(3alpha,5alpha)-3-hydroxypregnan-20-one)::1-((3R,5S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone::1-((3R,5S,10S,13S,17S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone::1-((3R,5S,10S,14S)-3-Hydroxy-10-methyl-13-(S)-methyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone::1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone::1-(3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-ethanone::3alpha-hydroxy-5alpha-pregnan-20-one::CHEMBL38856::US8575375, 10::allopregnanolone

ID: ALA38856

Chembl Id: CHEMBL38856

PubChem CID: 9883500

Max Phase: Preclinical

Molecular Formula: C21H34O2

Molecular Weight: 318.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)[C@H]1CCC2C3CC[C@H]4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C

Standard InChI:  InChI=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+/m0/s1

Standard InChI Key:  AURFZBICLPNKBZ-LOPWJTSLSA-N

Alternative Forms

1. Parent:

   

   ALA38856

   3alpha-Hydroxy-5alpha-pregnane-20-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 318.50

Molecular Weight (Monoisotopic): 318.2559

AlogP: 4.60

#Rotatable Bonds: 1

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 0

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: 2.21

References

1.  (2013)  Androstane and pregnane steroids with potent allosteric GABA receptor chloride ionophore modulating properties, 

2. Sun S, Fu J..  (2018)  Methyl-containing pharmaceuticals: Methylation in drug design.,  28  (20.0): [PMID:30243589] [10.1016/j.bmcl.2018.09.016]

Source

Source(2):

• Scientific Literature
• BindingDB Database