Methyl N-(2-chlorocinnamoyl)anthranilate

ID: ALA4569976

PubChem CID: 692625

Max Phase: Preclinical

Molecular Formula: C17H14ClNO3

Molecular Weight: 315.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1NC(=O)/C=C/c1ccccc1Cl

Standard InChI:  InChI=1S/C17H14ClNO3/c1-22-17(21)13-7-3-5-9-15(13)19-16(20)11-10-12-6-2-4-8-14(12)18/h2-11H,1H3,(H,19,20)/b11-10+

Standard InChI Key:  SZUZBVFPIJEWBV-ZHACJKMWSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   25.0343  -17.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0332  -18.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7413  -19.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4509  -18.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4481  -17.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7395  -17.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1542  -17.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8635  -17.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5697  -17.4342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2789  -17.8401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5666  -16.6170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9851  -17.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6903  -17.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3960  -17.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3934  -16.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6791  -16.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9764  -16.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6915  -18.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9843  -19.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3997  -19.0613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4009  -19.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1593  -19.0809    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  2  0
 18 20  1  0
 20 21  1  0
  4 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4569976

   Methyl 2-{[3-(2-chlorophenyl)acryloyl]amino}benzoate

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: 315.76

Molecular Weight (Monoisotopic): 315.0662

AlogP: 3.78

#Rotatable Bonds: 4

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 4.83

CX LogD: 4.83

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -1.08

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