7b-Hydroxydehydroepiandrosterone (CHEM035686)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:59:22 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035686
Identification
Common Name7b-Hydroxydehydroepiandrosterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3b,7b)-3,7-Dihydroxy-androst-5-en-17-oneHMDB
3b,7b-Dihydroxy-5-androsten-17-oneHMDB
3b,7b-Dihydroxy-5-androstene-17-oneHMDB
3b,7b-Dihydroxy-androst-5-en-17-oneHMDB
3b,7b-Dihydroxy-ost-5-en-17-oneHMDB
7-b-OH-DHEAHMDB
7-beta-OH-DHEAHMDB
7b-Hydroxy dehydroepiandrosteroneHMDB
7b-Hydroxy-dheaHMDB
Androst-5-ene-3b,7b-diol-17-oneHMDB
7-Hydroxydehydroepiandrosterone, (3beta)-isomerMeSH, HMDB
7beta-OH-DHEAMeSH, HMDB
7beta-HydroxydehydroepiandrosteroneMeSH, HMDB
7 alpha-HydroxydehydroepiandrosteroneMeSH, HMDB
7-Hydroxydehydroepiandrosterone, (3beta,7beta)-isomerMeSH, HMDB
7-HydroxydehydroepiandrosteroneMeSH, HMDB
Chemical FormulaC19H28O3
Average Molecular Mass304.424 g/mol
Monoisotopic Mass304.204 g/mol
CAS Registry Number2487-48-1
IUPAC Name(1S,2R,5S,9R,10R,11S,15S)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one
Traditional Name7b-Hydroxy-DHEA
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)C=C2C[C@@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h10,12-15,17,20-21H,3-9H2,1-2H3/t12-,13-,14-,15-,17-,18-,19-/m0/s1
InChI KeyOLPSAOWBSPXZEA-GCNMQWDSSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.84ALOGPS
logP2.21ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.1 m³·mol⁻¹ChemAxon
Polarizability35 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g0-0390000000-5b84fc74cc8c3d885c1bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1735900000-cde53af4934fd251f9d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-003d307a3c381597e38bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-0190000000-7563041720b768705389Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-3190000000-8012f9fad41969d73d46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-3459db2d82d83321802fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0098000000-6a1aaf578c3c1719798aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-2090000000-85d4a8001358a115f59bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-8b3060136e49afe5a336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0093000000-e42b11a1c3c059294db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0069000000-61a09d88b13611d21a89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0670-1981000000-b0f1410f207bdaec9fa1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05dl-3910000000-4b2efd9d887548375fc0Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004624
FooDB IDFDB023384
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7993704
ChEBI ID712193
PubChem Compound ID9817954
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pouzar, Vladimir; Slavikova, Tereza; Cerny, Ivan. On Steroids. 387. Synthesis of (19E)-3b,7b-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, new hapten for 7b-hydroxydehydroepiandrosterone (3b,7b-dihydroxyandrost-5-en-17-one). Collection of Czechoslovak Chemical Communications (1997), 62(1), 109-123.
2. Pouzar, Vladimir; Slavikova, Tereza; Cerny, Ivan. On Steroids. 387. Synthesis of (19E)-3b,7b-dihydroxy-17-oxoandrost-5-en-19-al 19-(O-carboxymethyl)oxime, new hapten for 7b-hydroxydehydroepiandrosterone (3b,7b-dihydroxyandrost-5-en-17-one). Collection of Czechoslovak Chemical Communications (1997), 62(1), 109-123.
3. Hennebert O, Chalbot S, Alran S, Morfin R: Dehydroepiandrosterone 7alpha-hydroxylation in human tissues: possible interference with type 1 11beta-hydroxysteroid dehydrogenase-mediated processes. J Steroid Biochem Mol Biol. 2007 May;104(3-5):326-33. Epub 2007 Mar 24.
4. Robinzon B, Michael KK, Ripp SL, Winters SJ, Prough RA: Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases? Arch Biochem Biophys. 2003 Apr 15;412(2):251-8.