Human Metabolome Database Version 3.5

Showing metabocard for 3a,7a-Dihydroxycoprostanic acid (HMDB00359)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:25:56 -0600
HMDB ID HMDB00359
Secondary Accession Numbers
  • HMDB01974
Metabolite Identification
Common Name 3a,7a-Dihydroxycoprostanic acid
Description 3a,7a-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID 864325 Link_out). 3a,7a-Dihydroxycoprostanic acid is the precursor to chenodeoxycholic acid. 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. 3a,7a-Dihydroxy-5b-cholestan-26-oate
  2. 3a,7a-Dihydroxy-5b-cholestan-26-oic acid
  3. 3a,7a-Dihydroxy-5b-cholestanoate
  4. 3a,7a-Dihydroxy-5b-cholestanoic acid
  5. 3a,7a-Dihydroxycoprostanate
  6. 3a,7a-Dihydroxycoprostanic acid
  7. 3a,7a-Hydroxy-5b-cholestan-26-oate
  8. 3a,7a-Hydroxy-5b-cholestan-26-oic acid
  9. 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oate
  10. 3alpha,7alpha-Dihydroxy-5beta-cholestan-26-oic acid
  11. 3alpha,7alpha-Dihydroxy-5beta-cholestanate
  12. 3alpha,7alpha-dihydroxy-5beta-cholestanic acid
  13. 3alpha,7alpha-Dihydroxy-5beta-cholestanoate
  14. 3alpha,7alpha-dihydroxy-5beta-cholestanoic acid
Chemical Formula C27H46O4
Average Molecular Weight 434.6517
Monoisotopic Molecular Weight 434.33960996
IUPAC Name (6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid
Traditional IUPAC Name (6R)-6-[(1S,2S,5R,7S,9R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanoic acid
CAS Registry Number 17974-66-2
SMILES [H][C@@]1(CC[C@@]2([H])C3[C@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C(O)=O
InChI Identifier InChI=1S/C27H46O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h16-24,28-29H,5-15H2,1-4H3,(H,30,31)/t16-,17?,18+,19-,20-,21+,22+,23-,24?,26+,27-/m1/s1
InChI Key ITZYGDKGRKKBSN-KLYSAGIUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Cholesterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 3 Hydroxy Steroid
  • 7 Hydroxy Steroid
  • Bicyclohexane
  • Bile Acid, Alcohol, Or Derivative
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Dihydroxy Bile Acid, Alcohol, Or Derivative
  • Hydroxy Bile Acid, Alcohol, Or Derivative
  • Secondary Alcohol
  • Sesterterpene
Direct Parent Cholesterols 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 0.0044 g/L ALOGPS
LogP 4.02 ALOGPS
LogP 5.15 ChemAxon
LogS -5.00 ALOGPS
pKa (strongest acidic) 4.83 ChemAxon
pKa (strongest basic) -0.54 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 123.05 ChemAxon
Polarizability 52.53 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
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 map00120 Link_out
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 FDB021979
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 HMDB00359 Link_out
Metagene Link HMDB00359 Link_out
METLIN ID 5348 Link_out
PubChem Compound 53477686 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Hanson, Russell Floyd. Isolation, identification, formation, and metabolism of 3a, 7a-hydroxy-5b-cholestan-26-oic acid in man. (1972), 73 pp. CAN 78:27152 AN 1973:27152
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Alme B, Bremmelgaard A, Sjovall J, Thomassen P: Analysis of metabolic profiles of bile acids in urine using a lipophilic anion exchanger and computerized gas-liquid chromatorgaphy-mass spectrometry. J Lipid Res. 1977 May;18(3):339-62. Pubmed: 864325 Link_out

Enzymes
Name: Aldehyde dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile acid-CoA:amino acid N-acyltransferase
Reactions: Not Available
Gene Name: BAAT
Uniprot ID: Q14032 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile acyl-CoA synthetase
Reactions: Not Available
Gene Name: SLC27A5
Uniprot ID: Q9Y2P5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
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