3-(5-(5-bromo-2-hydroxy-3-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-ylamino)benzoic acid

ID: ALA572150

PubChem CID: 135697783

Max Phase: Preclinical

Molecular Formula: C18H13BrN2O5S

Molecular Weight: 449.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Br)cc(/C=C2/SC(Nc3cccc(C(=O)O)c3)=NC2=O)c1O

Standard InChI:  InChI=1S/C18H13BrN2O5S/c1-26-13-8-11(19)5-10(15(13)22)7-14-16(23)21-18(27-14)20-12-4-2-3-9(6-12)17(24)25/h2-8,22H,1H3,(H,24,25)(H,20,21,23)/b14-7+

Standard InChI Key:  UYDUEDPSEYLRAT-VGOFMYFVSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   -0.0667   -3.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7584   -3.9795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0152   -4.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3458   -5.2505    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3192   -4.7637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7252   -5.1755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -4.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1532   -5.1794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -4.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -3.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4395   -3.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837   -5.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5817   -6.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2993   -4.7744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -3.2586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0376   -5.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7491   -4.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390   -3.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4495   -3.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682   -3.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717   -4.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4605   -5.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -2.6875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -5.9882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8879   -5.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6007   -4.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
 13 14  1  0
 13 15  2  0
  9 13  1  0
  2  3  2  0
  1 16  2  0
  7  8  2  0
  5 17  2  0
  3  4  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  9 10  2  0
 20 21  2  0
  5  1  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
  1  2  1  0
 20 24  1  0
 11 12  2  0
 23 25  1  0
 12  7  1  0
 22 26  1  0
  3  6  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA572150

   ---

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: 449.28

Molecular Weight (Monoisotopic): 447.9729

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 108.22

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.74

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 0.99

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -1.12

References

1. Gupta RK, Thakur TS, Desiraju GR, Tyagi JS..  (2009)  Structure-based design of DevR inhibitor active against nonreplicating Mycobacterium tuberculosis.,  52  (20): [PMID:19827833] [10.1021/jm900358q]

2. Al-Asri J, Fazekas E, Lehoczki G, Perdih A, Görick C, Melzig MF, Gyémánt G, Wolber G, Mortier J..  (2015)  From carbohydrates to drug-like fragments: Rational development of novel α-amylase inhibitors.,  23  (20): [PMID:26395057] [10.1016/j.bmc.2015.09.007]

Source

Source(1):

• Scientific Literature