4-((5-(5-bromo-2,4-dimethoxybenzylidene)-3-methyl-4-oxothiazolidin-2-ylidene)amino)benzoic acid

ID: ALA425782

PubChem CID: 9511578

Max Phase: Preclinical

Molecular Formula: C20H17BrN2O5S

Molecular Weight: 477.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(/C=C2\S/C(=N/c3ccc(C(=O)O)cc3)N(C)C2=O)cc1Br

Standard InChI:  InChI=1S/C20H17BrN2O5S/c1-23-18(24)17(9-12-8-14(21)16(28-3)10-15(12)27-2)29-20(23)22-13-6-4-11(5-7-13)19(25)26/h4-10H,1-3H3,(H,25,26)/b17-9-,22-20+

Standard InChI Key:  GVXOQTRNZPTULG-PAFNDRTPSA-N

Molfile:  

     RDKit          2D

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    2.8155   -7.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9882   -7.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5641   -8.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9660   -8.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965   -8.9040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -8.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -8.1575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3382   -7.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885   -6.6854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -6.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369   -6.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4781   -7.3341    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3614   -6.1300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -6.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -6.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4929   -6.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4728   -7.4196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433   -7.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0428   -7.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1839   -5.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4982   -6.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0443   -8.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4476   -8.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4660   -7.4951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7199   -8.6386    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762   -7.8507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -5.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9013   -7.4571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5334   -4.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  3  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  4  5  1  0
 10 20  2  0
  2  3  1  0
  9 21  1  0
  5  6  2  0
  9 10  1  0
 10 11  1  0
 22 23  1  0
 22 24  2  0
  6 22  1  0
 11 12  1  0
 18 25  1  0
 12  8  1  0
 17 26  1  0
  6  1  1  0
 15 27  1  0
 11 13  2  0
 26 28  1  0
  1  2  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA425782

   4-{[(2E,5Z)-5-(5-bromo-2,4-dimethoxybenzylidene)-3-methyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoic acid

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: 477.34

Molecular Weight (Monoisotopic): 476.0042

AlogP: 4.40

#Rotatable Bonds: 5

Polar Surface Area: 88.43

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.08

CX Basic pKa: 2.35

CX LogP: 4.11

CX LogD: 1.12

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.64

Np Likeness Score: -1.10

References

1. Dayam R, Aiello F, Deng J, Wu Y, Garofalo A, Chen X, Neamati N..  (2006)  Discovery of small molecule integrin alphavbeta3 antagonists as novel anticancer agents.,  49  (15): [PMID:16854058] [10.1021/jm051296s]

Source

Source(1):

• Scientific Literature