(2E,2'E)-N,N'-(2,2'-Disulfanediylbis(ethane-2,1-diyl))bis(3-(3-bromo-5-nitrophenyl)-2-(hydroxyimino)propanamide)

ID: ALA2047713

PubChem CID: 57326507

Max Phase: Preclinical

Molecular Formula: C22H22Br2N6O8S2

Molecular Weight: 722.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCSSCCNC(=O)/C(Cc1cc(Br)cc([N+](=O)[O-])c1)=N/O)/C(Cc1cc(Br)cc([N+](=O)[O-])c1)=N/O

Standard InChI:  InChI=1S/C22H22Br2N6O8S2/c23-15-5-13(7-17(11-15)29(35)36)9-19(27-33)21(31)25-1-3-39-40-4-2-26-22(32)20(28-34)10-14-6-16(24)12-18(8-14)30(37)38/h5-8,11-12,33-34H,1-4,9-10H2,(H,25,31)(H,26,32)/b27-19+,28-20+

Standard InChI Key:  ITRHKQKDSGILLP-MKYUKRCKSA-N

Molfile:  

     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
   11.0431   -4.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0443   -3.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3294   -2.8342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6130   -3.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6159   -4.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3312   -4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8979   -2.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1841   -3.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4689   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1854   -4.0748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9005   -4.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4676   -2.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7551   -3.2521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400   -2.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3262   -3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6111   -2.8429    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5348   -2.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5360   -2.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8211   -3.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1047   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076   -2.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8229   -1.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -3.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3242   -2.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -3.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3229   -2.0246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3922   -1.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0407   -4.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -2.8473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1821   -2.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8972   -3.2565    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -0.7872    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2527   -3.2680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2533   -4.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668   -2.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3317   -5.3161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0474   -5.7265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6185   -5.7307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7591   -2.8352    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  9 12  2  0
  6  1  1  0
  9 13  1  0
  1  2  2  0
 13 14  1  0
  4  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
 24 25  1  0
 20 21  1  0
 24 26  2  0
 18 19  1  0
 26 27  1  0
 21 22  2  0
 25 28  2  0
 22 17  1  0
 25 29  1  0
 17 18  2  0
 29 30  1  0
 20 23  1  0
 30 31  1  0
 19 20  2  0
 31 32  1  0
 23 24  1  0
 32 16  1  0
  7  8  1  0
 22 33  1  0
  8  9  1  0
  4  5  1  0
 34 35  2  0
 34 36  1  0
 18 34  1  0
  8 10  2  0
  2  3  1  0
 10 11  1  0
 37 38  2  0
 37 39  1  0
  6 37  1  0
  5  6  2  0
  2 40  1  0
M  CHG  4  34   1  36  -1  37   1  39  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2047713

   (2E)-3-(3-bromo-5-nitrophenyl)-N-[2-[2-[[(2E)-3-(3-bromo-5-nitrophenyl)-2-hydroxyiminopropanoyl]amino]ethyldisulfanyl]ethyl]-2-hydroxyiminopropanamide

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: 722.39

Molecular Weight (Monoisotopic): 719.9307

AlogP: 4.09

#Rotatable Bonds: 15

Polar Surface Area: 209.66

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.03

CX Basic pKa: ┄

CX LogP: 4.57

CX LogD: 4.47

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.05

Np Likeness Score: -0.24

References

1. Baud MG, Leiser T, Haus P, Samlal S, Wong AC, Wood RJ, Petrucci V, Gunaratnam M, Hughes SM, Buluwela L, Turlais F, Neidle S, Meyer-Almes FJ, White AJ, Fuchter MJ..  (2012)  Defining the mechanism of action and enzymatic selectivity of psammaplin A against its epigenetic targets.,  55  (4): [PMID:22280363] [10.1021/jm2016182]

Source

Source(1):

• Scientific Literature