#METABOLOMICS WORKBENCH suseha_20251208_050731 DATATRACK_ID:6853 STUDY_ID:ST004496 ANALYSIS_ID:AN007538 PROJECT_ID:PR002830
VERSION             	1
CREATED_ON             	December 27, 2025, 5:55 pm
#PROJECT
PR:PROJECT_TITLE                 	TIGAR Regulates Intestinal Mucus Barrier Integrity by Inhibiting Lactylation of
PR:PROJECT_TITLE                 	G6PD/6PGD in Ulcerative Colitis
PR:PROJECT_SUMMARY               	Oxidative stress and metabolic dysregulation in goblet cells represent
PR:PROJECT_SUMMARY               	significant contributors to the pathogenesis of ulcerative colitis (UC). TIGAR
PR:PROJECT_SUMMARY               	(TP53-induced glycolysis and apoptosis regulator) plays a critical role as a
PR:PROJECT_SUMMARY               	metabolic regulatory enzyme by promoting NADPH synthesis, thereby counteracting
PR:PROJECT_SUMMARY               	oxidative stress. However, the precise mechanisms through which TIGAR regulates
PR:PROJECT_SUMMARY               	NADPH synthesis and its impact on UC remain incompletely understood. Here, we
PR:PROJECT_SUMMARY               	demonstrate that TIGAR inhibits the lactylation of glucose-6-phosphate
PR:PROJECT_SUMMARY               	dehydrogenase (G6PD) and 6-phosphogluconate dehydrogenase (6PGD), both pivotal
PR:PROJECT_SUMMARY               	enzymes in the NADPH biosynthesis pathway, hence preserving their enzymatic
PR:PROJECT_SUMMARY               	activities. We further identify specific lactylation sites at lysine 432 (K432)
PR:PROJECT_SUMMARY               	in G6PD and lysine 38 (K38) in 6PGD. Lactylation modifications impact the
PR:PROJECT_SUMMARY               	formation of G6PD homodimers and the binding of 6PGD with NADP+. In male UC
PR:PROJECT_SUMMARY               	mice, persistently low TIGAR expression results in elevated lactic acid levels,
PR:PROJECT_SUMMARY               	which enhance the lactylation of G6PD and 6PGD, inhibit NADPH synthesis, and
PR:PROJECT_SUMMARY               	exacerbate oxidative stress in goblet cells. Consequently, these alterations
PR:PROJECT_SUMMARY               	lead to a reduction in thioredoxin 1 (Trx1) reductase activity, inducing
PR:PROJECT_SUMMARY               	S-nitrosylation of anterior gradient homolog 2 (AGR2), a key enzyme involved in
PR:PROJECT_SUMMARY               	MUC2 modification, thus impeding mature MUC2 production and compromising the
PR:PROJECT_SUMMARY               	integrity of the intestinal mucus barrier. Overall, our study elucidates the
PR:PROJECT_SUMMARY               	critical mechanisms by which TIGAR regulates NADPH synthesis, provides novel
PR:PROJECT_SUMMARY               	insights into how TIGAR maintains cellular redox homeostasis, and offers
PR:PROJECT_SUMMARY               	experimental evidence for considering TIGAR as a potential target for UC
PR:PROJECT_SUMMARY               	therapy.
PR:INSTITUTE                     	Southwest Hospital, Third Military Medical University
PR:DEPARTMENT                    	Clinical Medical Research Center
PR:LABORATORY                    	Clinical Medical Research Center
PR:LAST_NAME                     	Sen
PR:FIRST_NAME                    	Su
PR:ADDRESS                       	Gaotanyan Street, Shapingba District, Chongqing, China
PR:EMAIL                         	1441suse@163.com
PR:PHONE                         	0086015023351789
#STUDY
ST:STUDY_TITLE                   	Untargeted metabolomics of the colon tissues from TIGARf/f mice and
ST:STUDY_TITLE                   	TIGARf/fVil1-Cre mice
ST:STUDY_SUMMARY                 	In a previous untargeted metabolomics study, we observed significant
ST:STUDY_SUMMARY                 	accumulation of 6-phosphogluconate (6-PG) and elevated lactate levels in
ST:STUDY_SUMMARY                 	TIGAR-knockout HT-29 cells. To investigate whether this metabolic phenotype is
ST:STUDY_SUMMARY                 	conserved in vivo, we employed an intestinal epithelial cell–specific TIGAR
ST:STUDY_SUMMARY                 	knockout mouse model. TIGARf/f mice, harboring loxP sites flanking exon 2 of the
ST:STUDY_SUMMARY                 	TIGAR locus, were crossed with Villin1-Cre (Vil1-Cre) transgenic mice to
ST:STUDY_SUMMARY                 	generate TIGARf/fVil1-Cre mice with conditional deletion of TIGAR in the
ST:STUDY_SUMMARY                 	intestinal epithelium. Colon tissues (∼25 mg,n = 3 biological replicates per
ST:STUDY_SUMMARY                 	group) were collected from TIGARf/f mice and TIGARf/fVil1-Cre mice. Strikingly,
ST:STUDY_SUMMARY                 	levels of both 6-PG and lactate were significantly elevated in the colonic
ST:STUDY_SUMMARY                 	tissues of TIGARf/fVil1-Cre mice compared to controls. These results demonstrate
ST:STUDY_SUMMARY                 	that TIGAR plays a critical and conserved role in regulating glycolytic and
ST:STUDY_SUMMARY                 	pentose phosphate pathway metabolism in the intestinal epithelium in vivo.
ST:INSTITUTE                     	Southwest Hospital, Third Military Medical University
ST:LAST_NAME                     	Su
ST:FIRST_NAME                    	Sen
ST:ADDRESS                       	Gaotanyan Street 30, Shapingba District, Chongqing, Chongqing, 400038, China
ST:EMAIL                         	1441suse@163.com
ST:PHONE                         	0086015023351789
#SUBJECT
SU:SUBJECT_TYPE                  	Mammal
SU:SUBJECT_SPECIES               	Mus musculus
SU:TAXONOMY_ID                   	10090
#SUBJECT_SAMPLE_FACTORS:         	SUBJECT(optional)[tab]SAMPLE[tab]FACTORS(NAME:VALUE pairs separated by |)[tab]Raw file names and additional sample data
SUBJECT_SAMPLE_FACTORS           	-	Cont-1	Genotype:Wild-type | Sample source:colon	RAW_FILE_NAME(Raw file name)=Cont-1.raw
SUBJECT_SAMPLE_FACTORS           	-	Cont-2	Genotype:Wild-type | Sample source:colon	RAW_FILE_NAME(Raw file name)=Cont-2.raw
SUBJECT_SAMPLE_FACTORS           	-	Cont-3	Genotype:Wild-type | Sample source:colon	RAW_FILE_NAME(Raw file name)=Cont-3.raw
SUBJECT_SAMPLE_FACTORS           	-	KO-1	Genotype:TIGAR-knockout | Sample source:colon	RAW_FILE_NAME(Raw file name)=cre-1.raw
SUBJECT_SAMPLE_FACTORS           	-	KO-2	Genotype:TIGAR-knockout | Sample source:colon	RAW_FILE_NAME(Raw file name)=cre-2.raw
SUBJECT_SAMPLE_FACTORS           	-	KO-3	Genotype:TIGAR-knockout | Sample source:colon	RAW_FILE_NAME(Raw file name)=cre-3.raw
#COLLECTION
CO:COLLECTION_SUMMARY            	TIGARf/f mice have two lox sites on both sides of exon 2 in the TIGAR locus.
CO:COLLECTION_SUMMARY            	Floxed mice were crossed with Vil1-Cre mice to obtain tissue-specific knockout
CO:COLLECTION_SUMMARY            	of TIGAR. the mice were subjected to a 12-hour fasting period before treatment.
CO:SAMPLE_TYPE                   	Colon
#TREATMENT
TR:TREATMENT_SUMMARY             	No treatment
#SAMPLEPREP
SP:SAMPLEPREP_SUMMARY            	25 mg of colon tissue was weighed and mixed with 750 μL of pre-chilled 80%
SP:SAMPLEPREP_SUMMARY            	methanol for mouse colon samples. A low-temperature tissue grinder was utilized
SP:SAMPLEPREP_SUMMARY            	to homogenize the tissue for 60 seconds at -20°C, with a 30-second pause,
SP:SAMPLEPREP_SUMMARY            	repeated three times. The resulting homogenates from cells and colons were
SP:SAMPLEPREP_SUMMARY            	transferred and incubated at -20°C for 60 minutes. Subsequently, samples were
SP:SAMPLEPREP_SUMMARY            	centrifuged at 18,410 x g for 10 minutes at 4°C. The supernatant was collected
SP:SAMPLEPREP_SUMMARY            	after centrifugation, dried under a nitrogen gas, reconstituted, and centrifuged
SP:SAMPLEPREP_SUMMARY            	again to obtain the supernatant for subsequent analysis. A 20 μL aliquot from
SP:SAMPLEPREP_SUMMARY            	each sample was combined to prepare a quality control (QC) mixture for mass
SP:SAMPLEPREP_SUMMARY            	spectrometry analyses.
#CHROMATOGRAPHY
CH:CHROMATOGRAPHY_TYPE           	HILIC
CH:INSTRUMENT_NAME               	Thermo Vanquish
CH:COLUMN_NAME                   	Waters Atlantis Premier BEH Z-HILIC Column (2.1 × 100 mm, 1.7 μm)
CH:SOLVENT_A                     	5% acetonitrile/95% water; 15 mM ammonium acetate (pH 9.0)
CH:SOLVENT_B                     	95% acetonitrile/5% water; 15 mM ammonium acetate (pH 9.0)
CH:FLOW_GRADIENT                 	0-5 min: 90% B-65% B; 5-6 min: 65% B-65% B; 6 -8 min: 65% B-90% B; 8-10 min: 90%
CH:FLOW_GRADIENT                 	B
CH:FLOW_RATE                     	0.5 mL/min
CH:COLUMN_TEMPERATURE            	30℃
CH:METHODS_FILENAME              	Chromatography_methods0726.txt
#ANALYSIS
AN:ANALYSIS_TYPE                 	MS
AN:ANALYSIS_PROTOCOL_FILE        	MS_analysis_methods0726.txt
#MS
MS:INSTRUMENT_NAME               	Thermo Orbitrap Exploris 120
MS:INSTRUMENT_TYPE               	Orbitrap
MS:MS_TYPE                       	ESI
MS:ION_MODE                      	NEGATIVE
MS:MS_COMMENTS                   	The MS parameters for detection were: ESI source voltage 3.0 kV in negative ion
MS:MS_COMMENTS                   	scanning mode with scan range of m/z 70-1050 for mass spectrometry scanning,
MS:MS_COMMENTS                   	full scanning resolution of 120000, and MS2 scanning resolution of 60000, the
MS:MS_COMMENTS                   	top four precursor ions were broken up with the higher energy collisional
MS:MS_COMMENTS                   	dissociation cell in MS2 set to 30% normalized collision energy. the sheath gas
MS:MS_COMMENTS                   	was set at 60 arbitrary units, the auxiliary gas was set at 20 arbitrary units,
MS:MS_COMMENTS                   	and the blow air flow rate of 2Arb; the ion transport tube was set to 380 ° C;
MS:MS_COMMENTS                   	the vaporizer temperature of the ion source was set to 350 ° C. Software tools
MS:MS_COMMENTS                   	Xcalibur 4.3 (Thermo Fisher Scientific) and Compound Discover 3.3 (Thermo Fisher
MS:MS_COMMENTS                   	Scientific) were used for data processing and analyzing.Retention time alignment
MS:MS_COMMENTS                   	across all samples was achieved using the ChromeAlign node, with a pooled
MS:MS_COMMENTS                   	quality control (QC) sample serving as the reference. The pooled QC sample was
MS:MS_COMMENTS                   	prepared by combining equal aliquots from all biological samples. It was
MS:MS_COMMENTS                   	injected repeatedly—once every 10 analytical runs—to monitor instrument
MS:MS_COMMENTS                   	stability, enable batch effect correction, and support data normalization.
MS:MS_COMMENTS                   	Putative metabolite features were detected and grouped across all samples using
MS:MS_COMMENTS                   	the following key parameters (all other settings remained at default values):
MS:MS_COMMENTS                   	minimum peak intensity threshold of 1 × 10⁵ (area under the curve); mass
MS:MS_COMMENTS                   	tolerance of 5 ppm; retention time tolerance of 0.25 min; ionization modes
MS:MS_COMMENTS                   	limited to [M – H]⁻; and peak rating filter set to 4. Missing values were
MS:MS_COMMENTS                   	imputed using the built-in “Fill Gap” function, configured with a mass
MS:MS_COMMENTS                   	tolerance of 5 ppm and a signal-to-noise ratio threshold of 1.5. Metabolite
MS:MS_COMMENTS                   	identification was carried out through a tiered annotation strategy. Matching of
MS:MS_COMMENTS                   	both accurate mass (±5 ppm) and retention time (±0.5 min) to an in-house
MS:MS_COMMENTS                   	spectral library generated from authentic commercial standards, or spectral
MS:MS_COMMENTS                   	matching against the mzCloud database (https://www.mzcloud.org/) and mzVault
MS:MS_COMMENTS                   	database using MS/MS fragmentation data, with precursor and fragment mass
MS:MS_COMMENTS                   	tolerances of 10 ppm and a minimum match factor of 50.
#MS_METABOLITE_DATA
MS_METABOLITE_DATA:UNITS	peak area
MS_METABOLITE_DATA_START
Samples	Cont-1	Cont-2	Cont-3	KO-1	KO-2	KO-3
Factors	Genotype:Wild-type | Sample source:colon	Genotype:Wild-type | Sample source:colon	Genotype:Wild-type | Sample source:colon	Genotype:TIGAR-knockout | Sample source:colon	Genotype:TIGAR-knockout | Sample source:colon	Genotype:TIGAR-knockout | Sample source:colon
Acrylic acid	45601857	45942991	44923366	108243134	110370759	107149624
Glycine	37564133	37980472	40367452	108646827	108262854	107715899
Pyruvic acid	86789949	89876419	90712083	209864037	212724492	215801139
Isobutyric acid	13264890	30115737	25408396	8382824	9139238	8997462
β-Alanine	96051946	99495020	105777916	265877683	255769441	274882838
Lactic acid	1595026177	1638746422	1659031876	4630446203	4667004113	4790366933
Valeric acid	7873269	11622273	11648829	16125391	15025895	16033010
Malonic acid	23814224	4564271	20274530	29665984	24801805	5510998
3-Hydroxybutyric acid	18595510	20067945	18980493	50999843	51466409	49577891
Uracil	6902268	9857496	10058318	27556443	28171500	29000583
Glutaric anhydride	335904	516513	366798	1445109	1606907	1246876
Fumaric acid	6730961	7416501	7672116	12873127	12791355	12406041
5-Aminovaleric acid	112425648	118801920	116768513	355103534	360419445	364464505
Threonine	92584593	97158655	97387957	183079277	188682431	183285497
Taurine	5635959	5631849	5870226	11411751	11308434	11679872
4-Oxoproline	149915374	149102369	150234399	429017398	394042248	425926475
DL-β-Leucine	301879797	307507128	299604836	792797400	795249615	804273234
Asparagine	32100676	34323569	34519112	87058757	84006835	83231324
Malic acid	71434652	56307676	51840450	54165192	56205108	56938833
Adenine	47272177	62920761	62777259	111969634	118472324	119938155
Hypoxanthine	7804345	9978476	7294124	25379612	27664813	28514089
Xanthine	108560858	142826909	136372293	239584720	251033152	250243494
Glycolic acid	2871442	5018576	5734964	11727650	11407695	11706821
1-Chlorobenzotriazole	238525698	258561315	275987069	557595345	572646669	553443433
Glycerol 3-phosphate	3596310	739170	3540043	6797766	6293329	6227370
Nonanoic acid	9032401	24112073	29554899	40722724	39756533	36260007
L-Phenylalanine	71212887	75159227	73219712	190227201	192258938	169175918
7-Methylxanthine	6095462	10130696	9231223	24695335	21956330	24359825
(2R)-2,3-Dihydroxypropanoic acid	67201087	65395897	70273288	115479263	118575901	112593702
4-Phenolsulfonic acid	36120356	36755192	37273932	31359700	32033344	30690256
N-α-Acetyl-L-asparagine	2219190	1006963	893499	1967182	2251710	2117683
Theophylline	210676090	225960142	185419368	161962219	159419543	162491079
L-threo-3-Phenylserine	47547028	62184938	60211828	139678362	130289071	129740317
L-Iditol	12488170	8617893	7752204	6612498	6759714	7045465
4-Pyridoxic acid	10060507	12217817	11481962	20359479	20897697	20576624
6-Phosphogluconic acid	3572462	3203867	3575329	12212839	12911573	12622901
Salicylic acid	16328432	16573288	14054608	57783879	57568283	56649837
Guanosine	6691926	7060715	7048767	36759981	37716532	36395408
4-Dodecylbenzenesulfonic acid	28192708	40744694	28027302	34359507	30294320	28397655
Lithocholic Acid	35446741	49558142	42592685	22729513	20869887	15398001
Uridine 5'-diphosphoglucuronic acid	12878836	12149524	11885595	64909629	63588265	62950513
MS_METABOLITE_DATA_END
#METABOLITES
METABOLITES_START
metabolite_name	formula	quantified m/z	retention index	PubChem ID	KEGG ID	HMDB ID	SMILES	InChI Key	Classification Category
Acrylic acid	C3 H4 O2	71.0139	4.45	6581	C19501	HMDB0031647	OC(=O)C=C	NIXOWILDQLNWCW-UHFFFAOYSA-N	Organic acids and derivatives
Glycine	C2 H5 N O2	74.0248	4.61	750	C00037	HMDB0000123	NCC(O)=O	DHMQDGOQFOQNFH-UHFFFAOYSA-N	Organic acids and derivatives
Pyruvic acid	C3 H4 O3	87.0088	4.71	1060	C00022	HMDB0000243	CC(=O)C(O)=O	LCTONWCANYUPML-UHFFFAOYSA-N	Organic acids and derivatives
Isobutyric acid	C4 H8 O2	87.0452	1.48	6590	C02632	HMDB0001873	CC(C)C(O)=O	KQNPFQTWMSNSAP-UHFFFAOYSA-N	Organic acids and derivatives
β-Alanine	C3 H7 N O2	88.0404	5.31	239	C00099	HMDB0000056	NCCC(O)=O	UCMIRNVEIXFBKS-UHFFFAOYSA-N	Organic acids and derivatives
Lactic acid	C3 H6 O3	89.0244	2.70	107689	C00186	HMDB0000190	C[C@H](O)C(O)=O	JVTAAEKCZFNVCJ-REOHCLBHSA-N	Organic acids and derivatives
Valeric acid	C5 H10 O2	101.0608	1.05	7991	C00803	HMDB0000892	CCCCC(O)=O	NQPDZGIKBAWPEJ-UHFFFAOYSA-N	Lipids and lipid-like molecules
Malonic acid	C3 H4 O4	103.0037	3.98	867	C04025	HMDB0000691	OC(=O)CC(O)=O	OFOBLEOULBTSOW-UHFFFAOYSA-N	Organic acids and derivatives
3-Hydroxybutyric acid	C4 H8 O3	103.0401	2.08	92135	C01089	HMDB0000011	C[C@@H](O)CC(O)=O	WHBMMWSBFZVSSR-GSVOUGTGSA-N	Organic acids and derivatives
Uracil	C4 H4 N2 O2	111.0200	6.42	1174	C00106	HMDB0000300	O=C1NC=CC(=O)N1	ISAKRJDGNUQOIC-UHFFFAOYSA-N	Organoheterocyclic compounds
Glutaric anhydride	C5 H6 O3	113.0245	3.66			HMDB0252815	O=C1CCCC(=O)O1	VANNPISTIUFMLH-UHFFFAOYSA-N	Organoheterocyclic compounds
Fumaric acid	C4 H4 O4	115.0037	4.05	444972	C00122	HMDB0000134	OC(=O)C=CC(O)=O	VZCYOOQTPOCHFL-OWOJBTEDSA-N	Organic acids and derivatives
5-Aminovaleric acid	C5 H11 N O2	116.0717	2.97	138	C00431	HMDB0003355	NCCCCC(O)=O	JJMDCOVWQOJGCB-UHFFFAOYSA-N	Organic acids and derivatives
Threonine	C4 H9 N O3	118.0510	4.10	6288	C00188	HMDB0000167	C[C@@H](O)[C@H](N)C(O)=O	AYFVYJQAPQTCCC-GBXIJSLDSA-N	Organic acids and derivatives
Taurine	C2 H7 N O3 S	124.0074	4.36	1123	C00245	HMDB0000251	NCCS(O)(=O)=O	XOAAWQZATWQOTB-UHFFFAOYSA-N	Organic acids and derivatives
4-Oxoproline	C5 H7 N O3	128.0354	5.27	413589		HMDB0246561	OC(=O)C1CC(=O)CN1	HFXAFXVXPMUQCQ-UHFFFAOYSA-N	Organic acids and derivatives
DL-β-Leucine	C6 H13 N O2	130.0874	2.22	6106	C00123	HMDB0000687	CC(C)C[C@H](N)C(O)=O	ROHFNLRQFUQHCH-YFKPBYRVSA-N	Organic acids and derivatives
Asparagine	C4 H8 N2 O3	131.0462	4.59	6267	C00152	HMDB0000168	N[C@@H](CC(N)=O)C(O)=O	DCXYFEDJOCDNAF-REOHCLBHSA-N	Organic acids and derivatives
Malic acid	C4 H6 O5	133.0143	6.17	222656	C00149	HMDB0000156	O[C@@H](CC(O)=O)C(O)=O	BJEPYKJPYRNKOW-REOHCLBHSA-N	Organic acids and derivatives
Adenine	C5 H5 N5	134.0472	1.10	190	C00147	HMDB0000034	NC1=C2NC=NC2=NC=N1	GFFGJBXGBJISGV-UHFFFAOYSA-N	Organoheterocyclic compounds
Hypoxanthine	C5 H4 N4 O	135.0313	3.50	790	C00262	HMDB0000157	OC1=NC=NC2=C1NC=N2	FDGQSTZJBFJUBT-UHFFFAOYSA-N	Organoheterocyclic compounds
Xanthine	C5 H4 N4 O2	151.0262	1.70	1188	C00385	HMDB0000292	O=C1NC2=C(NC=N2)C(=O)N1	LRFVTYWOQMYALW-UHFFFAOYSA-N	Organoheterocyclic compounds
Glycolic acid	C2 H4 O3	151.0262	3.50	757	C03547	HMDB0000115	OCC(O)=O	AEMRFAOFKBGASW-UHFFFAOYSA-N	Organic acids and derivatives
1-Chlorobenzotriazole	C6 H4 Cl N3	152.0023	2.56	75771		HMDB0243899	ON1N=NC2=CC=CC=C12	ASOKPJOREAFHNY-UHFFFAOYSA-N	Organoheterocyclic compounds
Glycerol 3-phosphate	C3 H9 O6 P	152.9959	4.59	439162	C00093	HMDB0000126	OC[C@@H](O)COP(O)(O)=O	AWUCVROLDVIAJX-GSVOUGTGSA-N	Lipids and lipid-like molecules
Nonanoic acid	C9 H18 O2	157.1234	0.47	8158	C01601	HMDB0000847	CCCCCCCCC(O)=O	FBUKVWPVBMHYJY-UHFFFAOYSA-N	Lipids and lipid-like molecules
L-Phenylalanine	C9 H11 N O2	164.0717	2.11	6140	C00079	HMDB0000159	N[C@@H](CC1=CC=CC=C1)C(O)=O	COLNVLDHVKWLRT-QMMMGPOBSA-N	Organic acids and derivatives
7-Methylxanthine	C6 H6 N4 O2	165.0404	3.97	68374	C16353	HMDB0001991	CN1C=NC2=C1C(=O)NC(=O)N2	PFWLFWPASULGAN-UHFFFAOYSA-N	Organoheterocyclic compounds
(2R)-2,3-Dihydroxypropanoic acid	C3 H6 O4	165.0405	4.07	439194	C00258	HMDB0000139	OC[C@@H](O)C(O)=O	RBNPOMFGQQGHHO-UWTATZPHSA-N	Organic oxygen compounds
4-Phenolsulfonic acid	C6 H6 O4 S	172.9914	0.51	6101	C06677	HMDB0059933	CC1=CC=C(C=C1)S(O)(=O)=O	JOXIMZWYDAKGHI-UHFFFAOYSA-N	Benzenoids
N-α-Acetyl-L-asparagine	C6 H10 N2 O4	173.0568	3.50	99715		HMDB0006028	CC(=O)N[C@@H](CC(N)=O)C(O)=O	HXFOXFJUNFFYMO-BYPYZUCNSA-N	Organic acids and derivatives
Theophylline	C7 H8 N4 O2	179.0561	3.92	2153	C07130	HMDB0001889	CN1C2=C(NC=N2)C(=O)N(C)C1=O	ZFXYFBGIUFBOJW-UHFFFAOYSA-N	Organoheterocyclic compounds
L-threo-3-Phenylserine	C9 H11 N O3	180.0666	3.23	12314153		HMDB0002184	N[C@@H](C(O)C1=CC=CC=C1)C(O)=O	VHVGNTVUSQUXPS-JAMMHHFISA-N	Organic acids and derivatives
L-Iditol	C6 H14 O6	181.0718	3.21	5460044	C01507	HMDB0011632	OC[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO	FBPFZTCFMRRESA-UNTFVMJOSA-N	Organic oxygen compounds
4-Pyridoxic acid	C8 H9 N O4	182.0459	0.74	6723	C00847	HMDB0000017	CC1=NC=C(CO)C(C(O)=O)=C1O	HXACOUQIXZGNBF-UHFFFAOYSA-N	Organoheterocyclic compounds
6-Phosphogluconic acid	C6 H13 O10 P	275.0174	6.54	91493	C00345	HMDB0001316	O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O	BIRSGZKFKXLSJQ-SQOUGZDYSA-N	Organic oxygen compounds
Salicylic acid	C7 H6 O3	275.0540	3.28	10253	C07588	HMDB0000840	OC(=O)CNC(=O)C1=C(O)C=CC=C1	ONJSZLXSECQROL-UHFFFAOYSA-N	Benzenoids
Guanosine	C10 H13 N5 O5	282.0844	2.59	6802	C00387	HMDB0000133	NC1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=O)N1	NYHBQMYGNKIUIF-UUOKFMHZSA-N	Nucleosides, nucleotides, and analogues
4-Dodecylbenzenesulfonic acid	C18 H30 O3 S	325.1844	0.37	8485		HMDB0059915	CCCCCCCCCCCCC1=CC=C(C=C1)S(O)(=O)=O	KWXICGTUELOLSQ-UHFFFAOYSA-N	Benzenoids
Lithocholic Acid	C24 H40 O3	375.2899	0.44	164853	C17658	HMDB0000717	[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C	SMEROWZSTRWXGI-WFVDQZAMSA-N	Lipids and lipid-like molecules
Uridine 5'-diphosphoglucuronic acid	C15 H22 N2 O18 P2	579.0271	6.68	17473	C00167	HMDB0000935	O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)O[C@H]([C@@H]1O)N1C=CC(=O)NC1=O	HDYANYHVCAPMJV-LXQIFKJMSA-N	Organoheterocyclic compounds
METABOLITES_END
#END