3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate (PAMDB003557)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB003557
Identification
Name: 3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate
Description:3-Alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate is a steroid derivative or bile acid. It is a substrate for the enzyme 7-alpha-hydroxysteroid dehydrogenase, which catalyzes the following reaction: 3-alpha,7-alpha,12-alpha-trihydroxy-5-beta-cholanate + NAD+ = 3-alpha,12-alpha-dihydroxy-7-oxo-5-beta-cholanate + NADH.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oate
  • (3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-Oic acid
  • (3a,5b,7a,8a,12a,14b,17a)-3,7,12-Trihydroxycholan-24-Oate
  • (3a,5b,7a,8a,12a,14b,17a)-3,7,12-Trihydroxycholan-24-Oic acid
  • (3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholan-24-Oate
  • (3alpha,5beta,7alpha,12alpha)-3,7,12-trihydroxycholan-24-oic acid
  • (3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-Trihydroxycholan-24-Oate
  • (3alpha,5beta,7alpha,8alpha,12alpha,14beta,17alpha)-3,7,12-trihydroxycholan-24-oic acid
  • (3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-Oate
  • (3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-Oic acid
  • (3α,5β,7α,8α,12α,14β,17α)-3,7,12-Trihydroxycholan-24-Oate
  • (3α,5β,7α,8α,12α,14β,17α)-3,7,12-Trihydroxycholan-24-Oic acid
  • (4R)-4-(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopentaaphenanthren-17-ylpentanoate
  • (4R)-4-(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopentaaphenanthren-17-ylpentanoic acid
  • 3-a,7-a,12-a-Trihydroxy-5-b-cholanate
  • 3-a,7-a,12-a-Trihydroxy-5-b-cholanic acid
  • 3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholanic acid
  • 3-α,7-α,12-α-Trihydroxy-5-β-cholanate
  • 3-α,7-α,12-α-Trihydroxy-5-β-cholanic acid
  • 3a,7a,12a-Trihydroxy-5b-cholanate
  • 3a,7a,12a-Trihydroxy-5b-cholanic acid
  • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanate
  • 3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid
  • 3α,7α,12α-Trihydroxy-5β-cholanate
  • 3α,7α,12α-Trihydroxy-5β-cholanic acid
  • Cholate
  • Cholic acid
  • Cholsaeure
Chemical Formula: C24H40O5
Average Molecular Weight: 408.5714
Monoisotopic Molecular Weight: 408.28757439
InChI Key: BHQCQFFYRZLCQQ-OELDTZBJSA-N
InChI:InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
CAS number: Not Available
IUPAC Name:(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,??0??,???heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name: cholic acid
SMILES:[H][C@@](C)(CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@]([H])(O)C[C@]4([H])C[C@]([H])(O)CC[C@]4(C)[C@@]3([H])C[C@]([H])(O)[C@]12C
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Steroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct Parent Trihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 12-hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular Framework Aliphatic homopolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0738 mg/mLALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m3·mol-1ChemAxon
Polarizability46.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0009000000-85abf6e916e1cc1c46b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-476dc71e401cc2327292View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00nb-2109000000-0181c85f78bb9e29ea53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0009700000-63a8d2c748b3bc631c17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009200000-ba378537551be8134141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-caef890bd53da215442eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0596-9642000000-e425981b8a0ac72ea6eeView in MoNA
1D NMR13C NMR SpectrumNot Available
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16359
HMDB IDHMDB00619
Pubchem Compound ID221493
Kegg IDC00695
ChemSpider ID192176
Wikipedia IDCholic acid
BioCyc IDNot Available
Ligand ExpoCHD