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

ID: ALA2047706

PubChem CID: 11005732

Max Phase: Preclinical

Molecular Formula: C22H24F2N4O4S2

Molecular Weight: 510.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCSSCCNC(=O)/C(Cc1ccc(F)cc1)=N/O)/C(Cc1ccc(F)cc1)=N/O

Standard InChI:  InChI=1S/C22H24F2N4O4S2/c23-17-5-1-15(2-6-17)13-19(27-31)21(29)25-9-11-33-34-12-10-26-22(30)20(28-32)14-16-3-7-18(24)8-4-16/h1-8,31-32H,9-14H2,(H,25,29)(H,26,30)/b27-19+,28-20+

Standard InChI Key:  OGTDVWHHMIDAPH-MKYUKRCKSA-N

Molfile:  

     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
   11.6681   -2.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6693   -1.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9544   -1.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2380   -1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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
    9.5255   -2.7362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0926   -0.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3801   -1.5021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6650   -1.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9512   -1.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2361   -1.0929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -0.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110   -1.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1961   -1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4797   -1.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826   -0.2713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
   12.3827   -2.7368    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6244    0.1374    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1 33  1  0
  8  9  1  0
  4  5  1  0
  8 10  2  0
  2  3  1  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
  7  8  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
 17 34  1  0
 32 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047706

   (2E)-3-(4-fluorophenyl)-N-[2-[2-[[(2E)-3-(4-fluorophenyl)-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: 510.59

Molecular Weight (Monoisotopic): 510.1207

AlogP: 3.02

#Rotatable Bonds: 13

Polar Surface Area: 123.38

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.45

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.40

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.11

Np Likeness Score: -0.10

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