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Showing Compound Androstanediol (FDB022074)

Record Information
Version1.0
Creation date2011-09-21 00:08:03 UTC
Update date2015-10-09 22:30:52 UTC
Primary IDFDB022074
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAndrostanediol
DescriptionAndrostanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254, 16040068, 11744084) [HMDB]
CAS Number25126-76-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-a-androstanediolhmdb
3-alpha-androstanediolhmdb
3alpha-androstanediolhmdb
5 a-androstane-3 a, 17 b-diolhmdb
5 alpha-androstane-3 alpha, 17 beta-diolhmdb
5-a-androstane-3-a, 17-b-diolhmdb
5-alpha-androstan-3-alpha,17-beta-diolhmdb
5-alpha-androstane-3-a, 17-beta-diolhmdb
5-alpha-androstane-3-alpha-17-beta-diolhmdb
Androstane-3,17-diolhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP3.56ALOGPS
logP3.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability35.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H32O2
IUPAC name(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
InChI IdentifierInChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1
InChI KeyCBMYJHIOYJEBSB-UNPXRYTGSA-N
Isomeric SMILES[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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
Predicted GC-MSAndrostanediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bdSpectrum
Predicted GC-MSAndrostanediol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-2237900000-35be1627cada18777db8Spectrum
Predicted GC-MSAndrostanediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrostanediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrostanediol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrostanediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrostanediol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrostanediol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0090000000-22d60c19836ea8b4c2912016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0390000000-edb0fb77b27575b4b7292016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2980000000-cd6eafa93f3164ed780a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-bc689c3cdfdf044c011e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0090000000-bfbc140857bbdb62bcff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vm-1290000000-bced1e06a8686f3501af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-11452f48ce72555f1f282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-11452f48ce72555f1f282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-0090000000-ac9e93370094e8aebfa12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0090000000-36f4d97265b0d994d6282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-3940000000-b87bad8b672cc5fb32b02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-3900000000-0f8ce10c286f165d6e0f2021-09-22View Spectrum
NMRNot Available
ChemSpider ID390064
ChEMBL IDCHEMBL194532
KEGG Compound IDC07632
Pubchem Compound ID441301
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00495
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference