Back to Compounds

17-alpha,20-alpha-Dihydroxypregn-4-en-3-one (PC000927)

Record Information
Version1.0
Creation date2015-10-09 22:33:26 UTC
Update date2017-01-19 02:36:41 UTC
FoodComEx IDPC000927
FoodDB RecordFDB028344
Chemical Information
Name17-alpha,20-alpha-Dihydroxypregn-4-en-3-one
Description17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one (17 alpha, 20 alpha-OHP) is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labor and delivery (PMID: 6874891). 17 alpha, 20 alpha-dihydroxy-4-pregnen-3-one is known to be a substrate for the enzyme 20a-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hrs prior to parturition ovarian 20alpha-HSD activity is acutely stimulated. [HMDB]
CAS Number652-69-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(20S)-17,20-dihydroxypregn-4-en-3-onehmdb
17 alpha, 20 alpha-OHPhmdb
17 alpha, 20 alpha-Phmdb
17,20 alpha-OHPhmdb
17a,20a-Dihydroxypregn-4-en-3-onehmdb
17alpha,20alpha-Dihydroxypregn-4-en-3-onehmdb
17α,20α-dihydroxypregn-4-en-3-oneGenerator
Chemical FormulaC21H32O3
IUPAC name(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
InChI IdentifierInChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1
InChI KeyMASCESDECGBIBB-HNXXTFFGSA-N
Isomeric SMILES[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Average Molecular Weight332.477
Monoisotopic Molecular Weight332.23514489
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-hydroxysteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-diol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 17,20-dihydroxypregn-4-en-3-one (CHEBI:16418 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030183 )
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 5 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
Toronto Research Chemicals P712075