Chenodeoxycholic acid glycine conjugate (CHEM021887)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:14:53 UTC
Update Date2016-11-09 01:17:23 UTC
Accession NumberCHEM021887
Identification
Common NameChenodeoxycholic acid glycine conjugate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
Chemical FormulaC26H43NO5
Average Molecular Mass449.623 g/mol
Monoisotopic Mass449.314 g/mol
CAS Registry Number640-79-9
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
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
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 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
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.
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-0224900000-2c3ac66a1eb5dd4be992Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1001029000-2c90d59630fb6b214a2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-7001900000-5c674a4196bbe5921395Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9002100000-4253862988128e5343dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001000000-8c0e27e07cce4587ddaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001900000-1e432b0f0b5728b038dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-008a-3104900000-5e705b527c1bedaf73b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9101000000-bfc254147e11f3a6e4d2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000637
FooDB IDFDB022157
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45866
BioCyc IDNot Available
METLIN ID5610
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17215984
ChEBI IDNot Available
PubChem Compound ID22833540
Kegg Compound IDC05466
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Parmentier G; Eyssen H Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates. Steroids (1977), 30(5), 583-90.
2. Parmentier G; Eyssen H Synthesis and characteristics of the specific monosulfates of chenodeoxycholate, deoxycholate and their taurine or glycine conjugates. Steroids (1977), 30(5), 583-90.
3. 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.
4. 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.
5. Demers LM, Hepner G: Radioimmunoassay of bile acids in serum. Clin Chem. 1976 May;22(5):602-6.
6. 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.
7. 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.
8. 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.