(1S,9aR,11aS)-6,9a,11a-Trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid (2,5-bis-trifluoromethyl-phenyl)-amide

ID: ALA25183

Max Phase: Preclinical

Molecular Formula: C28H32F6N2O2

Molecular Weight: 542.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2NCC3C(CC[C@@]4(C)C3CC[C@@H]4C(=O)Nc3cc(C(F)(F)F)ccc3C(F)(F)F)[C@@]2(C)CCC1=O

Standard InChI:  InChI=1S/C28H32F6N2O2/c1-14-22(37)9-11-26(3)18-8-10-25(2)17(16(18)13-35-23(14)26)6-7-20(25)24(38)36-21-12-15(27(29,30)31)4-5-19(21)28(32,33)34/h4-5,12,16-18,20,35H,6-11,13H2,1-3H3,(H,36,38)/t16?,17?,18?,20-,25+,26-/m1/s1

Standard InChI Key:  VEBGFZDIXSWIAZ-NLVWCVCDSA-N

Molfile:  

     RDKit          2D

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    3.8542   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -6.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -5.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1417   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -3.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3000   -3.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8167   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5750   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -5.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0417   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7167   -6.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -0.5875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3750   -2.0000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -0.6042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.6750   -1.2500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8125   -2.6417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4417   -2.6625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -4.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -3.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -7.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  1  2  0
  5  9  1  0
  6  1  1  0
  7  2  1  0
  8 12  1  0
  9 15  1  0
 13 10  1  1
 11  5  1  0
 12 16  1  0
 13  3  1  0
 14 18  1  0
 15 10  1  0
 16  6  1  0
 17  4  1  0
 18 21  1  0
 19 22  1  0
 20  2  1  0
 21  9  2  0
 22  7  1  0
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 24  5  2  0
 25 23  1  0
 26 10  2  0
 27 17  1  0
 28 18  2  0
 29 17  2  0
 30 11  1  0
 31 11  1  0
 32 11  1  0
 33 14  1  0
 34 14  1  0
 35 14  1  0
  2 36  1  1
  3 37  1  1
 38  4  1  0
  7 12  1  0
 20 27  1  0
  3 19  1  0
 25 13  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA25183

   ---

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: 542.56

Molecular Weight (Monoisotopic): 542.2368

AlogP: 6.97

#Rotatable Bonds: 2

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 5.91

CX LogD: 5.91

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.40

Np Likeness Score: 0.40

References

1. Kenny B, Ballard S, Blagg J, Fox D..  (1997)  Pharmacological options in the treatment of benign prostatic hyperplasia.,  40  (9): [PMID:9135028] [10.1021/jm960697s]

2. Guarna, A A and 8 more authors.  2000-10-05  Benzo[c]quinolizin-3-ones: a novel class of potent and selective nonsteroidal inhibitors of human steroid 5alpha-reductase 1.  [PMID:11020287]

3. Hartmann, R W RW and 5 more authors.  2000-11-02  Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17 alpha-hydroxylase/C17-20-lyase) and 5 alpha-reductase types 1 and 2.  [PMID:11063622]

4. Occhiato, Ernesto G EG and 11 more authors.  2004-07-01  Synthesis, biological activity, and three-dimensional quantitative structure-activity relationship model for a series of benzo[c]quinolizin-3-ones, nonsteroidal inhibitors of human steroid 5alpha-reductase 1.  [PMID:15214782]

5. Handratta, Venkatesh D VD and 10 more authors.  2005-04-21  Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens: synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in the LAPC4 human prostate cancer xenograft model.  [PMID:15828836]

6. Lao, Kejing K and 6 more authors.  2017-09-01  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.  [PMID:28757062]

Source

Source(1):

• Scientific Literature