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5a-Androstane-3b,17b-diol (PC000479)

Record Information
Version1.0
Creation date2015-10-09 22:30:52 UTC
Update date2017-01-19 02:36:25 UTC
FoodComEx IDPC000479
FoodDB RecordFDB022073
Chemical Information
Name5a-Androstane-3b,17b-diol
DescriptionAndrostane-3,17-diol is a metabolite of dihydrotestosterone. It doesn't bind androgen receptors, but efficiently binds the estrogen receptor beta and inhibits prostate cancer cell migration through the activation of estrogen receptor beta. (PMID 15958594) [HMDB]
CAS Number571-20-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3b,5a,17b)-Androstane-3,17-diolGenerator
(3beta,5alpha,17beta)-Androstane-3,17-diolhmdb
(3β,5α,17β)-androstane-3,17-diolGenerator
3b,17b-Androstanediolhmdb
3b,17b-Dihydroxy-5a-androstanehmdb
3beta,17beta-Dihydroxy-5alpha-androstaneChEBI
3β,17β-dihydroxy-5α-androstaneGenerator
5-a-ANDROSTANE-3-b,17b-diolGenerator
5-ALPHA-ANDROSTANE-3-BETA,17BETA-diolChEBI
5-α-androstane-3-β,17β-diolGenerator
5a-Androstan-3b,17b-diolGenerator
5alpha-Androstan-3beta,17beta-diolhmdb
5alpha-Androstane-3beta,17beta-diolhmdb
5α-androstan-3β,17β-diolGenerator
Chemical FormulaC19H32O2
IUPAC name(1S,2S,5S,7S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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-YSZCXEEOSA-N
Isomeric SMILES[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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 9593AJ
Toronto Research Chemicals A637526