Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:56 UTC
HMDB IDHMDB00359
Secondary Accession Numbers
  • HMDB01974
Metabolite Identification
Common Name3a,7a-Dihydroxycoprostanic acid
Description3a,7a-Dihydroxycoprostanic acid is a bile acid excreted in small amounts in the urine of healthy subjects (PMID 864325 ). 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
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 FormulaC27H46O4
Average Molecular Weight434.6517
Monoisotopic Molecular Weight434.33960996
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 Number17974-66-2
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 KeyITZYGDKGRKKBSN-KLYSAGIUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassCholesterols 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 ParentCholesterols and Derivatives
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0044 g/LALOGPS
logP4.02ALOGPS
logP5.15ChemAxon
logS-5ALOGPS
pKa (strongest acidic)4.83ChemAxon
pKa (strongest basic)-0.54ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count3ChemAxon
polar surface area77.76ChemAxon
rotatable bond count6ChemAxon
refractivity123.05ChemAxon
polarizability52.53ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Bile Acid BiosynthesisSMP00035map00120
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021979
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00359
Metagene LinkHMDB00359
METLIN ID5348
PubChem Compound53477686
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceHanson, 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

Enzymes

Gene Name:
SLC27A5
Uniprot ID:
Q9Y2P5
Gene Name:
FABP6
Uniprot ID:
P51161

Transporters

Gene Name:
ABCB11
Uniprot ID:
O95342
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Gene Name:
SLC10A1
Uniprot ID:
Q14973