Human Metabolome Database Version 3.5

Showing metabocard for 1b,3a,12a-Trihydroxy-5b-cholanoic acid (HMDB00326)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:19 -0700
HMDB ID HMDB00326
Secondary Accession Numbers None
Metabolite Identification
Common Name 1b,3a,12a-Trihydroxy-5b-cholanoic acid
Description 1b,3a,12a-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. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3,12-Trihydroxy-(5b)-Cholan-24-oate
  2. 1,3,12-Trihydroxy-(5b)-Cholan-24-oic acid
  3. 1b,3a,12a-Trihydroxy-5b-cholan-24-oate
  4. 1b,3a,12a-Trihydroxy-5b-cholan-24-oic acid
  5. 1b,3a,12a-Trihydroxy-5b-cholanoate
  6. 1b,3a,12a-Trihydroxy-5b-cholanoic acid
Chemical Formula C24H40O5
Average Molecular Weight 408.5714
Monoisotopic Molecular Weight 408.28757439
IUPAC Name (4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(2S,3R,5S,15R,16S)-3,5,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number 80434-32-8
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 Key DAKYVYUAVGJDRK-LFMRMFNLSA-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
Substituents
  • 12 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
Direct Parent Dihydroxy Bile Acids, Alcohols and Derivatives
Ontology
Status Detected and 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 0.073 g/L ALOGPS
LogP 2.46 ALOGPS
LogP 2.49 ChemAxon
LogS -3.74 ALOGPS
pKa (strongest acidic) 4.65 ChemAxon
pKa (strongest basic) -0.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 110.67 ChemAxon
Polarizability 47.46 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Intestine
  • Gall Bladder
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.8 (0.2-2.0) uM Adult (>18 years old) Both Comment Biliary cirrhosis
Blood Detected and Quantified 0.2 (0.2-0.7) uM Adult (>18 years old) Both Comment Biliary cirrhosis
Urine Detected and Quantified 0.48 (0.11-1.0) umol/mmol creatinine Adult (>18 years old) Both Comment Biliary cirrhosis
Urine Detected and Quantified 0.44 (0.18-0.92) umol/mmol creatinine Adult (>18 years old) Both Comment Biliary cirrhosis
Associated Disorders and Diseases
Disease References
Primary biliary cirrhosis
  • Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. Pubmed: 2621422 Link_out
      Associated OMIM IDs
      • 109720 Link_out (Primary biliary cirrhosis)
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB021952
      KNApSAcK ID Not Available
      Chemspider ID Not Available
      KEGG Compound ID Not Available
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Not Available
      NuGOwiki Link HMDB00326 Link_out
      Metagene Link HMDB00326 Link_out
      METLIN ID 5315 Link_out
      PubChem Compound 53477683 Link_out
      PDB ID Not Available
      ChEBI ID Not Available
      References
      Synthesis Reference ohma, 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