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

ID: ALA4644930

PubChem CID: 156017867

Max Phase: Preclinical

Molecular Formula: C35H47N3O2S

Molecular Weight: 573.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@](O)(CN3CCN(C(=S)Nc4ccc5ccccc5c4)CC3)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12

Standard InChI:  InChI=1S/C35H47N3O2S/c1-33-15-16-35(40,22-26(33)8-10-28-29-11-12-31(39)34(29,2)14-13-30(28)33)23-37-17-19-38(20-18-37)32(41)36-27-9-7-24-5-3-4-6-25(24)21-27/h3-7,9,21,26,28-30,40H,8,10-20,22-23H2,1-2H3,(H,36,41)/t26-,28-,29-,30-,33-,34-,35+/m0/s1

Standard InChI Key:  XHTLWZSFBXQOQO-NZIHCCNHSA-N

Molfile:  

 
     RDKit          2D

 45 51  0  0  0  0  0  0  0  0999 V2000
    6.2256   -5.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9427   -5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558   -5.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558   -6.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9427   -6.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2256   -6.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4019   -6.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870   -6.9506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4019   -7.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870   -8.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655   -8.3814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507   -7.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655   -6.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7507   -9.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9251   -9.0948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5143   -9.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248  -10.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5149  -11.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890  -11.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792  -10.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6879   -9.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2759  -11.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6926  -12.6633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126  -12.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9234  -11.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1655   -9.8083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8137   -6.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3689   -6.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862   -6.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862   -5.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3689   -5.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3689   -4.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0863   -3.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7993   -4.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7993   -5.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5833   -5.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0683   -4.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5835   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7972   -3.1264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7993   -5.8271    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7993   -3.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3689   -5.8270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0862   -4.5906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558   -7.0628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558   -4.5905    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
 15 16  1  0
 17 16  2  0
 18 17  1  0
 19 18  2  0
 20 19  1  0
 21 20  2  0
 16 21  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18 25  1  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:

   

   ALA4644930

   ---

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: 573.85

Molecular Weight (Monoisotopic): 573.3389

AlogP: 6.50

#Rotatable Bonds: 3

Polar Surface Area: 55.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.88

CX Basic pKa: 7.71

CX LogP: 6.57

CX LogD: 6.09

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.41

Np Likeness Score: 0.46

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