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Showing metabocard for Adrenosterone (BMDB0006772)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:25:53 UTC
Update Date2020-04-22 15:18:33 UTC
BMDB IDBMDB0006772
Secondary Accession Numbers
  • BMDB06772
Metabolite Identification
Common NameAdrenosterone
DescriptionAdrenosterone, also known as Adrenosterone or NSC 12166, 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. Adrenosterone is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Adrenosterone can be biosynthesized from 11b-hydroxyandrost-4-ene-3,17-dione through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In cattle, adrenosterone is involved in the metabolic pathway called the androstenedione metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Keto-androstenedioneChEBI
11-KetoandrostenedioneChEBI
11-oxoChEBI
11-Oxoandrost-4-ene-3,17-dioneChEBI
11-OxoandrostenedioneChEBI
11-Oxy-4-androstenedioneChEBI
4-Androsten-3,11,17-trioneChEBI
AndrenosteroneChEBI
Androst-4-ene-3,11,17-trioneChEBI
NSC 12166ChEBI
Reichstein's substance gChEBI
4-Androstene-3,11,17-trioneHMDB
Adrenosterone, 3H-labeledHMDB
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
Description 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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
BioavailabilityYesChemAxon
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0596-3910000000-521e74db879ee9f81a3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0973000000-767c7b546b71c185a624View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0469000000-25e6987364697bc536e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-059fceb486c74e543289View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dd82c6133109d0e6e28eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-ff5973ba5b3491dd86a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-4190000000-b9abb2323ddbbd68f5caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-2789ee380fa1a8c91727View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0191000000-4cdffaa52886ce780121View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006772
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024074
KNApSAcK IDNot Available
Chemspider ID194597
KEGG Compound IDC05285
BioCyc IDCPD-18926
BiGG IDNot Available
Wikipedia LinkAdrenosterone
METLIN IDNot Available
PubChem Compound223997
PDB IDNot Available
ChEBI ID2495
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available