Record Information
Version1.0
Creation date2011-09-21 00:39:28 UTC
Update date2018-05-29 01:53:11 UTC
Primary IDFDB024074
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 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]. [HMDB]
CAS Number382-45-6
Structure
Thumb
Synonyms
SynonymSource
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H24O3
IUPAC name(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAdrenosterone, non-derivatized, GC-MS Spectrumsplash10-004l-3910000000-dda2aae9c4577545506cSpectrum
GC-MSAdrenosterone, non-derivatized, GC-MS Spectrumsplash10-004l-3910000000-dda2aae9c4577545506cSpectrum
Predicted GC-MSAdrenosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-1590000000-60fcf2c287c8dac542eeSpectrum
Predicted GC-MSAdrenosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ab9-2940000000-06e07dc51a896789d933Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0290000000-a6dda3c4c0b1e8e4c477Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0090000000-572505448243920d7c46Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-6a4af6e2a1477f91dfbbSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0190000000-57c8256a5ea31b9519f8Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1091000000-6b6dae7a99821b529938Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-1092000000-9361c41ea86f032c634bSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-6d600d8c52e480412d37Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0159-0290000000-af6aba5ffbd5525ba43aSpectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0ab9-2940000000-06e07dc51a896789d933Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0596-3910000000-521e74db879ee9f81a3bSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-0973000000-767c7b546b71c185a624Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0469000000-25e6987364697bc536e2Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-059fceb486c74e543289Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0069000000-51d9ddcfd1d7b8a3e20cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0l7i-0291000000-7b42bb8a716d4c0700e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9j-2490000000-c88e67e966734b1d65eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-34ecec5ab91ebc5e78ddSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-4c027780977d32f6a16eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-2090000000-cdcd813d0ed227d587c1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-dd82c6133109d0e6e28eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-ff5973ba5b3491dd86a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-4190000000-b9abb2323ddbbd68f5caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0029000000-2789ee380fa1a8c91727Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0191000000-4cdffaa52886ce780121Spectrum
NMRNot Available
ChemSpider ID194597
ChEMBL IDCHEMBL485683
KEGG Compound IDC05285
Pubchem Compound ID223997
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06772
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference