Showing metabocard for 1b,3a,12a-Trihydroxy-5b-cholanoic acid (BMDB0000326)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:28:40 UTC
Update Date2020-05-11 20:08:15 UTC
BMDB IDBMDB0000326
Secondary Accession Numbers
  • BMDB00326
Metabolite Identification
Common Name1b,3a,12a-Trihydroxy-5b-cholanoic acid
Description1b,3a,12a-Trihydroxy-5b-cholanoic acid 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. Based on a literature review a significant number of articles have been published on 1b,3a,12a-Trihydroxy-5b-cholanoic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1b,3a,12a-Trihydroxy-5b-cholanoateGenerator
1,3,12-Trihydroxy-(5b)-cholan-24-OateHMDB
1,3,12-Trihydroxy-(5b)-cholan-24-Oic acidHMDB
1b,3a,12a-Trihydroxy-5b-cholan-24-OateHMDB
1b,3a,12a-Trihydroxy-5b-cholan-24-Oic acidHMDB
(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-Trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateGenerator, HMDB
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
CAS Registry Number80434-32-8
SMILES
C[C@H](CCC(O)=O)C1CCC2C3CCC4C[C@H](O)C[C@@H](O)[C@]4(C)C3C[C@H](O)[C@]12C
InChI Identifier
InChI=1S/C24H40O5/c1-13(4-9-22(28)29)17-7-8-18-16-6-5-14-10-15(25)11-20(26)23(14,2)19(16)12-21(27)24(17,18)3/h13-21,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14?,15+,16?,17?,18?,19?,20-,21+,23+,24-/m1/s1
InChI KeyDAKYVYUAVGJDRK-LFMRMFNLSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 1-hydroxysteroid
  • 12-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP2.46ALOGPS
logP2.49ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.67 m³·mol⁻¹ChemAxon
Polarizability47.46 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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000326
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021952
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5315
PubChem Compound53477683
PDB IDNot Available
ChEBI ID89219
References
Synthesis Referenceohma, Masahiko; Mahara, Reijiro; Takeshita, Hiromi; Kurosawa, Takao; Ikegawa, Shigeo; Nittono, Hiroshi. Synthesis of the 1b-hydroxylated bile acids and identification of 1b,3a,7a-trihydroxy- and 1b,3a,7a,12a-tetrahydroxy-5b-cholan-24-oic acids in human meconium. Chemical & Pharmaceutical Bulletin (1985), 33(7), 3071-3.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available