Methyl N-(4-acetoxycinnamoyl)anthranilate

ID: ALA4514721

PubChem CID: 155539612

Max Phase: Preclinical

Molecular Formula: C19H17NO5

Molecular Weight: 339.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccccc1NC(=O)/C=C/c1ccc(OC(C)=O)cc1

Standard InChI:  InChI=1S/C19H17NO5/c1-13(21)25-15-10-7-14(8-11-15)9-12-18(22)20-17-6-4-3-5-16(17)19(23)24-2/h3-12H,1-2H3,(H,20,22)/b12-9+

Standard InChI Key:  QYZKQLJRMNXHFP-FMIVXFBMSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   14.8401  -24.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8390  -25.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5470  -25.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2567  -25.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2538  -24.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5452  -24.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9600  -24.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6692  -24.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3754  -24.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0846  -24.4148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3723  -23.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7908  -24.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4961  -24.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2017  -24.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1991  -23.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4849  -22.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7821  -23.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4972  -25.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7901  -25.6380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2055  -25.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2066  -26.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1309  -25.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4235  -25.2474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7155  -25.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4242  -24.4303    0.0000 O   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
  2 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514721

   ---

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: 339.35

Molecular Weight (Monoisotopic): 339.1107

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -0.36

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