Livestock Metabolome Database: Showing metabocard for Chenodeoxycholic acid glycine conjugate (LMDB00198)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:44:31 UTC

Update Date

2016-07-20 21:03:36 UTC

Lmdb

LMDB00198

Secondary Accession Numbers

None

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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Chenodeoxycholate glycine conjugate	Generator
Chenodeoxycholic acid glycine conjugic acid	Generator
(23R)-Hydroxychenodeoxycholylglycine	HMDB
12-Deoxycholylglycine	HMDB
12-Desoxycholylglycine	HMDB
3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amide	HMDB
Chenodeoxycholylglycine	HMDB
Glycine chenodeoxycholate	HMDB
Glycochenodeoxycholate	HMDB
Glycochenodeoxycholic acid	HMDB
Glycylchenodeoxycholate	HMDB
Glycylchenodeoxycholic acid	HMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-glycine	HMDB
N-(Carboxymethyl)-3a,7a-dihydroxy-5b-cholan-24-amide	HMDB
Acid, glycochenodeoxycholic	HMDB
Chenodeoxycholate, glycine	HMDB
3alpha,7alpha-Dihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide	HMDB
3α,7α-Dihydroxy-N-(carboxymethyl)-5β-cholan-24-amide	HMDB
Chenodeoxycholic acid glycine conjugate	HMDB
Chenodeoxyglycocholic acid	HMDB
N-[(3alpha,5beta,7alpha)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	HMDB
N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycine	HMDB

Chemical Formula

C₂₆H₄₃NO₅

Average Molecular Weight

449.6233

Monoisotopic Molecular Weight

449.314123491

IUPAC Name

2-[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

Traditional Name

[(4R)-4-[(2S,5R,7S,9R,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid

CAS Registry Number

640-79-9

SMILES

[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)[C@H](CCC3C1[C@H](O)C2)[C@H](C)CCC(=O)NCC(O)=O

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-AHBZRTSYSA-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

Not Available

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.4	ALOGPS
logP	2.61	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.77	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.08 m³·mol⁻¹	ChemAxon
Polarizability	52.08 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0560-0224900000-2c3ac66a1eb5dd4be992	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-1001029000-2c90d59630fb6b214a2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00e9-7001900000-5c674a4196bbe5921395	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9002100000-4253862988128e5343db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9001000000-8c0e27e07cce4587ddaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0001900000-1e432b0f0b5728b038db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-008a-3104900000-5e705b527c1bedaf73b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9101000000-bfc254147e11f3a6e4d2	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	Natalja P. Nørsko...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24477039	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	20231903	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	Pengcheng Zhou, J...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000637

FooDB ID

FDB022157

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

45866

BioCyc ID

Not Available

METLIN ID

5610

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

17215984

ChEBI ID

Not Available

PubChem Compound ID

22833540

Kegg Compound ID

C05466

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. Epub 2006 Sep 1. [16949895 ]

Showing metabocard for Chenodeoxycholic acid glycine conjugate (LMDB00198)

Structure for LMDB00198 (Chenodeoxycholic acid glycine conjugate)