Showing metabocard for 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid (BMDB0000447)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:30:53 UTC
Update Date2020-04-22 15:03:38 UTC
BMDB IDBMDB0000447
Secondary Accession Numbers
  • BMDB00447
Metabolite Identification
Common Name7a,12a-Dihydroxy-3-oxo-4-cholenoic acid
Description7a,12a-Dihydroxy-3-oxo-4-cholenoic acid, also known as 7alpha,12alpha-dihydroxy-3-oxochol-4-enoate, 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. Based on a literature review a significant number of articles have been published on 7a,12a-Dihydroxy-3-oxo-4-cholenoic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoateChEBI
7alpha,12alpha-Dihydroxy-3-oxochol-4-enoic acidChEBI
7a,12a-Dihydroxy-3-oxochol-4-enoateGenerator
7a,12a-Dihydroxy-3-oxochol-4-enoic acidGenerator
7Α,12α-dihydroxy-3-oxochol-4-enoateGenerator
7Α,12α-dihydroxy-3-oxochol-4-enoic acidGenerator
7a,12a-Dihydroxy-3-oxo-4-cholenoateGenerator
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-OateHMDB
7a,12a-Dihydroxy-3-oxo-chol-4-en-24-Oic acidHMDB
(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoateGenerator, HMDB
Chemical FormulaC24H36O5
Average Molecular Weight404.5396
Monoisotopic Molecular Weight404.256274262
IUPAC Name(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]pentanoic acid
CAS Registry Number13587-11-6
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])[C@H](O)CC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C24H36O5/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/h10,13,16-20,22,26-27H,4-9,11-12H2,1-3H3,(H,28,29)/t13-,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyZZUMXQCSMJCDDC-DFQOQHGMSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • 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
logP2.17ALOGPS
logP2.64ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.59 m³·mol⁻¹ChemAxon
Polarizability45.67 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 LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0000447
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022052
KNApSAcK IDNot Available
Chemspider ID4447084
KEGG Compound IDC15568
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5436
PubChem Compound5283996
PDB IDNot Available
ChEBI ID49269
References
Synthesis ReferenceKallner, Anders. Bile acids and steroids. 182. A method of synthesis of allochlanoic acids. Acta Chemica Scandinavica (1947-1973) (1967), 21(2), 322-8.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available