(2E,2'E)-N,N'-(2,2'-Disulfanediylbis(ethane-2,1-diyl))bis(2-(hydroxyimino)-3-(3-iodo-4,5-dimethoxyphenyl)-propanamide)

ID: ALA2047710

PubChem CID: 57326408

Max Phase: Preclinical

Molecular Formula: C26H32I2N4O8S2

Molecular Weight: 846.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C/C(=N\O)C(=O)NCCSSCCNC(=O)/C(Cc2cc(I)c(OC)c(OC)c2)=N/O)cc(I)c1OC

Standard InChI:  InChI=1S/C26H32I2N4O8S2/c1-37-21-13-15(9-17(27)23(21)39-3)11-19(31-35)25(33)29-5-7-41-42-8-6-30-26(34)20(32-36)12-16-10-18(28)24(40-4)22(14-16)38-2/h9-10,13-14,35-36H,5-8,11-12H2,1-4H3,(H,29,33)(H,30,34)/b31-19+,32-20+

Standard InChI Key:  BYISZXMGZIBNJF-GKTLAHRSSA-N

Molfile:  

     RDKit          2D

 42 43  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
   -1.2042    0.9667    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   12.3841   -1.0852    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6299    0.1395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3443   -0.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6238   -1.5151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6245   -2.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3774   -2.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0918   -2.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9605   -3.5584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6762   -3.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 22 33  1  0
  2 34  1  0
  8  9  1  0
  4  5  1  0
 35 36  1  0
 17 35  1  0
  8 10  2  0
  2  3  1  0
 37 38  1  0
 18 37  1  0
 10 11  1  0
  5  6  2  0
 39 40  1  0
  1 39  1  0
  9 12  2  0
  6  1  1  0
 41 42  1  0
  6 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047710

   (2E)-2-hydroxyimino-N-[2-[2-[[(2E)-2-hydroxyimino-3-(3-iodo-4,5-dimethoxyphenyl)propanoyl]amino]ethyldisulfanyl]ethyl]-3-(3-iodo-4,5-dimethoxyphenyl)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: 846.50

Molecular Weight (Monoisotopic): 845.9751

AlogP: 3.99

#Rotatable Bonds: 17

Polar Surface Area: 160.30

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.27

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 4.32

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.05

Np Likeness Score: 0.20

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