5-(5-(2-(allyloxy)-5-bromobenzylidene)-4-oxo-4,5-dihydrothiazol-2-ylamino)-2-chlorobenzoic acid

ID: ALA211705

PubChem CID: 135921848

Max Phase: Preclinical

Molecular Formula: C20H14BrClN2O4S

Molecular Weight: 493.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCOc1ccc(Br)cc1/C=C1\SC(Nc2ccc(Cl)c(C(=O)O)c2)=NC1=O

Standard InChI:  InChI=1S/C20H14BrClN2O4S/c1-2-7-28-16-6-3-12(21)8-11(16)9-17-18(25)24-20(29-17)23-13-4-5-15(22)14(10-13)19(26)27/h2-6,8-10H,1,7H2,(H,26,27)(H,23,24,25)/b17-9-

Standard InChI Key:  MQSHNYJRZDTWIS-MFOYZWKCSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    5.7944    0.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7932   -0.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5081   -0.7444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2245   -0.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2216    0.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5063    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9396   -0.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6534   -0.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4040   -0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9550   -0.0480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5414    0.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7347    0.4929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5765   -1.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8756    1.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7006    1.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1081    0.6992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9324    0.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3483    1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9339    2.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1110    2.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1733    1.4076    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3465    2.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1715    2.8422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9340    3.5567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5079   -1.5694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7933   -1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0789   -1.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643   -1.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5038    1.7336    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
 11 14  1  0
  4  7  1  0
 14 15  1  0
  3  4  1  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
 20 15  1  0
  2  3  2  0
 18 21  1  0
  5  6  1  0
 19 22  1  0
  9 10  1  0
 22 23  2  0
 10 11  2  0
 22 24  1  0
 11 12  1  0
  3 25  1  0
 12  8  1  0
 25 26  1  0
  6  1  2  0
 26 27  1  0
  9 13  2  0
 27 28  2  0
  1  2  1  0
  6 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA211705

   ---

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: 493.77

Molecular Weight (Monoisotopic): 491.9546

AlogP: 5.45

#Rotatable Bonds: 6

Polar Surface Area: 87.99

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.72

CX Basic pKa: ┄

CX LogP: 5.26

CX LogD: 1.96

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -1.67

References

1. Kim ND, Yoon J, Kim JH, Lee JT, Chon YS, Hwang MK, Ha I, Song WJ..  (2006)  Putative therapeutic agents for the learning and memory deficits of people with Down syndrome.,  16  (14): [PMID:16698266] [10.1016/j.bmcl.2006.04.042]

Source

Source(1):

• Scientific Literature