(3alpha,17alpha)-3-[(trans-2,5-Dimethyl-4-{[2-(trifluoromethyl)phenyl]sulfonyl}piperazin-1-yl)methyl]-pregn-20-yne-3,17-diol

ID: ALA4556519

PubChem CID: 155556930

Max Phase: Preclinical

Molecular Formula: C35H49F3N2O4S

Molecular Weight: 650.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C#C[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4C[C@@](O)(CN5CC(C)N(S(=O)(=O)c6ccccc6C(F)(F)F)CC5C)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C35H49F3N2O4S/c1-6-34(42)16-14-28-26-12-11-25-19-33(41,18-17-31(25,4)27(26)13-15-32(28,34)5)22-39-20-24(3)40(21-23(39)2)45(43,44)30-10-8-7-9-29(30)35(36,37)38/h1,7-10,23-28,41-42H,11-22H2,2-5H3/t23?,24?,25-,26+,27-,28-,31-,32-,33+,34-/m0/s1

Standard InChI Key:  BPSYMZDGGLPWHZ-TXFUIGSWSA-N

Molfile:  

 
     RDKit          2D

 49 54  0  0  0  0  0  0  0  0999 V2000
    6.1750  -17.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4621  -17.2951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4611  -18.1189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5427  -15.1728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9596  -14.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1336  -14.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9596  -13.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6721  -14.8685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6721  -13.2173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3846  -13.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3811  -14.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0903  -14.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8077  -14.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0974  -13.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8073  -13.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8241  -11.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1026  -12.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5340  -12.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5252  -13.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3043  -13.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7947  -12.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3187  -12.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5287  -11.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5203  -14.0637    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5823  -11.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7990  -12.8171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0902  -14.0470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3772  -12.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3730  -15.2812    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7169  -15.1679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942  -15.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4775  -15.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8827  -16.5852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7093  -16.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1305  -15.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6378  -17.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356  -16.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109  -16.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9906  -17.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011  -17.9930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2245  -17.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4890  -14.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1156  -17.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6323  -18.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0047  -19.3700    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3218  -19.5225    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4833  -18.8594    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1423  -12.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9678  -12.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  0
  5  6  1  1
  7  5  1  0
  7  9  1  0
  5  8  1  0
  8 11  1  0
 10  9  1  0
 10 11  1  0
 10 14  1  0
 11 12  1  0
 12 13  1  0
 13 15  1  0
 14 15  1  0
 14 17  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 23  1  1
 19 24  1  6
 22 25  1  1
 15 26  1  1
 14 27  1  6
 10 28  1  1
 11 29  1  6
  6 30  1  0
 30 31  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33  2  1  0
  2 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 36  1  0
 31 42  1  0
 34 43  1  0
 44 45  1  0
 44 46  1  0
 44 47  1  0
 41 44  1  0
 22 48  1  0
 48 49  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4556519

   ---

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: 650.85

Molecular Weight (Monoisotopic): 650.3365

AlogP: 5.93

#Rotatable Bonds: 4

Polar Surface Area: 81.08

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 7.37

CX LogP: 5.69

CX LogD: 5.40

Aromatic Rings: 1

Heavy Atoms: 45

QED Weighted: 0.40

Np Likeness Score: 0.27

References

1. Cortés-Benítez F, Roy J, Perreault M, Maltais R, Poirier D..  (2019)  A- and D-Ring Structural Modifications of an Androsterone Derivative Inhibiting 17β-Hydroxysteroid Dehydrogenase Type 3: Chemical Synthesis and Structure-Activity Relationships.,  62  (15): [PMID:31268309] [10.1021/acs.jmedchem.9b00624]

Source

Source(1):

• Scientific Literature