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

ID: ALA3976482

PubChem CID: 134152152

Max Phase: Preclinical

Molecular Formula: C28H40N2O

Molecular Weight: 420.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C(=O)N[C@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1

Standard InChI:  InChI=1S/C28H40N2O/c1-18(2)26(31)30-21-11-13-27(3)20(16-21)7-8-22-24-10-9-23(19-6-5-15-29-17-19)28(24,4)14-12-25(22)27/h5-6,9,15,17-18,20-22,24-25H,7-8,10-14,16H2,1-4H3,(H,30,31)/t20?,21-,22-,24-,25-,27-,28+/m0/s1

Standard InChI Key:  YRFIBCQGWPFBMW-RBYQFOCYSA-N

Molfile:  

     RDKit          2D

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   32.0075   -6.7092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3976482

   ---

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: 420.64

Molecular Weight (Monoisotopic): 420.3141

AlogP: 6.26

#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: 5.33

CX LogD: 5.33

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: 1.23

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