Record Information
Version3.6
Creation Date2008-08-08 10:29:51 UTC
Update Date2013-02-09 00:15:18 UTC
HMDB IDHMDB06773
Secondary Accession NumbersNone
Metabolite Identification
Common Name11b-Hydroxyandrost-4-ene-3,17-dione
Description11beta-Hydroxyandrost-4-ene-3,17-dione is an intermediate in adrenosterone production. 11beta-Hydroxyandrost-4-ene-3,17-dione is produced from androst-4-ene-3,17-dione, a reaction catalyzed by the enzyme cytochrome P450 B [EC:1.14.15.4]. 11beta-Hydroxyandrost-4-ene-3,17-dione is then converted into adrenosterone by the enzyme 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].
Structure
Thumb
Synonyms
  1. 11beta-Hydroxyandrost-4-ene-3,17-dione
  2. 4-Androsten-11beta-ol-3,17-dione
  3. Androst-4-ene-3,17-dione-11beta-ol
Chemical FormulaC19H26O3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
IUPAC Name(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
Traditional IUPAC Name(1S,2R,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
CAS Registry Number382-44-5
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1
InChI KeyWSCUHXPGYUMQEX-KCZNZURUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassAndrogens and Derivatives
Other Descriptors
  • 11beta-hydroxy steroid(ChEBI)
  • 17-oxo steroid(ChEBI)
  • 3-oxo steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C19 steroids (androgens) and derivatives(KEGG)
  • C19 steroids (androgens) and derivatives(Lipidmaps)
  • Hydroxysteroids
  • Ketosteroids
  • androstanoid(ChEBI)
Substituents
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Secondary Alcohol
  • Sesquiterpene Backbone
Direct ParentAndrogens 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 solubility0.082 g/LALOGPS
logP2ALOGPS
logP2.62ChemAxon
logS-3.6ALOGPS
pKa (strongest acidic)14.88ChemAxon
pKa (strongest basic)-2.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area54.37ChemAxon
rotatable bond count0ChemAxon
refractivity85.2ChemAxon
polarizability34ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB024075
KNApSAcK IDNot Available
Chemspider ID84958
KEGG Compound IDC05284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06773
Metagene LinkHMDB06773
METLIN IDNot Available
PubChem Compound94141
PDB IDNot Available
ChEBI ID27967
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

Gene Name:
CYP11B1
Uniprot ID:
P15538
Reactions
Reduced adrenal ferredoxin + Androstenedione + Oxygen unknown 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Waterdetails
Gene Name:
HSD17B2
Uniprot ID:
P37059
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
Gene Name:
HSD17B8
Uniprot ID:
Q92506
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
Gene Name:
HSD11B1
Uniprot ID:
P28845
Reactions
11b-Hydroxyandrost-4-ene-3,17-dione + NADP unknown Adrenosterone + NADPH + Hydrogen Iondetails
Gene Name:
HSD17B1
Uniprot ID:
P14061
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
Gene Name:
HSD17B7
Uniprot ID:
P56937
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
Gene Name:
HSD17B6
Uniprot ID:
O14756
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails
Gene Name:
CYP11B2
Uniprot ID:
P19099
Reactions
Reduced adrenal ferredoxin + Androstenedione + Oxygen unknown 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Waterdetails
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Reactions
11beta,17beta-Dihydroxy-4-androsten-3-one + NAD unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADH + Hydrogen Iondetails
11beta,17beta-Dihydroxy-4-androsten-3-one + NADP unknown 11b-Hydroxyandrost-4-ene-3,17-dione + NADPH + Hydrogen Iondetails