N-((3R,10R,13S,14R)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl)cyclopropanecarboxamide

ID: ALA3965598

PubChem CID: 89817119

Max Phase: Preclinical

Molecular Formula: C28H36N2O

Molecular Weight: 416.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H](NC(=O)C3CC3)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C28H36N2O/c1-27-13-11-21(30-26(31)18-5-6-18)16-20(27)7-8-22-24-10-9-23(19-4-3-15-29-17-19)28(24,2)14-12-25(22)27/h3-4,7,9,15,17-18,21-22,24-25H,5-6,8,10-14,16H2,1-2H3,(H,30,31)/t21-,22+,24+,25+,27+,28-/m1/s1

Standard InChI Key:  DZAWAUYONSMYGD-LLPCUEEJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3965598

   N-[(3R,8R,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-yl]cyclopropanecarboxamide

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: 416.61

Molecular Weight (Monoisotopic): 416.2828

AlogP: 5.93

#Rotatable Bonds: 3

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 4.46

CX LogD: 4.46

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: 0.83

References

1.  (2013)  C-17-heteroaryl steroidal compounds as inhibitors of CYP11B, CYP17, and/or CYP21, 

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data