3-((5aR,5bR,7aS,10aS,10bS,12aS)-5a,7a-dimethyl-3,4,5,5a,5b,6,7,7a,10,10a,10b,11,12,12a-tetradecahydro-1H-cyclopenta[5,6]naphtho[2,1-c]oxepin-8-yl)pyridine

ID: ALA3982387

PubChem CID: 68086704

Max Phase: Preclinical

Molecular Formula: C24H33NO

Molecular Weight: 351.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCCOC[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C24H33NO/c1-23-11-4-14-26-16-18(23)6-7-19-21-9-8-20(17-5-3-13-25-15-17)24(21,2)12-10-22(19)23/h3,5,8,13,15,18-19,21-22H,4,6-7,9-12,14,16H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1

Standard InChI Key:  IKGAOVKRBWWORL-VJLLXTKPSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   31.0973  -23.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8313  -23.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0461  -24.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0344  -25.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8041  -25.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3014  -24.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1056  -25.8638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.3223  -25.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3067  -26.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5894  -26.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8919  -26.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2398  -26.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4522  -26.5311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1045  -25.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4688  -25.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2742  -24.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9036  -25.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6168  -25.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6324  -24.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3486  -23.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6168  -25.8409    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.7008  -24.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9408  -27.0550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.3223  -24.6221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.1466  -23.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5548  -22.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8214  -21.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6229  -21.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1594  -22.2798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9034  -23.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  4  5  1  0
  6  5  1  0
  2  6  2  0
  4  7  1  6
  8  4  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
 13 14  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 11 17  1  0
 17 18  1  0
 19 18  1  0
 20 19  1  0
  3 20  1  0
  8 18  1  0
 18 21  1  6
 17 22  1  1
 11 23  1  6
  8 24  1  1
  3 25  1  1
 26  1  2  0
 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982387

   3-[(1S,2R,8R,11R,12S,16S)-2,16-dimethyl-6-oxatetracyclo[9.7.0.02,8.012,16]octadec-14-en-15-yl]pyridine

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: 351.53

Molecular Weight (Monoisotopic): 351.2562

AlogP: 5.74

#Rotatable Bonds: 1

Polar Surface Area: 22.12

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.64

Np Likeness Score: 1.49

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