3alpha-Hydroxy-3beta-methyl-21-(1',2',3'-triazol-2'-yl)-19-nor-5beta-pregnan-20-one

ID: ALA3427532

Chembl Id: CHEMBL3427532

Cas Number: 1430064-74-6

PubChem CID: 71553591

Max Phase: Preclinical

Molecular Formula: C23H35N3O2

Molecular Weight: 385.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(O)CC[C@H]2[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](C(=O)Cn4nccn4)CC[C@@H]32)C1

Standard InChI:  InChI=1S/C23H35N3O2/c1-22(28)9-7-16-15(13-22)3-4-18-17(16)8-10-23(2)19(18)5-6-20(23)21(27)14-26-24-11-12-25-26/h11-12,15-20,28H,3-10,13-14H2,1-2H3/t15-,16+,17-,18-,19+,20-,22-,23+/m1/s1

Standard InChI Key:  NNHRCSJWUBQYQV-YHWBJDLNSA-N

Alternative Forms

1. Parent:

   

   ALA3427532

   1-[(3R,5R,8R,9R,10S,13S,14S,17S)-3-hydroxy-3,13-dimethyl-2,4,5,6,7,8,9,10,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-(triazol-2-yl)ethanone

Molecule Features

Natural Product: No

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: 385.55

Molecular Weight (Monoisotopic): 385.2729

AlogP: 3.87

#Rotatable Bonds: 3

Polar Surface Area: 68.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.09

CX LogP: 3.39

CX LogD: 3.39

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.86

Np Likeness Score: 1.29

References

1. Martinez Botella G, Salituro FG, Harrison BL, Beresis RT, Bai Z, Shen K, Belfort GM, Loya CM, Ackley MA, Grossman SJ, Hoffmann E, Jia S, Wang J, Doherty JJ, Robichaud AJ..  (2015)  Neuroactive Steroids. 1. Positive Allosteric Modulators of the (γ-Aminobutyric Acid)A Receptor: Structure-Activity Relationships of Heterocyclic Substitution at C-21.,  58  (8): [PMID:25799373] [10.1021/acs.jmedchem.5b00032]

2. Martinez Botella G, Salituro FG, Harrison BL, Beresis RT, Bai Z, Blanco MJ, Belfort GM, Dai J, Loya CM, Ackley MA, Althaus AL, Grossman SJ, Hoffmann E, Doherty JJ, Robichaud AJ..  (2017)  Neuroactive Steroids. 2. 3α-Hydroxy-3β-methyl-21-(4-cyano-1H-pyrazol-1'-yl)-19-nor-5β-pregnan-20-one (SAGE-217): A Clinical Next Generation Neuroactive Steroid Positive Allosteric Modulator of the (γ-Aminobutyric Acid)A Receptor.,  60  (18): [PMID:28753313] [10.1021/acs.jmedchem.7b00846]

3. Blanco MJ, La D, Coughlin Q, Newman CA, Griffin AM, Harrison BL, Salituro FG..  (2018)  Breakthroughs in neuroactive steroid drug discovery.,  28  (2): [PMID:29223589] [10.1016/j.bmcl.2017.11.043]

Source

Source(1):

• Scientific Literature