N-(3-Ethoxy-4-hydroxycinnamoyl)anthranilic acid

ID: ALA4551396

PubChem CID: 155555048

Max Phase: Preclinical

Molecular Formula: C18H17NO5

Molecular Weight: 327.34

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCOc1cc(/C=C/C(=O)Nc2ccccc2C(=O)O)ccc1O

Standard InChI:  InChI=1S/C18H17NO5/c1-2-24-16-11-12(7-9-15(16)20)8-10-17(21)19-14-6-4-3-5-13(14)18(22)23/h3-11,20H,2H2,1H3,(H,19,21)(H,22,23)/b10-8+

Standard InChI Key:  NNTSHWHAMWNNPN-CSKARUKUSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   35.8601  -16.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8589  -17.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5670  -17.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2766  -17.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2738  -16.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5652  -16.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9800  -16.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6892  -16.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3954  -16.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1046  -16.6803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.3923  -15.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8108  -16.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5160  -16.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2217  -16.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2191  -15.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5049  -15.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8021  -15.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.5172  -17.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2255  -17.9015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.8101  -17.9035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5668  -18.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8590  -19.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8588  -19.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1509  -17.9222    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
  3 21  1  0
 21 22  1  0
 22 23  1  0
  2 24  1  0
M  END

Alternative Forms

  1. Parent:

    ALA4551396

    ---

Associated Targets(Human)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1847 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (1168 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 327.34Molecular Weight (Monoisotopic): 327.1107AlogP: 3.14#Rotatable Bonds: 6
Polar Surface Area: 95.86Molecular Species: ACIDHBA: 4HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 3.55CX Basic pKa: CX LogP: 3.77CX LogD: 0.41
Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.71Np Likeness Score: -0.33

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