Back to Compounds

Epiandrosterone (PC000384)

Record Information
Version1.0
Creation date2015-10-09 22:30:22 UTC
Update date2017-01-19 02:36:21 UTC
FoodComEx IDPC000384
FoodDB RecordFDB021984
Chemical Information
NameEpiandrosterone
DescriptionEpiandrosterone is a naturally occurring steroid synthesized in the adrenal cortex, gonads, brain, and gastrointestinal tract. It is less active than androsterone and excreted in small amounts in normal human urine. Epiandrosterone is a metabolite of the most abundant adrenal androgenic steroid dehydroepiandrosterone (DHEA) in young adult humans, but is not completely inactive and is considered an effector as well. Epiandrosterone is a precursor or substrate for cytochrome P450 species and enzymes (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase) that produce 7alpha- and 7beta-hydroxylated metabolites in the human brain and other organs. These 7-hydroxylated derivatives exert anti-glucocorticoid and neuroprotective effects. (PMID: 17017935, 12475725, 15650074, 15784286) [HMDB]
CAS Number481-29-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
3-Epiandrosteronehmdb
3b-Androsteronehmdb
3b-Hydroxy-17-oxo-5a-androstanehmdb
3b-Hydroxy-5a-androstan-17-onehmdb
3b-Hydroxy-5a-androstane-17-onehmdb
3b-Hydroxyandrostan-17-onehmdb
3b-Hydroxyetioallocholan-17-onehmdb
3b-OH-5a-Androstane-17-onehmdb
5a-Androstan-3b-ol-17-onehmdb
5a-Androstane-3b-ol-17-onehmdb
d-Epiandrosteronehmdb
epi-andosteronehmdb
epi-Androsteronehmdb
iso-Androsteronehmdb
Isoandrosteronehmdb
trans-Androsteronehmdb
Chemical FormulaC19H30O2
IUPAC name(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
InChI IdentifierInChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12?,13-,14-,15-,16-,18-,19-/m0/s1
InChI KeyQGXBDMJGAMFCBF-QRIARFFBSA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
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-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 300 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci H110
AKSci J10456
Glentham GP6146
Toronto Research Chemicals E578000
Toronto Research Chemicals KIT1140