(8R,9S,10R,13S,14S)-17-(5-(difluoromethyl)pyridin-3-yl)-6,10,13-trimethyl-6,7, 8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3973535

PubChem CID: 68087375

Max Phase: Preclinical

Molecular Formula: C26H31F2NO

Molecular Weight: 411.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1C[C@@H]2[C@H](CC[C@]3(C)C(c4cncc(C(F)F)c4)=CC[C@@H]23)[C@@]2(C)CCC(=O)C=C12

Standard InChI:  InChI=1S/C26H31F2NO/c1-15-10-19-21-5-4-20(16-11-17(24(27)28)14-29-13-16)25(21,2)9-7-22(19)26(3)8-6-18(30)12-23(15)26/h4,11-15,19,21-22,24H,5-10H2,1-3H3/t15?,19-,21-,22-,25+,26+/m0/s1

Standard InChI Key:  NHUAZHCIDQXGIK-DBUIOMFGSA-N

Molfile:  

     RDKit          2D

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   16.8946  -25.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7632  -25.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3925  -25.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6834  -22.4486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   16.1891  -26.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0561  -25.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1676  -26.1203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8884  -24.8786    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0725  -22.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.1669  -24.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1743  -25.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1257  -21.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8798  -24.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4805  -26.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5996  -26.1077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4356  -23.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6786  -23.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4541  -24.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6074  -25.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7569  -21.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9522  -21.5976    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.0020  -20.6281    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1935  -27.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3503  -26.9747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3973535

   (8R,9S,10R,13S,14S)-17-[5-(difluoromethyl)pyridin-3-yl]-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

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: 411.54

Molecular Weight (Monoisotopic): 411.2374

AlogP: 6.79

#Rotatable Bonds: 2

Polar Surface Area: 29.96

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.10

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.54

Np Likeness Score: 1.45

References

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

Source

Source(1):

• Patent Bioactivity Data