#METABOLOMICS WORKBENCH anderbra_20230502_093501 DATATRACK_ID:3996 STUDY_ID:ST003302 ANALYSIS_ID:AN005412 PROJECT_ID:PR002052
VERSION             	1
CREATED_ON             	July 7, 2024, 6:25 pm
#PROJECT
PR:PROJECT_TITLE                 	Untargeted Dialysate Metabolomics Identification and Detection of Novel
PR:PROJECT_TITLE                 	Neurochemicals via Benzoyl Chloride Derivatization
PR:PROJECT_SUMMARY               	This study combines these strategies to obtain in-depth untargeted chemical
PR:PROJECT_SUMMARY               	identification of dialysate. We target the rat dorsal and ventral striatum,
PR:PROJECT_SUMMARY               	given its importance in motivation, movement, and reward processing and identify
PR:PROJECT_SUMMARY               	489 compounds. Despite the depth of analysis, many well-known neurochemicals,
PR:PROJECT_SUMMARY               	such as all neurotransmitters, were not identified in the untargeted method.
PR:PROJECT_SUMMARY               	These compounds could be detected using BzCl derivation in a targeted method
PR:PROJECT_SUMMARY               	though. By tracking isotopic BzCl feature pair detection and filtering of MS/MS
PR:PROJECT_SUMMARY               	spectra by known benzoyl fragment ions, we found 872 unique features in
PR:PROJECT_SUMMARY               	dialysate suggesting many unknown compounds remain to be identified in
PR:PROJECT_SUMMARY               	dialysate.
PR:INSTITUTE                     	University of Michigan
PR:LAST_NAME                     	Anderson
PR:FIRST_NAME                    	Brady
PR:ADDRESS                       	930 N. University Ann Arbor, MI 48109
PR:EMAIL                         	anderbra@umich.edu
PR:PHONE                         	6519256798
PR:FUNDING_SOURCE                	NIH (NINDD,NIEHS)
PR:PUBLICATIONS                  	to be updated later
PR:CONTRIBUTORS                  	Brady Anderson, Pavlo Popov, Amanda Cicali, Adana Nwamba, Charles R. Evans,
PR:CONTRIBUTORS                  	Robert T. Kennedy
#STUDY
ST:STUDY_TITLE                   	Untargeted Dialysate Metabolomics Identification and Detection of Novel
ST:STUDY_TITLE                   	Neurochemicals via Benzoyl Chloride Derivatization
ST:STUDY_SUMMARY                 	This study combines these strategies to obtain in-depth untargeted chemical
ST:STUDY_SUMMARY                 	identification of dialysate. We target the rat dorsal and ventral striatum,
ST:STUDY_SUMMARY                 	given its importance in motivation, movement, and reward processing and identify
ST:STUDY_SUMMARY                 	489 compounds. Despite the depth of analysis, many well-known neurochemicals,
ST:STUDY_SUMMARY                 	such as all neurotransmitters, were not identified in the untargeted method.
ST:STUDY_SUMMARY                 	These compounds could be detected using BzCl derivation in a targeted method
ST:STUDY_SUMMARY                 	though. By tracking isotopic BzCl feature pair detection and filtering of MS/MS
ST:STUDY_SUMMARY                 	spectra by known benzoyl fragment ions, we found 872 unique features in
ST:STUDY_SUMMARY                 	dialysate suggesting many unknown compounds remain to be identified in
ST:STUDY_SUMMARY                 	dialysate.
ST:INSTITUTE                     	University of Michigan
ST:LAST_NAME                     	Anderson
ST:FIRST_NAME                    	Brady
ST:ADDRESS                       	930 N. University Ann Arbor, MI, 48109, USA
ST:EMAIL                         	anderbra@umich.edu
ST:PHONE                         	734-615-4376
ST:NUM_GROUPS                    	1
ST:TOTAL_SUBJECTS                	6
ST:NUM_MALES                     	6
ST:STUDY_COMMENTS                	Sprague Dawley Rats
ST:PUBLICATIONS                  	to be updated later
#SUBJECT
SU:SUBJECT_TYPE                  	Mammal
SU:SUBJECT_SPECIES               	Rattus norvegicus
SU:TAXONOMY_ID                   	10116
SU:AGE_OR_AGE_RANGE              	75 days (average)
SU:WEIGHT_OR_WEIGHT_RANGE        	340-375 g
SU:GENDER                        	Male
SU:ANIMAL_ANIMAL_SUPPLIER        	Charles River Laboratory
SU:ANIMAL_HOUSING                	Group housed (3 per cage)
SU:ANIMAL_LIGHT_CYCLE            	Reversed light cycle (12 h on, 12 h off)
SU:ANIMAL_FEED                   	Lab diet 5LOD rat chow
SU:SPECIES_GROUP                 	Sprague Dawley
#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           	-	RPLC_1x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_1x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_10x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_10x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_aCSF_Pos	Sample type:aCSF | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_aCSF_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Pos_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_Blank_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Pos_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_Blank_Pos_MS1_02.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_1x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_1x_Dialysate_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_10x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_10x_Dialysate_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_aCSF_Neg	Sample type:aCSF | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_aCSF_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Neg_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_Blank_Neg_01
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Neg_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_Blank_Neg_02
SUBJECT_SAMPLE_FACTORS           	-	HILIC_1x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_1x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_10x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_10x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Pos_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_Blank_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Pos_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_Blank_Pos_MS1_02.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_1x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_1x_Dialysate_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_10x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_10x_Dialysate_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Neg_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_Blank_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Neg_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_Blank_Neg_MS1_02.mzML
#COLLECTION
CO:COLLECTION_SUMMARY            	For this study, animal treatment was approved by the University Committee on Use
CO:COLLECTION_SUMMARY            	and Care of Animals (UCUCA) at the University of Michigan, the National
CO:COLLECTION_SUMMARY            	Institute of Health (NIH) Guidelines for the Care and Use of Laboratory Animals.
CO:COLLECTION_SUMMARY            	For dialysate sample collection, we used six male Sprague-Dawley rats (Charles
CO:COLLECTION_SUMMARY            	River Laboratories; Wilmington, MA), approximately 75 days old and weighing 340
CO:COLLECTION_SUMMARY            	to 375 g. Rats were group-housed before and after stereotaxic surgery in a
CO:COLLECTION_SUMMARY            	reverse light cycle vivarium (12 h on/12 h off; lights off 6 AM) with ad libitum
CO:COLLECTION_SUMMARY            	access to food and water. Before dialysate collection, a single microdialysis
CO:COLLECTION_SUMMARY            	cannula was implanted using stereotaxic surgery targeting the striatum with
CO:COLLECTION_SUMMARY            	coordinates from bregma: +1.8 AP, ±1.8 ML, -4.0 DV. Animals recovered for 36 to
CO:COLLECTION_SUMMARY            	48 h before microdialysis probe placement. On the day of sample collection (at
CO:COLLECTION_SUMMARY            	the beginning of the rat dark cycle), a microdialysis probe was inserted under
CO:COLLECTION_SUMMARY            	isoflurane anesthesia. CMA 12 Elite microdialysis probes with a 4 mm long
CO:COLLECTION_SUMMARY            	membrane (0.5 mm O.D.) and 20,000-dalton molecular weight cutoff were used
CO:COLLECTION_SUMMARY            	(Harvard Apparatus; Holliston, MA). After insertion, the microdialysis probe
CO:COLLECTION_SUMMARY            	membrane spanned the rostral areas of the dorsomedial striatum, the nucleus
CO:COLLECTION_SUMMARY            	accumbens core, and the lateral nucleus accumbens shell.Before sample
CO:COLLECTION_SUMMARY            	collection, aCSF solution was perfused at a flow rate of 2 uL/min for 45 min,
CO:COLLECTION_SUMMARY            	followed by 30 min at 1 uL/min. After probe conditioning, all samples were
CO:COLLECTION_SUMMARY            	collected at a 1 uL/min perfusion rate and 30-min fractions for 12 continuous
CO:COLLECTION_SUMMARY            	hours. The collected dialysate fractions were kept in a -20 ºC freezer during
CO:COLLECTION_SUMMARY            	the 12-h sampling period and stored in a -80 ºC freezer after.
CO:SAMPLE_TYPE                   	Brain
CO:COLLECTION_METHOD             	Microdialysate
CO:COLLECTION_LOCATION           	Dorsal and ventral striatum
CO:COLLECTION_FREQUENCY          	Continuous
CO:COLLECTION_DURATION           	12 h
CO:VOLUMEORAMOUNT_COLLECTED      	4 mL
CO:STORAGE_CONDITIONS            	-80℃
CO:COLLECTION_TUBE_TEMP          	0 C
#TREATMENT
TR:TREATMENT_SUMMARY             	No treatment was administered. Rats were freely moving with access to food and
TR:TREATMENT_SUMMARY             	water.
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	For underivatized experiments, aliquots of pooled dialysate were transferred to
SP:SAMPLEPREP_SUMMARY            	tapered glass HPLC vials (Thermo Fisher Scientific; Waltham, MA) and dried in an
SP:SAMPLEPREP_SUMMARY            	EZ-2 vacuum centrifuge (GeneVac; Ipswich, United Kingdom) for three hours.
SP:SAMPLEPREP_SUMMARY            	Samples were then preconcentrated 10-fold by volume in 9:1 water:methanol or
SP:SAMPLEPREP_SUMMARY            	85:15 acetonitrile:water for RPLC and HILIC analyses.
SP:PROCESSING_STORAGE_CONDITIONS 	On ice
SP:EXTRACT_STORAGE               	-80℃
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_SUMMARY        	Hydrophilic interaction liquid chromatography (HILIC)
CH:CHROMATOGRAPHY_TYPE           	HILIC
CH:INSTRUMENT_NAME               	Thermo Vanquish
CH:COLUMN_NAME                   	Waters ACQUITY UPLC BEH Amide (100 x 2.1mm,1.7um)
CH:SOLVENT_A                     	95:5 water:acetonitrile with 0.125% v/v formic acid and 10 mM ammonium formate
CH:SOLVENT_B                     	5:95 acetonitrile:water with 0.125% v/v formic acid and 10 mM ammonium formate
CH:FLOW_GRADIENT                 	0-0.5 min, 100%B; 0.5-7, 100-85%B; 7-9, 85%B; 9-16, 85-50%B; 16-16.1, 50-100%B;
CH:FLOW_GRADIENT                 	16.1-20, 100%B
CH:FLOW_RATE                     	0.300 mL/min
CH:COLUMN_TEMPERATURE            	55 C
CH:SAMPLE_INJECTION              	2 uL
CH:WASHING_BUFFER                	85:15 acetonitrile:water
CH:TARGET_SAMPLE_TEMPERATURE     	4 C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Thermo Orbitrap ID-X tribrid
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	NEGATIVE
MS:MS_COMMENTS                   	Mass spectrometer settings for all full scan (MS1) methods were set as follows:
MS:MS_COMMENTS                   	sheath gas, 40; aux gas, 10; sweep gas, 1; ion transfer tube temp, 325 ºC;
MS:MS_COMMENTS                   	vaporizer temp, 300 ºC; orbitrap resolution. 120000; scan range, 70-800 m/z; RF
MS:MS_COMMENTS                   	lens, 45%; normalized AGC target, 25%; maximum injection time, auto; microscans,
MS:MS_COMMENTS                   	1; data type, profile; internal mass calibration, EASY-ICTM. Spray voltages were
MS:MS_COMMENTS                   	set to 3200 V and -3200 V for positive and negative ionization modes. For MS/MS
MS:MS_COMMENTS                   	methods, the instrument settings above were maintained except for full scan
MS:MS_COMMENTS                   	orbitrap resolution, which was lowered to maximize MS/MS spectra collection. The
MS:MS_COMMENTS                   	data-dependent acquisition methods utilized the following settings: full scan
MS:MS_COMMENTS                   	orbitrap resolution, 60000; intensity threshold, 1.0x104; dynamic exclusion
MS:MS_COMMENTS                   	properties; exclusion duration 3 seconds (exclude after one time with +/- 5
MS:MS_COMMENTS                   	ppm); isolation mode, quadrupole; isolation window, 1.2 m/z; activation type,
MS:MS_COMMENTS                   	HCD; collision energy mode, assisted; collision energies, 20, 40, and 80%;
MS:MS_COMMENTS                   	detector type, orbitrap; orbitrap resolution, 30000; normalized AGC target, 20%;
MS:MS_COMMENTS                   	maximum injection time, 54 ms; microscans, 1; data type, centroid; cycle time,
MS:MS_COMMENTS                   	1.2 s. Five iterative injections (i.e., rolling precursor ion exclusion) were
MS:MS_COMMENTS                   	performed for underivatized samples to better collect MS/MS spectra of lower
MS:MS_COMMENTS                   	abundance metabolites.
MS:CAPILLARY_TEMPERATURE         	325 C
MS:DRY_GAS_FLOW                  	Sheath 40, Auxiliary 10, Sweep 1
MS:ION_SOURCE_TEMPERATURE        	300 C
MS:ION_SPRAY_VOLTAGE             	-3200
MS:IONIZATION_ENERGY             	negative
MS:MASS_ACCURACY                 	120,000 resolution
MS:AUTOMATIC_GAIN_CONTROL        	45%
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	Peak area
MS_METABOLITE_DATA_START
Samples	HILIC_1x_Dialysate_Neg	HILIC_10x_Dialysate_Neg	HILIC_Blank_Neg_01	HILIC_Blank_Neg_02
Factors	Sample type:Dialysate | Dialysate concentration:1x	Sample type:Dialysate | Dialysate concentration:10x	Sample type:Blank | Dialysate concentration:N/A	Sample type:Blank | Dialysate concentration:N/A
N-ACETYLPHENYLALANINE	87637	5814058	3836	5438
URIDINE	9297190	17058982	2498	2291
DEOXYURIDINE	7585705	26209558	2367	2169
ADENOSINE	4655816	16227646	6437	3324
(2,5-DIOXOIMIDAZOLIDIN-4-YL)UREA	9551477	11459107	3787	7979
KETOLEUCINE	21206118	86684064	191206	59028
4-(1-BUTYLHEPTYL)BESYLIC ACID	2241787	4907431	1464879	1658444
2-KETO-3,3-DIMETHYL-BUTYRIC ACID	21206118	86684064	59824	47576
2-HYDROXY-3-(4-HYDROXYPHENYL)PROPANOIC ACID	4274019	6316664	7672	2392.25
4-DODECYLBENZENE-1-SULFONIC ACID	119866	99204	137274	2874871
SULFURIC ACID LAURYL ESTER	725567	15034991	1651508	1158501
4-(1-PROPYLHEPTYL)BESYLIC ACID	200812	691427	438688	436031
MONOISOBUTYL PHTHALIC ACID	432089	2413221	42508	56187
ETHYLMALONIC ACID	92239	444216	71405	88323
OCTYL HYDROGEN SULFATE	3662890	411796	152605	271067
3-(3,5-DIMETHOXYPHENYL)PROP-2-ENOIC ACID	8966885	3895841	478214	10232821
2-AMINO-5-CHLORO-4-METHYL-BESYLIC ACID	553653	9883109	3857	6987
SULFURIC ACID [(8R,9S,10R,13S,14S,17R)-3-KETO-10,13-DIMETHYL-1,2,6,7,8,9,11,12,14,15,16,17-DODECAHYDROCYCLOPENTA[A]PHENANTHREN-17-YL] ESTER	1052706	6336980	362028	476813
3,4-DIMETHYLBESYLIC ACID	1749913	29215094	6153	6721
SALICYLIC ACID	2249711	7846557	101010	78386
2,3-DIMETHYLBESYLIC ACID	1745201	9866695	6153	6721
2-(3-KETO-4H-1,4-BENZOXAZIN-2-YL)ACETIC ACID	2535419	3685440	4313	4211
HIPPURIC ACID	1166870	1922689	22616	56021
PERFLUOROOCTANOIC ACID	685335	4540274	3463	5171
HEPTADECAFLUORONONANOIC ACID	122113	829472	2578	2696
PERFLUOROBUTANOIC ACID	66804792	68153752	506545	395362
2,2,3,3,4,4,5,5,6,6,7,7,7-TRIDECAFLUOROENANTHIC ACID	786055	5082822	14864	12728
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	ID.level	Match.type	Retention.time	Precursor.M.Z	Adduct	Collision.energy	Entropy	Total.intensity	Prec.Purity	Compound.name	IUPAC.or.systematic.name	RefMet.name	Database.ID	Source.database	Formula	InChIKey	SMILES	Score	MSMS.entropy.score	Dot.product	Reverse.dot.product	MSMS.library.name	CF.Kingdom	CF.Superclass	CF.Class	CF.Subclass	CF.Direct.parent	RTP
N-ACETYLPHENYLALANINE	MSI1	Regular	2.545	206.0814	[M-H]-	20	1.824	1241112	0.949	N-Acetyl-L-phenylalanine	(2S)-2-acetamido-3-phenylpropanoic acid	N-Acetylphenylalanine	HMDB0000512	HMDB	C11H13NO3	CBQJSKKFNMDLON-JTQLQIEISA-N	CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	864	0.874	929	995	NIST20 HighRes MSMS	Organic compounds	Organic acids and derivatives	Carboxylic acids and derivatives	Amino acids, peptides, and analogues	Phenylalanine and derivatives	4.35
URIDINE	MSI1	Regular	4.367	243.0609	[M-H]-	20	2.214	1277472	0.943	Uridine	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione	Uridine	HMDB0000296	HMDB	C9H12N2O6	DRTQHJPVMGBUCF-XVFCMESISA-N	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O	855	0.845	904	985	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Pyrimidine nucleosides	NA	Pyrimidine nucleosides	4.87
DEOXYURIDINE	MSI1	InSource	2.884	273.0726	[M-H]-	20	1.161	1991663	0.883	Deoxyuridine	1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione	Deoxyuridine	HMDB0000012	HMDB	C9H12N2O5	MXHRCPNRJAMMIM-SHYZEUOFSA-N	OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O	233	0.792	476	880	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Pyrimidine nucleosides	Pyrimidine 2'-deoxyribonucleosides	Pyrimidine 2'-deoxyribonucleosides	3.52
ADENOSINE	MSI1	InSource	4.326	312.0947	[M-H]-	20	0.454	1506402	0.942	Adenosine	(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol	Adenosine	HMDB0000050	HMDB	C10H13N5O4	OIRDTQYFTABQOQ-KQYNXXCUSA-N	NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1	341	0.859	949	999	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Purine nucleosides	NA	Purine nucleosides	6.71
(2,5-DIOXOIMIDAZOLIDIN-4-YL)UREA	MSI1	Regular	5.449	157.0361	[M-H]-	20	1.166	636755	0.95	Allantoin	(2,5-dioxoimidazolidin-4-yl)urea		HMDB0000462	HMDB	C4H6N4O3	POJWUDADGALRAB-UHFFFAOYSA-N	NC(=O)NC1NC(=O)NC1=O	849	0.962	972	997	MONA	Organic compounds	Organoheterocyclic compounds	Azoles	Imidazoles	Imidazoles	5.73
KETOLEUCINE	MSI2A	Regular	2.131	129.0551	[M-H]-	20	0.424	394338	0.952	Ketoleucine	4-methyl-2-oxopentanoic acid	Ketoleucine	HMDB0000695	HMDB	C6H10O3	BKAJNAXTPSGJCU-UHFFFAOYSA-N	CC(C)CC(=O)C(O)=O	782	0.828	925	926	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Keto acids and derivatives	Short-chain keto acids and derivatives	Short-chain keto acids and derivatives	2.34
4-(1-BUTYLHEPTYL)BESYLIC ACID	MSI2A	InSource	1.127	339.1995	[M-H]-	80	1.726	679069	0.694	5-(4-Sulfophenyl)undecane	4-(1-butylheptyl)besylic acid		15593874	PubChem	C17H28O3S	FERBTPHUEYEGDN-UHFFFAOYSA-N	CCCCCCC(CCCC)C1=CC=C(C=C1)S(=O)(=O)O	860	0.755	924	984	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.41
2-KETO-3,3-DIMETHYL-BUTYRIC ACID	MSI2A	Regular	2.301	129.0551	[M-H]-	20	0.43	555871	0.961	3,3-Dimethyl-2-oxobutyric acid	2-keto-3,3-dimethyl-butyric acid		13150	PubChem	C6H10O3	IAWVHZJZHDSEOC-UHFFFAOYSA-N	CC(C)(C)C(=O)C(=O)O	320	0.783	618	999	NIST20 HighRes MSMS	Organic compounds	Organic acids and derivatives	Keto acids and derivatives	Short-chain keto acids and derivatives	Short-chain keto acids and derivatives	2.83
2-HYDROXY-3-(4-HYDROXYPHENYL)PROPANOIC ACID	MSI2A	Regular	3.57	181.0497	[M-H]-	20	2.412	276454	0.587	Hydroxyphenyllactic acid	2-hydroxy-3-(4-hydroxyphenyl)propanoic acid		HMDB0000755	HMDB	C9H10O4	JVGVDSSUAVXRDY-UHFFFAOYSA-N	OC(CC1=CC=C(O)C=C1)C(O)=O	728	0.671	836	973	NIST17 MSMS	Organic compounds	Phenylpropanoids and polyketides	Phenylpropanoic acids	NA	Phenylpropanoic acids	4.14
4-DODECYLBENZENE-1-SULFONIC ACID	MSI2A	Regular	2.194	325.184	[M-H]-	80	1.766	770503	0.603	4-Dodecylbenzenesulfonic Acid	4-dodecylbenzene-1-sulfonic acid		HMDB0059915	HMDB	C18H30O3S	KWXICGTUELOLSQ-UHFFFAOYSA-N	CCCCCCCCCCCCC1=CC=C(C=C1)S(O)(=O)=O	672	0.686	871	973	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.28
SULFURIC ACID LAURYL ESTER	MSI2A	Regular	1.044	265.1477	[M-H]-	40	1.106	6992495	0.613	Lauryl sulfate	sulfuric acid lauryl ester		8778	PubChem	C12H26O4S	MOTZDAYCYVMXPC-UHFFFAOYSA-N	CCCCCCCCCCCCOS(=O)(=O)O	745	0.653	946	964	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Organic sulfuric acids and derivatives	Sulfuric acid esters	Sulfuric acid monoesters	1.48
4-(1-PROPYLHEPTYL)BESYLIC ACID	MSI2A	InSource	1.884	325.184	[M-H]-	80	2.078	367713	0.596	4-(Decan-4-yl)benzenesulfonic acid	4-(1-propylheptyl)besylic acid		14921167	PubChem	C16H26O3S	NANHIUZYPFDGJS-UHFFFAOYSA-N	CCCCCCC(CCC)C1=CC=C(C=C1)S(=O)(=O)O	743	0.665	879	991	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.41
MONOISOBUTYL PHTHALIC ACID	MSI2A	Regular	1.194	221.0809	[M-H]-	20	3.099	385834	0.789	Monoisobutyl phthalic acid	2-[(2-methylpropoxy)carbonyl]benzoic acid	Monoisobutyl phthalic acid	HMDB0002056	HMDB	C12H14O4	RZJSUWQGFCHNFS-UHFFFAOYSA-N	CC(C)COC(=O)C1=CC=CC=C1C(O)=O	656	0.741	790	982	NIST17 MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Benzoic acid esters	1.48
ETHYLMALONIC ACID	MSI2A	InSource	2.868	130.9919	[M-H]-	20	1.986	48452	0.783	Ethylmalonic acid	2-ethylpropanedioic acid	Ethylmalonic acid	HMDB0000622	HMDB	C5H8O4	UKFXDFUAPNAMPJ-UHFFFAOYSA-N	CCC(C(O)=O)C(O)=O	235	0.675	713	999	NIST17 MSMS	Organic compounds	Lipids and lipid-like molecules	Fatty Acyls	Fatty acids and conjugates	Branched fatty acids	3.16
OCTYL HYDROGEN SULFATE	MSI2A	InSource	2.47	265.1477	[M-H]-	40	1.34	628955	0.604	octyl hydrogen sulfate	octyl hydrogen sulfate		CHEBI:83122	ChEBI	C8H18O4S	UZZYXUGECOQHPU-UHFFFAOYSA-N	CCCCCCCCOS(O)(=O)=O	525	0.658	870	990	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Organic sulfuric acids and derivatives	Sulfuric acid esters	Sulfuric acid monoesters	1.88
3-(3,5-DIMETHOXYPHENYL)PROP-2-ENOIC ACID	MSI2A	InSource	1.211	100.9337	[M-H]-	40	0	6901	0.976	3-(3,5-dimethoxyphenyl)prop-2-enoic acid	3-(3,5-dimethoxyphenyl)prop-2-enoic acid		HMDB0127491	HMDB	C11H12O4	VLSRUFWCGBMYDJ-UHFFFAOYSA-N	COC1=CC(C=CC(O)=O)=CC(OC)=C1	364	0.689	999	999	MONA	Organic compounds	Phenylpropanoids and polyketides	Cinnamic acids and derivatives	Hydroxycinnamic acids and derivatives	Coumaric acids and derivatives	1.58
2-AMINO-5-CHLORO-4-METHYL-BESYLIC ACID	MSI2A	InSource	1.348	212.0023	[M-H]-	40	0.278	425739	0.979	2-Amino-5-chloro-4-methylbenzenesulfonic acid	2-amino-5-chloro-4-methyl-besylic acid		6936	PubChem	C7H8ClNO3S	VYZCFAPUHSSYCC-UHFFFAOYSA-N	CC1=CC(=C(C=C1Cl)S(=O)(=O)O)N	526	0.653	968	988	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	p-Methylbenzenesulfonates	2.14
SULFURIC ACID [(8R,9S,10R,13S,14S,17R)-3-KETO-10,13-DIMETHYL-1,2,6,7,8,9,11,12,14,15,16,17-DODECAHYDROCYCLOPENTA[A]PHENANTHREN-17-YL] ESTER	MSI2A	InSource	1.002	293.1787	[M-H]-	40	0.659	1821276	0.925	Epitestosterone sulfate	sulfuric acid [(8R,9S,10R,13S,14S,17R)-3-keto-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] ester		12133250	PubChem	C19H28O5S	WAQBISPOEAOCOG-KZYORJDKSA-N	C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2OS(=O)(=O)O)CCC4=CC(=O)CC[C@]34C	724	0.74	956	965	NIST17 MSMS	Organic compounds	Lipids and lipid-like molecules	Steroids and steroid derivatives	Sulfated steroids	Sulfated steroids	1.61
3,4-DIMETHYLBESYLIC ACID	MSI2A	Regular	2.159	185.0271	[M-H]-	20	0.29	529875	0.939	3,4-Dimethylbenzenesulfonic Acid	3,4-dimethylbesylic acid		14756	PubChem	C8H10O3S	WYCOJIVDCGJKDB-UHFFFAOYSA-N	CC1=C(C=C(C=C1)S(=O)(=O)O)C	482	0.869	763	983	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	p-Methylbenzenesulfonates	1.45
SALICYLIC ACID	MSI2A	Regular	1.504	137.0246	[M-H]-	40	1.44	244155	0.928	Salicylic acid	2-hydroxybenzoic acid	Salicylic acid	HMDB0001895	HMDB	C7H6O3	YGSDEFSMJLZEOE-UHFFFAOYSA-N	OC(=O)C1=CC=CC=C1O	642	0.697	951	998	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Salicylic acids	2.1
2,3-DIMETHYLBESYLIC ACID	MSI2A	Regular	2.003	185.0279	[M-H]-	40	0	850637	0.979	2,3-Dimethylbenzenesulfonic acid	2,3-dimethylbesylic acid		172623	PubChem	C8H10O3S	ZZXDRXVIRVJQBT-UHFFFAOYSA-N	CC1=C(C(=CC=C1)S(=O)(=O)O)C	492	0.859	947	984	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.77
2-(3-KETO-4H-1,4-BENZOXAZIN-2-YL)ACETIC ACID	MSI2B	Regular	1.983	206.045	[M-H]-	20	0.688	622814	0.879	(3-Oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetic acid	2-(3-keto-4H-1,4-benzoxazin-2-yl)acetic acid		2783999	PubChem	C10H9NO4	GBWCBWJRILQTBI-UHFFFAOYSA-N	C1=CC=C2C(=C1)NC(=O)C(O2)CC(=O)O	432	0.706	880	988	NIST20 HighRes MSMS	Organic compounds	Organoheterocyclic compounds	Benzoxazines	Benzoxazinones	Benzoxazinones	3.89
HIPPURIC ACID	MSI2B	Regular	2.826	178.05	[M-H]-	20	1.623	100258	0.938	Hippuric acid	2-(phenylformamido)acetic acid	Hippuric acid	HMDB0000714	HMDB	C9H9NO3	QIAFMBKCNZACKA-UHFFFAOYSA-N	OC(=O)CNC(=O)C1=CC=CC=C1	397	0.654	850	985	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Hippuric acids	4.96
PERFLUOROOCTANOIC ACID	MSI2B	Regular	0.861	412.9664	[M-H]-	20	1.224	1472896	0.873	Perfluorooctanoic acid	pentadecafluorooctanoic acid	Perfluorooctanoic acid	HMDB0059587	HMDB	C8HF15O2	SNGREZUHAYWORS-UHFFFAOYSA-N	[H]OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F	756	0.791	893	914	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	2.75
HEPTADECAFLUORONONANOIC ACID	MSI2B	Regular	0.837	462.9635	[M-H]-	20	2.402	330524	0.549	Perfluorononanoic acid	heptadecafluorononanoic acid	Heptadecafluorononanoic acid	HMDB0061739	HMDB	C9HF17O2	UZUFPBIDKMEQEQ-UHFFFAOYSA-N	OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F	719	0.719	814	965	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluorooctanoic acid and derivatives	2.77
PERFLUOROBUTANOIC ACID	MSI2B	Regular	0.966	212.9791	[M-H]-	20	0	3374248	0.962	PERFLUOROBUTANOIC ACID		Perfluorobutanoic acid	9777	PubChem	C4HF7O2	YPJUNDFVDDCYIH-UHFFFAOYSA-N	C(=O)(C(C(C(F)(F)F)(F)F)(F)F)O	604	0.689	992	999	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	3.61
2,2,3,3,4,4,5,5,6,6,7,7,7-TRIDECAFLUOROENANTHIC ACID	MSI2B	Regular	0.885	362.9694	[M-H]-	20	1.361	838178	0.878	Perfluoroheptanoic acid	2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroenanthic acid		67818	PubChem	C7HF13O2	ZWBAMYVPMDSJGQ-UHFFFAOYSA-N	C(=O)(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O	746	0.786	921	966	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	2.92
METABOLITES_END
#END


#METABOLOMICS WORKBENCH anderbra_20230502_093501 DATATRACK_ID:3996 STUDY_ID:ST003302 ANALYSIS_ID:AN005412 PROJECT_ID:PR002052
VERSION             	1
CREATED_ON             	July 7, 2024, 6:25 pm
#PROJECT
PR:PROJECT_TITLE                 	Untargeted Dialysate Metabolomics Identification and Detection of Novel
PR:PROJECT_TITLE                 	Neurochemicals via Benzoyl Chloride Derivatization
PR:PROJECT_SUMMARY               	This study combines these strategies to obtain in-depth untargeted chemical
PR:PROJECT_SUMMARY               	identification of dialysate. We target the rat dorsal and ventral striatum,
PR:PROJECT_SUMMARY               	given its importance in motivation, movement, and reward processing and identify
PR:PROJECT_SUMMARY               	489 compounds. Despite the depth of analysis, many well-known neurochemicals,
PR:PROJECT_SUMMARY               	such as all neurotransmitters, were not identified in the untargeted method.
PR:PROJECT_SUMMARY               	These compounds could be detected using BzCl derivation in a targeted method
PR:PROJECT_SUMMARY               	though. By tracking isotopic BzCl feature pair detection and filtering of MS/MS
PR:PROJECT_SUMMARY               	spectra by known benzoyl fragment ions, we found 872 unique features in
PR:PROJECT_SUMMARY               	dialysate suggesting many unknown compounds remain to be identified in
PR:PROJECT_SUMMARY               	dialysate.
PR:INSTITUTE                     	University of Michigan
PR:LAST_NAME                     	Anderson
PR:FIRST_NAME                    	Brady
PR:ADDRESS                       	930 N. University Ann Arbor, MI 48109
PR:EMAIL                         	anderbra@umich.edu
PR:PHONE                         	6519256798
PR:FUNDING_SOURCE                	NIH (NINDD,NIEHS)
PR:PUBLICATIONS                  	to be updated later
PR:CONTRIBUTORS                  	Brady Anderson, Pavlo Popov, Amanda Cicali, Adana Nwamba, Charles R. Evans,
PR:CONTRIBUTORS                  	Robert T. Kennedy
#STUDY
ST:STUDY_TITLE                   	Untargeted Dialysate Metabolomics Identification and Detection of Novel
ST:STUDY_TITLE                   	Neurochemicals via Benzoyl Chloride Derivatization
ST:STUDY_SUMMARY                 	This study combines these strategies to obtain in-depth untargeted chemical
ST:STUDY_SUMMARY                 	identification of dialysate. We target the rat dorsal and ventral striatum,
ST:STUDY_SUMMARY                 	given its importance in motivation, movement, and reward processing and identify
ST:STUDY_SUMMARY                 	489 compounds. Despite the depth of analysis, many well-known neurochemicals,
ST:STUDY_SUMMARY                 	such as all neurotransmitters, were not identified in the untargeted method.
ST:STUDY_SUMMARY                 	These compounds could be detected using BzCl derivation in a targeted method
ST:STUDY_SUMMARY                 	though. By tracking isotopic BzCl feature pair detection and filtering of MS/MS
ST:STUDY_SUMMARY                 	spectra by known benzoyl fragment ions, we found 872 unique features in
ST:STUDY_SUMMARY                 	dialysate suggesting many unknown compounds remain to be identified in
ST:STUDY_SUMMARY                 	dialysate.
ST:INSTITUTE                     	University of Michigan
ST:LAST_NAME                     	Anderson
ST:FIRST_NAME                    	Brady
ST:ADDRESS                       	930 N. University Ann Arbor, MI, 48109, USA
ST:EMAIL                         	anderbra@umich.edu
ST:PHONE                         	734-615-4376
ST:NUM_GROUPS                    	1
ST:TOTAL_SUBJECTS                	6
ST:NUM_MALES                     	6
ST:STUDY_COMMENTS                	Sprague Dawley Rats
ST:PUBLICATIONS                  	to be updated later
#SUBJECT
SU:SUBJECT_TYPE                  	Mammal
SU:SUBJECT_SPECIES               	Rattus norvegicus
SU:TAXONOMY_ID                   	10116
SU:AGE_OR_AGE_RANGE              	75 days (average)
SU:WEIGHT_OR_WEIGHT_RANGE        	340-375 g
SU:GENDER                        	Male
SU:ANIMAL_ANIMAL_SUPPLIER        	Charles River Laboratory
SU:ANIMAL_HOUSING                	Group housed (3 per cage)
SU:ANIMAL_LIGHT_CYCLE            	Reversed light cycle (12 h on, 12 h off)
SU:ANIMAL_FEED                   	Lab diet 5LOD rat chow
SU:SPECIES_GROUP                 	Sprague Dawley
#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           	-	RPLC_1x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_1x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_10x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_10x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_aCSF_Pos	Sample type:aCSF | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_aCSF_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Pos_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_Blank_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Pos_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Positive; RAW_FILE_NAME=2023_0128_RPLC_Blank_Pos_MS1_02.mzML
SUBJECT_SAMPLE_FACTORS           	-	RPLC_1x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_1x_Dialysate_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_10x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_10x_Dialysate_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_aCSF_Neg	Sample type:aCSF | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_aCSF_Neg
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Neg_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_Blank_Neg_01
SUBJECT_SAMPLE_FACTORS           	-	RPLC_Blank_Neg_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Reversed phase; Ionization mode=Negative; RAW_FILE_NAME=2023_0128_RPLC_Blank_Neg_02
SUBJECT_SAMPLE_FACTORS           	-	HILIC_1x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_1x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_10x_Dialysate_Pos	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_10x_Dialysate_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Pos_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_Blank_Pos_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Pos_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Positive; RAW_FILE_NAME=2023_0130_HILIC_Blank_Pos_MS1_02.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_1x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:1x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_1x_Dialysate_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_10x_Dialysate_Neg	Sample type:Dialysate | Dialysate concentration:10x	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_10x_Dialysate_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Neg_01	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_Blank_Neg_MS1_01.mzML
SUBJECT_SAMPLE_FACTORS           	-	HILIC_Blank_Neg_02	Sample type:Blank | Dialysate concentration:N/A	Chromatography=Hydrophilic interaction liquid chromatography; Ionization mode=Negative; RAW_FILE_NAME=2023_0130_HILIC_Blank_Neg_MS1_02.mzML
#COLLECTION
CO:COLLECTION_SUMMARY            	For this study, animal treatment was approved by the University Committee on Use
CO:COLLECTION_SUMMARY            	and Care of Animals (UCUCA) at the University of Michigan, the National
CO:COLLECTION_SUMMARY            	Institute of Health (NIH) Guidelines for the Care and Use of Laboratory Animals.
CO:COLLECTION_SUMMARY            	For dialysate sample collection, we used six male Sprague-Dawley rats (Charles
CO:COLLECTION_SUMMARY            	River Laboratories; Wilmington, MA), approximately 75 days old and weighing 340
CO:COLLECTION_SUMMARY            	to 375 g. Rats were group-housed before and after stereotaxic surgery in a
CO:COLLECTION_SUMMARY            	reverse light cycle vivarium (12 h on/12 h off; lights off 6 AM) with ad libitum
CO:COLLECTION_SUMMARY            	access to food and water. Before dialysate collection, a single microdialysis
CO:COLLECTION_SUMMARY            	cannula was implanted using stereotaxic surgery targeting the striatum with
CO:COLLECTION_SUMMARY            	coordinates from bregma: +1.8 AP, ±1.8 ML, -4.0 DV. Animals recovered for 36 to
CO:COLLECTION_SUMMARY            	48 h before microdialysis probe placement. On the day of sample collection (at
CO:COLLECTION_SUMMARY            	the beginning of the rat dark cycle), a microdialysis probe was inserted under
CO:COLLECTION_SUMMARY            	isoflurane anesthesia. CMA 12 Elite microdialysis probes with a 4 mm long
CO:COLLECTION_SUMMARY            	membrane (0.5 mm O.D.) and 20,000-dalton molecular weight cutoff were used
CO:COLLECTION_SUMMARY            	(Harvard Apparatus; Holliston, MA). After insertion, the microdialysis probe
CO:COLLECTION_SUMMARY            	membrane spanned the rostral areas of the dorsomedial striatum, the nucleus
CO:COLLECTION_SUMMARY            	accumbens core, and the lateral nucleus accumbens shell.Before sample
CO:COLLECTION_SUMMARY            	collection, aCSF solution was perfused at a flow rate of 2 uL/min for 45 min,
CO:COLLECTION_SUMMARY            	followed by 30 min at 1 uL/min. After probe conditioning, all samples were
CO:COLLECTION_SUMMARY            	collected at a 1 uL/min perfusion rate and 30-min fractions for 12 continuous
CO:COLLECTION_SUMMARY            	hours. The collected dialysate fractions were kept in a -20 ºC freezer during
CO:COLLECTION_SUMMARY            	the 12-h sampling period and stored in a -80 ºC freezer after.
CO:SAMPLE_TYPE                   	Brain
CO:COLLECTION_METHOD             	Microdialysate
CO:COLLECTION_LOCATION           	Dorsal and ventral striatum
CO:COLLECTION_FREQUENCY          	Continuous
CO:COLLECTION_DURATION           	12 h
CO:VOLUMEORAMOUNT_COLLECTED      	4 mL
CO:STORAGE_CONDITIONS            	-80℃
CO:COLLECTION_TUBE_TEMP          	0 C
#TREATMENT
TR:TREATMENT_SUMMARY             	No treatment was administered. Rats were freely moving with access to food and
TR:TREATMENT_SUMMARY             	water.
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	For underivatized experiments, aliquots of pooled dialysate were transferred to
SP:SAMPLEPREP_SUMMARY            	tapered glass HPLC vials (Thermo Fisher Scientific; Waltham, MA) and dried in an
SP:SAMPLEPREP_SUMMARY            	EZ-2 vacuum centrifuge (GeneVac; Ipswich, United Kingdom) for three hours.
SP:SAMPLEPREP_SUMMARY            	Samples were then preconcentrated 10-fold by volume in 9:1 water:methanol or
SP:SAMPLEPREP_SUMMARY            	85:15 acetonitrile:water for RPLC and HILIC analyses.
SP:PROCESSING_STORAGE_CONDITIONS 	On ice
SP:EXTRACT_STORAGE               	-80℃
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_SUMMARY        	Hydrophilic interaction liquid chromatography (HILIC)
CH:CHROMATOGRAPHY_TYPE           	HILIC
CH:INSTRUMENT_NAME               	Thermo Vanquish
CH:COLUMN_NAME                   	Waters ACQUITY UPLC BEH Amide (100 x 2.1mm,1.7um)
CH:SOLVENT_A                     	95:5 water:acetonitrile with 0.125% v/v formic acid and 10 mM ammonium formate
CH:SOLVENT_B                     	5:95 acetonitrile:water with 0.125% v/v formic acid and 10 mM ammonium formate
CH:FLOW_GRADIENT                 	0-0.5 min, 100%B; 0.5-7, 100-85%B; 7-9, 85%B; 9-16, 85-50%B; 16-16.1, 50-100%B;
CH:FLOW_GRADIENT                 	16.1-20, 100%B
CH:FLOW_RATE                     	0.300 mL/min
CH:COLUMN_TEMPERATURE            	55 C
CH:SAMPLE_INJECTION              	2 uL
CH:WASHING_BUFFER                	85:15 acetonitrile:water
CH:TARGET_SAMPLE_TEMPERATURE     	4 C
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
#MS
MS:INSTRUMENT_NAME               	Thermo Orbitrap ID-X tribrid
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	NEGATIVE
MS:MS_COMMENTS                   	Mass spectrometer settings for all full scan (MS1) methods were set as follows:
MS:MS_COMMENTS                   	sheath gas, 40; aux gas, 10; sweep gas, 1; ion transfer tube temp, 325 ºC;
MS:MS_COMMENTS                   	vaporizer temp, 300 ºC; orbitrap resolution. 120000; scan range, 70-800 m/z; RF
MS:MS_COMMENTS                   	lens, 45%; normalized AGC target, 25%; maximum injection time, auto; microscans,
MS:MS_COMMENTS                   	1; data type, profile; internal mass calibration, EASY-ICTM. Spray voltages were
MS:MS_COMMENTS                   	set to 3200 V and -3200 V for positive and negative ionization modes. For MS/MS
MS:MS_COMMENTS                   	methods, the instrument settings above were maintained except for full scan
MS:MS_COMMENTS                   	orbitrap resolution, which was lowered to maximize MS/MS spectra collection. The
MS:MS_COMMENTS                   	data-dependent acquisition methods utilized the following settings: full scan
MS:MS_COMMENTS                   	orbitrap resolution, 60000; intensity threshold, 1.0x104; dynamic exclusion
MS:MS_COMMENTS                   	properties; exclusion duration 3 seconds (exclude after one time with +/- 5
MS:MS_COMMENTS                   	ppm); isolation mode, quadrupole; isolation window, 1.2 m/z; activation type,
MS:MS_COMMENTS                   	HCD; collision energy mode, assisted; collision energies, 20, 40, and 80%;
MS:MS_COMMENTS                   	detector type, orbitrap; orbitrap resolution, 30000; normalized AGC target, 20%;
MS:MS_COMMENTS                   	maximum injection time, 54 ms; microscans, 1; data type, centroid; cycle time,
MS:MS_COMMENTS                   	1.2 s. Five iterative injections (i.e., rolling precursor ion exclusion) were
MS:MS_COMMENTS                   	performed for underivatized samples to better collect MS/MS spectra of lower
MS:MS_COMMENTS                   	abundance metabolites.
MS:CAPILLARY_TEMPERATURE         	325 C
MS:DRY_GAS_FLOW                  	Sheath 40, Auxiliary 10, Sweep 1
MS:ION_SOURCE_TEMPERATURE        	300 C
MS:ION_SPRAY_VOLTAGE             	-3200
MS:IONIZATION_ENERGY             	negative
MS:MASS_ACCURACY                 	120,000 resolution
MS:AUTOMATIC_GAIN_CONTROL        	45%
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	Peak area
MS_METABOLITE_DATA_START
Samples	HILIC_1x_Dialysate_Neg	HILIC_10x_Dialysate_Neg	HILIC_Blank_Neg_01	HILIC_Blank_Neg_02
Factors	Sample type:Dialysate | Dialysate concentration:1x	Sample type:Dialysate | Dialysate concentration:10x	Sample type:Blank | Dialysate concentration:N/A	Sample type:Blank | Dialysate concentration:N/A
N-ACETYLPHENYLALANINE	87637	5814058	3836	5438
URIDINE	9297190	17058982	2498	2291
DEOXYURIDINE	7585705	26209558	2367	2169
ADENOSINE	4655816	16227646	6437	3324
(2,5-DIOXOIMIDAZOLIDIN-4-YL)UREA	9551477	11459107	3787	7979
KETOLEUCINE	21206118	86684064	191206	59028
4-(1-BUTYLHEPTYL)BESYLIC ACID	2241787	4907431	1464879	1658444
2-KETO-3,3-DIMETHYL-BUTYRIC ACID	21206118	86684064	59824	47576
2-HYDROXY-3-(4-HYDROXYPHENYL)PROPANOIC ACID	4274019	6316664	7672	2392.25
4-DODECYLBENZENE-1-SULFONIC ACID	119866	99204	137274	2874871
SULFURIC ACID LAURYL ESTER	725567	15034991	1651508	1158501
4-(1-PROPYLHEPTYL)BESYLIC ACID	200812	691427	438688	436031
MONOISOBUTYL PHTHALIC ACID	432089	2413221	42508	56187
ETHYLMALONIC ACID	92239	444216	71405	88323
OCTYL HYDROGEN SULFATE	3662890	411796	152605	271067
3-(3,5-DIMETHOXYPHENYL)PROP-2-ENOIC ACID	8966885	3895841	478214	10232821
2-AMINO-5-CHLORO-4-METHYL-BESYLIC ACID	553653	9883109	3857	6987
SULFURIC ACID [(8R,9S,10R,13S,14S,17R)-3-KETO-10,13-DIMETHYL-1,2,6,7,8,9,11,12,14,15,16,17-DODECAHYDROCYCLOPENTA[A]PHENANTHREN-17-YL] ESTER	1052706	6336980	362028	476813
3,4-DIMETHYLBESYLIC ACID	1749913	29215094	6153	6721
SALICYLIC ACID	2249711	7846557	101010	78386
2,3-DIMETHYLBESYLIC ACID	1745201	9866695	6153	6721
2-(3-KETO-4H-1,4-BENZOXAZIN-2-YL)ACETIC ACID	2535419	3685440	4313	4211
HIPPURIC ACID	1166870	1922689	22616	56021
PERFLUOROOCTANOIC ACID	685335	4540274	3463	5171
HEPTADECAFLUORONONANOIC ACID	122113	829472	2578	2696
PERFLUOROBUTANOIC ACID	66804792	68153752	506545	395362
2,2,3,3,4,4,5,5,6,6,7,7,7-TRIDECAFLUOROENANTHIC ACID	786055	5082822	14864	12728
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	ID.level	Match.type	Retention.time	Precursor.M.Z	Adduct	Collision.energy	Entropy	Total.intensity	Prec.Purity	Compound.name	IUPAC.or.systematic.name	RefMet.name	Database.ID	Source.database	Formula	InChIKey	SMILES	Score	MSMS.entropy.score	Dot.product	Reverse.dot.product	MSMS.library.name	CF.Kingdom	CF.Superclass	CF.Class	CF.Subclass	CF.Direct.parent	RTP
N-ACETYLPHENYLALANINE	MSI1	Regular	2.545	206.0814	[M-H]-	20	1.824	1241112	0.949	N-Acetyl-L-phenylalanine	(2S)-2-acetamido-3-phenylpropanoic acid	N-Acetylphenylalanine	HMDB0000512	HMDB	C11H13NO3	CBQJSKKFNMDLON-JTQLQIEISA-N	CC(=O)N[C@@H](CC1=CC=CC=C1)C(O)=O	864	0.874	929	995	NIST20 HighRes MSMS	Organic compounds	Organic acids and derivatives	Carboxylic acids and derivatives	Amino acids, peptides, and analogues	Phenylalanine and derivatives	4.35
URIDINE	MSI1	Regular	4.367	243.0609	[M-H]-	20	2.214	1277472	0.943	Uridine	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione	Uridine	HMDB0000296	HMDB	C9H12N2O6	DRTQHJPVMGBUCF-XVFCMESISA-N	OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O	855	0.845	904	985	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Pyrimidine nucleosides	NA	Pyrimidine nucleosides	4.87
DEOXYURIDINE	MSI1	InSource	2.884	273.0726	[M-H]-	20	1.161	1991663	0.883	Deoxyuridine	1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione	Deoxyuridine	HMDB0000012	HMDB	C9H12N2O5	MXHRCPNRJAMMIM-SHYZEUOFSA-N	OC[C@H]1O[C@H](C[C@@H]1O)N1C=CC(=O)NC1=O	233	0.792	476	880	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Pyrimidine nucleosides	Pyrimidine 2'-deoxyribonucleosides	Pyrimidine 2'-deoxyribonucleosides	3.52
ADENOSINE	MSI1	InSource	4.326	312.0947	[M-H]-	20	0.454	1506402	0.942	Adenosine	(2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol	Adenosine	HMDB0000050	HMDB	C10H13N5O4	OIRDTQYFTABQOQ-KQYNXXCUSA-N	NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1	341	0.859	949	999	MONA	Organic compounds	Nucleosides, nucleotides, and analogues	Purine nucleosides	NA	Purine nucleosides	6.71
(2,5-DIOXOIMIDAZOLIDIN-4-YL)UREA	MSI1	Regular	5.449	157.0361	[M-H]-	20	1.166	636755	0.95	Allantoin	(2,5-dioxoimidazolidin-4-yl)urea		HMDB0000462	HMDB	C4H6N4O3	POJWUDADGALRAB-UHFFFAOYSA-N	NC(=O)NC1NC(=O)NC1=O	849	0.962	972	997	MONA	Organic compounds	Organoheterocyclic compounds	Azoles	Imidazoles	Imidazoles	5.73
KETOLEUCINE	MSI2A	Regular	2.131	129.0551	[M-H]-	20	0.424	394338	0.952	Ketoleucine	4-methyl-2-oxopentanoic acid	Ketoleucine	HMDB0000695	HMDB	C6H10O3	BKAJNAXTPSGJCU-UHFFFAOYSA-N	CC(C)CC(=O)C(O)=O	782	0.828	925	926	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Keto acids and derivatives	Short-chain keto acids and derivatives	Short-chain keto acids and derivatives	2.34
4-(1-BUTYLHEPTYL)BESYLIC ACID	MSI2A	InSource	1.127	339.1995	[M-H]-	80	1.726	679069	0.694	5-(4-Sulfophenyl)undecane	4-(1-butylheptyl)besylic acid		15593874	PubChem	C17H28O3S	FERBTPHUEYEGDN-UHFFFAOYSA-N	CCCCCCC(CCCC)C1=CC=C(C=C1)S(=O)(=O)O	860	0.755	924	984	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.41
2-KETO-3,3-DIMETHYL-BUTYRIC ACID	MSI2A	Regular	2.301	129.0551	[M-H]-	20	0.43	555871	0.961	3,3-Dimethyl-2-oxobutyric acid	2-keto-3,3-dimethyl-butyric acid		13150	PubChem	C6H10O3	IAWVHZJZHDSEOC-UHFFFAOYSA-N	CC(C)(C)C(=O)C(=O)O	320	0.783	618	999	NIST20 HighRes MSMS	Organic compounds	Organic acids and derivatives	Keto acids and derivatives	Short-chain keto acids and derivatives	Short-chain keto acids and derivatives	2.83
2-HYDROXY-3-(4-HYDROXYPHENYL)PROPANOIC ACID	MSI2A	Regular	3.57	181.0497	[M-H]-	20	2.412	276454	0.587	Hydroxyphenyllactic acid	2-hydroxy-3-(4-hydroxyphenyl)propanoic acid		HMDB0000755	HMDB	C9H10O4	JVGVDSSUAVXRDY-UHFFFAOYSA-N	OC(CC1=CC=C(O)C=C1)C(O)=O	728	0.671	836	973	NIST17 MSMS	Organic compounds	Phenylpropanoids and polyketides	Phenylpropanoic acids	NA	Phenylpropanoic acids	4.14
4-DODECYLBENZENE-1-SULFONIC ACID	MSI2A	Regular	2.194	325.184	[M-H]-	80	1.766	770503	0.603	4-Dodecylbenzenesulfonic Acid	4-dodecylbenzene-1-sulfonic acid		HMDB0059915	HMDB	C18H30O3S	KWXICGTUELOLSQ-UHFFFAOYSA-N	CCCCCCCCCCCCC1=CC=C(C=C1)S(O)(=O)=O	672	0.686	871	973	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.28
SULFURIC ACID LAURYL ESTER	MSI2A	Regular	1.044	265.1477	[M-H]-	40	1.106	6992495	0.613	Lauryl sulfate	sulfuric acid lauryl ester		8778	PubChem	C12H26O4S	MOTZDAYCYVMXPC-UHFFFAOYSA-N	CCCCCCCCCCCCOS(=O)(=O)O	745	0.653	946	964	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Organic sulfuric acids and derivatives	Sulfuric acid esters	Sulfuric acid monoesters	1.48
4-(1-PROPYLHEPTYL)BESYLIC ACID	MSI2A	InSource	1.884	325.184	[M-H]-	80	2.078	367713	0.596	4-(Decan-4-yl)benzenesulfonic acid	4-(1-propylheptyl)besylic acid		14921167	PubChem	C16H26O3S	NANHIUZYPFDGJS-UHFFFAOYSA-N	CCCCCCC(CCC)C1=CC=C(C=C1)S(=O)(=O)O	743	0.665	879	991	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.41
MONOISOBUTYL PHTHALIC ACID	MSI2A	Regular	1.194	221.0809	[M-H]-	20	3.099	385834	0.789	Monoisobutyl phthalic acid	2-[(2-methylpropoxy)carbonyl]benzoic acid	Monoisobutyl phthalic acid	HMDB0002056	HMDB	C12H14O4	RZJSUWQGFCHNFS-UHFFFAOYSA-N	CC(C)COC(=O)C1=CC=CC=C1C(O)=O	656	0.741	790	982	NIST17 MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Benzoic acid esters	1.48
ETHYLMALONIC ACID	MSI2A	InSource	2.868	130.9919	[M-H]-	20	1.986	48452	0.783	Ethylmalonic acid	2-ethylpropanedioic acid	Ethylmalonic acid	HMDB0000622	HMDB	C5H8O4	UKFXDFUAPNAMPJ-UHFFFAOYSA-N	CCC(C(O)=O)C(O)=O	235	0.675	713	999	NIST17 MSMS	Organic compounds	Lipids and lipid-like molecules	Fatty Acyls	Fatty acids and conjugates	Branched fatty acids	3.16
OCTYL HYDROGEN SULFATE	MSI2A	InSource	2.47	265.1477	[M-H]-	40	1.34	628955	0.604	octyl hydrogen sulfate	octyl hydrogen sulfate		CHEBI:83122	ChEBI	C8H18O4S	UZZYXUGECOQHPU-UHFFFAOYSA-N	CCCCCCCCOS(O)(=O)=O	525	0.658	870	990	NIST17 MSMS	Organic compounds	Organic acids and derivatives	Organic sulfuric acids and derivatives	Sulfuric acid esters	Sulfuric acid monoesters	1.88
3-(3,5-DIMETHOXYPHENYL)PROP-2-ENOIC ACID	MSI2A	InSource	1.211	100.9337	[M-H]-	40	0	6901	0.976	3-(3,5-dimethoxyphenyl)prop-2-enoic acid	3-(3,5-dimethoxyphenyl)prop-2-enoic acid		HMDB0127491	HMDB	C11H12O4	VLSRUFWCGBMYDJ-UHFFFAOYSA-N	COC1=CC(C=CC(O)=O)=CC(OC)=C1	364	0.689	999	999	MONA	Organic compounds	Phenylpropanoids and polyketides	Cinnamic acids and derivatives	Hydroxycinnamic acids and derivatives	Coumaric acids and derivatives	1.58
2-AMINO-5-CHLORO-4-METHYL-BESYLIC ACID	MSI2A	InSource	1.348	212.0023	[M-H]-	40	0.278	425739	0.979	2-Amino-5-chloro-4-methylbenzenesulfonic acid	2-amino-5-chloro-4-methyl-besylic acid		6936	PubChem	C7H8ClNO3S	VYZCFAPUHSSYCC-UHFFFAOYSA-N	CC1=CC(=C(C=C1Cl)S(=O)(=O)O)N	526	0.653	968	988	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	p-Methylbenzenesulfonates	2.14
SULFURIC ACID [(8R,9S,10R,13S,14S,17R)-3-KETO-10,13-DIMETHYL-1,2,6,7,8,9,11,12,14,15,16,17-DODECAHYDROCYCLOPENTA[A]PHENANTHREN-17-YL] ESTER	MSI2A	InSource	1.002	293.1787	[M-H]-	40	0.659	1821276	0.925	Epitestosterone sulfate	sulfuric acid [(8R,9S,10R,13S,14S,17R)-3-keto-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] ester		12133250	PubChem	C19H28O5S	WAQBISPOEAOCOG-KZYORJDKSA-N	C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2OS(=O)(=O)O)CCC4=CC(=O)CC[C@]34C	724	0.74	956	965	NIST17 MSMS	Organic compounds	Lipids and lipid-like molecules	Steroids and steroid derivatives	Sulfated steroids	Sulfated steroids	1.61
3,4-DIMETHYLBESYLIC ACID	MSI2A	Regular	2.159	185.0271	[M-H]-	20	0.29	529875	0.939	3,4-Dimethylbenzenesulfonic Acid	3,4-dimethylbesylic acid		14756	PubChem	C8H10O3S	WYCOJIVDCGJKDB-UHFFFAOYSA-N	CC1=C(C=C(C=C1)S(=O)(=O)O)C	482	0.869	763	983	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	p-Methylbenzenesulfonates	1.45
SALICYLIC ACID	MSI2A	Regular	1.504	137.0246	[M-H]-	40	1.44	244155	0.928	Salicylic acid	2-hydroxybenzoic acid	Salicylic acid	HMDB0001895	HMDB	C7H6O3	YGSDEFSMJLZEOE-UHFFFAOYSA-N	OC(=O)C1=CC=CC=C1O	642	0.697	951	998	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Salicylic acids	2.1
2,3-DIMETHYLBESYLIC ACID	MSI2A	Regular	2.003	185.0279	[M-H]-	40	0	850637	0.979	2,3-Dimethylbenzenesulfonic acid	2,3-dimethylbesylic acid		172623	PubChem	C8H10O3S	ZZXDRXVIRVJQBT-UHFFFAOYSA-N	CC1=C(C(=CC=C1)S(=O)(=O)O)C	492	0.859	947	984	NIST20 HighRes MSMS	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzenesulfonic acids and derivatives	Benzenesulfonic acids and derivatives	1.77
2-(3-KETO-4H-1,4-BENZOXAZIN-2-YL)ACETIC ACID	MSI2B	Regular	1.983	206.045	[M-H]-	20	0.688	622814	0.879	(3-Oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl)acetic acid	2-(3-keto-4H-1,4-benzoxazin-2-yl)acetic acid		2783999	PubChem	C10H9NO4	GBWCBWJRILQTBI-UHFFFAOYSA-N	C1=CC=C2C(=C1)NC(=O)C(O2)CC(=O)O	432	0.706	880	988	NIST20 HighRes MSMS	Organic compounds	Organoheterocyclic compounds	Benzoxazines	Benzoxazinones	Benzoxazinones	3.89
HIPPURIC ACID	MSI2B	Regular	2.826	178.05	[M-H]-	20	1.623	100258	0.938	Hippuric acid	2-(phenylformamido)acetic acid	Hippuric acid	HMDB0000714	HMDB	C9H9NO3	QIAFMBKCNZACKA-UHFFFAOYSA-N	OC(=O)CNC(=O)C1=CC=CC=C1	397	0.654	850	985	MONA	Organic compounds	Benzenoids	Benzene and substituted derivatives	Benzoic acids and derivatives	Hippuric acids	4.96
PERFLUOROOCTANOIC ACID	MSI2B	Regular	0.861	412.9664	[M-H]-	20	1.224	1472896	0.873	Perfluorooctanoic acid	pentadecafluorooctanoic acid	Perfluorooctanoic acid	HMDB0059587	HMDB	C8HF15O2	SNGREZUHAYWORS-UHFFFAOYSA-N	[H]OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F	756	0.791	893	914	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	2.75
HEPTADECAFLUORONONANOIC ACID	MSI2B	Regular	0.837	462.9635	[M-H]-	20	2.402	330524	0.549	Perfluorononanoic acid	heptadecafluorononanoic acid	Heptadecafluorononanoic acid	HMDB0061739	HMDB	C9HF17O2	UZUFPBIDKMEQEQ-UHFFFAOYSA-N	OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F	719	0.719	814	965	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluorooctanoic acid and derivatives	2.77
PERFLUOROBUTANOIC ACID	MSI2B	Regular	0.966	212.9791	[M-H]-	20	0	3374248	0.962	PERFLUOROBUTANOIC ACID		Perfluorobutanoic acid	9777	PubChem	C4HF7O2	YPJUNDFVDDCYIH-UHFFFAOYSA-N	C(=O)(C(C(C(F)(F)F)(F)F)(F)F)O	604	0.689	992	999	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	3.61
2,2,3,3,4,4,5,5,6,6,7,7,7-TRIDECAFLUOROENANTHIC ACID	MSI2B	Regular	0.885	362.9694	[M-H]-	20	1.361	838178	0.878	Perfluoroheptanoic acid	2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroenanthic acid		67818	PubChem	C7HF13O2	ZWBAMYVPMDSJGQ-UHFFFAOYSA-N	C(=O)(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O	746	0.786	921	966	MONA	Organic compounds	Organohalogen compounds	Alkyl halides	Alkyl fluorides	Perfluoroalkyl carboxylic acid and derivatives	2.92
METABOLITES_END
#END