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

ID: ALA2047693

PubChem CID: 57326406

Max Phase: Preclinical

Molecular Formula: C22H22Br2F2N4O4S2

Molecular Weight: 668.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NCCSSCCNC(=O)/C(Cc1ccc(F)c(Br)c1)=N/O)/C(Cc1ccc(F)c(Br)c1)=N/O

Standard InChI:  InChI=1S/C22H22Br2F2N4O4S2/c23-15-9-13(1-3-17(15)25)11-19(29-33)21(31)27-5-7-35-36-8-6-28-22(32)20(30-34)12-14-2-4-18(26)16(24)10-14/h1-4,9-10,33-34H,5-8,11-12H2,(H,27,31)(H,28,32)/b29-19+,30-20+

Standard InChI Key:  KVADKHILEASNMV-CZYCKNNWSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
   28.0556  -11.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0568  -10.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3420  -10.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6255  -10.9850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6284  -11.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3438  -12.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9104  -10.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1966  -10.9873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4815  -10.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1979  -11.8123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9130  -12.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4802   -9.7509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7677  -10.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.0525  -10.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3387  -10.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6236  -10.5804    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.3462  -13.0497    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   28.7702  -12.2243    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.4777   -9.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4766  -10.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1914  -11.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9078  -10.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9050   -9.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1896   -9.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6230  -11.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3368  -10.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0519  -10.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3355   -9.7621    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6204   -9.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0532  -11.8235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7657  -10.5849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4808  -10.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1947  -10.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9098  -10.9940    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1871   -8.5247    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.7632   -9.3501    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0
  8  9  1  0
  4  5  1  0
 19 20  2  0
  8 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
  9 12  2  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
  9 13  1  0
 26 27  1  0
  1  2  2  0
 26 28  2  0
 13 14  1  0
 28 29  1  0
  4  7  1  0
 27 30  2  0
 14 15  1  0
 27 31  1  0
  3  4  2  0
 31 32  1  0
 15 16  1  0
 32 33  1  0
  7  8  1  0
 33 34  1  0
  6 17  1  0
 24 35  1  0
 19 36  1  0
 34 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047693

   (2E)-3-(3-bromo-4-fluorophenyl)-N-[2-[2-[[(2E)-3-(3-bromo-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: 668.38

Molecular Weight (Monoisotopic): 665.9417

AlogP: 4.55

#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: 8.06

CX Basic pKa: ┄

CX LogP: 4.97

CX LogD: 4.88

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.08

Np Likeness Score: -0.18

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