Methyl N-(a-methylcinnamoyl)anthranilate

ID: ALA4581992

PubChem CID: 2189279

Max Phase: Preclinical

Molecular Formula: C18H17NO3

Molecular Weight: 295.34

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H17NO3/c1-13(12-14-8-4-3-5-9-14)17(20)19-16-11-7-6-10-15(16)18(21)22-2/h3-12H,1-2H3,(H,19,20)/b13-12+

Standard InChI Key:  HTVMXIJYSZOPTD-OUKQBFOZSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    2.1612   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1601   -4.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8681   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5778   -4.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -3.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -3.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2811   -3.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9904   -3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4058   -3.7910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6935   -2.5679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1120   -3.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8172   -3.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5229   -3.3768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5203   -2.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8060   -2.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1033   -2.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8184   -4.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1112   -5.0142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5266   -5.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5278   -5.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9935   -4.6135    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
M  END

Alternative Forms

1. Parent:

   

   ALA4581992

   methyl 2-[[(E)-2-methyl-3-phenylprop-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: 295.34

Molecular Weight (Monoisotopic): 295.1208

AlogP: 3.52

#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: 12.91

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: -0.61

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