(8R,9S,10R,13S)-10,13-dimethyl-6-phenyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13-octahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3981801

PubChem CID: 68087035

Max Phase: Preclinical

Molecular Formula: C30H31NO

Molecular Weight: 421.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC(c4ccccc4)C4=CC(=O)CC[C@@]43C)C1=CC=C2c1cccnc1

Standard InChI:  InChI=1S/C30H31NO/c1-29-15-13-27-24(26(29)11-10-25(29)21-9-6-16-31-19-21)18-23(20-7-4-3-5-8-20)28-17-22(32)12-14-30(27,28)2/h3-11,16-17,19,23-24,27H,12-15,18H2,1-2H3/t23?,24-,27-,29+,30+/m0/s1

Standard InChI Key:  RJUWDMZQCCRHJY-NDOZEIIQSA-N

Molfile:  

     RDKit          2D

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   32.5650  -26.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1375  -26.6711    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:

   

   ALA3981801

   (8R,9S,10R,13S)-10,13-dimethyl-6-phenyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12-octahydrocyclopenta[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: 421.58

Molecular Weight (Monoisotopic): 421.2406

AlogP: 6.92

#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: 4.77

CX LogP: 5.55

CX LogD: 5.55

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: 1.43

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