Record Information
Version3.6
Creation Date2008-08-14 18:14:34 UTC
Update Date2013-05-29 19:45:26 UTC
HMDB IDHMDB06894
Secondary Accession NumbersNone
Metabolite Identification
Common Name3a,7a-Dihydroxy-5b-cholestan-26-al
Description3alpha,7alpha-Dihydroxy-5beta-cholestan-26-al is an intermediate involved in bile acid biosynthesis, specifically in the synthesis of chenodeoxyglycocholate and lithocholate. 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. (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).
Structure
Thumb
Synonyms
  1. 3alpha,7alpha-dihydroxy-5beta-cholestan-27-al
  2. 5beta-cholestan-27-al-3alpha,7alpha-diol
  3. 5beta-cholestane-3alpha,7alpha-diol-27-al
Chemical FormulaC27H46O3
Average Molecular Weight418.6523
Monoisotopic Molecular Weight418.344695338
IUPAC Name6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanal
Traditional IUPAC Name6-[(2S,5R,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2-methylheptanal
CAS Registry NumberNot Available
SMILES
CC(CCCC(C)C1CCC2C3[C@H](O)CC4C[C@H](O)CC[C@]4(C)C3CC[C@]12C)C=O
InChI Identifier
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)21-8-9-22-25-23(11-13-27(21,22)4)26(3)12-10-20(29)14-19(26)15-24(25)30/h16-25,29-30H,5-15H2,1-4H3/t17?,18?,19?,20-,21?,22?,23?,24-,25?,26+,27-/m1/s1
InChI KeyYWGOKHMOJTZGBN-SBOSHUFNSA-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
  • Aldehyde
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Secondary Alcohol
  • Sesterterpene
Direct ParentCholesterols and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 solubility6.970E-04 g/LALOGPS
logP4.91ALOGPS
logP4.99ChemAxon
logS-5.8ALOGPS
pKa (strongest acidic)16.07ChemAxon
pKa (strongest basic)-0.54ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area57.53ChemAxon
rotatable bond count6ChemAxon
refractivity122.12ChemAxon
polarizability51.14ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024141
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05445
BioCyc IDNot Available
BiGG ID45826
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06894
Metagene LinkHMDB06894
METLIN IDNot Available
PubChem Compound53477906
PDB IDNot Available
ChEBI ID27428
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. Pubmed: 11316487
  2. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. Pubmed: 16037564
  3. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. Pubmed: 12576301
  4. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. Pubmed: 11907135

Enzymes

Gene Name:
ALDH9A1
Uniprot ID:
P49189
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Iondetails
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Iondetails
Gene Name:
ALDH2
Uniprot ID:
P05091
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Iondetails
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Iondetails
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Reactions
3a,7a-Dihydroxy-5b-cholestan-26-al + NAD + Water unknown 3a,7a-Dihydroxy-5b-cholestanate + NADH + Hydrogen Iondetails
Gene Name:
ADH5
Uniprot ID:
P11766
Gene Name:
ADH1B
Uniprot ID:
P00325
Gene Name:
ADH1A
Uniprot ID:
P07327
Gene Name:
ADH6
Uniprot ID:
P28332
Gene Name:
ADH1C
Uniprot ID:
P00326
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Reactions
3 alpha,7 alpha,26-Trihydroxy-5beta-cholestane unknown 3a,7a-Dihydroxy-5b-cholestan-26-aldetails
3a,7a-Dihydroxy-5b-cholestan-26-al + NADPH + Oxygen + Hydrogen Ion unknown 3a,7a-Dihydroxy-5b-cholestanate + NADP + Waterdetails