(3aR,3bS,5aS,8bR)-3a,5a-dimethyl-6-(pyridin-3-yl)-1a,2,3,3a,3b,4,5,5a,8b,9-decahydrocyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10(1H)-one

ID: ALA3974498

PubChem CID: 68086760

Max Phase: Preclinical

Molecular Formula: C24H27NO

Molecular Weight: 345.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC(=O)C45CC4CC[C@]35C)C1=CC=C2c1cccnc1

Standard InChI:  InChI=1S/C24H27NO/c1-22-9-8-20-17(12-21(26)24-13-16(24)7-10-23(20,24)2)19(22)6-5-18(22)15-4-3-11-25-14-15/h3-6,11,14,16-17,20H,7-10,12-13H2,1-2H3/t16?,17-,20-,22+,23+,24?/m0/s1

Standard InChI Key:  OUHVEACSDYIANY-DZRNBHKKSA-N

Molfile:  

     RDKit          2D

 28 33  0  0  0  0  0  0  0  0999 V2000
   27.3738  -11.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6859  -10.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9880  -11.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2959  -10.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3004   -9.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9982   -9.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6916   -9.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3812   -9.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0775   -9.9338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7712   -9.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5301   -9.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0050   -9.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5397   -8.4913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7769   -8.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8620   -7.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0877   -8.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3898   -8.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0717  -10.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0775   -9.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.3812  -10.3236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.6961   -9.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3667  -11.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7975   -7.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5973   -7.5531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8552   -6.7785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3123   -6.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5082   -6.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2541   -7.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 10 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17  8  1  0
 18  9  1  0
  1 18  1  0
  9 19  1  1
  8 20  1  6
  7 21  1  1
  2  7  1  0
  4  2  1  0
  1 22  2  0
 13 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974498

   (1S,2R,10R,15S)-2,15-dimethyl-14-pyridin-3-ylpentacyclo[8.7.0.02,7.05,7.011,15]heptadeca-11,13-dien-8-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: 345.49

Molecular Weight (Monoisotopic): 345.2093

AlogP: 5.22

#Rotatable Bonds: 1

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: 3.92

CX LogD: 3.92

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: 1.88

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