N-(4-Hydroxycinnamoyl)anthranilic acid

ID: ALA4516367

Cas Number: 53901-55-6

PubChem CID: 6443019

Max Phase: Preclinical

Molecular Formula: C16H13NO4

Molecular Weight: 283.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)Nc1ccccc1C(=O)O

Standard InChI:  InChI=1S/C16H13NO4/c18-12-8-5-11(6-9-12)7-10-15(19)17-14-4-2-1-3-13(14)16(20)21/h1-10,18H,(H,17,19)(H,20,21)/b10-7+

Standard InChI Key:  INBHLTYBRKASIZ-JXMROGBWSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.1765  -23.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1754  -24.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834  -24.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5931  -24.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5903  -23.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817  -22.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2964  -22.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057  -23.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7119  -22.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4211  -23.3210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7088  -22.0979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1273  -22.9098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8325  -23.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5382  -22.9069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5356  -22.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8213  -21.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1186  -22.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8337  -24.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5419  -24.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1265  -24.5442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674  -24.5629    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  1  0
 18 20  2  0
  2 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4516367

   Avenanthramide D

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: 283.28

Molecular Weight (Monoisotopic): 283.0845

AlogP: 2.74

#Rotatable Bonds: 4

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.55

CX Basic pKa: ┄

CX LogP: 3.57

CX LogD: 0.21

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.75

Np Likeness Score: -0.26

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