(E)-7-(2-carboxystyryl)-3-hydroxy-2-naphthoic acid

ID: ALA4514951

PubChem CID: 155539447

Max Phase: Preclinical

Molecular Formula: C20H14O5

Molecular Weight: 334.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2cc(/C=C/c3ccccc3C(=O)O)ccc2cc1O

Standard InChI:  InChI=1S/C20H14O5/c21-18-11-14-8-6-12(9-15(14)10-17(18)20(24)25)5-7-13-3-1-2-4-16(13)19(22)23/h1-11,21H,(H,22,23)(H,24,25)/b7-5+

Standard InChI Key:  OOJPDDXARGNMFN-FNORWQNLSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.1591   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1580   -3.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8660   -4.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8642   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5728   -3.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5736   -3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2821   -4.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9904   -3.9029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9857   -3.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2766   -2.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4486   -2.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4484   -1.8671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7410   -3.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4499   -4.3188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6909   -2.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4010   -3.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1063   -2.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8142   -3.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5189   -2.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5144   -1.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7992   -1.4326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0974   -1.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3853   -1.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3768   -0.6314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6819   -1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 11 13  1  0
  1 11  1  0
  2 14  1  0
  9 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  1  0
 23 25  2  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514951

   ---

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: 334.33

Molecular Weight (Monoisotopic): 334.0841

AlogP: 4.11

#Rotatable Bonds: 4

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.66

CX Basic pKa: ┄

CX LogP: 4.96

CX LogD: -1.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: 0.19

References

1. Irvine MW, Fang G, Sapkota K, Burnell ES, Volianskis A, Costa BM, Culley G, Collingridge GL, Monaghan DT, Jane DE..  (2019)  Investigation of the structural requirements for N-methyl-D-aspartate receptor positive and negative allosteric modulators based on 2-naphthoic acid.,  164  [PMID:30622023] [10.1016/j.ejmech.2018.12.054]

Source

Source(1):

• Scientific Literature