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

ID: ALA4521793

PubChem CID: 155542595

Max Phase: Preclinical

Molecular Formula: C20H14O5

Molecular Weight: 334.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(/C=C/c2ccc3cc(O)c(C(=O)O)cc3c2)c1

Standard InChI:  InChI=1S/C20H14O5/c21-18-11-14-7-6-13(9-16(14)10-17(18)20(24)25)5-4-12-2-1-3-15(8-12)19(22)23/h1-11,21H,(H,22,23)(H,24,25)/b5-4+

Standard InChI Key:  VAGJZEYJEXAKKE-SNAWJCMRSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.2540  -13.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2529  -14.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9609  -15.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9591  -13.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6678  -13.9216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6685  -14.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3771  -15.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0853  -14.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0806  -13.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3715  -13.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5435  -13.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5433  -12.7011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8359  -13.9270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5449  -15.1528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7858  -13.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4960  -13.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2012  -13.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9091  -13.9009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6138  -13.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6093  -12.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8942  -12.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1924  -12.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8862  -11.4489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5900  -11.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1746  -11.0472    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
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521793

   ---

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: 2.67

CX Basic pKa: ┄

CX LogP: 4.96

CX LogD: -1.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.62

Np Likeness Score: 0.28

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