(E)-3-(1H-Benzoimidazol-2-yl)-4-[1-(1,1-dioxo-tetrahydro-1lambda(6)-thiophen-3-yl)-3,5-dimethyl-1H-pyrazol-4-yl]-but-3-enoic acid

ID: ALA4863408

PubChem CID: 164624009

Max Phase: Preclinical

Molecular Formula: C20H22N4O4S

Molecular Weight: 414.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1nn(C2CCS(=O)(=O)C2)c(C)c1/C=C(\CC(=O)O)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C20H22N4O4S/c1-12-16(13(2)24(23-12)15-7-8-29(27,28)11-15)9-14(10-19(25)26)20-21-17-5-3-4-6-18(17)22-20/h3-6,9,15H,7-8,10-11H2,1-2H3,(H,21,22)(H,25,26)/b14-9+

Standard InChI Key:  IGCYYSSHKAGBGU-NTEUORMPSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   21.5291   -1.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5333   -2.4292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.2457   -2.0131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0569   -4.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0557   -5.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7706   -5.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7688   -4.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4841   -4.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4843   -5.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2705   -5.7946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7561   -5.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2701   -4.4574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5811   -5.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9939   -5.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9934   -4.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8183   -4.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5816   -6.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9944   -7.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7566   -6.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3006   -5.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0852   -4.8223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0849   -3.9972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3001   -3.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0450   -5.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0437   -2.9586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7521   -3.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5344   -3.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0190   -3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7494   -2.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 14 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 16  2  0
 20 24  1  0
 23 25  1  0
 22 26  1  0
 26 27  1  0
 27 28  1  0
 28  2  1  0
  2 29  1  0
 29 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4863408

   ---

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: 414.49

Molecular Weight (Monoisotopic): 414.1362

AlogP: 2.75

#Rotatable Bonds: 5

Polar Surface Area: 117.94

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.09

CX Basic pKa: 5.24

CX LogP: -0.39

CX LogD: -2.15

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.49

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