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

2022-08-30 23:57:48 UTC

MiMeDB 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

Not Available

Chemical Formula

C₂₆H₄₃NO₅

Average Molecular Weight

449.6233

Monoisotopic Molecular Weight

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

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

Proteins

#<MetaboliteProteinLink:0x0000564abf7ceb78>

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Biliary atresia		This associated disease is originally imported from HMDB metabolite HMDB0000637 concentration id 59605	Association	Human Urine		3944741	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Firmicutes	102	Human ; Human Feces; Pig	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction;
	Bacteroidetes	51	Human Feces; Human	Microbial culture; Metabolic reconstruction
	Actinobacteria	37	Human ; Human Feces	Microbial culture; Metabolic reconstruction;
	Proteobacteria	5	Human Feces; Human	Metabolic reconstruction;
	Fusobacteria	3	Human Feces	Metabolic reconstruction
	Euryarchaeota	2	Human Feces; Human	Metabolic reconstruction
	Planctomycetes	1	Human Feces	Metabolic reconstruction
NULL	Firmicutes	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	>0.01				Adult (>18 years old)	Both	Normal	HMDB	659989	details
Human	Detected and Quantified	0.032	0.058			Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741	details
Human	Detected and Quantified	0.0013	0.0026			Infant (0-1 year old)	Both	Normal	HMDB	3944741	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	CCD	HMDB	19636438	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19636438	details
Human	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	19636438	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Ileal Crohn's disease	HMDB	19636438	details
Human	Detected and Quantified	22.28	15.65			Not Specified	Not Specified	Normal	HMDB	22664055	details
Human	Detected but not Quantified					Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963	details
Human	Detected but not Quantified					Not Specified	Not Specified	Recurrent Clostridium difficile infection	HMDB	24284963	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Clostridium difficile infection	HMDB	24284963	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Colorectal cancer	HMDB	25037050	details
Human	Detected and Quantified	6.5		3.3	13.3	Infant (0-1 year old)	Both	Severe acute malnutrition	HMDB	27163928	details
Human	Detected and Quantified	1.3		1.1	1.4	Infant (0-1 year old)	Both	Normal	HMDB	27163928	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Colorectal Cancer	HMDB	27275383	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details
Human	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details
Human	Detected and Quantified	0.06	0.01			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.	details
Human	Detected and Quantified	0.032	0.058			Adult (>18 years old)	Both	Biliary atresia	HMDB	3944741	details
Human	Detected and Quantified	>0.01				Adult (>18 years old)	Both	Normal	HMDB	659989	details
Human	Detected and Quantified	0.0013	0.0026			Infant (0-1 year old)	Both	Normal	HMDB	3944741	details
Human	Detected and Quantified	1.3		1.1	1.4	Infant (0-1 year old)	Both	Normal	HMDB	27163928	details
Human	Detected and Quantified	22.28	15.65			Not Specified	Not Specified	Normal	HMDB	22664055	details
Human	Detected and Quantified	0.06	0.01			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.	details
Human Placenta	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Prostate	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	19636438	details
Human Feces	Detected but not Quantified					Children (1-13 years old)	Both	Normal	HMDB	19636438	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	27543620	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	25037050	details
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030	details
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057	details

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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:0x0000564abf6276a8>

3D MOL for #<Metabolite:0x0000564abf6276a8>

3D SDF for #<Metabolite:0x0000564abf6276a8>

3D-SDF for #<Metabolite:0x0000564abf6276a8>

PDB for #<Metabolite:0x0000564abf6276a8>

3D PDB for #<Metabolite:0x0000564abf6276a8>

SMILES for #<Metabolite:0x0000564abf6276a8>

INCHI for #<Metabolite:0x0000564abf6276a8>

Structure for #<Metabolite:0x0000564abf6276a8>

3D Structure for #<Metabolite:0x0000564abf6276a8>