Showing Metabocard for 3alpha-hydroxy-5beta-pregnan-20-one (BASm0000058)

Common Name3alpha-hydroxy-5beta-pregnan-20-one
Description3alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).
Structure
Molecular FormulaC21H34O2
Average Mass318.49350
Monoisotopic Mass318.25588
IUPAC Name1-[(2S,5R,7R,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional NamePregnanolone
CAS Registry NumberNot Available
SMILESCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI IdentifierInChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15-,16?,17-,18?,19?,20+,21-/m1/s1
InChI KeyAURFZBICLPNKBZ-KCZNCWLVSA-N
CHEBI IDCHEBI:1712
HMDB IDHMDB0006759
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 Solubility1.36e-03 g/l
logP4.28
logS-5.37
pKa (Strongest Acidic)18.30
pKa (Strongest Basic)-1.36
Hydrogen Acceptor Count2
Hydrogen Donor Count1
Polar Surface Area37.3 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity92.91 m³·mol⁻¹
Polarizability38.36

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