(1S,9aR,11aS)-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 (3,3-dimethyl-butyl)-amide

ID: ALA24033

Max Phase: Preclinical

Molecular Formula: C25H40N2O2

Molecular Weight: 400.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)CCNC(=O)[C@H]1CCC2C3CNC4=CC(=O)CC[C@]4(C)C3CC[C@@]21C

Standard InChI:  InChI=1S/C25H40N2O2/c1-23(2,3)12-13-26-22(29)20-7-6-18-17-15-27-21-14-16(28)8-10-25(21,5)19(17)9-11-24(18,20)4/h14,17-20,27H,6-13,15H2,1-5H3,(H,26,29)/t17?,18?,19?,20-,24+,25-/m1/s1

Standard InChI Key:  DRDSSIFDXYDAAO-YMYWZCFKSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    4.0375   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -6.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5 13  1  0
  6  4  1  0
  7  1  1  0
  8 12  1  0
  9  3  2  0
  7 10  1  1
 11  1  1  0
 12  6  1  0
 13 11  1  0
 14  4  1  0
 15  2  1  0
 16  7  1  0
 17 21  1  0
 18 10  2  0
 19 10  1  0
 20 17  2  0
 21 15  1  0
 22 26  1  0
  1 23  1  1
  2 24  1  1
 25 19  1  0
 26 25  1  0
 27 22  1  0
 28 22  1  0
 29 22  1  0
 16 14  1  0
  5  6  1  0
  8  3  1  0
 17  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA24033

   ---

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: 400.61

Molecular Weight (Monoisotopic): 400.3090

AlogP: 4.45

#Rotatable Bonds: 3

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.65

CX LogD: 3.65

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: 1.07

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]

Source

Source(1):

• Scientific Literature