#METABOLOMICS WORKBENCH sinkwarr_20250324_105430 DATATRACK_ID:5775 STUDY_ID:ST003845 ANALYSIS_ID:AN006319 PROJECT_ID:PR002403 VERSION 1 CREATED_ON April 4, 2025, 9:52 pm #PROJECT PR:PROJECT_TITLE Shift in the urinary metabolome associated with PR:PROJECT_TITLE 2,3,7,8-tetrachlorodibenzo-p-dioxin activation of the hepatic aryl hydrocarbon PR:PROJECT_TITLE receptor PR:PROJECT_SUMMARY Epidemiological evidence suggests an association between dioxin and dioxin-like PR:PROJECT_SUMMARY compound (DLC) exposure and human liver disease. In rodents, the prototypical PR:PROJECT_SUMMARY DLC, 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), has been shown to induce the PR:PROJECT_SUMMARY progression of reversible hepatic steatosis to steatohepatitis with periportal PR:PROJECT_SUMMARY fibrosis and biliary hyperplasia. Although the effects of TCDD toxicity are PR:PROJECT_SUMMARY mediated by aryl hydrocarbon receptor (AHR) activation, the underlying PR:PROJECT_SUMMARY mechanisms of TCDD-induced liver toxicity are not well understood. In the PR:PROJECT_SUMMARY present study, male C57BL/6NCrl mice were gavaged every 4 days for 28 days with PR:PROJECT_SUMMARY 0.03 - 30 µg/kg TCDD or sesame oil vehicle and evaluated for liver PR:PROJECT_SUMMARY histopathology and gene expression as well as complementary 1-dimensional proton PR:PROJECT_SUMMARY magnetic resonance (1-D 1H NMR) urinary metabolic profiling. Urinary PR:PROJECT_SUMMARY trimethylamine (TMA), trimethylamine N-oxide (TMAO), and 1-methylnicotinamide PR:PROJECT_SUMMARY (1MN) levels were altered by TCDD at doses ≤ 3 µg/kg; other urinary PR:PROJECT_SUMMARY metabolites, like glycolate, urocanate, and 3-hydroxyisovalerate, were only PR:PROJECT_SUMMARY altered at doses that induced moderate to severe steatohepatitis. Hepatic PR:PROJECT_SUMMARY differential gene expression of rate-limiting enzymes of choline, gloxylate, and PR:PROJECT_SUMMARY amino acid metabolism coincided with the altered urinary metabolites. Published PR:PROJECT_SUMMARY single-nuclear RNA-seq (snRNA-seq), AHR ChIP-seq, and AHR knockout gene PR:PROJECT_SUMMARY expression datasets provided further support for hepatic PR:INSTITUTE Michigan State University PR:DEPARTMENT Biochemistry and Molecular Biology PR:LAST_NAME Sink PR:FIRST_NAME Warren PR:ADDRESS 603 Wilson Rd, East Lansing, Michigan, 48824, USA PR:EMAIL sinkwarr@msu.edu PR:PHONE 6162953496 PR:PROJECT_COMMENTS The urine samples were collected by the Zacharewski lab at Michigan State PR:PROJECT_COMMENTS University. The samples were evaluated with 1-dimensional 1H NMR by Dr. Ali PR:PROJECT_COMMENTS Yilmaz at Corewell Health Research Institute. The data upload was done by Warren PR:PROJECT_COMMENTS Sink from the Zacharewski lab. #STUDY ST:STUDY_TITLE Shift in the urinary metabolome associated with ST:STUDY_TITLE 2,3,7,8-tetrachlorodibenzo-p-dioxin activation of the hepatic aryl hydrocarbon ST:STUDY_TITLE receptor ST:STUDY_SUMMARY Epidemiological evidence suggests an association between dioxin and dioxin-like ST:STUDY_SUMMARY compound (DLC) exposure and human liver disease. In rodents, the prototypical ST:STUDY_SUMMARY DLC, 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), has been shown to induce the ST:STUDY_SUMMARY progression of reversible hepatic steatosis to steatohepatitis with periportal ST:STUDY_SUMMARY fibrosis and biliary hyperplasia. Although the effects of TCDD toxicity are ST:STUDY_SUMMARY mediated by aryl hydrocarbon receptor (AHR) activation, the underlying ST:STUDY_SUMMARY mechanisms of TCDD-induced liver toxicity are not well understood. In the ST:STUDY_SUMMARY present study, male C57BL/6NCrl mice were gavaged every 4 days for 28 days with ST:STUDY_SUMMARY 0.03 - 30 µg/kg TCDD or sesame oil vehicle and evaluated for liver ST:STUDY_SUMMARY histopathology and gene expression as well as complementary 1-dimensional proton ST:STUDY_SUMMARY magnetic resonance (1-D 1H NMR) urinary metabolic profiling. Urinary ST:STUDY_SUMMARY trimethylamine (TMA), trimethylamine N-oxide (TMAO), and 1-methylnicotinamide ST:STUDY_SUMMARY (1MN) levels were altered by TCDD at doses ≤ 3 µg/kg; other urinary ST:STUDY_SUMMARY metabolites, like glycolate, urocanate, and 3-hydroxyisovalerate, were only ST:STUDY_SUMMARY altered at doses that induced moderate to severe steatohepatitis. Hepatic ST:STUDY_SUMMARY differential gene expression of rate-limiting enzymes of choline, gloxylate, and ST:STUDY_SUMMARY amino acid metabolism coincided with the altered urinary metabolites. Published ST:STUDY_SUMMARY single-nuclear RNA-seq (snRNA-seq), AHR ChIP-seq, and AHR knockout gene ST:STUDY_SUMMARY expression datasets provided further support for hepatic cell-type and ST:STUDY_SUMMARY AHR-regulated dependency for the affected metabolic pathways. ST:INSTITUTE Michigan State University ST:DEPARTMENT Biochemistry and Molecular Biology ST:LAST_NAME Sink ST:FIRST_NAME Warren ST:ADDRESS 603 Wilson Rd, East Lansing, Michigan, 48824, USA ST:EMAIL sinkwarr@msu.edu ST:PHONE 6162953496 #SUBJECT SU:SUBJECT_TYPE Mammal SU:SUBJECT_SPECIES Mus musculus SU:TAXONOMY_ID 10090 SU:GENOTYPE_STRAIN C56BL/6NCrl SU:AGE_OR_AGE_RANGE post-natal day 58 SU:WEIGHT_OR_WEIGHT_RANGE 16 - 24 grams SU:GENDER Male SU:ANIMAL_ANIMAL_SUPPLIER Charles River #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 56 2 Sample source:Urine | Dose:0 µg/kg TCDD RAW_FILE_NAME(Raw file name)=20 SUBJECT_SAMPLE_FACTORS 3 6 Sample source:Urine | Dose:0 µg/kg TCDD RAW_FILE_NAME(Raw file name)=60 SUBJECT_SAMPLE_FACTORS 2 14 Sample source:Urine | Dose:0 µg/kg TCDD RAW_FILE_NAME(Raw file name)=140 SUBJECT_SAMPLE_FACTORS 29 22 Sample source:Urine | Dose:0 µg/kg TCDD RAW_FILE_NAME(Raw file name)=220 SUBJECT_SAMPLE_FACTORS 30 40 Sample source:Urine | Dose:0 µg/kg TCDD RAW_FILE_NAME(Raw file name)=400 SUBJECT_SAMPLE_FACTORS 36 8 Sample source:Urine | Dose:0.03 µg/kg TCDD RAW_FILE_NAME(Raw file name)=80 SUBJECT_SAMPLE_FACTORS 62 12 Sample source:Urine | Dose:0.03 µg/kg TCDD RAW_FILE_NAME(Raw file name)=120 SUBJECT_SAMPLE_FACTORS 34 16 Sample source:Urine | Dose:0.03 µg/kg TCDD RAW_FILE_NAME(Raw file name)=160 SUBJECT_SAMPLE_FACTORS 35 26 Sample source:Urine | Dose:0.03 µg/kg TCDD RAW_FILE_NAME(Raw file name)=260 SUBJECT_SAMPLE_FACTORS 63 34 Sample source:Urine | Dose:0.03 µg/kg TCDD RAW_FILE_NAME(Raw file name)=340 SUBJECT_SAMPLE_FACTORS 37 3 Sample source:Urine | Dose:0.1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=30 SUBJECT_SAMPLE_FACTORS 38 19 Sample source:Urine | Dose:0.1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=190 SUBJECT_SAMPLE_FACTORS 39 29 Sample source:Urine | Dose:0.1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=290 SUBJECT_SAMPLE_FACTORS 64 31 Sample source:Urine | Dose:0.1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=310 SUBJECT_SAMPLE_FACTORS 66 38 Sample source:Urine | Dose:0.1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=380 SUBJECT_SAMPLE_FACTORS 41 5 Sample source:Urine | Dose:0.3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=50 SUBJECT_SAMPLE_FACTORS 40 11 Sample source:Urine | Dose:0.3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=110 SUBJECT_SAMPLE_FACTORS 69 18 Sample source:Urine | Dose:0.3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=180 SUBJECT_SAMPLE_FACTORS 67 21 Sample source:Urine | Dose:0.3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=210 SUBJECT_SAMPLE_FACTORS 68 30 Sample source:Urine | Dose:0.3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=300 SUBJECT_SAMPLE_FACTORS 44 7 Sample source:Urine | Dose:1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=70 SUBJECT_SAMPLE_FACTORS 45 15 Sample source:Urine | Dose:1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=150 SUBJECT_SAMPLE_FACTORS 18 23 Sample source:Urine | Dose:1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=230 SUBJECT_SAMPLE_FACTORS 70 32 Sample source:Urine | Dose:1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=320 SUBJECT_SAMPLE_FACTORS 71 37 Sample source:Urine | Dose:1 µg/kg TCDD RAW_FILE_NAME(Raw file name)=370 SUBJECT_SAMPLE_FACTORS 19 1 Sample source:Urine | Dose:3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=10 SUBJECT_SAMPLE_FACTORS 20 13 Sample source:Urine | Dose:3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=130 SUBJECT_SAMPLE_FACTORS 46 20 Sample source:Urine | Dose:3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=200 SUBJECT_SAMPLE_FACTORS 73 27 Sample source:Urine | Dose:3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=270 SUBJECT_SAMPLE_FACTORS 74 36 Sample source:Urine | Dose:3 µg/kg TCDD RAW_FILE_NAME(Raw file name)=360 SUBJECT_SAMPLE_FACTORS 49 4 Sample source:Urine | Dose:10 µg/kg TCDD RAW_FILE_NAME(Raw file name)=40 SUBJECT_SAMPLE_FACTORS 76 9 Sample source:Urine | Dose:10 µg/kg TCDD RAW_FILE_NAME(Raw file name)=90 SUBJECT_SAMPLE_FACTORS 50 17 Sample source:Urine | Dose:10 µg/kg TCDD RAW_FILE_NAME(Raw file name)=170 SUBJECT_SAMPLE_FACTORS 77 24 Sample source:Urine | Dose:10 µg/kg TCDD RAW_FILE_NAME(Raw file name)=240 SUBJECT_SAMPLE_FACTORS 22 33 Sample source:Urine | Dose:10 µg/kg TCDD RAW_FILE_NAME(Raw file name)=330 SUBJECT_SAMPLE_FACTORS 79 10 Sample source:Urine | Dose:30 µg/kg TCDD RAW_FILE_NAME(Raw file name)=100 SUBJECT_SAMPLE_FACTORS 52 25 Sample source:Urine | Dose:30 µg/kg TCDD RAW_FILE_NAME(Raw file name)=250 SUBJECT_SAMPLE_FACTORS 54 28 Sample source:Urine | Dose:30 µg/kg TCDD RAW_FILE_NAME(Raw file name)=280 SUBJECT_SAMPLE_FACTORS 53 35 Sample source:Urine | Dose:30 µg/kg TCDD RAW_FILE_NAME(Raw file name)=350 SUBJECT_SAMPLE_FACTORS 80 39 Sample source:Urine | Dose:30 µg/kg TCDD RAW_FILE_NAME(Raw file name)=390 #COLLECTION CO:COLLECTION_SUMMARY TCDD elicits similar effects of steatohepatitis and hepatotoxicity in both sexes CO:COLLECTION_SUMMARY of C57BL/6NCrl mice as previously reported. However, male C57BL/6NCrl mice CO:COLLECTION_SUMMARY exhibit heightened sensitivity to TCDD-elicited liver toxicity compared to CO:COLLECTION_SUMMARY female C57BL/6NCrl mice (i.e., the TCDD dose-response curve of female CO:COLLECTION_SUMMARY C57BL/6NCrl liver toxicity is right-shifted). To observe the range of CO:COLLECTION_SUMMARY histological, gene expression, and metabolic differences elicited by TCDD, CO:COLLECTION_SUMMARY C57BL/6NCrl males were prioritized. Post-natal day (PND) 25 C57BL/6NCrl males CO:COLLECTION_SUMMARY from Charles River Breeding Laboratories (Kingston, NY) were acclimatized for CO:COLLECTION_SUMMARY five days prior to treatment. Mice were housed in Innovive Innocages (San Diego, CO:COLLECTION_SUMMARY CA) containing ALPHA-dri bedding (Shepherd Specialty Papers, Chicago) at an CO:COLLECTION_SUMMARY ambient temperature of 21° C with 30-40 % humidity and a 12 h/12 light/dark CO:COLLECTION_SUMMARY cycle. All mice were fed the TEKLAD diet 8940 (Madison, WI) ad libitum. At PND CO:COLLECTION_SUMMARY 30, mice were orally gavaged with 0.1 ml sesame oil vehicle (Sigma-Aldrich, St. CO:COLLECTION_SUMMARY Louis, MO) or 0.03, 0.1, 0.3, 1, 3, 10, or 30 µg/kg TCDD (AccuStandard, New CO:COLLECTION_SUMMARY Haven, CT) every 4 days for 28 days from Zeitgeber (ZT) 0 – 3 for a total of 7 CO:COLLECTION_SUMMARY administered doses to induce steady-state levels of TCDD. Moreover, the doses CO:COLLECTION_SUMMARY used in the current study were chosen to account for the relatively short study CO:COLLECTION_SUMMARY duration as opposite to lifelong cumulative human exposure from diverse AhR CO:COLLECTION_SUMMARY ligands, the bioaccumulative nature of halogenated AhR ligands, and different CO:COLLECTION_SUMMARY half-lives of TCDD in humans (1−11 years) and mice (8−12 days). The same CO:COLLECTION_SUMMARY dose range and treatment regimen has been used in previous studies where we CO:COLLECTION_SUMMARY found that mouse hepatic tissue levels were comparable to serum levels following CO:COLLECTION_SUMMARY the intentional poisoning of Viktor Yushchenko (1 – 30 μg/kg) and following CO:COLLECTION_SUMMARY the accidental exposure from a 1976 chemical plant accident of Seveso women with CO:COLLECTION_SUMMARY and without chloracne (0.03 – 0.3 μg/kg). On PND 55, urine and feces were CO:COLLECTION_SUMMARY collected from individual mice from ZT 0 – 3, snap-frozen in liquid nitrogen, CO:COLLECTION_SUMMARY and stored at -80° C. Three days later, PND 58 mice were euthanized by CO2. CO:COLLECTION_SUMMARY Blood, liver, kidney, and epididymal adipose tissues were collected. Whole CO:COLLECTION_SUMMARY livers were weighed, snap-frozen in liquid nitrogen, and stored at -80° C. Mice CO:COLLECTION_SUMMARY were monitored every day for fluctuations in body weight and changes in chow CO:COLLECTION_SUMMARY weight from ZT 0 – 3. Food consumption per day was calculated by dividing the CO:COLLECTION_SUMMARY difference in chow weight from the previous day by the number of mice per cage. CO:COLLECTION_SUMMARY This study was conducted in accordance with relevant guidelines and regulations. CO:COLLECTION_SUMMARY All animal procedures were approved by the Michigan State University CO:COLLECTION_SUMMARY Institutional Animal Care and Use Committee (IACUC; PROTO 202100219) and meet CO:COLLECTION_SUMMARY the ARRIVE guidelines. CO:SAMPLE_TYPE Urine #TREATMENT TR:TREATMENT_SUMMARY TCDD elicits similar effects of steatohepatitis and hepatotoxicity in both sexes TR:TREATMENT_SUMMARY of C57BL/6NCrl mice as previously reported. However, male C57BL/6NCrl mice TR:TREATMENT_SUMMARY exhibit heightened sensitivity to TCDD-elicited liver toxicity compared to TR:TREATMENT_SUMMARY female C57BL/6NCrl mice (i.e., the TCDD dose-response curve of female TR:TREATMENT_SUMMARY C57BL/6NCrl liver toxicity is right-shifted). To observe the range of TR:TREATMENT_SUMMARY histological, gene expression, and metabolic differences elicited by TCDD, TR:TREATMENT_SUMMARY C57BL/6NCrl males were prioritized. Post-natal day (PND) 25 C57BL/6NCrl males TR:TREATMENT_SUMMARY from Charles River Breeding Laboratories (Kingston, NY) were acclimatized for TR:TREATMENT_SUMMARY five days prior to treatment. Mice were housed in Innovive Innocages (San Diego, TR:TREATMENT_SUMMARY CA) containing ALPHA-dri bedding (Shepherd Specialty Papers, Chicago) at an TR:TREATMENT_SUMMARY ambient temperature of 21° C with 30-40 % humidity and a 12 h/12 light/dark TR:TREATMENT_SUMMARY cycle. All mice were fed the TEKLAD diet 8940 (Madison, WI) ad libitum. At PND TR:TREATMENT_SUMMARY 30, mice were orally gavaged with 0.1 ml sesame oil vehicle (Sigma-Aldrich, St. TR:TREATMENT_SUMMARY Louis, MO) or 0.03, 0.1, 0.3, 1, 3, 10, or 30 µg/kg TCDD (AccuStandard, New TR:TREATMENT_SUMMARY Haven, CT) every 4 days for 28 days from Zeitgeber (ZT) 0 – 3 for a total of 7 TR:TREATMENT_SUMMARY administered doses to induce steady-state levels of TCDD. Moreover, the doses TR:TREATMENT_SUMMARY used in the current study were chosen to account for the relatively short study TR:TREATMENT_SUMMARY duration as opposite to lifelong cumulative human exposure from diverse AhR TR:TREATMENT_SUMMARY ligands, the bioaccumulative nature of halogenated AhR ligands, and different TR:TREATMENT_SUMMARY half-lives of TCDD in humans (1−11 years) and mice (8−12 days). #SAMPLEPREP SP:SAMPLEPREP_SUMMARY Urine samples (500 µl) in a 1.5 mL Eppendorf tube were centrifuged at 12,000 g SP:SAMPLEPREP_SUMMARY for 10 minutes at 4° C to remove debris. The supernatant (300 µL) was SP:SAMPLEPREP_SUMMARY transferred to a clean 1.5 mL Eppendorf tube containing 35 μL of D2O and 15 μL SP:SAMPLEPREP_SUMMARY of buffer (11.667 mM DSS [disodium-2,2-dimethyl-2-silapentane-5-sulphonate], 730 SP:SAMPLEPREP_SUMMARY mM imidazole, and 0.47 % NaN3 in H2O). Samples (350 μL) were then transferred SP:SAMPLEPREP_SUMMARY to a standard 3 mm thin-walled glass NMR tube for 1H NMR spectral analysis. All SP:SAMPLEPREP_SUMMARY 1H NMR spectra were randomly collected on a Bruker Ascend HD 600 MHz SP:SAMPLEPREP_SUMMARY spectrometer equipped with a 5 mm TCI cryoprobe and acquired at 25° C using the SP:SAMPLEPREP_SUMMARY modified version of the first transient of the Bruker noesy-presaturation pulse SP:SAMPLEPREP_SUMMARY sequence providing a high degree of quantitative accuracy. Spectra were SP:SAMPLEPREP_SUMMARY collected with 128 transients and 16 steady-state scans using a 5-second SP:SAMPLEPREP_SUMMARY acquisition time and a 5.1-second recycle delay. Prior to spectral analysis, all SP:SAMPLEPREP_SUMMARY FIDs were zero-filled to 128K data points, and line broadened by 0.5 Hz. The SP:SAMPLEPREP_SUMMARY methyl singlet produced by a known quantity of DSS (1000 μM) was used as an SP:SAMPLEPREP_SUMMARY internal standard for chemical shift referencing (set to 0 ppm) and for SP:SAMPLEPREP_SUMMARY quantification. All 1H NMR spectra were processed and analyzed using Chenomx NMR SP:SAMPLEPREP_SUMMARY Suite Professional software package version 8.3 (Chenomx Inc., Edmonton, CA). SP:SAMPLEPREP_SUMMARY Prior to statistical analysis, all NMR spectra were manually inspected for SP:SAMPLEPREP_SUMMARY technical faults. Analysis identified 107 unique metabolites in the mouse urine SP:SAMPLEPREP_SUMMARY samples. #ANALYSIS AN:ANALYSIS_TYPE NMR #NMR NM:INSTRUMENT_NAME 600 HHz Avance III HD NM:INSTRUMENT_TYPE FT-NMR NM:NMR_EXPERIMENT_TYPE 1D-1H NM:SPECTROMETER_FREQUENCY 600 MHz NM:NMR_PROBE TCI- croprobe NM:NMR_SOLVENT Water- D2O (90/10) NM:NMR_TUBE_SIZE 3.00 mm NM:SHIMMING_METHOD Topshim 3d NM:PULSE_SEQUENCE 1dnoesy NM:WATER_SUPPRESSION presat NM:RECEIVER_GAIN 80.6 NM:NUMBER_OF_SCANS 128 NM:ACQUISITION_TIME 5.3 sec NM:SPECTRAL_WIDTH 20.8 NM:LINE_BROADENING no NM:APODIZATION Exponential NM:BASELINE_CORRECTION_METHOD BXR-spline NM:CHEMICAL_SHIFT_REF_STD 0.0 ppm (DSS) #NMR_METABOLITE_DATA NMR_METABOLITE_DATA:UNITS micromolar NMR_METABOLITE_DATA_START Samples 2 6 14 22 40 8 12 16 26 34 3 19 29 31 38 5 11 18 21 30 7 15 23 32 37 1 13 20 27 36 4 9 17 24 33 10 25 28 35 39 Factors Sample source:Urine | Dose:0 µg/kg TCDD Sample source:Urine | Dose:0 µg/kg TCDD Sample source:Urine | Dose:0 µg/kg TCDD Sample source:Urine | Dose:0 µg/kg TCDD Sample source:Urine | Dose:0 µg/kg TCDD Sample source:Urine | Dose:0.03 µg/kg TCDD Sample source:Urine | Dose:0.03 µg/kg TCDD Sample source:Urine | Dose:0.03 µg/kg TCDD Sample source:Urine | Dose:0.03 µg/kg TCDD Sample source:Urine | Dose:0.03 µg/kg TCDD Sample source:Urine | Dose:0.1 µg/kg TCDD Sample source:Urine | Dose:0.1 µg/kg TCDD Sample source:Urine | Dose:0.1 µg/kg TCDD Sample source:Urine | Dose:0.1 µg/kg TCDD Sample source:Urine | Dose:0.1 µg/kg TCDD Sample source:Urine | Dose:0.3 µg/kg TCDD Sample source:Urine | Dose:0.3 µg/kg TCDD Sample source:Urine | Dose:0.3 µg/kg TCDD Sample source:Urine | Dose:0.3 µg/kg TCDD Sample source:Urine | Dose:0.3 µg/kg TCDD Sample source:Urine | Dose:1 µg/kg TCDD Sample source:Urine | Dose:1 µg/kg TCDD Sample source:Urine | Dose:1 µg/kg TCDD Sample source:Urine | Dose:1 µg/kg TCDD Sample source:Urine | Dose:1 µg/kg TCDD Sample source:Urine | Dose:3 µg/kg TCDD Sample source:Urine | Dose:3 µg/kg TCDD Sample source:Urine | Dose:3 µg/kg TCDD Sample source:Urine | Dose:3 µg/kg TCDD Sample source:Urine | Dose:3 µg/kg TCDD Sample source:Urine | Dose:10 µg/kg TCDD Sample source:Urine | Dose:10 µg/kg TCDD Sample source:Urine | Dose:10 µg/kg TCDD Sample source:Urine | Dose:10 µg/kg TCDD Sample source:Urine | Dose:10 µg/kg TCDD Sample source:Urine | Dose:30 µg/kg TCDD Sample source:Urine | Dose:30 µg/kg TCDD Sample source:Urine | Dose:30 µg/kg TCDD Sample source:Urine | Dose:30 µg/kg TCDD Sample source:Urine | Dose:30 µg/kg TCDD Creatine 635.5 1899.8 440.8 996.3 935.4 198 1642.7 457 915 951.3 631 2377.1 1145.2 1491.1 1160.9 1632.9 409.7 434.1 1292 1675.6 536.6 1098.6 722 354.6 857.6 548 1228.3 474.5 978.4 261.7 908.3 525.9 340.7 744.1 348.5 536.3 268.7 269.3 359.1 1291.5 Ethanol 1535.4 4259 267.6 373.7 699 435.9 210.9 732.3 721.6 455.7 546.1 2582.2 1010 796.4 1024.6 818 369.9 283.4 486.5 849.9 2293.8 2253.4 715.8 5334.5 614.4 591.7 2086.8 406.7 1988.1 490 468.2 999.5 2237.2 663.8 275.1 2642.1 1214.4 18347.2 229.4 407.6 Glycolate 209 4740 216 295.3 222.6 228 1078 381.4 570.1 560.3 420.2 4253.9 838.1 1029.9 1980.7 689.2 363.7 314.8 748.3 465.6 485.9 656.7 483.7 584.2 541.7 553.4 645.5 570.9 1073.2 664.9 2004.6 2119.1 1239.5 2919 1146.7 2238.3 2607.5 2085.5 2003.3 5391 D-Glucose 732.3 1178.4 663.2 1229.8 1011.4 671.2 1817.1 950.1 1272.3 1043.1 916.1 2767.2 1384 2011 2514.5 1157.7 770.6 1011.9 1185.6 842.1 942.5 1212.9 1408 754.8 1269.3 1023.7 1292.5 892.3 1560.8 1178.8 682.6 1021.8 423.9 1580 776.5 627.8 871 364.5 606.4 2119.7 Glycine 194.6 344.7 4.4 187.8 223.1 89.2 311.6 149 226.1 155.5 166.7 102.7 416.4 253.1 103.1 171.7 208.4 135.9 197.4 192.2 155.3 215.6 118 199 288.7 118.5 214.5 121.2 184.6 128.8 111.2 195.8 172.2 292.8 100.4 125 83 102.5 77.6 307.1 Guanidoacetate 673.2 1267 582.3 606.7 692.3 463.9 953.7 425.1 735.6 551.4 673.6 1511.7 1315.8 1086.6 871.8 848.4 428.4 478.9 854 719.9 528.7 787.1 905 654.8 885 747.2 863.8 556 524.1 442 415.1 575.9 349.1 934.8 533.1 373.2 385.2 281.1 456.8 890.5 Glycerol 237.3 932.1 199.9 356.8 267.7 228.8 379.1 193.3 304.5 189 146.5 994.6 646.9 549.7 1045.5 457.2 172.3 250.7 626 394.1 116 167 384 197.6 306.1 280.8 431.4 288.7 275.7 337.7 150.1 442.8 96 684.5 191.9 123.2 246.1 75.1 242.4 1038.4 Fumaric acid 554.6 590.8 291.1 353.6 749.4 307.3 497.3 344 471.9 294.3 347.9 609 314.7 497.2 353.2 573.1 323.1 382.1 371 318.2 408.7 399.4 356.5 1739.9 380.6 354.2 509.8 326.6 427.7 290.7 244.6 201 262.8 469.9 535.5 281.7 203.1 232.6 160.7 423.8 D-Galactose 372.4 666.7 163.6 216.3 300.2 190.5 761.7 339.2 522.6 232.3 140 1378.4 921.5 370.3 813.3 366.7 179.8 290.9 562.1 717.4 282.2 402.4 653.2 53.7 475.8 256.8 462.4 163.5 338.9 225.5 146.9 345.8 183 436 274.7 107.5 178.6 149.2 236.5 261.3 L-Glutamic acid 1104 3661.2 547.2 606.8 1605.4 460.7 2394.7 1052.6 1552.3 1788.1 774.2 4321.9 1234.1 1835.9 1719.7 1214.8 663.7 1059.6 1183.4 2700.1 1164.8 1058.4 1247.5 1559.5 1074 816.8 1521.8 444 1490.9 908.1 926 1121.8 743.6 1290.8 1251.6 1019.3 1903.6 770.7 1569.4 3291.9 Hypoxanthine 0.9 4.7 0.8 1 1.6 0.7 2.9 0.8 1.2 0.8 0.7 2.6 1.6 1.7 306.2 1.1 0.6 0.8 1.5 4.6 0.8 0.8 1 1 0.8 0.9 1.3 0.6 0.8 0.6 1.5 0.7 0.5 3.5 0.8 0.6 2.5 0.5 3.6 7.2 Tyrosine 100.9 290.2 91.6 147.9 137.3 79.8 224.9 211.3 201.5 128.7 151.6 295.8 227 257.6 183.7 197.4 110.4 117.5 164.7 314.8 115.5 164.6 177.1 164.9 142.6 131.3 165.5 113 138.7 102.5 210.9 153.5 116.7 148.7 170.8 159.9 144 88.2 157.6 334.5 L-Phenylalanine 720.2 1564.1 390.9 554.6 879.8 483.1 928.3 584.6 710.9 687.8 520 11240.4 897.2 955.5 855.1 859 416 646 716.2 1416.2 464.8 614.6 967.2 461 689.6 525.3 855.4 644.5 728.3 457.7 630.3 514.7 426.9 735 460.2 451.6 509.4 486.4 271.7 1356.8 L-Alanine 32.1 95.2 20 30.7 29.5 17.6 48.8 29.9 29.2 26.5 30.3 56.1 42.6 57.5 60.7 27.3 14.7 29 45.1 50.7 23.1 33.8 23.8 31.1 25.7 23.3 31.6 16.3 30.7 21.1 17.4 26.2 25.5 25.8 16.5 15.4 25.1 9.8 17.4 29.7 Methylamine 527.1 1792.6 610.2 843.6 738.6 509.7 1128.6 959.6 1136.1 775.8 927.1 2704.9 1244.3 1385.9 1135.8 1300 797.5 688.9 926.9 1285.6 846.5 922.8 730.1 713.5 855.3 844.3 792.8 645.5 700.5 590.6 520.6 582.6 370 646.5 381.9 301.9 270.5 244.6 440.8 616.4 L-Threonine 308 372.3 139.7 171.5 256.8 144 413.7 228.1 295.7 148.9 205.5 370.6 328.5 331.8 285.7 235.8 146.9 221 278.1 540 173.8 185.9 239 184.4 213.2 166.8 190.7 185.7 282.3 190 137.3 154.9 117.1 209.4 159.1 101.5 203.5 67.4 185.5 199.7 L-Asparagine 35.39448362 158.083335 24.72695301 58.10285948 58.69120187 23.2163727 81.02657179 50.46487176 80.48358221 62.28172218 45.65482799 167.6253029 118.6030667 124.053796 85.08161359 71.55710765 23.55862708 24.18237339 80.53766192 71.25099437 14.3185344 76.54478959 70.43442379 39.60495796 73.39413852 40.50104726 73.2182211 28.98897318 55.80965252 43.86583166 47.19913329 39.10693359 29.22180116 74.60514657 28.61106942 41.9432407 28.8736289 39.14747105 30.63073201 70.12742833 Isoleucine 134.6 500.8 45.2 128.9 178.4 42.7 320.8 156.9 265.9 82.1 89.6 645.8 393 358.1 428.9 181.4 72 77.5 64.9 440.8 51 159.2 205.4 99 97.3 65 216.6 41.7 214.1 49.7 78.9 99.5 27 173.8 76.8 26.9 172.8 29.6 42.5 301 L-Fucose 252.3 289.3 150.4 155.8 212.8 166 314.6 173 246.5 167.9 183.4 606.9 306.4 351.2 347.7 105.2 137 108.3 172 328.4 227.7 203.5 140.2 142.4 208.6 161.6 271.6 133.2 155.3 134.6 81.7 162.6 76.2 230.3 190.6 123.6 93.8 167.9 196.1 323.2 L-Histidine 6630.4 39546.5 7394.8 15337.9 10107.8 10220.4 22437.2 16706.1 23095.5 17550.8 20463.5 8384.4 22615 20598.4 3418.4 22863.1 10291.9 5356.7 13721.3 23546.7 20994.3 20429.3 27317.7 13443.8 14679.5 22374.4 27240.9 19771.4 18884.9 14036.3 13813.3 17086.1 8126.5 18700.3 7942.4 11174.4 8008.9 5051.1 6808.9 309.9 L-Lysine 602.5 1001.4 356.8 423 641.1 283.6 953.7 804.3 806.5 559.3 688.6 1249.5 1008.3 968 757.6 785.9 575.1 581 696.3 742.5 668.7 546.1 675.4 461.8 645.5 569.8 847.7 612.9 724.1 583.1 442 404.1 258.4 536 374.9 317.1 159.1 237.7 226.9 287.2 L-Serine 98.10237308 84.41410476 88.81110372 74.34919786 91.6765793 98.15729642 98.11734455 77.12149936 59.56818056 63.83716478 84.05865467 317.332997 147.5806049 107.3220462 98.84700136 86.15824044 50.9815299 60.68507194 54.36816867 106.3708189 92.17831002 118.447603 115.3526731 129.4124733 116.9053089 140.2175419 137.9944067 60.40683388 73.37276516 87.83164109 103.9900126 119.3193551 73.98197615 175.7403291 115.6475697 77.03119526 101.2517137 59.30879026 135.7556069 253.6463218 L-Lactic acid 283 489.8 210.2 217.9 385 233.2 1735.8 310.5 332.5 369.4 406.6 426.8 337.7 463.6 650.4 330.4 202.8 241.6 624.9 517.7 243.3 306.8 272.3 400.8 375.3 244.5 535.9 235.1 2059.8 512.8 205.1 202.5 273.7 269.9 224.4 126.5 377.3 203.5 228.9 479.9 Aspartate 425.2 1557.7 369.8 600.2 290.3 402.8 624.7 691.9 509.4 598.1 766.1 7993.2 1099.6 1014.5 786 708.6 556 439 336.9 1016.8 643.4 618.4 695 320.1 614.3 442.1 534.9 398.2 533.6 284.9 234.4 249.5 234.8 681.2 340.8 321.6 340.1 208.7 411.6 692.9 L-Cystine 218.1 386.8 173.5 310.7 227 229.8 412 125.1 421 253.5 518.2 383.8 344.3 532.7 438.7 365.1 234.5 159.1 197.1 457.7 376.5 255.4 265 171 302.8 352 395.5 209.6 189.4 317.5 280 146.6 118.4 285.8 205.2 176 319.3 161.9 361.5 357.2 Methylmalonic acid 125.1 171.4 150.8 222 91 122.8 194.2 177.2 187.1 219.9 94.6 211.3 185.2 91.7 149.3 124.3 99.4 148.3 136.4 72 181.7 141.1 181.4 68.6 218.8 108.6 376.1 123.3 195.7 133.3 80.8 61.4 53.8 124.3 81.9 39.9 117.7 0 122.3 96.7 Phenylacetate 18.9 34.8 11.5 22.4 19.7 13.7 19.8 16.1 25.4 21.8 27.5 0 36.8 37.6 174.7 20.1 9.5 25.7 26.3 19.2 15.7 24.8 38 17.3 24.8 19.7 24.3 18.6 23.4 15.3 12.1 20 13.2 25.4 19.6 13.7 26.3 20.8 21.9 23.7 Myo-inositol 240.9 944.3 158.8 233 240.6 213.3 309.9 301.3 300.5 206 210.7 2108.1 1011.3 496.3 674.3 208.5 211.7 189.4 296.8 790.9 163.1 273.3 515.2 225 379.1 216.7 183.4 174 147.6 295.9 254.3 344.5 114.2 546.4 159.9 211.1 304.4 140.9 273.9 342.7 Pyruvic acid 298.3 541.5 137.3 129.4 282.7 126.8 824.4 169.8 376.7 380.5 227.1 617.7 368.3 491.6 553.7 182.9 134.5 333 349.6 958.4 177.2 379.6 240.5 387.1 184.2 163.8 221.4 168.9 390 193.4 351.8 697.2 213.5 439.1 316.3 383.2 1106.2 298.5 1197 2328.7 Sorbitol 185.8 1215.9 171.6 251.9 289.5 249.2 495.3 332.9 430.3 361.2 380.5 2172 986 708 576.9 392.7 223.1 259.8 692.4 871.7 194.7 485.3 617 172.3 439.4 276.7 407.7 238 514.2 307.4 237.2 244.2 140.3 349.1 187 163.8 230.4 140.5 308.1 545 Taurine 5582.5 12121.9 204.7 252.4 4019.7 176.8 8338.3 1023.5 3682.8 737.9 311.2 21926.1 4665.7 7444.8 5977.4 4822 67.3 1035.4 4325.8 4820.5 306.8 2747.7 1248.3 1730.7 1236.2 531 2760.9 189.8 1130.5 945.1 3723.7 11161.2 1044.2 10130.2 1895.2 1892.6 2947 301.8 226.6 14162.7 Succinate 2813.8 6703.4 1882 2871.9 3387.1 2445 5139.6 2827.5 4523.4 2754.6 3358.1 8701.8 5192.2 6172.8 4733.9 4735.8 3116.7 3136.7 5541.8 4755.4 3809.5 4707.3 4411.6 2703.8 4828.6 3906.6 4990.9 3997.5 3743.5 3692.8 1537.5 2091.5 2073.5 3515.4 2941 982 1313.3 1086.4 992.5 1808.4 Pyroglutamic acid 612.9 823.3 366.5 390.5 489.9 440 845.9 351.6 577.8 352.2 590 1488.3 677.8 925.3 792.4 649.9 375.9 491.4 565.5 505.4 421.8 336.3 594.2 465.7 532.5 519.1 576.5 426.9 440 341.7 206.1 339.5 203.7 643.6 434.4 278 416.9 240.6 429.1 1349.7 Sarcosine 222.5 663.2 164.3 282.6 346.9 257.4 718 295.4 283.2 351.6 378 699.4 816.2 713.1 1038.1 671.6 124 180.9 238 821.2 298.2 245.1 302.8 530.7 362.4 193.5 258.6 249.2 423.6 235.2 162.9 216.9 626.7 339.4 50.4 117.3 163.8 85.6 221.1 912.1 Urea 170516.3 578804.9 40738.1 84484.4 258043.7 49805.5 402223.8 101705.8 180982.5 117452.6 116432.7 812049 347816.5 444263.3 540830.8 257898 73583.7 112842.6 238832.1 445821.4 77765.5 141414 112247.8 132174.4 149119.1 83062.9 167493.5 81318.5 184331.9 142437.7 191402.4 234386.7 88507.4 360722.8 138736.7 110569.4 166001.4 51231.2 168782.9 353899.7 Uracil 25.1 398.7 184.2 210.1 238.2 199 0 278.7 253.2 157.2 61.9 544.1 316.1 218.7 327 202 191.8 153.5 297.8 243.2 121.4 12.7 307.2 122.6 152.3 169.9 220.9 161.8 107.1 142.9 53.5 0 40.2 57 83 140.7 116.6 90.9 164 618.9 3-Hydroxybutyric acid 291.4 513.6 232.8 352.8 344.4 216.8 407.7 538 418.5 346.5 374.9 743.1 401.8 424.4 536.7 346.2 335.7 296.9 198.1 369.5 314.4 397.5 319.3 299.9 272.8 213.2 394.3 242.3 302.1 251.1 174.2 170.4 118.4 303.2 146.6 236.3 130.8 342.7 135.2 184.8 3-Methylhistidine 808.6 2515.1 449 466.3 1033.2 358.2 1218.7 468.1 797 344.5 560.4 1250.4 453.8 1192.2 816.1 519.1 341.1 732.5 699.8 2003 677.7 426.3 0 624.8 363.2 409.5 256.1 470.9 404.7 608.7 354.9 571 327 1462.3 554.9 470.8 596.5 211.4 272.2 665.4 L-Arginine 273.5 867.8 213.4 532.4 390.5 184.6 650.4 300.5 588.7 250.6 351.4 1524.2 965.4 744.8 690.1 541.1 102.6 268.7 538.3 554.4 0 322 115.1 341.9 496.7 254.8 616.3 129 295.6 264.2 241.3 446.4 367.7 560.7 279 171.8 264.4 190.7 359.5 638.5 L-Cysteine 0 1616.1 964.5 1508.3 356 1004.1 820.5 676.1 978.5 1256.1 1344.6 889.5 1592.9 1095.3 883 511.3 824.2 626 691.3 1331.8 936.2 681.7 806.7 597.1 856.2 1091.2 596 410.3 757.4 690.4 485.5 659.6 437.3 1012.8 996 490.3 327.3 366.8 530.5 981.7 Gluconic acid 789.6 1111.6 300.9 367.3 714.9 315 1264.1 643.1 603.1 371.4 670.3 1568.8 1011.9 1318.1 1044 774.8 448.1 549.6 952.2 905.7 545.4 607.8 869.7 382.7 698.9 376.3 513.8 486.5 616.8 488.6 284.5 506.1 255 814.1 338.7 200.7 385.3 217.1 483.7 693.9 L-Glutamine 590.5 2231.7 0 705.3 709.6 420.4 1420.9 562.2 757.3 1150.7 663.2 1455.2 1366.9 1239.7 1049.1 548.2 301.7 215.2 884.7 0 444.3 590.5 345.7 0 509.4 174.3 601.9 46.8 678.5 73.1 348 561.6 227.8 499.9 0 275 390.3 50.2 289.7 669.6 L-Leucine 209.1 369.7 114.8 212.9 181.2 120.5 238.7 157.7 221.6 117.1 167.9 497.7 425.2 353 270.8 148.3 112 163 329.8 279 176.6 214.2 160.9 129.9 197 230.4 268.4 205.8 212.4 132.4 120.2 188.3 133.9 285 143 62.7 185.5 77.7 103.1 268.9 Malonate 120.8 1774.3 99 50.9 1275.8 40.5 1611.6 37.6 95.3 19 26.7 1423.9 1301 1492.8 1668.7 102.8 17.3 0 200.5 1469.4 41.2 38.4 0 7 58.4 24.9 25.8 52.7 197.7 46.2 771.1 913.9 626 1466.4 90.2 234 1285 0 1311.7 2016.6 Methionine 81.7 271.5 48.9 31.9 57.4 32.3 160 64.9 119 28.4 50.6 51.1 128.6 103.9 102.7 60 28.6 39.7 86.3 114 26.9 11.3 8.2 46.6 54.5 33.6 48.2 33.6 42.3 42.3 48.7 77.7 41.6 69.4 35.1 33.1 0 23.3 17.3 0 Hippuric acid 641.1 3029.3 940.3 1115.8 1460.6 654.3 1475.3 1437.5 1545.7 1291.4 1456.6 3522.2 1777.3 2305.8 1612.5 1677.8 1033.1 906.3 1365.9 1452.4 1063.7 1358.9 1406.3 855.8 1397.5 934 1388.2 1028.6 969.2 903.7 724 713.9 486.9 985.8 565.8 608.3 677.5 484.4 1001.7 1205.6 Isovaleric acid 231.5 249.8 99.2 152.2 187.6 136.4 271.4 305.3 305.8 135.8 139.7 321.6 206.2 204.8 196.4 212.8 146.2 184.9 228.9 358.4 161.5 165.9 273.3 160.9 216.6 184.9 178.6 210 152.2 146.9 71.9 76 73.7 227.1 96.7 51.6 146.2 51.7 113 258.2 Valine 53.4 98.2 40.8 68.5 55.1 13.2 134.2 61.1 78.4 59.3 31.6 52.2 0 54.9 121.6 35.4 48.8 56.5 48 73.7 49.9 58.1 68.2 38.5 54.1 32.5 76.8 30.3 0 46.4 27.4 35.5 28.6 43.8 22.9 28.2 38.4 19.7 27.7 18.2 Tryptophan 433.3 576.8 353.9 499.4 214.7 401.7 367.2 577 575 546.4 500.7 1261.3 385.3 487.7 498.3 671.1 326 502.2 289.1 381.5 393.5 687.8 647.7 260.2 547.5 370.7 508 385.1 326.8 295.2 218.7 207.2 381.4 176 345 192.4 177 289.6 195.9 432.5 Phosphorylcholine 21.2 0 62.1 114.1 28.1 111.1 55.9 35.1 3.1 55.9 46.4 11.9 37.3 23.3 40.5 49.7 45.4 25.7 35.7 41.3 41.3 89.2 7.3 11.7 35.7 50.8 0 0 31 24.8 22.2 33.6 37.9 26.3 19 24 15.6 6 9.6 0 Acetone 59.6 83.3 22.6 40.5 61.4 41.6 76 48.1 55 47.6 36.1 85.6 56.7 78.6 50.3 59.4 29.5 37.8 45.1 88.9 42.1 38.6 18.2 79.1 44.8 37.3 47.7 37.8 45.9 41.5 30.6 26.6 27.8 56.2 50.9 45.7 50 28.3 31.9 80 Caffeine 35 77.3 36.6 37.3 22.1 32.6 94.8 71.9 74 31.9 22.1 63.4 59.1 49.8 55.4 39.7 26.9 33.2 31.8 74.3 31.5 32.8 24.6 64.8 33.3 29 30.2 22 27.8 20.9 37.6 35.1 23.4 59.1 22.4 19.4 23.3 15.9 14.2 20.6 Methanol 1266.3 1337.7 1353 150.8 2678.2 2780.2 2051.5 493 1092.8 1639.4 3142.1 418.1 2046.9 2072.7 628.1 2096.8 3028.3 1155.3 2049.2 680.9 1419.7 1660.6 1034.6 782.2 1407.8 1017.8 2706.9 2728 3156.8 1065.3 1467.4 2266 2226.3 2130.8 1621.4 1514.3 1179.1 3507.5 2213 446.1 Propylene glycol 6.9 22.9 6.5 8.2 9.4 6 16.2 11.3 8.1 7.3 10.3 10.4 15.9 6 15.7 7 6.6 10.8 14.5 15 8.7 7.4 12 6.5 7.5 6.6 11.2 8.9 10.3 7.7 7.4 8.2 6.6 10.7 8.1 5.4 7.9 5.3 9.7 15.6 5-Aminopentanoate 574.2 692.2 250.5 295.9 612.1 214.6 819.9 524.9 616.3 390.5 415 869.5 672 809 605.4 467.6 324.9 414 502.9 732.5 439.8 381.5 533.1 443.7 500.7 385.2 512 405.9 483.8 442.9 224.4 290.7 216 438.7 344.9 145.5 380.5 129 316.5 427.3 Dimethyl sulfone 367.1 800.6 316.4 301 367.2 185.8 400.1 324.6 429.6 233.2 370.4 987.4 317.9 523.5 348.9 332.6 283.7 181 439.7 348.3 213.2 350.6 312.5 211.2 299.2 458.4 456.7 194.2 262.4 229.5 133.2 183.9 145.4 253 181.6 207.9 176.2 182.4 134.1 434.6 p-Cresol sulfate 32.8 87.9 16 30.5 40.6 21.1 66.9 50.9 42.1 56.4 41.9 58.4 57.2 106.1 76.6 50.1 20.2 49.5 49.1 96.4 31.9 43.8 64.5 47 43.7 33.7 36.3 44.1 51.6 35.6 40 51.5 28.1 55.9 42.5 34 29.9 19.8 37.6 82 1-Methylnicotinamide 40.1 62.4 32.3 32.3 23.1 24.2 34.5 20.9 10.4 44.9 3.7 86.6 22 48.2 36.2 5.3 3.6 20.4 47.7 18.6 20.5 25 24.1 2 13.7 5.5 21.6 7.6 10.9 5.5 8.8 6.5 4.6 16.7 3.1 3.1 2.1 0.8 1.7 7.6 2-Hydroxyisovalerate 17.4 62.8 20.2 28.2 32.9 17.5 65 23.7 53.3 21.7 19.1 74.2 61.4 56.5 52.6 35.6 15 17.1 38.2 74.1 24.9 37.8 37.8 13.3 37.1 35.9 43.6 27.9 48.3 29.3 31.9 51 29.2 57.4 35.2 31.5 53.3 28.9 43.5 87.9 2-Hydroxyvalerate 396.5 595.4 231.9 328.2 451.5 232.7 622.4 512.1 596.8 281.5 307.4 547.2 436.7 465.1 447.8 429.3 327.3 342.7 564.5 549.1 360.7 388.4 429.7 357.7 461.7 374.4 389.3 337.8 378.5 328.1 122.1 164.8 202.8 381.2 187.5 95.1 164.1 82.5 180.6 190.6 3-Aminoisobutyrate 852.2 1852.9 259.1 191 344.5 225.8 152.3 396.5 337 212.3 359.8 805.2 416.3 414.3 562.1 474.8 323.2 218 279.6 419.9 549.4 1075 341.7 72.1 329.2 288.9 1317.9 148.2 978.3 218.1 246.7 572.8 1158.6 326.2 172.5 1314.9 543.3 105.2 111 127 3-Hydroxyisovalerate 16.7 21.9 16.8 14.7 19.8 14.5 22.7 22.7 29 12.9 14.1 63 47.4 37.1 42.5 19.6 9.1 58.6 23 116 71.2 32 17.4 28.5 18.2 18.5 17 22.4 27.5 24.7 37.3 52.3 18 41.9 15.7 69.7 31.7 20.6 63.1 75.9 3-Indoxylsulfate 112.7 91.7 197.1 314 209.7 140.5 52.3 47.7 72.7 76.2 89 235.9 65.6 95.4 150.2 126.4 44.6 92.5 45.9 339.2 84.1 236.8 54.6 27.6 268.9 136.5 107.5 54.7 134.6 60.2 136.8 35.8 115.8 47.3 78 85.5 47.8 106.8 82.9 237 4-Aminobutyrate 129.5 223.5 92.8 130.8 121.6 86.9 99 150.4 136.2 67.6 238 271.9 204 170.1 181.4 130.7 98.7 88.7 195.1 189.4 203.6 113.6 145.5 136 102.7 213.7 163.1 121.8 114.5 98.3 96.3 88.3 68.1 135.4 58.4 40.7 60 38.7 47.1 145 Acetamide 42.8 41.6 41.2 42.5 53 34.9 44.3 49.7 16.6 41.6 43.5 98 88.2 93.5 59.4 62.8 39.9 32.8 56.3 82.9 33.7 44.6 49.7 62.3 60 31.8 69.5 20.1 62.8 34.4 25.6 29.6 27.4 27.7 24.7 13.8 16.8 72.2 24.3 44.6 Acetate 269 755.5 235.8 518.1 259.3 276.7 540.6 259.9 587 331 409.3 931.1 828.8 657.4 566.6 482.4 240.3 291.2 644.7 594.6 340.3 413.8 405.9 300.2 442.2 354.6 553.5 473.4 729 438.2 249.3 418.4 497.4 327.3 281 199.1 254.6 272.2 388.4 400.5 Acetoacetate 53.4 211.4 51.8 117.9 86.1 72.2 181.3 60.3 50.6 80.8 57.3 285.6 194.1 140.7 459.9 149.4 45.8 53 98.9 202.3 73.2 84.9 99.1 76.4 104 95.7 96.2 51.6 72.6 76.6 49.8 81.1 18 125 45.4 53.9 60.2 29 63.8 171 Adenine 13.9 48.1 6.5 35 11.5 10.2 58.5 21.2 40.7 43.8 35.2 71.4 14.2 15.4 179.6 39.3 7.8 16.4 34.4 18.8 24.1 33.6 24.5 16.2 16.4 14.6 26.7 22.3 32.8 7.4 17.1 10 9.8 4.8 9 29.8 18.6 7.2 8.5 20.8 Adenosine 15.2 17 12.6 13.9 20.3 20.1 25.2 14.8 16.2 10.7 13.5 36 13.7 16.8 20.9 9.2 9.7 9.8 11.3 18.6 12.2 13.7 14.1 7.8 11.8 14.8 16.5 11.6 14.3 8.4 13.7 15.7 5 25.8 11.8 14.4 14.9 9 14.5 42.1 Adipate 34.9 180.7 26.2 19.1 71.5 17.1 42.7 35.1 101.2 49.9 54.8 40.9 108.3 36.8 114.7 20.9 33.1 27.9 64.5 124.3 42.9 23.3 9.9 25.2 40.1 44 61.5 41.8 58.7 44.3 18.3 52.6 18.7 35.8 57.9 27.3 102.3 39.8 18.4 68.8 ADP 26 42.8 5.3 9.9 29.9 11.9 34.8 11 23.4 22.6 6.9 48.2 34.4 32.3 33.1 28.4 3.4 9.1 21.5 30.5 11.4 4.8 8.7 18.3 6.3 8.5 10.3 5.6 20.4 16.4 16.8 21.3 16.1 33 18.1 18.4 6.5 4.2 8.7 15.3 AMP 2.4 9.3 4.3 5.2 5.5 1.8 9.3 7.4 7.4 4.2 8.1 17.4 7.6 9.2 9.3 9.9 4.5 4.8 9.2 7.5 6.1 5.4 6.2 3.3 5.6 4.1 8.8 4.8 7.7 6.3 3.1 4 4.2 4.1 4.9 1.4 3.1 4.6 5.5 6.6 Anserine 163.6 126.3 138.9 180.7 118.4 67.6 91.5 188.6 144.3 76.5 127.4 448.9 180.4 265.5 217.3 185.4 87.2 102.4 242.2 147.8 110.2 142.9 145.4 49.6 139.8 163.8 68.4 80.6 122.9 73.6 74 189.1 61.1 246 61.4 49.4 43.2 16.9 54.4 88 ATP 16.3 34.2 8.5 7 32.8 12.6 21.8 5.8 24 10 19 51.7 35.4 24.4 43 23.4 9.7 11 11.9 19.8 10.9 20.8 10.8 15.4 9.4 19.2 8.3 4.7 28.2 30 15.4 11 6.2 10.6 19.5 5.3 13.2 14.3 13.9 33.7 Butyrate 178.6 440.3 139.6 184.7 191.8 141.8 384.9 205.3 209.6 159.6 167.6 465.2 284.4 337.7 306.1 218.7 127.4 176 227.3 380.1 180 221.2 251.9 160.6 200.7 215.6 258.7 187.1 271.3 166.9 183.5 251.7 165 325.1 212.3 174.7 264.6 148 288 556.3 Cadaverine 79 117.4 45.9 51.1 46.2 62.2 109.6 66.5 158.7 59.4 138.8 77.2 53.1 83.5 113 56.3 100.5 130.7 42.4 60.9 93.2 30.9 22.1 35.9 54.9 90.2 135.9 40.5 19.6 45.7 71.6 51.9 36.7 78.3 49.4 32.3 69.5 33 24.4 30.4 Carnitine 67.4 26.2 177.8 93.1 60.1 50.4 163.8 54.4 84.8 86.7 125 26.5 144.4 188.8 143.6 136.6 82 74.2 98.7 113.6 79.8 184.9 107.7 35.4 92.9 128.5 80.3 69.9 95.4 74.4 74.8 111.7 82.1 150.8 82.7 34.6 19.4 15.1 23.6 62.9 Choline 38.3 159.3 49.8 78.1 56.3 37.2 101.3 61.2 83.8 60.2 49.7 185.8 95.2 111.6 90.1 69.8 39 51.3 76 92.2 46.1 56.4 59.7 173.9 61.4 43 57.3 37.3 39.9 30.1 24.9 34.7 24 52.6 23.6 15.6 17.6 11.6 21.1 38 cis-Aconitate 1562.5 1919.3 1452.7 1427.7 1078 1310.9 2252.7 1457.9 1652.9 1152 1502.4 2968.7 1758.4 2502.3 2015.5 1359.5 1161.1 1441.9 1783.7 1662.6 1511.8 1421.9 1368.1 1639.9 1548.1 1413.3 1781.3 1301.8 1324.3 1171.3 976.9 1289.1 953 1901.3 1156.3 1031.6 1544.2 1245.3 1533.3 2176.5 Citrate 23144.6 41952.7 21925.1 19229.3 23398.8 19304.9 27448.6 19536 25623.5 14486.5 21149.9 50450.4 23227.8 33969.3 26861.3 21506.6 13345.3 15228.5 204788.5 10723.9 13191.3 22851.9 21359.3 15503.4 8398.7 20150.4 25917.8 19346.4 20934.3 16097.5 16283 16168.5 9753.8 27273.4 18191.2 18333.2 14324.2 11647.4 19871.7 36188.8 Creatinine 1175.8 5321.2 945.1 898.7 1012.4 807.7 2081.2 1280.2 1063.8 858.4 1306.3 5600.8 1673.6 1232.2 2202 1186.1 770.7 812.4 1466.4 2500.8 1014.9 963.6 667.4 706.3 944.2 1165.6 449.5 938 1266.5 1033.9 882.1 1947.1 690.1 1988.4 934 744.9 1057.9 558.7 816.1 1653.9 Cytosine 33.6 26.4 31.8 39.5 36.3 51.2 52.6 36.9 33.2 33.8 28 32.8 34.1 49.7 45.7 45.4 49.4 36.9 35.9 101 35.8 28 33 25.9 37.3 33.7 28.8 31.7 24.8 37.2 19.3 21.4 38.2 26 55.3 18 42.5 32.1 30.8 40.4 Dimethylamine 628.5 2317.5 699.7 980.6 1042.1 592.2 1589 1653.2 1462.5 1021.3 1285.3 3550.4 1808.1 2293.7 1824.8 1755 1185.2 998.9 1659.3 1909.2 1135.8 1416.5 1262.7 467.3 1240.6 679.4 858.5 754.3 906 818.7 409.9 439.2 491.3 553.2 356.9 1430.7 1236.8 251.3 434.2 3094.4 Ethanolamine 365.1 544.6 143.8 137.8 179.7 240.4 146.6 55.3 407.4 198.7 291.7 307.9 448.6 453 425.8 202.6 188.1 233.7 305.3 302.2 89.6 193.5 77.3 258.8 208.5 339.7 147.1 159.1 298.9 112.2 148.9 321.2 244.6 491.8 186.4 79.8 80.4 47.9 73.3 432.5 Formate 72.7 566.8 130.4 172.4 172.5 115.6 242.3 151.9 333.6 224.3 173.4 915.8 428 501.6 329.8 190.5 131.5 137.9 453 294.3 126.5 218.2 215.9 153.6 291.7 166 199.4 226.3 276.8 237.3 204.9 258.8 172.6 275.9 174.9 252.3 166.6 327.7 693.5 258.4 Glucose 94.3 489.7 107.4 189.8 75.5 97.8 184.6 104.9 261.8 159.4 180.1 679.1 373.8 529.7 368.5 224 212.5 181.8 44.1 711.3 138.9 221.9 193.9 51.1 277.9 182.7 246.1 165.9 216.3 37 186.2 63.3 152.4 147.4 134.7 180.2 211.3 142.9 274.9 374.1 Glucuronate 63.8 290.8 71.9 146.4 111 56.8 165 151.4 148.1 147.3 125.4 355.7 315.6 288 304.4 184.7 83.6 106 160.1 196.9 90.8 111 149.1 92.3 161.1 124.6 185.7 117.4 141.9 138.1 92.6 92.1 57.4 84.2 87.4 61.5 159.2 84.5 154.9 257.6 Glutarate 44.7 186 51.9 103.5 138.1 60 79 143.4 182.6 156 48.9 297.6 216.5 159.1 207.6 102.3 88 98.4 188.3 254.5 78.4 57 92.6 160.8 159.2 65.4 184.1 102.8 161.5 127 35.4 81.2 80.2 133 81.1 52.5 141.3 66.3 99.9 152.1 Guanosine 44.8 28.9 13.4 12.4 11.8 15.9 22.7 12.6 32 16.5 14.7 56.6 45.7 32.5 35.5 86.9 11.6 10.8 80 24.8 14.4 14.2 11.8 37.9 25.6 10.3 20.7 14.5 71.8 22.3 68.4 22.7 23.1 28 59.8 39.7 52.2 15.5 66 24.3 Histamine 48.4 108.4 59.3 91.2 47.9 90 49.7 41 87.6 57.9 35.5 79 115 86.2 238 73 19.9 109.7 85.7 42.1 86.3 81.1 67.1 65.1 53.5 116.1 131 111 29.9 33 51.7 35.3 16.9 47.6 40.7 125 37.7 36.5 50.4 35.6 Imidazole 87917.4 93591.2 92243.4 93083.6 69953.2 87198.6 87747.1 85771.6 91490.1 84314.2 90253.5 104591 87161.8 59686.1 85948.7 96620.2 85517.7 84113.3 67712 79150.5 101930 89534.8 85158.1 80033.2 91799 87579.9 93527.6 90325.4 80644.6 69188.5 96655 90452.2 104596.7 90781 82066.2 90063.8 92814.8 84656 91260.1 98260.8 Indole-3-lactate 62.3 144.2 58.1 54.5 69.1 25.9 140.3 56 78.3 97 22.2 138.4 111.5 91.4 132.8 130.4 15.2 74.6 78.1 124.2 58 146.5 93.7 105 175.2 141.6 103.3 58.3 61.9 111.6 81.7 82.4 150.4 102 36.1 35.9 95.8 179 82.6 106.2 Inosine 7.7 7.2 5.1 11.9 45.7 16.6 24.2 13.2 24.6 11 10.1 38.2 24.5 39.7 30.9 7.1 13.2 11.7 14 25.9 5.5 10.8 7.9 16.8 19.4 9.3 11.9 13 20.2 10.2 3.2 7.1 15.6 24.8 14.6 7.7 19.9 9.6 31.1 54.9 Isobutyrate 80.4 178.8 60.6 74.9 75.4 59.4 151.4 78 90 68.8 73.8 185.5 114.6 134.5 124.7 82.7 54 71.3 97.3 141.2 74.5 91.3 100.9 58.3 85.8 72.2 111.8 82.2 109.2 73.5 77.6 104.6 68.9 115.8 87.5 66.5 114.8 60.5 107.5 205.9 Isocitrate 354.4 2060.5 375.3 185.6 943.2 161.6 762.8 331.1 527.9 445.6 759.6 1126 563.1 1490.4 1653.6 566.8 416.1 211.5 422.9 387.5 411.3 364.2 270.2 555.3 414.1 228.7 1155.1 108.6 237.4 397.6 853.8 585.9 270.3 1548.8 695.1 129 894 397.5 585.9 685.7 Mandelate 62 283.7 22.6 29.8 45.7 40.1 30.9 38.8 54.2 22.3 83.4 107.1 45.3 38.9 93 174 55.4 35.1 53.3 51.3 37 97.6 58.2 26.7 34 44 63.5 59.4 74.3 40.9 95.3 87 19.3 37.7 32.5 36 59.7 48 47.7 36.7 Mannitol 82.8 320.3 97.4 128.7 53 80.7 59.2 111 93.7 55.6 65.8 551.8 213.9 279.1 248.9 241.4 143.4 93.6 126.6 122.9 94.9 100.7 103.1 101.8 85.1 64.1 91.3 126.1 95.8 110.7 119.1 144.9 119.3 163.7 78 137.7 128.6 94.9 112.8 244.5 Methylguanidine 20 352.3 62.5 101.8 113.1 39.5 162.2 115.4 151.3 128.2 102.1 299.7 221.3 267 160 185.5 88.7 97.2 143.6 182.1 64 151.2 152.1 84.5 156 142 185.8 95 119.8 106.5 91 89.4 50.4 134.6 78.6 73 87.6 63.4 93 129.5 Methylmalonate 35.2 80.2 23.7 36 46.6 15.1 61.5 26.5 52.3 33 26.9 86.4 49.4 70.3 56.1 49.8 17.8 27 37.6 87.3 28.3 47.4 34.6 21.9 36.8 50.4 53.1 19 40 26.6 18.5 22.9 26.7 37.8 46.1 41.2 25.4 24.8 24.5 89.1 Methylsuccinate 61.1 134.7 47.8 40.7 56.5 182.5 153.6 74.3 56.5 47 51 164.5 68.6 81.6 92.1 47.8 35.5 43.2 75.6 90.5 47.8 76.7 44.9 65 48.8 42 88.5 45.5 162.9 55.1 78.5 111.2 57.9 73.9 58.5 64.7 176.9 118.3 194.8 330.4 N,N-Dimethylglycine 93.2 394.2 57.3 98.2 77.1 57.3 277.2 118.1 194.9 129 98.6 394.6 250.3 268.3 234.1 152.9 68.1 82.4 214.1 227.9 80.7 110.2 73.5 111.3 107.2 68.6 84.2 53.6 104.3 85 74.1 83.6 55.1 70 61.9 54.4 43.6 38.7 30.4 54 O-Acetylcarnitine 23.2 45 14.3 28.9 32.6 13.4 50 22.4 37.6 34.4 43.1 130.2 48.1 58.3 49.2 38.7 27.1 22.9 53.8 54.8 25.2 37.7 32.7 16 35.1 26.3 29.7 25.3 35.6 23.2 20.9 30.2 15.4 35.5 22.6 15.9 22.5 10.4 19.5 35.2 Pyridoxine 11 117.2 25 30.5 46.3 16 9.5 23.6 24.2 26.7 10 143.9 44.4 69.5 87.7 21.6 25.4 28.1 25.7 31.7 31.1 27.5 28 23 14.3 31.6 34.6 27 20.8 26.3 12.5 19.1 11 15.1 17.3 13.2 14.3 6.6 20.6 25.5 Pyruvate 257.1 506.4 117.9 155.7 350.8 98.7 621.3 157.7 278.7 320.7 172 208.5 260.4 416.9 489.2 192 103.6 271.8 258.9 798 133.2 310.3 212.6 294.6 174.3 164.6 225.8 144.9 318.4 186.9 275.2 520.3 187.1 363.5 291.2 354.7 885.5 230.2 991.7 2124.1 Thymine 78.1 78.2 33.2 41.3 70.5 36.7 69.8 56.3 71.2 38.1 43.3 65.6 52.3 55.8 61.9 46.2 36.5 54.3 45.1 74.2 37.1 54.6 57.7 36.4 54.6 37.4 70 42.6 63.2 46.5 16.4 43.2 20.3 48.9 48.5 18.5 32.1 23.1 22 47 trans-Aconitate 243.4 1457.5 210.5 403.3 267.7 141.4 727.7 242.9 579.2 423.2 345.4 1982 831.1 1033.5 679.7 730.9 308.4 188.6 651.5 645 259.4 361.2 201.9 227.6 448.3 453.5 450.9 165.3 440.8 322 402.5 431.9 155.2 584.9 186.7 264.3 186.5 115.6 97.6 401.5 Trigonelline 170.2 722.8 203.1 289.6 237.1 130.7 446.6 231.6 336.2 308.5 282.9 1034.9 559.6 657.6 510.1 451.1 243.4 183.8 406 411.8 260.5 316.6 225.6 210.8 322 287 326.7 211.5 252.1 261.3 268.7 249.7 132.6 355.5 160 150.7 93.4 99.8 77.7 248.6 Trimethylamine 65.9 127.2 160.2 223.2 288 125.5 111.9 102.1 84.9 61.2 273.9 245 148.7 406.9 103.8 95.5 61.2 222.9 19.4 62.5 55.9 65.8 110.1 111 54.5 10.9 14.2 56.6 97.3 15.1 3.6 4.9 4.7 106 5.2 5.6 43 22.6 6.6 12.3 Trimethylamine N-oxide 616.6 2322.3 885 927.8 1162.6 692.4 1456.3 993.7 1524.9 1186.4 1480.4 3608.4 1760 2244.9 1514.3 2046.8 1315.8 1027.8 1818.2 1523.5 1821.4 2070.8 2231.8 2098.3 2099.9 3829 5527.1 5237.9 3988 4950.4 3177.3 2693.1 2479.6 3180.6 2001.4 2017.2 1230.1 1165.7 1073.2 2484.8 Tyramine 203.1 773.3 207 276.7 322.8 146.1 510.6 390.4 388.3 166.4 234.4 505.5 497.1 594.1 524.2 451 226.6 241.7 301.9 479.3 249.3 280 212.9 473 272 275 366.1 240 363.3 203.9 651.3 669.5 308.6 695.1 427.6 420.1 394.7 277.2 459.3 1064.7 Urocanate 23.6 61.8 21.7 23 31.9 12.8 37.5 20.9 23 35.9 29.3 79.6 45.6 48.8 59.2 39.5 20.9 22.2 29.8 35.7 26.5 28.1 21.7 35.3 54.6 29.1 29.6 21.9 29.5 38.5 45.1 44.7 32 115.7 33.1 55.9 62 27.8 89.7 87.5 NMR_METABOLITE_DATA_END #METABOLITES METABOLITES_START metabolite_name PubChem ID KEGG ID Creatine 586 C00300 Ethanol 702 C00469 Glycolate 757 C03547 D-Glucose 5739 C00031 Glycine 750 C00037 Guanidoacetate 763 C00581 Glycerol 753 C00116 Fumaric acid 444972 C00122 D-Galactose 6036 C00124 L-Glutamic acid 33032 C00025 Hypoxanthine 135398638 C00262 Tyrosine 6057 C00082 L-Phenylalanine 6140 C00079 L-Alanine 5950 C00041 Methylamine 6329 C00218 L-Threonine 6288 C00188 L-Asparagine 6267 C00152 Isoleucine 6306 C00407 L-Fucose 17106 C01019 L-Histidine 6274 C00135 L-Lysine 5962 C00047 L-Serine 5951 C00065 L-Lactic acid 107689 C00186 Aspartate 5960 C00049 L-Cystine 67678 C00491 Methylmalonic acid 487 C02170 Phenylacetate 4409936 Myo-inositol 892 Pyruvic acid 1060 C00022 Sorbitol 5780 C00794 Taurine 1123 C00245 Succinate 1110 C00042 Pyroglutamic acid 7405 C01879 Sarcosine 1088 C00213 Urea 1176 C00086 Uracil 1174 C00106 3-Hydroxybutyric acid 441 3-Methylhistidine 64969 C01152 L-Arginine 6322 C00062 L-Cysteine 5862 C00097 Gluconic acid 10690 C00257 L-Glutamine 5961 C00064 L-Leucine 6106 C00123 Malonate 867 C02028 Methionine 6137 C00073 Hippuric acid 464 C01586 Isovaleric acid 10430 C08262 Valine 6287 C00183 Tryptophan 6305 C00078 Phosphorylcholine 135437 Acetone 180 C00207 Caffeine 2519 C07481 Methanol 887 C00132 Propylene glycol 1030 C00583 5-Aminopentanoate 138 C00431 Dimethyl sulfone 6213 C11142 p-Cresol sulfate 4615423 1-Methylnicotinamide 457 C02918 2-Hydroxyisovalerate 99823 2-Hydroxyvalerate 98009 3-Aminoisobutyrate 64956 C05145 3-Hydroxyisovalerate 69362 C20827 3-Indoxylsulfate 10258 4-Aminobutyrate 119 C00334 Acetamide 178 C06244 Acetate 176 C00033 Acetoacetate 96 C00164 Adenine 190 C00147 Adenosine 60961 C00212 Adipate 196 C06104 ADP 6022 C00008 AMP 6083 C00020 Anserine 112072 C01262 ATP 5957 C00002 Butyrate 264 C00246 Cadaverine 273 C01672 Carnitine 288 Choline 305 C00114 cis-Aconitate 643757 C00417 Citrate 311 C00158 Creatinine 588 C00791 Cytosine 597 C00380 Dimethylamine 674 C00543 Ethanolamine 700 C00189 Formate 284 C00058 Glucose 5793 C00031 Glucuronate 94715 C00191 Glutarate 743 C00489 Guanosine 135398635 C00387 Histamine 774 C00388 Imidazole 795 C01589 Indole-3-lactate 92904 C02043 Inosine 135398641 C00294 Isobutyrate 6590 C02632 Isocitrate 1198 C00311 Mandelate 1292 Mannitol 6251 C00392 Methylguanidine 10111 C02294 Methylmalonate 487 C02170 Methylsuccinate 10349 N,N-Dimethylglycine 673 C01026 O-Acetylcarnitine 7045767 Pyridoxine 1054 C00314 Pyruvate 1060 C00022 Thymine 1135 C00178 trans-Aconitate 444212 C00417 Trigonelline 5570 C01004 Trimethylamine 1146 C00565 Trimethylamine N-oxide 1145 C01104 Tyramine 5610 C00483 Urocanate 736715 C00785 METABOLITES_END #END