MiMeDB: Showing metabocard for Chenodeoxycholic acid glycine conjugate (MMDBc0000128)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:36:54 UTC

Update Date

2024-10-13 14:01:44 UTC

Metabolite ID

MMDBc0000128

Metabolite Identification

Common Name

Chenodeoxycholic acid glycine conjugate

Description

Chenodeoxycholic acid glycine conjugate is an acyl glycine and a bile acid-glycine conugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). This compound usually exists as the sodium salt and acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Chenodeoxycholylglycine	ChEBI
Chenodeoxyglycocholate	ChEBI
Chenodeoxyglycocholic acid	ChEBI
GCDCA	ChEBI
Glycine chenodeoxycholate	ChEBI
Glycochenodeoxycholate	ChEBI
Glycochenodeoxycholic acid	Kegg
Glycine chenodeoxycholic acid	Generator
Chenodeoxycholate glycine conjugate	Generator
Chenodeoxycholic acid glycine conjugic acid	Generator
Acid, glycochenodeoxycholic	HMDB
Chenodeoxycholate, glycine	HMDB

Molecular Formula

C₂₆H₄₃NO₅

Average Mass

449.6233

Monoisotopic Mass

449.314123491

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

640-79-9

SMILES

Not Available

InChI Identifier

InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21-,24+,25+,26-/m1/s1

InChI Key

GHCZAUBVMUEKKP-GYPHWSFCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Glycinated bile acids and derivatives

Alternative Parents

Substituents

Glycinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid glycine conjugate (CHEBI:36274 )
C26 bile acids, alcohols, and derivatives (C05466 )
Glycine conjugates (LMST05030008 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Bile
Blood
Feces
Placenta
Prostate
Urine

Tissue Locations

Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo sapiens
MMDBp0194143	Glycine N-acyltransferase	Enzyme	Q6IB77	Homo sapiens
MMDBp0194144	Glycine N-acyltransferase-like protein 1	Enzyme	Q969I3	Homo sapiens
MMDBp0194145	Glycine N-acyltransferase-like protein 2	Enzyme	Q8WU03	Homo sapiens
MMDBp0194146	Glycine N-acyltransferase-like protein 3	Enzyme	Q5SZD4	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000368	Chenodeoxyglycocholoyl Coenzyme A	Chenodeoxycholic acid glycine conjugate	bile acid CoA:amino acid N-acyltransferase	VMH	30371894
MMDBr0000369	Chenodeoxycholoyl-CoA	Chenodeoxycholic acid glycine conjugate	bile acid CoA:amino acid N-acyltransferase	VMH	30371894
MMDBr0002722	Chenodeoxycholoyl-CoA	Chenodeoxycholic acid glycine conjugate	bile acid CoA:amino acid N-acyltransferase	VMH	12810727 6884990
MMDBr0012622	Chenodeoxycholic acid glycine conjugate	Chenodeoxycholic acid	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Biliary atresia		Association	Human Urine	HMDB	3944741

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	103	Human ; Human mucosa; Human feces; Human saliva; Human stool; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Bacteroidetes	51	Human feces; Human ; Human urine; Human appendix biopsy; Human stool; Human saliva	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	37	Human ; Human feces; Human saliva; Human mucosa; Human stool	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	5	Human feces; Human	Metabolic reconstruction
Bacteria	Fusobacteria	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Bile	Detected and Quantified	>0.01				uM	Adult (>18 years old)	Both	Normal	HMDB	659989
Human Urine	Detected and Quantified	0.032	0.058			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Urine	Detected and Quantified	0.0013	0.0026			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	3944741
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	CCD	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Ileal Crohn's disease	HMDB	19636438
Human Feces	Detected and Quantified	22.28	15.65			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Clostridium difficile infection	HMDB	24284963
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050
Human Blood	Detected and Quantified	6.5		3.3	13.3	uM	Infant (0-1 year old)	Both	Severe acute malnutrition	HMDB	27163928
Human Blood	Detected and Quantified	1.3		1.1	1.4	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected and Quantified	0.06	0.01			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	0.032	0.058			umol/mmol creatinine	Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741
Human Bile	Detected and Quantified	>0.01				uM	Adult (>18 years old)	Both	Normal	HMDB	659989
Human Urine	Detected and Quantified	0.0013	0.0026			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	3944741
Human Blood	Detected and Quantified	1.3		1.1	1.4	uM	Infant (0-1 year old)	Both	Normal	HMDB	27163928
Human Feces	Detected and Quantified	22.28	15.65			nmol/g dry feces	Not Specified	Not Specified	Normal	HMDB	22664055
Human Blood	Detected and Quantified	0.06	0.01			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Children (1-13 years old)	Both	Normal	HMDB	19636438
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000637

DrugBank ID

DB02123

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05466

BioCyc ID

GLYCOCHENODEOXYCHOLIC_ACID

BiGG ID

Not Available

Wikipedia Link

Glycochenodeoxycholic_acid

METLIN ID

Not Available

PubChem Compound

12544

PDB ID

Not Available

ChEBI ID

36274

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bloch CA, Watkins JB: Determination of conjugated bile acids in human bile and duodenal fluid by reverse-phase high-performance liquid chromatography. J Lipid Res. 1978 May;19(4):510-3. [PubMed:659989 ]
Hepner GW, Demers LM: Dynamics of the enterohepatic circulation of the glycine conjugates of cholic, chenodeoxycholic, deoxycholic, and sulfolithocholic acid in man. Gastroenterology. 1977 Mar;72(3):499-501. [PubMed:832799 ]
Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6. [PubMed:1261008 ]
Makino I, Shinozaki K, Nakagawa S, Mashimo K: Measurement of sulfated and nonsulfated bile acids in human serum and urine. J Lipid Res. 1974 Mar;15(2):132-8. [PubMed:4832755 ]
Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. doi: 10.1016/j.jchromb.2006.08.013. Epub 2006 Sep 1. [PubMed:16949895 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Chenodeoxycholic acid glycine conjugate (MMDBc0000128)

MOL for #<Metabolite:0x00007fdb2b222fc8>

3D MOL for #<Metabolite:0x00007fdb2b222fc8>

3D SDF for #<Metabolite:0x00007fdb2b222fc8>

3D-SDF for #<Metabolite:0x00007fdb2b222fc8>

PDB for #<Metabolite:0x00007fdb2b222fc8>

3D PDB for #<Metabolite:0x00007fdb2b222fc8>

SMILES for #<Metabolite:0x00007fdb2b222fc8>

INCHI for #<Metabolite:0x00007fdb2b222fc8>

Structure for #<Metabolite:0x00007fdb2b222fc8>

3D Structure for #<Metabolite:0x00007fdb2b222fc8>