Methyl N-(4-trifluoromethylcinnamoyl)anthranilate

ID: ALA4554194

PubChem CID: 30255267

Max Phase: Preclinical

Molecular Formula: C18H14F3NO3

Molecular Weight: 349.31

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H14F3NO3/c1-25-17(24)14-4-2-3-5-15(14)22-16(23)11-8-12-6-9-13(10-7-12)18(19,20)21/h2-11H,1H3,(H,22,23)/b11-8+

Standard InChI Key:  PNFQYDULONSPIB-DHZHZOJOSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   27.9647  -10.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9635  -10.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6716  -11.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3812  -10.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3784  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6698   -9.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0846   -9.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7938  -10.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5000   -9.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2092  -10.1139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4969   -8.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9154   -9.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6206  -10.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3263   -9.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3237   -8.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6095   -8.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9067   -8.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6218  -10.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9147  -11.3371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3301  -11.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3312  -12.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2555  -11.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5481  -10.9466    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.2549  -12.1729    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.5422  -11.7585    0.0000 F   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
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554194

   methyl 2-[[(E)-3-[4-(trifluoromethyl)phenyl]prop-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: 349.31

Molecular Weight (Monoisotopic): 349.0926

AlogP: 4.14

#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: 5.10

CX LogD: 5.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -0.89

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