(E)-3-(benzo[d]thiazol-2-yl)-4-(4-(carboxymethyl)phenyl)but-3-enoic acid

ID: ALA4877301

PubChem CID: 164629158

Max Phase: Preclinical

Molecular Formula: C19H15NO4S

Molecular Weight: 353.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C/C(=C\c1ccc(CC(=O)O)cc1)c1nc2ccccc2s1

Standard InChI:  InChI=1S/C19H15NO4S/c21-17(22)10-13-7-5-12(6-8-13)9-14(11-18(23)24)19-20-15-3-1-2-4-16(15)25-19/h1-9H,10-11H2,(H,21,22)(H,23,24)/b14-9+

Standard InChI Key:  KWBLAUNNBJHJNI-NTEUORMPSA-N

Molfile:  

 
     RDKit          2D

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   17.0482   -9.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0470  -10.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7551  -10.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7533   -9.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4619   -9.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4622  -10.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2408  -10.4985    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7218   -9.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2404   -9.1739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5390   -9.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9479  -10.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5395  -11.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7224  -11.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9484  -11.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9474   -9.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7646   -9.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1690   -9.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9854   -9.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3946   -9.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9813   -8.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1663   -8.4215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2118   -9.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6216   -9.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2142  -10.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4388   -9.8322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 10 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877301

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 353.40

Molecular Weight (Monoisotopic): 353.0722

AlogP: 3.94

#Rotatable Bonds: 6

Polar Surface Area: 87.49

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.22

CX Basic pKa: 1.96

CX LogP: 3.89

CX LogD: -1.64

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.84

References

1. Azuma M, Inoue M, Nishida A, Akahane H, Kitajima M, Natani S, Chimori R, Yoshimori A, Mano Y, Uchiro H, Tanuma SI, Takasawa R..  (2021)  Addition of hydrophobic side chains improve the apoptosis inducibility of the human glyoxalase I inhibitor, TLSC702.,  40  [PMID:33711442] [10.1016/j.bmcl.2021.127918]

Source

Source(1):

• Scientific Literature