4-Pregnen-21-ol-3,20-dione-21-(4-nitrobenzenesufonate)

ID: ALA1093760

PubChem CID: 44550019

Max Phase: Preclinical

Molecular Formula: C27H33NO7S

Molecular Weight: 515.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(=O)COS(=O)(=O)c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C27H33NO7S/c1-26-13-11-19(29)15-17(26)3-8-21-22-9-10-24(27(22,2)14-12-23(21)26)25(30)16-35-36(33,34)20-6-4-18(5-7-20)28(31)32/h4-7,15,21-24H,3,8-14,16H2,1-2H3/t21-,22-,23-,24+,26-,27-/m0/s1

Standard InChI Key:  CSFFQWPGTTYNBO-YNHSGCSHSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
    5.4603   -9.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4603   -9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720   -8.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1720  -10.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879   -9.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6038  -10.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3196   -9.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3196   -9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0313   -8.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8160   -8.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3007   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8156   -7.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2285   -6.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0527   -6.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0313   -7.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0313   -6.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3196   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6038   -7.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6038   -8.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879   -9.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8879   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6038   -9.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3196   -8.1750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0313   -9.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7455  -10.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8146   -6.0815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4624   -6.0762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2864   -6.1165    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1099   -6.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2708   -6.9414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3037   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5276   -6.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3502   -6.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7550   -6.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3310   -5.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5097   -5.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5825   -6.0819    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9862   -5.3624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0037   -6.7913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 19  1  0
  8 19  1  0
 19 20  1  0
  3 20  1  0
  5 20  1  0
 20 21  1  1
 19 22  1  6
  8 23  1  1
  9 24  1  6
  1 25  2  0
  1  2  1  0
 13 26  2  0
  2  3  1  0
 14 27  1  0
  1  4  1  0
 27 28  1  0
  4  5  2  0
 28 29  1  0
  5  6  1  0
 28 30  2  0
  6  7  1  0
 28 31  2  0
  7  8  1  0
 29 32  2  0
  8  9  1  0
 32 33  1  0
  9 10  1  0
 33 34  2  0
 10 11  1  0
 34 35  1  0
 11 12  1  0
 35 36  2  0
 36 29  1  0
 12 13  1  1
 13 14  1  0
 12 15  1  0
 37 38  2  0
 37 39  1  0
 34 37  1  0
M  CHG  2  37   1  39  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1093760

   [2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 4-nitrobenzenesulfonate

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: 515.63

Molecular Weight (Monoisotopic): 515.1978

AlogP: 5.02

#Rotatable Bonds: 6

Polar Surface Area: 120.65

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.32

CX LogD: 5.32

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.30

Np Likeness Score: 0.84

References

1. Dexheimer TS, Gediya LK, Stephen AG, Weidlich I, Antony S, Marchand C, Interthal H, Nicklaus M, Fisher RJ, Njar VC, Pommier Y..  (2009)  4-Pregnen-21-ol-3,20-dione-21-(4-bromobenzenesulfonate) (NSC 88915) and related novel steroid derivatives as tyrosyl-DNA phosphodiesterase (Tdp1) inhibitors.,  52  (22): [PMID:19883083] [10.1021/jm901061s]

Source

Source(1):

• Scientific Literature