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Showing Compound Chenodeoxycholic acid glycine conjugate (FDB022157)

Record Information
Version1.0
Creation date2011-09-21 00:09:18 UTC
Update date2015-07-21 06:57:01 UTC
Primary IDFDB022157
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChenodeoxycholic acid glycine conjugate
DescriptionChenodeoxycholic 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. [HMDB]
CAS Number640-79-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Chenodeoxycholate glycine conjugateGenerator
Chenodeoxycholic acid glycine conjugic acidGenerator
(23R)-HydroxychenodeoxycholylglycineHMDB
12-DeoxycholylglycineHMDB
12-DesoxycholylglycineHMDB
3a,7a-Dihydroxy-N-(carboxymethyl)-5b-cholan-24-amideHMDB
ChenodeoxycholylglycineHMDB
Glycine chenodeoxycholateHMDB
GlycochenodeoxycholateHMDB
Glycochenodeoxycholic acidHMDB
GlycylchenodeoxycholateHMDB
Glycylchenodeoxycholic acidHMDB
N-(3a,7a-Dihydroxy-5b-cholan-24-oyl)-glycineHMDB
N-(Carboxymethyl)-3a,7a-dihydroxy-5b-cholan-24-amideHMDB
Acid, glycochenodeoxycholicHMDB
Chenodeoxycholate, glycineHMDB
3alpha,7alpha-Dihydroxy-N-(carboxymethyl)-5beta-cholan-24-amideHMDB
3α,7α-Dihydroxy-N-(carboxymethyl)-5β-cholan-24-amideHMDB
Chenodeoxycholic acid glycine conjugateHMDB
Chenodeoxyglycocholic acidHMDB
N-[(3alpha,5beta,7alpha)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineHMDB
N-[(3α,5β,7α)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineHMDB
N-(3a,7a-dihydroxy-5b-cholan-24-oyl)-Glycinehmdb
N-(carboxymethyl)-3a,7a-dihydroxy-5b-Cholan-24-amidehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0079 g/LALOGPS
logP2.4ALOGPS
logP2.61ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.08 m³·mol⁻¹ChemAxon
Polarizability52.08 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H43NO5
IUPAC name2-[(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
InChI IdentifierInChI=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 KeyGHCZAUBVMUEKKP-AHBZRTSYSA-N
Isomeric 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
Average Molecular Weight449.6233
Monoisotopic Molecular Weight449.314123491
Classification
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated 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 FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSChenodeoxycholic acid glycine conjugate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0560-0224900000-2c3ac66a1eb5dd4be992Spectrum
Predicted GC-MSChenodeoxycholic acid glycine conjugate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1001029000-2c90d59630fb6b214a2eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-7001900000-5c674a4196bbe59213952016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9002100000-4253862988128e5343db2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-8c0e27e07cce4587ddaa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001900000-1e432b0f0b5728b038db2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008a-3104900000-5e705b527c1bedaf73b82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9101000000-bfc254147e11f3a6e4d22016-08-03View Spectrum
NMRNot Available
ChemSpider ID17215984
ChEMBL IDNot Available
KEGG Compound IDC05466
Pubchem Compound ID22833540
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00637
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45866
KNApSAcK IDNot Available
HET ID1FMC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Glycine N-acyltransferase-like protein 3GLYATL3Q5SZD4
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference