Showing Metabocard for 5alpha-pregnane-3,20-dione (BASm0001637)

Common Name5alpha-pregnane-3,20-dione
Description5a-Pregnane-3,20-dione is a biologically active 5-alpha-reduced metabolite of plasma progesterone. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (allopregnanolone), a neuroactive steroid that binds with GABA(A) receptor.
Structure
Molecular FormulaC21H32O2
Average Mass316.47760
Monoisotopic Mass316.24023
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
Traditional Name5α-dihydroprogesterone
CAS Registry Number566-65-4
SMILESCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI IdentifierInChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyXMRPGKVKISIQBV-BJMCWZGWSA-N
CHEBI IDCHEBI:28952
HMDB IDHMDB0003759
Pathways
NameSMPDB/PathBank
Steroidogenesis
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency
17-alpha-hydroxylase deficiency (CYP17)
11-beta-hydroxylase deficiency (CYP11B1)
21-hydroxylase deficiency (CYP21)
Corticosterone methyl oxidase I deficiency (CMO I)
Corticosterone methyl oxidase II deficiency - CMO II
Apparent mineralocorticoid excess syndrome
3-Beta-Hydroxysteroid Dehydrogenase Deficiency
StateNot Available
Water Solubility1.29e-03 g/l
logP4.06
logS-5.39
pKa (Strongest Acidic)19.34
pKa (Strongest Basic)-7.05
Hydrogen Acceptor Count2
Hydrogen Donor Count0
Polar Surface Area34.14 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity91.88 m³·mol⁻¹
Polarizability37.86

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