(4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-dimethyl-2-oxo-N-phenylhexadecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide

ID: ALA4064645

PubChem CID: 10500864

Max Phase: Preclinical

Molecular Formula: C25H34N2O2

Molecular Weight: 394.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(=O)N[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)Nc3ccccc3)CC[C@@H]12

Standard InChI:  InChI=1S/C25H34N2O2/c1-24-14-12-19-17(8-11-21-25(19,2)15-13-22(28)27-21)18(24)9-10-20(24)23(29)26-16-6-4-3-5-7-16/h3-7,17-21H,8-15H2,1-2H3,(H,26,29)(H,27,28)/t17-,18-,19-,20+,21+,24-,25+/m0/s1

Standard InChI Key:  CXCHAQSCCCXEAH-QKONGSNMSA-N

Molfile:  

     RDKit          2D

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    3.4875   -8.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1928   -9.3482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3023   -7.3176    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -8.5351    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -8.5516    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8866   -9.7568    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8835   -5.7462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446   -5.2870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4204   -6.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511   -7.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6872   -7.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2163   -6.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 20  2  0
  5 21  1  1
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  9 23  1  6
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  6 25  1  6
 19 26  1  0
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 26 28  1  0
 28 29  2  0
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 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4064645

   (1S,3aS,3bS,5aR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-N-phenyl-1,2,3,3a,3b,4,5,5a,6,8,9,9b,10,11-tetradecahydroindeno[5,4-f]quinoline-1-carboxamide

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: 394.56

Molecular Weight (Monoisotopic): 394.2620

AlogP: 4.76

#Rotatable Bonds: 2

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.76

Np Likeness Score: 0.71

References

1. Lao K, Sun J, Wang C, Wang Y, You Q, Xiao H, Xiang H..  (2017)  Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists.,  27  (17): [PMID:28757062] [10.1016/j.bmcl.2017.05.078]

Source

Source(1):

• Scientific Literature