(2E,2'E)-N,N'-(2,2'-Disulfanediylbis(ethane-2,1-diyl))bis(3-(3-bromo-4-(methylthio)phenyl)-2-(hydroxyimino)propanamide)

ID: ALA2047709

PubChem CID: 57326407

Max Phase: Preclinical

Molecular Formula: C24H28Br2N4O4S4

Molecular Weight: 724.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(C/C(=N\O)C(=O)NCCSSCCNC(=O)/C(Cc2ccc(SC)c(Br)c2)=N/O)cc1Br

Standard InChI:  InChI=1S/C24H28Br2N4O4S4/c1-35-21-5-3-15(11-17(21)25)13-19(29-33)23(31)27-7-9-37-38-10-8-28-24(32)20(30-34)14-16-4-6-22(36-2)18(26)12-16/h3-6,11-12,33-34H,7-10,13-14H2,1-2H3,(H,27,31)(H,28,32)/b29-19+,30-20+

Standard InChI Key:  AFPVJGBDFQJXBO-CZYCKNNWSA-N

Molfile:  

     RDKit          2D

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   10.2409   -2.3281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9562   -2.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5229   -1.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8091   -1.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0939   -1.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8104   -2.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2354   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9479   -0.2746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2328    0.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -2.3360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3782   -1.0973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -1.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8071   -1.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5222   -1.5065    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6244    0.1374    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2042    0.9667    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.3841   -1.0852    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3750   -3.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  2  0
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  4  7  1  0
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  3  4  2  0
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  7  8  1  0
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 17 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047709

   (2E)-3-(3-bromo-4-methylsulfanylphenyl)-N-[2-[2-[[(2E)-3-(3-bromo-4-methylsulfanylphenyl)-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: 724.59

Molecular Weight (Monoisotopic): 721.9360

AlogP: 5.71

#Rotatable Bonds: 15

Polar Surface Area: 123.38

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.43

CX Basic pKa: ┄

CX LogP: 5.94

CX LogD: 5.91

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.05

Np Likeness Score: 0.03

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