Showing metabocard for 3b,12a-Dihydroxy-5b-cholanoic acid (BMDB0000438)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:45 UTC
Update Date2020-05-11 20:20:54 UTC
BMDB IDBMDB0000438
Secondary Accession Numbers
  • BMDB00438
Metabolite Identification
Common Name3b,12a-Dihydroxy-5b-cholanoic acid
Description3b,12a-Dihydroxy-5b-cholanoic acid, also known as 3-epideoxycholic acid or (3b,5b,12a)-3,12-dihydroxycholan-24-Oate, belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups. 3b,12a-Dihydroxy-5b-cholanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-Oic acidChEBI
3-Epideoxycholic acidChEBI
3beta-Deoxycholic acidChEBI
Isodeoxycholic acidChEBI
(3b,5b,12a)-3,12-Dihydroxycholan-24-OateGenerator
(3b,5b,12a)-3,12-Dihydroxycholan-24-Oic acidGenerator
(3beta,5beta,12alpha)-3,12-Dihydroxycholan-24-OateGenerator
(3Β,5β,12α)-3,12-dihydroxycholan-24-OateGenerator
(3Β,5β,12α)-3,12-dihydroxycholan-24-Oic acidGenerator
3-EpideoxycholateGenerator
3b-DeoxycholateGenerator
3b-Deoxycholic acidGenerator
3beta-DeoxycholateGenerator
3Β-deoxycholateGenerator
3Β-deoxycholic acidGenerator
IsodeoxycholateGenerator
3b,12a-Dihydroxy-5b-cholanoateGenerator
3b,12a-Dihydroxy-5b-cholan-24-OateHMDB
3b,12a-Dihydroxy-5b-cholan-24-Oic acidHMDB
3b,12a-Dihydroxy-5b-cholanateHMDB
3b,12a-Dihydroxy-5b-cholanic acidHMDB
3b,12a-DihydroxycholanoateHMDB
3b,12a-Dihydroxycholanoic acidHMDB
5b-Cholanic acid-3b,12a-diolHMDB
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name3-epideoxycholic acid
CAS Registry Number570-63-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17+,18-,19+,20+,21+,23+,24-/m1/s1
InChI KeyKXGVEGMKQFWNSR-OFYXWCICSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.3ALOGPS
logP3.79ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-0.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.2 m³·mol⁻¹ChemAxon
Polarizability46.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Gallbladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000438
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022045
KNApSAcK IDNot Available
Chemspider ID141062
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5427
PubChem Compound160530
PDB IDNot Available
ChEBI ID88098
References
Synthesis ReferenceDanielsson, Henry; Eneroth, Peter; Hellstrom, Kjell; Sjovall, Jan. Bile acids and steroids. CXXIII. Synthesis of some 3b-hydroxylated bile acids and the isolation of 3b,12a-dihydroxy-5b-cholanic acid from feces. Journal of Biological Chemistry (1962), 237 3657-9.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available