Human Metabolome Database Version 3.5

Showing metabocard for 12b-Hydroxy-5b-cholanoic acid (HMDB02431)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:53 -0600
Update Date 2013-05-29 13:36:17 -0600
HMDB ID HMDB02431
Secondary Accession Numbers None
Metabolite Identification
Common Name 12b-Hydroxy-5b-cholanoic acid
Description 12-hydroxy-(5b,12b)-Cholan-24-oic acid is a naturally occurring bile acid that has been identified in human bile. (PMID: 14167657 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 12-Hydroxy-(5b,12b)-Cholan-24-oate
  2. 12-Hydroxy-(5b,12b)-Cholan-24-oic acid
  3. 12b-Hydroxy-5b-Cholan-24-oate
  4. 12b-Hydroxy-5b-Cholan-24-oic acid
  5. 12b-Hydroxy-5b-cholanic acid
  6. 12b-Hydroxy-5b-cholanoate
  7. 12b-Hydroxy-5b-cholanoic acid
  8. 12beta-Hydroxy-5beta-cholanoate
  9. 12beta-Hydroxy-5beta-cholanoic acid
Chemical Formula C24H40O3
Average Molecular Weight 376.5726
Monoisotopic Molecular Weight 376.297745146
IUPAC Name (4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(1S,2S,7S,10R,11S,14R,15R,16R)-16-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number 15173-23-6
SMILES [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier InChI=1S/C24H40O3/c1-15(7-12-22(26)27)18-10-11-19-17-9-8-16-6-4-5-13-23(16,2)20(17)14-21(25)24(18,19)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16+,17+,18-,19+,20+,21-,23+,24-/m1/s1
InChI Key OBUOWZOYJNAMCZ-ORVKXXEISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Bile Acids, Alcohols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Bile Acids, Alcohols and Derivatives
  • C24 bile acids, alcohols, and derivatives(Lipidmaps)
  • Monohydroxy Bile Acids, Alcohols and Derivatives
Substituents
  • 12 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct Parent Hydroxy Bile Acids, Alcohols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0011 g/L ALOGPS
LogP 4.50 ALOGPS
LogP 5.18 ChemAxon
LogS -5.52 ALOGPS
pKa (strongest acidic) 4.65 ChemAxon
pKa (strongest basic) -0.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 107.53 ChemAxon
Polarizability 45.28 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023003
KNApSAcK ID Not Available
Chemspider ID 4446900 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02431 Link_out
Metagene Link HMDB02431 Link_out
METLIN ID Not Available
PubChem Compound 5283812 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. ENEROTH P: THIN-LAYER CHROMATOGRAPHY OF BILE ACIDS. J Lipid Res. 1963 Jan;4:11-6. Pubmed: 14167657 Link_out

Enzymes
Name: Gastrotropin
Reactions: Not Available
Gene Name: FABP6
Uniprot ID: P51161 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Solute carrier organic anion transporter family member 1B3
Reactions: Not Available
Gene Name: SLCO1B3
Uniprot ID: Q9NPD5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1B1
Reactions: Not Available
Gene Name: SLCO1B1
Uniprot ID: Q9Y6L6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Canalicular multispecific organic anion transporter 2
Reactions: Not Available
Gene Name: ABCC3
Uniprot ID: O15438 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt export pump
Reactions: Not Available
Gene Name: ABCB11
Uniprot ID: O95342 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ileal sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A2
Uniprot ID: Q12908 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sodium/bile acid cotransporter
Reactions: Not Available
Gene Name: SLC10A1
Uniprot ID: Q14973 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 1A2
Reactions: Not Available
Gene Name: SLCO1A2
Uniprot ID: P46721 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Solute carrier organic anion transporter family member 4A1
Reactions: Not Available
Gene Name: SLCO4A1
Uniprot ID: Q96BD0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA