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

ID: ALA4871220

PubChem CID: 5891263

Max Phase: Preclinical

Molecular Formula: C19H15NO4S

Molecular Weight: 353.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc(/C=C(\CC(=O)O)c2nc3ccccc3s2)cc1

Standard InChI:  InChI=1S/C19H15NO4S/c1-24-19(23)13-8-6-12(7-9-13)10-14(11-17(21)22)18-20-15-4-2-3-5-16(15)25-18/h2-10H,11H2,1H3,(H,21,22)/b14-10+

Standard InChI Key:  HMPQDKFMNIOTIO-GXDHUFHOSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   -0.3989   -9.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978  -10.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3134  -10.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116   -8.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0202   -9.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0205  -10.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991  -10.2838    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2802   -9.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987   -8.9593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0974   -9.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062  -10.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979  -11.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2807  -11.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5067  -11.7440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5057   -8.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3229   -8.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7273   -9.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5438   -9.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9529   -8.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5397   -8.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -8.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7701   -8.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1799   -9.6190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1775   -8.2036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -8.2022    0.0000 C   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  2  0
 22 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871220

   (E)-3-(1,3-benzothiazol-2-yl)-4-(4-methoxycarbonylphenyl)but-3-enoic acid

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: 4.10

#Rotatable Bonds: 5

Polar Surface Area: 76.49

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.24

CX Basic pKa: 1.96

CX LogP: 4.26

CX LogD: 1.25

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: -0.85

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