Methyl N-(a-phenylcinnamoyl)anthranilate

ID: ALA4558012

PubChem CID: 1183336

Max Phase: Preclinical

Molecular Formula: C23H19NO3

Molecular Weight: 357.41

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H19NO3/c1-27-23(26)19-14-8-9-15-21(19)24-22(25)20(18-12-6-3-7-13-18)16-17-10-4-2-5-11-17/h2-16H,1H3,(H,24,25)/b20-16+

Standard InChI Key:  OWCNSRQYBWQSPI-CAPFRKAQSA-N

Molfile:  

 
     RDKit          2D

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   13.1190   -3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1179   -4.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8259   -4.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5356   -4.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5328   -3.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8242   -2.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2389   -2.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9482   -3.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6543   -2.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3636   -3.2957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6513   -2.0726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698   -2.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7750   -3.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4807   -2.8816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4780   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7638   -1.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0611   -2.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7762   -4.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0690   -4.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4844   -4.5169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4856   -5.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9513   -4.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2460   -4.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2487   -5.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9585   -5.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6670   -5.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6608   -4.5188    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
  8 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558012

   methyl 2-[[(E)-2,3-diphenylprop-2-enoyl]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: 357.41

Molecular Weight (Monoisotopic): 357.1365

AlogP: 4.65

#Rotatable Bonds: 5

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: 12.63

CX Basic pKa: ┄

CX LogP: 5.89

CX LogD: 5.89

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.41

Np Likeness Score: -0.63

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