4-(4-(2,5-dimethylphenyl)-3-(methoxycarbonyl)-5-methylthiophen-2-ylamino)-4-oxobut-2-enoic acid

ID: ALA4786630

PubChem CID: 1002591

Max Phase: Preclinical

Molecular Formula: C19H19NO5S

Molecular Weight: 373.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1c(NC(=O)/C=C/C(=O)O)sc(C)c1-c1cc(C)ccc1C

Standard InChI:  InChI=1S/C19H19NO5S/c1-10-5-6-11(2)13(9-10)16-12(3)26-18(17(16)19(24)25-4)20-14(21)7-8-15(22)23/h5-9H,1-4H3,(H,20,21)(H,22,23)/b8-7+

Standard InChI Key:  ZKYIULIRTLREAV-BQYQJAHWSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    3.1449   -8.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9621   -8.6012    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2165   -7.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5535   -7.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8948   -7.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637   -9.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5509   -6.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2580   -6.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -6.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2568   -5.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197   -7.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505   -6.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740   -6.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -7.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397   -7.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160   -8.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6885   -8.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0041   -5.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9940   -7.5730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6006   -8.1207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3781   -7.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4295   -8.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9846   -8.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7622   -8.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3704   -8.7118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9349   -7.3650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  1  6  1  0
  7  8  1  0
  7  9  2  0
  4  7  1  0
  8 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 11  1  0
 16 17  1  0
 13 18  1  0
  3 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4786630

   4-{[4-(2,5-Dimethylphenyl)-3-(methoxycarbonyl)-5-methyl-2-thienyl]amino}-4-oxo-2-butenoic 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: 373.43

Molecular Weight (Monoisotopic): 373.0984

AlogP: 3.71

#Rotatable Bonds: 5

Polar Surface Area: 92.70

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.79

CX Basic pKa: ┄

CX LogP: 5.31

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.78

References

1. Hou X,Sun JP,Ge L,Liang X,Li K,Zhang Y,Fang H.  (2020)  Inhibition of striatal-enriched protein tyrosine phosphatase by targeting computationally revealed cryptic pockets.,  190  [PMID:32078861] [10.1016/j.ejmech.2020.112131]

Source

Source(1):

• Scientific Literature