(E)-3-(3-Bromo-4-hydroxyphenyl)-N-(3-(2-((E)-3-(3-bromo-4-hydroxyphenyl)-2-(hydroxyimino)propanamido)ethylthio)-propyl)-2-(hydroxyimino)propanamide

ID: ALA2047705

PubChem CID: 57326508

Max Phase: Preclinical

Molecular Formula: C23H26Br2N4O6S

Molecular Weight: 646.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H26Br2N4O6S/c24-16-10-14(2-4-20(16)30)12-18(28-34)22(32)26-6-1-8-36-9-7-27-23(33)19(29-35)13-15-3-5-21(31)17(25)11-15/h2-5,10-11,30-31,34-35H,1,6-9,12-13H2,(H,26,32)(H,27,33)/b28-18+,29-19+

Standard InChI Key:  BDYSKDIFUSBAPW-UOSOPFLXSA-N

Molfile:  

     RDKit          2D

 36 37  0  0  0  0  0  0  0  0999 V2000
    1.7862    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.8562    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296    1.4437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3585    0.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0730    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9296   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -3.0938    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3585    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730    3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0730    1.4438    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  2  6  2  0
  8  9  1  0
  9 10  1  0
 12 13  1  0
 11 12  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 14 18  1  0
 19 20  1  0
 15 19  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 24 27  1  0
 23 28  1  0
 16 21  1  0
 13 18  1  0
 10 11  1  0
  5  8  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 29 34  2  0
 32 35  1  0
 31 36  1  0
  3 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2047705

   (2E)-3-(3-bromo-4-hydroxyphenyl)-N-[3-[2-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]ethylsulfanyl]propyl]-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: 646.36

Molecular Weight (Monoisotopic): 643.9940

AlogP: 3.42

#Rotatable Bonds: 13

Polar Surface Area: 163.84

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.71

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 3.97

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.08

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