N-(2-Chlorocinnamoyl)anthranilic acid

ID: ALA4517528

PubChem CID: 11514966

Max Phase: Preclinical

Molecular Formula: C16H12ClNO3

Molecular Weight: 301.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1Cl)Nc1ccccc1C(=O)O

Standard InChI:  InChI=1S/C16H12ClNO3/c17-13-7-3-1-5-11(13)9-10-15(19)18-14-8-4-2-6-12(14)16(20)21/h1-10H,(H,18,19)(H,20,21)/b10-9+

Standard InChI Key:  QUAFNALOLHHWGL-MDZDMXLPSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.5483  -10.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5471  -11.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2552  -11.9964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9648  -11.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9620  -10.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2534  -10.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6682  -10.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3774  -10.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0836  -10.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7928  -10.7536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0805   -9.5305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4990  -10.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2042  -10.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9099  -10.3395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9073   -9.5214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1931   -9.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4903   -9.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2054  -11.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9137  -11.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4983  -11.9768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6732  -11.9944    0.0000 Cl  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
  4 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4517528

   2-[[(E)-3-(2-chlorophenyl)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: 301.73

Molecular Weight (Monoisotopic): 301.0506

AlogP: 3.69

#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: 4.48

CX LogD: 1.12

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.85

Np Likeness Score: -1.03

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]

Source

Source(1):

• Scientific Literature