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)-2,2,2-trifluoroacetamide

ID: ALA3978938

PubChem CID: 134151913

Max Phase: Preclinical

Molecular Formula: C26H33F3N2O

Molecular Weight: 446.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H](NC(=O)C(F)(F)F)CC1CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C26H33F3N2O/c1-24-11-9-18(31-23(32)26(27,28)29)14-17(24)5-6-19-21-8-7-20(16-4-3-13-30-15-16)25(21,2)12-10-22(19)24/h3-4,7,13,15,17-19,21-22H,5-6,8-12,14H2,1-2H3,(H,31,32)/t17?,18-,19-,21-,22-,24-,25+/m0/s1

Standard InChI Key:  UMSYICAEHRJDIF-HSLNWIHESA-N

Molfile:  

     RDKit          2D

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   32.2458   -7.7262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   31.5411   -6.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5136   -6.9255    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3978938

   ---

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: 446.56

Molecular Weight (Monoisotopic): 446.2545

AlogP: 6.16

#Rotatable Bonds: 2

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: 8.33

CX Basic pKa: 4.81

CX LogP: 5.22

CX LogD: 5.17

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.59

Np Likeness Score: 1.13

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