84 C8 H7 N O4 S 189740.7885 509105.3158 33093711.38 34718487.17 37374424.45 16263011.95 19005330.56 21736632.2 19525471.12 C5 H10 N6 O S 132635.5083 104433.8847 26852995.09 26969400.59 17875587.16 16917938.17 23521588.62 19958035.06 22987015.62 C6 H8 O8 4997400.64 7670560.958 22887263.23 23518824.17 22640108.37 19284556.74 18707508.19 18956965.93 24038443.52 C6 H7 Cl O6 2471173.052 171717.1903 32845607.79 32872070.07 24747311.51 23485974.78 24216686.94 27859119.06 31104516.95 C6 H10 O9 P2 6868276.943 8753640.047 18667667.12 39013977.33 36579995.59 18515206.51 32349211.11 15170972.97 37506893.44 C2 H6 O8 S3 433318.0701 914200.3263 27869838.66 21882949.91 22603045.44 19014916.5 22860968.56 20085451.1 21743275.09 C16 H27 N O13 157964.2111 150931.8266 21352049.8 22558138.9 19685336.68 10428315.14 19356591.39 14653298.83 12079591.81 C23 H13 N10 O11 P3 2651391.843 2719366.951 20439037.72 27798177.3 27360742.79 24133824.17 18316393.29 25248084 27977059.19 C15 H17 N O5 S 379713.5657 805701.8278 37110765.45 33430012.27 29383886.28 18169807.97 35795198.71 22901212.93 17404367.84 C7 H17 N O7 P2 131254.2849 83280.96472 12800822.61 26903317.21 27150991.43 20898695.21 21532607.41 27831534.59 28386338.94 C8 H14 N10 O14 P2 S2 2591195.923 2856311.932 20437617.82 26871710.33 26375717.03 24497174.96 18519867.78 24952304.34 25689702.98 C6 H9 N O7 6734923.774 3807793.941 31706465.95 35079076.51 36683650.74 37718931.81 30825035.73 29960545.79 26902348.77 C22 H9 N10 O11 P3 2878203.238 3134044.45 20562805.76 27567854.25 25595792.3 24855112.56 17991394.42 25714788.49 27621884.85 C7 H23 N7 P2 S 88476.96086 121845.1781 6902317.582 7062619.156 11537945.49 4760560.254 5344620.506 6138942.609 2998564.211 C6 H10 N10 O2 313494.1924 367489.1581 19255228.74 22866275.69 25609730.9 19096075.73 19663596.97 21638858.71 22194833.43 C17 H17 N O10 173774.2565 432375.6441 14151526.3 20362157.98 24256827.03 20806430.38 11399279.86 15057180.7 14876886.32 C7 H11 N O7 1782418.101 2419608.357 7836026.2 14834089.18 17929754.39 5187535.202 20996476.12 17987644.84 4666024.842 C21 H35 O8 P 108198.2363 108661.7646 15756485.17 16119216.01 11433389.3 4079301.39 14308563.34 6521409.201 4097639.744 C3 H8 N6 O P2 S 197068.8631 293151.857 13959123.37 7607761.318 7514553.897 9141407.431 9730938.42 10758301.71 7442723.595 C12 H12 O14 4463084.701 330604.6847 11414912.92 13618146.22 13768427.6 16625734.25 9648715.685 10858502.19 13419347.44 C6 H2 O3 S3 76473.8357 99367.58867 12061580.52 12605447.12 14253324.81 13540646.7 11074903.86 12432379.94 11358077.27 C5 H16 N8 O6 75881.50149 85204.2416 9817874.099 7537667.816 9560656.573 10418188.13 6890179.5 11168264.3 7092698.214 C5 H12 N6 O4 S2 408505.6519 1036226.215 23412201.13 30451144.24 31780617.13 21091898.01 18539849.32 20423237.64 24441367.69 C10 H12 N2 O8 173966.5098 160698.7286 10707733.6 11806870.61 11056545.65 9984717.445 9398051.375 10593442.76 11667302.65 C10 H15 O11 P3 S 2187381.33 2918046.599 14589958.5 17353858.2 17297065.1 16259661.98 6933886.507 17955627.05 17096777.78 C18 H21 N2 P3 S 124600.829 313348.2638 11360646.4 13990508.99 14852678.97 10553120.37 9422174.664 10408575 13320427.26 C11 H6 N10 O3 P2 S2 2664082.049 1648034.947 21407491.55 22734235.11 22185525.14 12125127.15 20770343.38 21092849.2 23457007.51 C26 H54 N O9 P 93140.61201 92069.24764 1781703.24 19267095.5 12336354.57 3650333.739 3719091.464 1783325.394 7109872.825 C9 H18 N2 O8 146215.244 153954.8031 15805399.56 12777969.76 11364977.27 16863974.79 13787433.61 10104221.72 6728739.959 C3 H12 N2 O4 P2 7908836.29 141427.0975 11610638.12 23206516.02 21896669.27 21010641.53 20632295.28 19940609.83 21258392.21 C6 H2 N10 O8 S 2340931.633 2091294.977 13092398.79 19221899.64 13502503.24 15914857.83 9965821.212 13387893.74 26547036.1 C5 H5 N5 O10 1838318.591 1157489.347 26640241.86 29418098.73 28943490.01 26882573.01 25603877.4 47463531.24 52814058.95 C11 H15 N O10 72125.43747 73312.22346 13737643.84 11189631.57 8648902.58 11884727.02 14366634.49 14137709.27 13044581.48 C17 H13 O13 P3 1731716.737 2088582.478 14443196.11 17668962.21 16521971.64 16340193.56 13124340.32 17205242.5 17346471.23 C5 H11 N O6 S 200047.0077 446067.6107 14193810.16 16519732.57 17734917.81 4887471.427 7177818.006 12607479.29 15426447.06 C9 H13 N3 O9 108840.4197 191816.7615 10569468.16 7825568.858 6306860.537 18627252.94 10586945.57 12550903.4 8027082.534 C8 H9 N8 O2 P3 S 3791764.304 2582159.407 38428511.57 45483550.04 45704823.46 28574592.54 37224302.83 48289100.2 52497384.1 C5 H20 N9 O5 P3 285219.8367 709668.469 14869864.32 20270350.83 22004894.34 13969234.76 10955892.16 15012018.84 18693054.14 C31 H12 N8 O18 P2 1732849.227 1710991.141 11199759.15 14719917.38 14719196.1 14142643.35 9414429.822 13374530.69 15264087.16 C34 H13 N4 O17 P 1384673.46 1410567.614 10323140.48 14088613.47 13359345.48 11820078.65 8958219.487 12974031.33 14236857.31 C6 H9 Br O6 361365.6991 68715.17922 8723397.035 7400771.264 11370402.88 9295984.516 9187410.124 11314606.8 7517808.303 C5 H9 Br O7 195682.22 125395.3543 10379648.02 9993283.349 9011898.101 8235206.884 7612531.886 9127380.263 9541715.603 C11 H13 N O9 70565.26444 71726.37861 10164332.16 8662411.024 6185602.868 9014518.815 10597016.14 10675482.16 9844517.892 C5 H7 Cl O6 369455.5395 333364.6445 8956836.886 9083800.61 8202178.91 7172976.285 5491949.764 7544280.483 8596844.17 C5 H14 N2 O13 153170.0481 97186.53666 13442935.82 15415022.37 14372056.75 12343297.94 12093555.42 16118951.73 7640902.865 C14 H18 O15 2686907.265 416930.3106 6632426.102 10953929.98 10439916.2 4244000.791 6626715.873 7201635.232 8848787.009 C3 H2 N2 O3 P2 190972.8848 180053.4198 10306368.53 19596610.77 23282720.03 22965379.17 20060589.96 20839675.44 22099285.09 C14 H11 N O8 1621031.33 514196.7811 5364256.45 6633857.6 7294093.809 9561443.559 4969120.381 6230112.007 5200487.941 C7 H13 N7 S 186293.1703 199378.0655 10693162.97 11244950.81 9328263.243 5416650.416 8788913.546 6440123.858 4950099.814 C44 H62 N6 O13 P2 33323.60262 32101.566 282833.498 3755800.254 3393938.022 2324599.714 4908888.562 2217610.705 4439507.734 C5 H4 N6 O9 P2 2042735.302 2524348.622 11547426.91 9723596.857 13427725.1 11645339.54 11485775.47 13581085.53 12905994.16 C16 H35 Br N5 O6 P 171124.5275 263118.4215 5234505.352 2586256.414 2393023.389 992654.7763 849505.5969 4944230.917 2009690.838 C14 H35 Br N4 O3 P2 200685.6977 204057.9684 8339839.986 9134235.049 7601882.935 4854253.287 7534074.224 5350926.95 4447536.01 C6 H11 N O7 S 62722.76722 62246.39788 3815090.755 5513452.652 6117972.03 5849541.672 3905416.304 5412934.728 7330209.933 C9 H11 N O6 S 107871.0055 87212.32169 9454218.848 9592648.45 10837028.29 8687576.008 8071821.052 11817390.71 9543763.795 C13 H28 N5 O16 P3 S 841163.7414 296119.4844 5341111.347 7162776.444 2564540.862 6407801.834 4627726.638 3354169.945 3816442.211 C8 H20 N2 O7 P2 506562.7656 261981.1388 2143501.294 3817685.289 4163523.985 2981764.444 2725108.148 3547314.938 2889010.765 C14 H26 O5 S 17884.82186 17678.21703 634489.9739 2440036.435 1118798.782 324347.3628 797660.5012 617589.9046 1299080.574 C5 H20 N9 O5 P3 (2) 933062.5854 64064.25357 4962288.499 5705413.839 5859902.73 6643153.099 3308175.677 4875924.696 5698763.075 C23 H12 O 269289.9899 337402.8626 5845666.314 7458937.765 6574791.608 5859857.212 5887933.423 7416220.784 7331123.337 C9 H18 O10 179780.7927 436256.7128 6738383.751 7824640.6 7647938.711 5256564.707 5768279.697 6036123.903 7354906.99 C31 H5 N10 O16 P 859340.9626 984892.4857 7511241.648 10457818.94 10363281.88 9504101.107 6968774.475 9656543.873 10251880.95 C7 H23 N4 P3 134964.3081 128376.8641 13430483.49 10536590.33 11208773.37 13192596.05 16628712.96 15038069.61 9674967.269 C9 H13 Cl N2 O6 98268.12247 173184.494 10300224.37 8675454.706 7536636.757 4249650.861 10779710.98 11262177.09 9851564.485 C15 H23 N O11 125293.0857 131925.1797 6488977.957 8482305.57 8050600.27 2704055.349 6440945.537 5434603.276 5777539.875 C8 H21 N3 O9 P2 222421.267 527400.4628 8447613.403 11199167.53 11275301.18 6863457.627 5411320.618 7055374.294 7296526.123 C37 H11 O15 P3 699883.2119 777940.6804 7400734.05 9573467.526 9192051.012 8739628.408 6066977.065 8804244.972 9689706.523 C11 H28 Cl N8 O2 P3 S 126269.4503 139435.0488 2367385.788 4591992.389 4078655.527 2268044.165 3879721.582 2466334.785 2192540.231 C17 H40 Br N7 O4 P2 150740.0215 331762.6256 1014747.879 1946442.024 10711802.58 2992124.611 2576570.632 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886839.2627 1166382.583 C6 H16 N2 O2 P2 S2 98648.18894 88645.36516 1457165.688 1387670.623 863173.556 2447427.976 1279856.414 2179749.819 1993801.765 C4 H12 Cl N2 O4 P 103064.6939 100828.7745 2384634.692 2924635.421 3488312.08 1979191.594 2588106.566 2512711.469 2832068.329 C6 H18 Br N3 O16 P2 251029.3608 161770.2208 2932978.972 3230059.753 961510.6692 1168220.108 1486357.785 1205737.371 3134622.834 C9 H8 O6 S 100757.2432 96716.3823 1726427.864 1498247.328 1344225.041 1854630.198 1336207.746 2223285.954 2310112.129 C15 H35 N9 O3 S 47736.27866 45352.02089 709612.2129 1460487.781 1198311.445 368882.8312 668321.532 589839.2944 895607.1045 C24 H19 N4 O3 P S 88525.64453 69047.63202 1039946.519 1503363.479 1666411.446 544137.8011 946257.588 1391176.547 1364065.311 C14 H23 O3 P S 65361.57037 64447.92341 1076781.599 1347086.929 1699765.206 656632.076 1208172.848 860019.6311 1053375.636 C2 H4 O10 S4 69505.7024 69416.27206 1476710.207 1123526.004 1398785.993 995751.6698 1136551.545 1194413.234 1150423.417 C7 H7 Br O2 S 87442.72285 102212.9064 1221500.825 828984.3944 970407.6659 817140.1153 1045226.552 1249056.922 1244719.044 C2 H3 O14 P S 162847.2224 156316.2481 1451383.584 2414602.564 3063890.331 2795648.627 3058020.403 2870191.636 2917483.35 C17 H26 O4 S 48127.9754 45724.15378 257437.6407 940345.9037 1091875.603 248718.21 786321.5326 433095.8335 896383.3119 C13 H28 N6 O S 38397.82536 37075.75906 311173.5192 356689.9899 415426.5842 902835.5719 946473.2246 714951.8665 314892.8072 C6 H22 N8 O8 P2 71432.01823 81965.49919 700036.4394 713306.8333 1438961.93 850287.7641 232007.2579 830178.3358 962932.0167 C7 H22 N3 O8 P3 1518365.901 145552.2158 3681382.654 4453443.227 3641539.972 3047211.709 1463411.768 3759237.666 4126362.599 C4 H7 Cl3 N2 O3 S3 115339.1019 88981.6501 1057715.792 720693.3478 735938.8948 843670.4187 998004.3902 1070918.197 759447.4211 C4 H N6 O P3 87790.13242 67281.81658 850157.3484 909705.5541 821863.8357 629212.3598 675225.986 795212.5433 835195.9182 C13 H28 N6 O2 S 30363.05123 30012.29834 185649.3026 338040.3252 350046.5302 495719.3904 737892.0579 662083.0389 297361.2559 C6 H20 N4 O P2 S 95374.68889 101034.1257 3120334.061 3200472.217 3095042.414 1189635.005 2971480.658 1820489.826 2941723.43 C H3 Br O3 107481.0866 82919.35933 851415.1592 1006486.6 851591.2195 783748.1639 874888.3809 752565.7383 805072.2096 C4 H15 Cl N9 P 93254.34859 98190.54759 1403670.681 1228885.007 1348920.606 254478.3116 987222.6006 819318.6056 844143.376 C10 H15 N O5 58682.61065 51412.56304 1287910.963 1067244.929 1212997.539 529330.5425 1052971.559 850773.9852 838176.0556 C11 H18 Cl O P S 76086.03401 85265.65061 1010127.541 1138104.232 1485680.347 201382.7252 991948.617 852526.7636 1089389.337 C8 H3 Cl4 N O3 88559.44835 79579.61238 1042435.405 1105275.109 851924.5695 617134.8315 810414.9188 840427.9024 1199873.137 C4 H14 Br N4 P3 154321.5524 98890.97609 889888.2681 980990.1029 910725.1936 667251.2639 557699.3155 731266.7585 1058196.402 C6 H10 Br N O6 120473.4373 85045.91647 820973.2834 833351.3951 758911.8429 668759.014 814995.6146 1014501.947 861470.8758 C31 H7 N3 112219.6259 68731.48122 376251.5641 752706.6566 975815.6147 331178.7993 927947.6863 992925.5954 243700.0337 C3 H7 Cl N8 O5 P2 S3 68432.29664 65221.23643 772376.6002 474811.5897 523778.5154 413050.5862 732370.4537 445897.4205 552690.6888 C32 H67 N7 O3 40609.2703 36660.99369 61740.7861 1005220.41 475441.057 42376.71539 119022.0133 101186.8614 442753.644 C15 H24 N10 O5 S2 69736.30856 122900.9674 786409.6929 536145.7389 352635.2387 402624.1223 557933.4773 1058405.831 580320.8391 C45 H84 N3 P3 49541.45878 45598.57826 262916.5071 933213.9067 921232.7257 252098.1242 357237.3992 222421.1939 468824.8758 C11 H16 Br Cl2 N4 O P S 60603.19342 54458.09263 383812.1829 484560.0865 533823.6801 512016.5675 432376.2981 826367.7935 641276.9326 C8 H8 O S4 95752.49331 93675.20712 953042.0142 372223.0305 453467.1055 836031.9033 279393.1028 1370230.19 1364511.918 C16 H17 Br N2 O2 44827.23016 81073.37475 495985.8057 520566.9693 723102.713 544794.2418 395679.657 620351.592 531499.8823 C3 H7 Cl2 O5 P 112827.5204 58683.25594 790425.5016 759813.9123 737615.5681 829559.1721 590535.3386 650064.0928 721161.7341 C16 H28 O5 58976.57529 56945.96699 636348.6812 419643.858 371199.2962 394085.7527 255611.7462 439842.6221 646800.1703 C19 H20 Br N3 O 56773.25473 100055.3094 415448.1491 428696.6222 333328.5664 159403.4387 373529.6807 509918.737 632719.8962 C8 H2 Cl2 N3 P3 93496.36045 84015.92672 1042435.405 1235248.808 851924.5695 617134.8315 810414.9188 1010289.05 1199873.137 C3 H12 N6 O S5 79561.58568 78833.99998 699967.5234 774280.2412 1026969.879 1147571.659 253456.3367 1317602.452 1460663.545 C45 H55 N O4 53702.42068 51020.17529 380721.6241 695989.2665 354803.2029 56766.04886 352436.7871 100116.2107 273840.9014 C12 H15 N O4 S 47439.23536 45805.86644 548894.0962 571240.3294 568810.0498 169336.6316 336534.5251 539725.2287 445023.5354 C4 H7 Br2 N2 O2 P3 S 74653.02712 59170.00603 506496.566 347669.6207 448985.6471 252232.0962 369511.0568 367854.9263 325414.952 C4 H N6 O5 P3 S 131839.4379 129139.9457 222640.5781 1580961.563 1648219.085 1558183.187 1403927.372 1445258.988 1770280.916 C17 H44 N8 O4 P2 52195.81042 50331.97301 146801.8589 620580.7337 734714.4558 168282.124 232814.8261 118733.4154 489959.1907 C15 H29 N4 O4 P 45774.57578 44198.52236 260851.6858 566859.8612 609051.8734 293441.1647 262651.5463 521550.3818 509079.5643 C5 H12 Cl N3 O13 S 196398.3549 100981.2569 899579.6036 1418616.215 1415291.995 1101295.325 689027.8388 1064010.395 1351452.427 C5 H17 N10 O7 P3 70024.48943 103520.4263 282729.2129 846878.0323 801361.2877 459261.2019 332900.0035 488919.011 733460.8922 C13 H18 Cl N8 O4 P 89135.31267 157089.1316 901267.3909 955714.2685 706286.4948 480253.4286 737335.4725 617358.0265 988435.7364 C5 H12 Cl N10 P 62814.24334 61936.20381 564455.0134 791350.2272 942896.9738 61158.10296 635409.8419 611916.8055 722862.672 C13 H26 Br N5 O5 S 76593.22184 134985.3649 624382.2744 675627.1336 505045.0884 438108.1972 641270.6563 794719.8904 723743.2559 C2 H6 Cl N3 O3 S2 74683.64166 74587.54906 413585.1625 463452.2656 283588.827 611695.5626 594511.4059 512125.967 391904.944 C12 H10 Br Cl 64123.36306 66465.99868 448364.2959 546212.016 619194.8297 297816.8478 700865.3638 571830.2779 119721.4562 C7 H8 Cl2 N2 S2 57661.32346 53655.274 422097.3079 391536.1239 465224.176 292993.9908 489696.4526 564269.1533 322261.231 C6 H22 N9 O2 P3 45065.74191 44435.79716 324796.7356 453013.9419 443706.6702 198208.2701 228590.5161 308559.8574 252005.6381 C7 H12 Cl N O6 162681.676 171058.0891 481696.0601 913068.8366 889122.7633 99033.86882 724134.5307 879405.0972 537159.2107 C4 H7 Cl N O5 P 56587.25613 57225.83511 377720.3188 382753.2264 340286.1612 460552.5281 206749.67 255277.2753 304357.063 C6 H17 N4 O6 P 42936.62138 40419.52665 521244.3895 453382.3895 400718.3611 472838.5578 651171.2877 330747.0678 416482.015 C5 H19 N9 O3 P2 S 53470.82381 94235.21417 357832.2236 435210.1975 352742.3103 246268.5807 273252.0712 299627.5467 384897.3276 C3 H7 Br N8 O3 53570.73804 54175.27605 195394.1047 381320.7293 388456.4793 69516.35541 292177.505 358462.6874 92781.32605 C4 H4 Cl4 N3 O3 P 37400.45308 37822.51177 205632.4091 135011.6058 156878.388 135880.8337 133549.2738 152079.1391 139096.3993 MS_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name Tags XYLOSE/ARABINOSE/LYXOSE A Veronal F valine A;F uridine A URATE B;D Uracil degenerate Uracil degenerate (2) A;F uracil A;B;C;F tyrosine A;F tryptophan A;B;F TI0889000 Thymine F thymidine A;F threonine A;B;C;F Tauropine taurine A;B;F Sulfuric acid Stearic acid F Spaglumic acid sorbitol A Serine degenerate serine A;F Sebacic acid Rivastigmine Retinyl acetate F Quinolinic acid Pyridoxal A;F pseudouridine A;F Protocatechuic acid proline A;B;F Portulacaxanthin I F Pivagabine Piracetam Pipecolate A;F Picein Phosphoric acid phenylalanine A;F Paraldehyde F PANTOTHENATE A;F Palustrine F OXOPROLINE/PYROGLUTAMATE A;F Oxalosuccinic acid Orotic acid D Ornithine degenerate (RT = 9.874) F Ornithine degenerate (RT = 14.706) F ornithine A;F O-Acetyl-L-serine N~2~-Acetyl-L-ornithine F Nitrosoguvacoline (RT = 2.163) F Nitrosoguvacoline (RT = 2.163) (2) F Niacin N6-METHYLLYSINE F N-ACETYLSERINE A N-Acetylnorvaline N-acetylmethionine A N-Acetylgalactosamine 6-sulfate N-Acetylaspartic acid N-ACETYLALANINE A N-Acetyl-L-leucine N-Acetyl-L-aspartic acid "N(3)-(4-Methoxyfumaroyl)-2,3-diaminopropionic acid" N(2)-succinyl-L-citrulline F myo-inositol A;F MW_946.36560@RT_1.650 F MW_886.56034@RT_1.647 F MW_884.54470@RT_1.649 F MW_867.56624@RT_1.697 F MW_858.53001@RT_1.652 F MW_843.56688@RT_1.705 F MW_819.56496@RT_1.710 F MW_793.54972@RT_1.717 F MW_750.50849@RT_1.757 F MW_747.52194@RT_1.684 F MW_701.44562@RT_1.745 F MW_687.43064@RT_1.751 F MW_641.40835@RT_1.745 F MW_585.36445@RT_1.872 F MW_557.33318@RT_1.931 F MW_473.09572@RT_4.840 F MW_466.10637@RT_4.823 F MW_448.14117@RT_1.779 F MW_438.24739@RT_1.771 F MW_412.13438@RT_6.720 F MW_411.22806@RT_1.761 F MW_391.24662@RT_1.765 F MW_375.25184@RT_1.754 F MW_370.20516@RT_14.713 F MW_344.21960@RT_2.034 F MW_344.19851@RT_1.985 F MW_332.27121@RT_1.719 F MW_330.19806@RT_1.649 F MW_323.22056@RT_1.961 F MW_320.07046@RT_14.104 F MW_314.19267@RT_14.110 F MW_310.10822@RT_2.186 F MW_303.15422@RT_11.640 F MW_298.17749@RT_2.175 F MW_294.08461@RT_2.769 F MW_290.04391@RT_6.262 F MW_282.14936@RT_1.796 F MW_280.13409@RT_2.151 F MW_275.14740@RT_11.657 F MW_273.04782@RT_2.767 F MW_271.21416@RT_1.957 F MW_261.05277@RT_6.228 F MW_246.08459@RT_4.999 F MW_228.00319@RT_8.794 F MW_224.08912@RT_6.649 F MW_219.03745@RT_3.495 F MW_215.04261@RT_1.974 F MW_202.02961@RT_2.007 F MW_196.09328@RT_14.706 E;F MW_184.04800@RT_2.285 F MW_182.10569@RT_2.096 F MW_168.12646@RT_2.542 F MW_156.08958@RT_2.615 F Mimosine (RT = 2.465) F mH MFCD12546417 F METHYL GALACTOSIDE F Methionine sulfoxide A;F methionine A;F Malonic acid MALEATE B malate B;D lysine A;F leucine A;B;C;D;F lactide Lactic Acid (tail) D lactic acid C;D L-coprine Juniperic acid F Itaconic acid isoleucine A;B;C;D;F isocitrate A;D Isethionic acid Isethionic acid (2) F inosine A;F Imidazolelactate hypoxanthine A;F hydroxyprolie/5-aminolevulinic acid A;B;D hydroxyacetone phosphate Hydroquinone Hydrogen bromide Hopantenic acid Homovanillic acid Homo-L-arginine F histidine (tail) F Hippuric acid glutamine A;C;F GLUCURONATE A glucose A GLUCONATE A;B Formylisoglutamine F Fomepizole Ethylparaben Ethopabate F Erythrose F epsilon-(gamma-Glutamyl)-lysine F dihydroxyphenylalanine F Dihydrothymine DEOXYURIDINE A D-Gluconic acid D-(+)-Pyroglutamic Acid F cytidine A;F Cysteine-glutathione disulfide F Creatinine degenerate F creatinine A;F creatine A;B;D;F citrulline A;F Cinnamic acid Chlorogenic acid Beta-Hydroxybutyric acid asymmetric dimethylarginine (ADMA) A;F Aspartame F ascorbic acid 2-sulfate argininosuccinate A;F arginine A;B;C;F Arachidonic acid F anthopleurine AMPA Aminolevulinic acid alpha-Ketoglutaric acid C Aloin B E allantoin A;B alanine A;B;C;D;F afegostat afegostat (2) F Aceglutamide 7-Methylguanosine F 6-Deoxy-D-arabino-hexos-2-ulose 5-Methoxy-3-indoleaceate 5'-O-[(3-Amino-6-hydroxy-6-imino-2-oxohexyl)(hydroxy)phosphoryl]adenosine 4-tert-Octylphenol monoethoxylate F 4-phenolsulfonic acid E;F 4-ACETAMIDOBUTANOATE A 4-(Hydroxymethyl)benzenesulfonic acid 3-Sulfinoalanine 3-OH-isovaleric acid 3-O-feruloyl-D-quinic acid 3-methyl-2-oxopentanoic_acid A;F 3-HYDROXYMETHYLGLUTARATE A 3-hydroxyisobutyric_acid A 3-hydroxybutyric_acid A "3'-Hydroxycotinine, Cis-" 2-O-Sulfo-L-idopyranuronic acid 2-Hydroxybenzyl 1-hydroxy-6-oxo-2-cyclohexene-1-carboxylate 2-Furoic acid 2-Descarboxy-betanidin 2-arachidonoylglycerol "2,3,6-Pyridinetriol" E "2,3,-DIHYDROXYBENZOYLSERINE" 1-Stearoyl-2-hydroxy-sn-glycero-3-PE F 1-(sn-glycero-3-phospho)-1D-myo-inositol F "1,3,4-Trihydroxy-5-oxocyclohexanecarboxylic acid" .alpha.-Aminoadipic acid "(3S,4R)-3,4,5-Trihydroxy-4'-oxo-3',4,4',5-tetrahydro-2'H,3H-spiro[furan-2,1'-naphthalene]-6'-carboxylic acid" "(2S,3R)-3-[(2-Nitro-1H-imidazol-1-yl)methoxy]-1,2,4-butanetriol" (2-Pyridinyloxy)methanesulfonic acid (2-butyl-1H-imidazol-4-yl)methanol F (+)-castanospermine C15 H16 O8 C8 H12 N4 O5 P2 C11 H18 O11 P2 C6 H9 Cl O7 C4 H9 N O4 S C7 H13 O4 P S C5 H11 O3 P S C4 H6 O P2 S2 C9 H16 O10 P2 C10 H20 N2 O15 P2 C7 H13 N4 O6 P3 S C7 H14 N2 O14 P2 C5 H6 N4 O4 P2 C11 H14 N8 O16 P2 C10 H10 N10 O6 P2 C14 H7 N8 O11 P C14 H30 N8 O8 C8 H12 O10 P2 C6 H9 Br O7 C4 H15 N2 O5 P3 C16 H17 N4 O16 P C6 H9 Cl O7 (2) C17 H11 N10 O17 P C14 H15 N4 O15 P C5 H7 Br O5 C8 H16 O8 C4 H14 N2 O7 P2 S C5 H7 Cl O5 C7 H10 O6 S C6 H10 O12 S C23 H37 N3 O5 C11 H7 N10 O14 P C20 H19 N4 O18 P C12 H5 N8 O10 P C15 H9 N10 O16 P C21 H23 N O10 C33 H9 N8 O12 P C12 H22 O7 S C2 H Cl N10 O C6 H8 N6 O9 P2 C H4 O6 S2 C4 H10 O5 S C10 H14 O6 S C12 H18 N8 O16 P2 C8 H7 N O4 S C5 H10 N6 O S C6 H8 O8 C6 H7 Cl O6 C6 H10 O9 P2 C2 H6 O8 S3 C16 H27 N O13 C23 H13 N10 O11 P3 C15 H17 N O5 S C7 H17 N O7 P2 C8 H14 N10 O14 P2 S2 C6 H9 N O7 C22 H9 N10 O11 P3 C7 H23 N7 P2 S C6 H10 N10 O2 C17 H17 N O10 C7 H11 N O7 C21 H35 O8 P C3 H8 N6 O P2 S C12 H12 O14 C6 H2 O3 S3 C5 H16 N8 O6 C5 H12 N6 O4 S2 C10 H12 N2 O8 C10 H15 O11 P3 S C18 H21 N2 P3 S C11 H6 N10 O3 P2 S2 C26 H54 N O9 P C9 H18 N2 O8 C3 H12 N2 O4 P2 C6 H2 N10 O8 S C5 H5 N5 O10 C11 H15 N O10 C17 H13 O13 P3 C5 H11 N O6 S C9 H13 N3 O9 C8 H9 N8 O2 P3 S C5 H20 N9 O5 P3 C31 H12 N8 O18 P2 C34 H13 N4 O17 P C6 H9 Br O6 C5 H9 Br O7 C11 H13 N O9 C5 H7 Cl O6 C5 H14 N2 O13 C14 H18 O15 C3 H2 N2 O3 P2 C14 H11 N O8 C7 H13 N7 S C44 H62 N6 O13 P2 C5 H4 N6 O9 P2 C16 H35 Br N5 O6 P C14 H35 Br N4 O3 P2 C6 H11 N O7 S C9 H11 N O6 S C13 H28 N5 O16 P3 S C8 H20 N2 O7 P2 C14 H26 O5 S C5 H20 N9 O5 P3 (2) C23 H12 O C9 H18 O10 C31 H5 N10 O16 P C7 H23 N4 P3 C9 H13 Cl N2 O6 C15 H23 N O11 C8 H21 N3 O9 P2 C37 H11 O15 P3 C11 H28 Cl N8 O2 P3 S C17 H40 Br N7 O4 P2 C37 H86 N7 O6 P3 C6 H17 N3 O8 P2 C12 H22 N5 O P3 C3 H4 N6 O10 S C22 H7 N6 O18 P S C6 H16 N6 O4 P2 S2 C H2 N5 O10 P C18 H18 Cl N7 O2 P2 S3 E C8 H24 N7 P3 C15 H14 O6 S C41 H83 N3 O7 P2 C5 H18 N3 P3 C12 H32 N10 O5 S2 C10 H17 N O5 C3 H5 Cl O16 C8 H14 N6 O8 C7 H8 N10 O4 S C7 H18 N9 O4 P C6 H10 Cl N O6 C5 H10 O3 S C15 H15 N O2 P2 C37 H84 N7 O13 P C3 H6 N10 O3 P2 C31 H14 N10 O8 P2 C11 H15 N O10 (2) C H3 Cl O3 C9 H8 O P2 C7 H8 O5 S C13 H26 N10 S C6 H10 O4 S C6 H18 N9 O4 P C11 H12 N2 O11 C10 H24 N7 O12 P C5 H19 N9 O5 S C6 H12 N8 O2 C H4 Br N8 O P C7 H21 Br N9 O3 P C7 H10 O6 S5 C8 H9 Br N9 O2 P C15 H11 N O9 C19 H49 N9 O11 C29 H54 N5 O5 P C18 H23 Br N2 O3 C4 H4 P2 S2 C7 H14 Br N7 O7 S2 C9 H15 O12 P C8 H11 N O5 C9 H10 N8 O6 C2 H5 O2 P S C10 H27 N9 O6 P2 S C4 H5 O8 P3 S2 C11 H22 N2 O5 P2 S C5 H7 N8 P3 S C9 H18 N8 O P2 S C3 H8 O10 S4 C10 H11 N O8 C2 H5 N3 O4 P2 S C12 H29 Br N4 O17 C17 H17 N5 P2 C48 H78 N2 O5 C10 H15 N O11 S C13 H26 Br N7 P2 C17 H30 Br O P C4 H14 N9 O5 P3 C13 H14 O12 C9 H19 N O5 C4 H15 N10 O8 P3 C25 H51 N9 O4 P2 C5 H9 N7 O2 C5 H8 N6 O11 P2 C9 H15 N4 O3 P3 C7 H15 Cl N O8 P S2 C21 H32 N4 S C14 H10 O2 P2 C7 H21 Br N8 P2 C2 H6 Cl N O4 S4 C2 H6 Cl2 N4 O6 P2 C9 H19 N8 P C7 H17 Cl N O8 P S2 C3 H3 O6 P S C18 H19 N2 O3 P S C6 H13 N O9 C7 H20 Br N7 O2 C9 H10 O6 S C7 H8 O5 S (2) C2 H3 N5 O2 P2 S2 C7 H11 N O8 C7 H27 N10 O2 P3 C H3 N8 O P S C25 H30 S C6 H19 N7 O11 P2 C11 H12 O11 C16 H28 Br O2 P C15 H22 N9 O3 P S C12 H13 N2 O3 P E C11 H27 N2 O14 P S C5 H4 O P2 S3 C4 H8 Cl3 P3 C23 H40 N P3 C27 H32 O S C4 H12 N5 O2 P C9 H7 Cl N5 O2 P S C H N5 P2 S C42 H49 O7 P C21 H3 Cl N6 O P2 C5 H17 N7 O10 P2 C6 H16 N2 O2 P2 S2 C4 H12 Cl N2 O4 P C6 H18 Br N3 O16 P2 C9 H8 O6 S C15 H35 N9 O3 S C24 H19 N4 O3 P S C14 H23 O3 P S C2 H4 O10 S4 C7 H7 Br O2 S C2 H3 O14 P S C17 H26 O4 S C13 H28 N6 O S C6 H22 N8 O8 P2 C7 H22 N3 O8 P3 C4 H7 Cl3 N2 O3 S3 C4 H N6 O P3 C13 H28 N6 O2 S C6 H20 N4 O P2 S C H3 Br O3 C4 H15 Cl N9 P C10 H15 N O5 C11 H18 Cl O P S C8 H3 Cl4 N O3 C4 H14 Br N4 P3 C6 H10 Br N O6 C31 H7 N3 C3 H7 Cl N8 O5 P2 S3 C32 H67 N7 O3 C15 H24 N10 O5 S2 C45 H84 N3 P3 C11 H16 Br Cl2 N4 O P S C8 H8 O S4 C16 H17 Br N2 O2 C3 H7 Cl2 O5 P C16 H28 O5 C19 H20 Br N3 O C8 H2 Cl2 N3 P3 C3 H12 N6 O S5 C45 H55 N O4 C12 H15 N O4 S C4 H7 Br2 N2 O2 P3 S C4 H N6 O5 P3 S C17 H44 N8 O4 P2 C15 H29 N4 O4 P C5 H12 Cl N3 O13 S C5 H17 N10 O7 P3 C13 H18 Cl N8 O4 P C5 H12 Cl N10 P C13 H26 Br N5 O5 S C2 H6 Cl N3 O3 S2 C12 H10 Br Cl C7 H8 Cl2 N2 S2 C6 H22 N9 O2 P3 C7 H12 Cl N O6 C4 H7 Cl N O5 P C6 H17 N4 O6 P C5 H19 N9 O3 P2 S C3 H7 Br N8 O3 C4 H4 Cl4 N3 O3 P METABOLITES_END #END