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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-08 10:19:11 UTC
Update Date2017-12-07 01:59:44 UTC
HMDB IDHMDB0006772
Secondary Accession Numbers
  • HMDB06772
Metabolite Identification
Common NameAdrenosterone
DescriptionAdrenosterone is a steroid hormone with weak androgenic effect. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichstein's substance G.(Wikipedia). Andrenosterone is created from androst-4-ene-3,17-dione by the work of two enzymes, CYP11B (E1.14.15.4) and 11beta-hydroxysteroid dehydrogenase [EC:1.1.1.146].
Structure
Thumb
Synonyms
ValueSource
11-KetoandrostenedioneMeSH
4-Androstene-3,11,17-trioneMeSH
Adrenosterone, 3H-labeledMeSH
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione
Traditional Nameadrenosterone
CAS Registry Number382-45-6
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H24O3/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/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1
InChI KeyRZRPTBIGEANTGU-IRIMSJTPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 17-oxosteroid
  • 11-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    System 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 Solubility0.055 g/LALOGPS
logP2.42ALOGPS
logP3.01ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)17.99ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.21 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.27 m³·mol⁻¹ChemAxon
Polarizability33.28 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-dda2aae9c4577545506cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-dda2aae9c4577545506cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-1590000000-60fcf2c287c8dac542eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ab9-2940000000-06e07dc51a896789d933View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0290000000-a6dda3c4c0b1e8e4c477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-572505448243920d7c46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-6a4af6e2a1477f91dfbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-57c8256a5ea31b9519f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1091000000-6b6dae7a99821b529938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1092000000-9361c41ea86f032c634bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-6d600d8c52e480412d37View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-af6aba5ffbd5525ba43aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ab9-2940000000-06e07dc51a896789d933View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0069000000-51d9ddcfd1d7b8a3e20cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l7i-0291000000-7b42bb8a716d4c0700e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9j-2490000000-c88e67e966734b1d65eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-34ecec5ab91ebc5e78ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-4c027780977d32f6a16eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-2090000000-cdcd813d0ed227d587c1View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Androstenedione MetabolismPw031290Pw031290 greyscalePw031290 simpleNot 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 IDFDB024074
KNApSAcK IDNot Available
Chemspider ID194597
KEGG Compound IDC05285
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound223997
PDB IDNot Available
ChEBI ID607862
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:
HSD11B2
Uniprot ID:
P80365
Molecular weight:
44126.06
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular weight:
32400.665
Reactions
11b-Hydroxyandrost-4-ene-3,17-dione + NADP → Adrenosterone + NADPH + Hydrogen Iondetails