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Record Information
StatusExpected but not Quantified
Creation Date2008-08-14 18:10:28 UTC
Update Date2017-12-20 20:32:56 UTC
Secondary Accession Numbers
  • HMDB06892
Metabolite Identification
Common Name7a-Hydroxy-5b-cholestan-3-one
Description7alpha-Hydroxy-5beta-cholestan-3-one is an intermediate in bile acid synthesis. 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 ).
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name(2S,9S,15R)-9-hydroxy-2,15-dimethyl-14-(6-methylheptan-2-yl)tetracyclo[²,⁷.0¹¹,¹⁵]heptadecan-5-one
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
  • Cholesterol-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available

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  Biofluid and excreta:

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Physiological effect

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility8.8e-05 g/LALOGPS
pKa (Strongest Acidic)19.99ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.33 m³·mol⁻¹ChemAxon
Polarizability50.43 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-059l-1429000000-36dd7661988002ae7048View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-4553900000-095eadc0e820bc80b096View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0019400000-4dd1a559cbcc4562e70dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-3119100000-f5ee2373268e16d7dfa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3139000000-8871a8cc4f848fcb3ea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0002900000-36cc7f2c2ca5297e94f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0004900000-2cf478d98ec9f18cfc00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-2009000000-56c5e620409babd7e456View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
27-Hydroxylase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Bile Acid BiosynthesisThumbThumb?image type=greyscaleThumb?image type=simpleMap00120
Cerebrotendinous Xanthomatosis (CTX)ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIIThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB024139
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05451
BioCyc IDNot Available
BiGG ID45839
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477905
PDB IDNot Available
ChEBI ID2290
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 ]


General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
Uniprot ID:
Molecular weight:
3a,7a-Dihydroxy-5b-cholestane + NAD → 7a-Hydroxy-5b-cholestan-3-one + NADH + Hydrogen Iondetails
3a,7a-Dihydroxy-5b-cholestane + NADP → 7a-Hydroxy-5b-cholestan-3-one + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
Uniprot ID:
Molecular weight:
7a-Hydroxy-5b-cholestan-3-one + NADP → 7a-Hydroxy-cholestene-3-one + NADPH + Hydrogen Iondetails