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

ID: ALA2047714

PubChem CID: 51033159

Max Phase: Preclinical

Molecular Formula: C26H34N4O6S4

Molecular Weight: 626.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C/C(=N\O)C(=O)NCCSSCCNC(=O)/C(Cc2ccc(SC)c(OC)c2)=N/O)ccc1SC

Standard InChI:  InChI=1S/C26H34N4O6S4/c1-35-21-15-17(5-7-23(21)37-3)13-19(29-33)25(31)27-9-11-39-40-12-10-28-26(32)20(30-34)14-18-6-8-24(38-4)22(16-18)36-2/h5-8,15-16,33-34H,9-14H2,1-4H3,(H,27,31)(H,28,32)/b29-19+,30-20+

Standard InChI Key:  GVLQQIPTRAJGBJ-CZYCKNNWSA-N

Molfile:  

     RDKit          2D

 40 41  0  0  0  0  0  0  0  0999 V2000
   10.8264   -2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1127   -1.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3963   -1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3992   -2.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1145   -2.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6812   -1.1112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9674   -1.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2522   -1.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9687   -2.3498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6838   -2.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2509   -0.2884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5384   -1.5271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8233   -1.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1095   -1.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3944   -1.1179    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7514   -0.2999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526   -1.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377   -1.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3213   -1.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3242   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395    0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6062   -1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8228   -1.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063   -0.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088    0.1118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241   -2.3610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -1.1223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2517   -1.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9655   -1.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806   -1.5315    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0421    0.9382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7577    1.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1188   -3.5834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8345   -3.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4715    0.1145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1859   -0.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5357   -2.7604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.2501   -2.3478    0.0000 C   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
 33 34  1  0
 22 33  1  0
  8  9  1  0
  4  5  1  0
 35 36  1  0
  6 35  1  0
  8 10  2  0
  2  3  1  0
 37 38  1  0
 17 37  1  0
 10 11  1  0
  5  6  2  0
 39 40  1  0
  1 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047714

   (2E)-2-hydroxyimino-N-[2-[2-[[(2E)-2-hydroxyimino-3-(3-methoxy-4-methylsulfanylphenyl)propanoyl]amino]ethyldisulfanyl]ethyl]-3-(3-methoxy-4-methylsulfanylphenyl)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: 626.85

Molecular Weight (Monoisotopic): 626.1361

AlogP: 4.21

#Rotatable Bonds: 17

Polar Surface Area: 141.84

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.72

CX Basic pKa: ┄

CX LogP: 4.09

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.05

Np Likeness Score: 0.00

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