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

ID: ALA2047712

PubChem CID: 51033160

Max Phase: Preclinical

Molecular Formula: C22H24N6O8S2

Molecular Weight: 564.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCSSCCNC(=O)/C(Cc1cccc([N+](=O)[O-])c1)=N/O)/C(Cc1cccc([N+](=O)[O-])c1)=N/O

Standard InChI:  InChI=1S/C22H24N6O8S2/c29-21(19(25-31)13-15-3-1-5-17(11-15)27(33)34)23-7-9-37-38-10-8-24-22(30)20(26-32)14-16-4-2-6-18(12-16)28(35)36/h1-6,11-12,31-32H,7-10,13-14H2,(H,23,29)(H,24,30)/b25-19+,26-20+

Standard InChI Key:  XSCWTGRIWSPFBD-FQHZWJPGSA-N

Molfile:  

     RDKit          2D

 38 39  0  0  0  0  0  0  0  0999 V2000
   11.2014   -3.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2026   -2.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4877   -2.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7713   -2.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7742   -3.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4895   -3.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0562   -2.1821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3424   -2.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6272   -2.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3437   -3.4207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0588   -3.8321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9134   -2.5980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983   -2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4845   -2.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7694   -2.1888    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1978   -2.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4813   -1.3705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2338   -0.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1991   -3.4319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9116   -2.1932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6267   -2.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3405   -2.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556   -2.6024    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6686   -0.1272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842    0.2832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9553    0.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9195   -2.1802    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9201   -1.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6336   -2.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
  5  6  2  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
  8  9  1  0
 33 34  2  0
 33 35  1  0
 22 33  1  0
  4  5  1  0
  8 10  2  0
  2  3  1  0
 36 37  2  0
 36 38  1  0
  2 36  1  0
M  CHG  4  33   1  35  -1  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2047712

   (2E)-2-hydroxyimino-N-[2-[2-[[(2E)-2-hydroxyimino-3-(3-nitrophenyl)propanoyl]amino]ethyldisulfanyl]ethyl]-3-(3-nitrophenyl)propanamide

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: 564.60

Molecular Weight (Monoisotopic): 564.1097

AlogP: 2.56

#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: 8.37

CX Basic pKa: ┄

CX LogP: 3.03

CX LogD: 2.99

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.06

Np Likeness Score: -0.25

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