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

ID: ALA2115222

Max Phase: Preclinical

Molecular Formula: C27H29ClF6N2O2

Molecular Weight: 562.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CNC4=C(Cl)C(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(=O)Nc1c(C(F)(F)F)cccc1C(F)(F)F

Standard InChI:  InChI=1S/C27H29ClF6N2O2/c1-24-10-8-15-13(12-35-22-20(28)19(37)9-11-25(15,22)2)14(24)6-7-18(24)23(38)36-21-16(26(29,30)31)4-3-5-17(21)27(32,33)34/h3-5,13-15,18,35H,6-12H2,1-2H3,(H,36,38)/t13-,14-,15-,18+,24-,25+/m0/s1

Standard InChI Key:  FIRKCWVDFVAVJO-QNLPRMKJSA-N

Molfile:  

     RDKit          2D

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    5.3267   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -7.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -2.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2510   -3.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8899   -7.7915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1763   -4.1275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938   -6.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3190   -6.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3703   -4.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8000   -3.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5883   -5.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8213   -3.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561   -6.5533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -8.6131    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0436   -7.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3002   -3.2981    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.8736    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5370   -2.2701    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5391   -4.5830    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6060   -3.6329    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0602   -4.1703    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5080   -2.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1529   -1.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3190   -4.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9590   -1.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6064   -5.7322    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3190   -6.9733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8938   -6.9617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4 11  1  0
  5  1  2  0
  6  3  1  0
  7  3  2  0
  8  1  1  0
  9 12  1  0
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 15 17  1  0
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 27 18  2  0
 28 13  1  0
 29 13  1  0
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 32 14  1  0
 33 14  1  0
  2 34  1  1
 35  7  1  0
 36  6  2  0
  4 37  1  1
 38 35  2  0
 15 10  1  0
 25 20  1  0
 19  4  1  0
 16 23  1  0
 38 36  1  0
 15 39  1  1
 11 40  1  6
 10 41  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2115222

   ---

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: 562.98

Molecular Weight (Monoisotopic): 562.1822

AlogP: 7.14

#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: 11.80

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.90

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.38

Np Likeness Score: 0.49

References

1. Frye SV, Haffner CD, Maloney PR, Hiner RN, Dorsey GF, Noe RA, Unwalla RJ, Batchelor KW, Bramson HN, Stuart JD..  (1995)  Structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase by 6-azaandrost-4-en-3-ones: optimization of the C17 substituent.,  38  (14): [PMID:7629802] [10.1021/jm00014a015]

2. Frye SV, Haffner CD, Maloney PR, Hiner RN, Dorsey GF, Noe RA, Unwalla RJ, Batchelor KW, Bramson HN, Stuart JD..  (1995)  Structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase by 6-azaandrost-4-en-3-ones: optimization of the C17 substituent.,  38  (14): [PMID:7629802] [10.1021/jm00014a015]

Source

Source(1):

• Scientific Literature