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Showing Compound 7a-Hydroxytestosterone (FDB023273)

Record Information
Version1.0
Creation date2011-09-21 00:27:16 UTC
Update date2015-07-21 06:57:37 UTC
Primary IDFDB023273
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name7a-Hydroxytestosterone
Description4-Hydroxytestosterone is the 17-hydroxylated analog to formestane. It is commercially available on the internet as anabolic steroid for oral self-administration and does not have any therapeutic indication. Hence, only little information is available about its metabolism. So far, most studies dealt with 4-hydroxytestosterone as metabolite of formestane while one study investigated the glucuronic acid conjugates of metabolic products of 4-hydroxytestosterone. This substance is prohibited in sports by the World Anti-Doping Agency; there is to a considerable increase of structurally related steroids with anabolic effects offered via the internet. 4-Hydroxytestosterone is a metabolite of the steroidal aromatase inhibitor 4-hydroxyandrost-4-ene-3,17-dione (4OHA). (PMID: 17724580, 17610244, 17207827, 1284430) [HMDB]
CAS Number2141-17-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(17beta)-4,17-Dihydroxy-androst-4-en-3-oneHMDB
(3b,17a)-Androst-5-ene-3,17-diolHMDB
3b,17a-Dihydroxyandrost-5-eneHMDB
4,17beta-Dihydroxy-4-androstene-3-oneHMDB
4-Androstene-7alpha-17beta-diol-3-oneHMDB
4-OHTHMDB
7alpha-HydroxytestosteroneHMDB
Androst-5-ene-3b,17a-diolHMDB
D5-Androstene-3b,17a-diolHMDB
4,17 beta-Dihydroxy-4-androstene-3-oneHMDB
(17beta)-4,17-dihydroxy-Androst-4-en-3-onehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP2.48ALOGPS
logP2.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.4 m³·mol⁻¹ChemAxon
Polarizability34.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H28O3
IUPAC name(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11?,12?,13?,16-,18+,19-/m0/s1
InChI KeyBQOIJSIMMIDHMO-XRJYYLNASA-N
Isomeric SMILESC[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
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
  • 4-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Enol
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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-MS7a-Hydroxytestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004j-0090000000-f8c70e9c073ebf34b059Spectrum
Predicted GC-MS7a-Hydroxytestosterone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1022900000-600be045d8943f743d57Spectrum
Predicted GC-MS7a-Hydroxytestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS7a-Hydroxytestosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0095000000-1ed1d6e3a92671fd2ad0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0391000000-688b70f5d7af33f8cee6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0041-6690000000-280160a24bfda119b38cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-e348bdb79d40a4c67d8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-414113628118ffc4436dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-1090000000-78462554e3a1a05a840cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-92df155d883a35606e36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0095000000-c78824a01c7b942a579aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0049000000-dee580cc76c7cfcdaec8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0590000000-4682faf86ab20fed64d6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-4910000000-82ee78b7109f9f4b5333Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC05291
Pubchem Compound ID53477776
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03956
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
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference