N-(4-Methylcinnamoyl)anthranilic acid

ID: ALA4557362

PubChem CID: 11666329

Max Phase: Preclinical

Molecular Formula: C17H15NO3

Molecular Weight: 281.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(/C=C/C(=O)Nc2ccccc2C(=O)O)cc1

Standard InChI:  InChI=1S/C17H15NO3/c1-12-6-8-13(9-7-12)10-11-16(19)18-15-5-3-2-4-14(15)17(20)21/h2-11H,1H3,(H,18,19)(H,20,21)/b11-10+

Standard InChI Key:  RYGGYSHFHOMWTD-ZHACJKMWSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   36.0417  -10.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0405  -10.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7486  -11.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4582  -10.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4554  -10.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7468   -9.6904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1616   -9.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8708  -10.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5770   -9.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2862  -10.0850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.5739   -8.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9924   -9.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6976  -10.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4033   -9.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4007   -8.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6865   -8.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9837   -8.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6988  -10.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4071  -11.3062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9917  -11.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3325  -11.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 13 18  1  0
 18 19  1  0
 18 20  2  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557362

   2-[[(E)-3-(4-methylphenyl)prop-2-enoyl]amino]benzoic 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: 281.31

Molecular Weight (Monoisotopic): 281.1052

AlogP: 3.35

#Rotatable Bonds: 4

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 1.03

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -0.65

References

1. Chandrabalan A, McPhillie MJ, Morice AH, Boa AN, Sadofsky LR..  (2019)  N-Cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.,  170  [PMID:30878828] [10.1016/j.ejmech.2019.02.074]

2. Zhang H, Yu P, Lin H, Jin Z, Zhao S, Zhang Y, Xu Q, Jin H, Liu Z, Yang W, Zhang L..  (2021)  The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both In Vitro and In Vivo.,  64  (7.0): [PMID:33784097] [10.1021/acs.jmedchem.0c02129]

Source

Source(1):

• Scientific Literature