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Record Information
Version4.0
Creation Date2006-05-22 14:17:41 UTC
Update Date2017-09-27 08:24:13 UTC
HMDB IDHMDB0002197
Secondary Accession Numbers
  • HMDB02197
Metabolite Identification
Common Name7a,12a-Dihydroxy-cholestene-3-one
Description7a,12a-Dihydroxy-cholestene-3-one is an intermediate in bile acid synthesis; is considerably higher in patients with cerebrotendinous xanthomatosis (CTX) than in the normal liver. (PMID 7017048 ).
Structure
Thumb
Synonyms
ValueSource
7-a,12-a-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-a-Dihydroxycholest-4-en-3-oneHMDB
7-a,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-a,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7-alpha,12-alpha-Dihydroxy-4-cholesten-3-oneHMDB
7-alpha,12-alpha-Dihydroxycholest-4-en-3-oneHMDB
7alpha,12alpha-Dihydroxy-cholestene-3-oneHMDB
Chemical FormulaC27H44O3
Average Molecular Weight416.6365
Monoisotopic Molecular Weight416.329045274
IUPAC Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
Traditional Name(1S,2R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)CC2CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)20-9-10-21-25-22(15-24(30)27(20,21)5)26(4)12-11-19(28)13-18(26)14-23(25)29/h11-12,16-18,20-25,29-30H,6-10,13-15H2,1-5H3/t17-,18?,20-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyVJGNBLOGSXHTLR-JFXJTJEYSA-N
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
Substituents
  • Cholesterol-skeleton
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 7-hydroxysteroid
  • Oxosteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.0029 g/LALOGPS
logP4.69ALOGPS
logP5.18ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-0.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.94 m³·mol⁻¹ChemAxon
Polarizability50.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0957100000-f9ca360b20be30aee5cdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-6421590000-060d19b9863c108036eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009200000-ca011752a678df923d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007k-2109000000-fe2eac67f433d8e5ffd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-7209000000-dd9edd2da2f8a7cfa3b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0004900000-9a4838827d7cc0003b0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0009800000-d99dd5a2761313bbd19cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0012-1109000000-12f6e81d23b56a07105cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Familial Hypercholanemia (FHCA)Pw000194Pw000194 greyscalePw000194 simpleNot Available
Zellweger SyndromePw000195Pw000195 greyscalePw000195 simpleNot Available
Displaying entries 6 - 7 of 7 in total
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 IDFDB022899
KNApSAcK IDNot Available
Chemspider ID13628315
KEGG Compound IDC05457
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6539
PubChem Compound21252277
PDB IDNot Available
ChEBI ID28477
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bjorkhem I, Oftebro H, Skrede S, Pedersen JI: Assay of intermediates in bile acid biosynthesis using isotope dilution--mass spectrometry: hepatic levels in the normal state and in cerebrotendinous xanthomatosis. J Lipid Res. 1981 Feb;22(2):191-200. [PubMed:7017048 ]

Enzymes

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:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
7a,12a-Dihydroxy-5b-cholestan-3-one + NADP → 7a,12a-Dihydroxy-cholestene-3-one + NADPH + Hydrogen Iondetails
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A2
Uniprot ID:
P31213
Molecular weight:
28407.035
General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
General function:
Involved in monooxygenase activity
Specific function:
Involved in bile acid synthesis and is responsible for the conversion of 7 alpha-hydroxy-4-cholesten-3-one into 7 alpha, 12 alpha-dihydroxy-4-cholesten-3-one. Responsible for the balance between formation of cholic acid and chenodeoxycholic acid. Has a rather broad substrate specificity including a number of 7-alpha-hydroxylated C27 steroids.
Gene Name:
CYP8B1
Uniprot ID:
Q9UNU6
Molecular weight:
58068.01
Reactions
7a-Hydroxy-cholestene-3-one + NADPH + Oxygen → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails
7a-Hydroxy-cholestene-3-one + Hydrogen Ion + Oxygen + NADPH → 7a,12a-Dihydroxy-cholestene-3-one + NADP + Waterdetails