Human Metabolome Database Version 3.5

Showing metabocard for 1b,3a,7a-Trihydroxy-5b-cholanoic acid (HMDB00414)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:32 -0700
HMDB ID HMDB00414
Secondary Accession Numbers None
Metabolite Identification
Common Name 1b,3a,7a-Trihydroxy-5b-cholanoic acid
Description 1b,3a,7a-Trihydroxy-5b-cholanoic acid is a bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1 beta,3a,7a-Trihydroxy-5b-cholanoate
  2. 1 beta,3a,7a-Trihydroxy-5b-cholanoic acid
  3. 1b,3 alpha,7a-Trihydroxy-5b-cholanoate
  4. 1b,3 alpha,7a-Trihydroxy-5b-cholanoic acid
  5. 1b,3a,7 alpha-Trihydroxy-5b-cholanoate
  6. 1b,3a,7 alpha-Trihydroxy-5b-cholanoic acid
  7. 1b,3a,7a-Trihydroxy-5 beta-cholanoate
  8. 1b,3a,7a-Trihydroxy-5 beta-cholanoic acid
  9. 1b,3a,7a-Trihydroxy-5b-cholan-24-oate
  10. 1b,3a,7a-Trihydroxy-5b-cholan-24-oic acid
  11. 1b,3a,7a-Trihydroxy-5b-cholanoate
  12. 1b,3a,7a-Trihydroxy-5b-cholanoic acid
  13. 1b-Hydroxychenodeoxycholate
  14. 1b-Hydroxychenodeoxycholic acid
  15. 3-a,7-a,12-a-Trihydroxy-5-a-cholanoate
  16. 3-a,7-a,12-a-Trihydroxy-5-a-cholanoic acid
  17. 3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoate
  18. 3-a,7-a,12-alpha-Trihydroxy-5-alpha-cholanoic acid
Chemical Formula C24H40O5
Average Molecular Weight 408.5714
Monoisotopic Molecular Weight 408.28757439
IUPAC Name (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(1S,2S,3R,5S,7S,9R,10S,11S,14R,15R)-3,5,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number 99598-04-6
SMILES [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@H](O)C[C@@H](O)[C@]12C
InChI Identifier InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(8-9-23(16,17)2)24(3)14(11-19(22)26)10-15(25)12-20(24)27/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
InChI Key GYUVAHWOVINGNE-RWXZXXAWSA-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)
Substituents
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct Parent Dihydroxy 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 238 - 240 °C 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 0.08 g/L ALOGPS
LogP 2.21 ALOGPS
LogP 2.41 ChemAxon
LogS -3.71 ALOGPS
pKa (strongest acidic) 4.6 ChemAxon
pKa (strongest basic) -0.61 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 110.75 ChemAxon
Polarizability 47.11 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations Not Available
Tissue Location
  • Intestine
  • Kidney
  • Liver
  • Gall Bladder
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 FDB022030
KNApSAcK ID Not Available
Chemspider ID 4446934 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00414 Link_out
Metagene Link HMDB00414 Link_out
METLIN ID 5403 Link_out
PubChem Compound 5283846 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Tohma, 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 References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
  2. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. Pubmed: 10203155 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