Methyl N-cinnamoylanthranilate

ID: ALA4588544

Cas Number: 55695-68-6

PubChem CID: 732144

Max Phase: Preclinical

Molecular Formula: C17H15NO3

Molecular Weight: 281.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1NC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C17H15NO3/c1-21-17(20)14-9-5-6-10-15(14)18-16(19)12-11-13-7-3-2-4-8-13/h2-12H,1H3,(H,18,19)/b12-11+

Standard InChI Key:  MAHZJDOWUGDBCV-VAWYXSNFSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   13.9362  -10.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9351  -11.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6431  -11.8313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3528  -11.4219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3500  -10.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6413  -10.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0561  -10.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7654  -10.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4715  -10.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1808  -10.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4685   -9.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8869  -10.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5922  -10.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2979  -10.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2952   -9.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5810   -8.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8783   -9.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5933  -11.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8862  -11.8117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3016  -11.8097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3028  -12.6269    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  2  0
 18 20  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4588544

   methyl 2-((2E)-3-phenylprop-2-enoylamino)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: 281.31

Molecular Weight (Monoisotopic): 281.1052

AlogP: 3.13

#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: 4.22

CX LogD: 4.22

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: -0.59

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