3-{[2-Ethyl-10-oxo-9,10-dihydroanthracene-9-ylidene]amino}benzoicacid

ID: ALA2283225

PubChem CID: 76330905

Max Phase: Preclinical

Molecular Formula: C23H17NO3

Molecular Weight: 355.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc2c(c1)/C(=N/c1cccc(C(=O)O)c1)c1ccccc1C2=O

Standard InChI:  InChI=1S/C23H17NO3/c1-2-14-10-11-19-20(12-14)21(17-8-3-4-9-18(17)22(19)25)24-16-7-5-6-15(13-16)23(26)27/h3-13H,2H2,1H3,(H,26,27)/b24-21+

Standard InChI Key:  WEJDWBALHUTSBL-DARPEHSRSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   22.6947   -3.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6936   -4.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4126   -4.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1290   -4.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1262   -3.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4107   -2.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8432   -2.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8402   -2.0478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9802   -2.8835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5588   -3.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9800   -2.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9893   -0.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7020   -0.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6978   -1.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4083   -2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1237   -1.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1240   -0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4128   -0.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2696   -1.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2735   -0.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5633   -0.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8490   -0.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8492   -1.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5598   -2.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1335   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4202   -1.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9939    0.4174    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
  1  9  1  0
  7 10  1  0
  9 11  2  0
 11 14  1  0
 11 19  1  0
 13 12  1  0
 12 20  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 23 25  1  0
 25 26  1  0
 12 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283225

   3-{[2-Ethyl-10-oxo-9,10-dihydroanthracene-9-ylidene]amino}benzoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 355.39

Molecular Weight (Monoisotopic): 355.1208

AlogP: 4.66

#Rotatable Bonds: 3

Polar Surface Area: 66.73

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.59

CX Basic pKa: 0.70

CX LogP: 5.70

CX LogD: 2.96

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -0.39

References

1. Bansal SK, Sinha BN, Khosa RL.  (2013)  -Amino butyric acid analogs as novel potent GABA-AT inhibitors: molecular docking, synthesis, and biological evaluation,  22  (1): [10.1007/s00044-012-0023-0]

Source

Source(1):

• Scientific Literature