(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-3-[[4-(2-naphthylsulfonyl)piperazin-1-yl]methyl]-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one

ID: ALA4643563

PubChem CID: 156018276

Max Phase: Preclinical

Molecular Formula: C34H46N2O4S

Molecular Weight: 578.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@](O)(CN3CCN(S(=O)(=O)c4ccc5ccccc5c4)CC3)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12

Standard InChI:  InChI=1S/C34H46N2O4S/c1-32-15-16-34(38,22-26(32)8-10-28-29-11-12-31(37)33(29,2)14-13-30(28)32)23-35-17-19-36(20-18-35)41(39,40)27-9-7-24-5-3-4-6-25(24)21-27/h3-7,9,21,26,28-30,38H,8,10-20,22-23H2,1-2H3/t26-,28-,29-,30-,32-,33-,34+/m0/s1

Standard InChI Key:  SLFPTSAMLBNMLN-UJBQZKNZSA-N

Molfile:  

 
     RDKit          2D

 45 51  0  0  0  0  0  0  0  0999 V2000
    7.3871  -12.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1043  -12.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8174  -12.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8174  -13.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1043  -14.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3871  -13.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5634  -13.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1485  -14.5332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5634  -15.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1485  -15.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228  -15.9641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9122  -15.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228  -14.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9122  -16.6775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228  -17.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1486  -17.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5607  -18.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1498  -18.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3259  -18.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096  -18.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178  -19.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3334  -20.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473  -20.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5572  -19.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968  -16.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968  -17.0871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9752  -14.5326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5305  -14.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2478  -13.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2478  -12.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5305  -12.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5305  -11.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2479  -11.3481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -11.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -12.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7450  -12.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2300  -12.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7452  -11.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9589  -10.7047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -13.4097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -10.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5305  -13.4097    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2478  -12.1690    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8174  -14.6454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8174  -12.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  6  5  1  0
  1  6  1  0
  6  7  1  1
  7  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13 12  1  0
  8 13  1  0
 11 14  1  0
 14 15  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 18 24  1  0
 14 25  2  0
 14 26  2  0
  6 27  1  0
  4 28  1  0
 29 28  1  0
 30 29  1  0
 31 30  1  0
  3 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 30 35  1  0
 35 36  1  0
 37 36  1  0
 38 37  1  0
 34 38  1  0
 38 39  2  0
 35 40  1  6
 34 41  1  1
 31 42  1  6
 30 43  1  1
  4 44  1  6
  3 45  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4643563

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 578.82

Molecular Weight (Monoisotopic): 578.3178

AlogP: 5.49

#Rotatable Bonds: 4

Polar Surface Area: 77.92

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 6.92

CX LogP: 5.38

CX LogD: 5.26

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.52

Np Likeness Score: 0.44

References

1. Boutin S, Roy J, Maltais R, Poirier D..  (2020)  Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells - Identifying inhibitors of non-classical pathways producing the most potent androgen.,  30  (2): [PMID:31753699] [10.1016/j.bmcl.2019.126783]

Source

Source(1):

• Scientific Literature