3-[(2,3,5,6-Tetramethyl-4-oxocyclohexa-2,5-dien-1-ylidene)amino]benzoicacid

ID: ALA2283228

PubChem CID: 76330906

Max Phase: Preclinical

Molecular Formula: C17H17NO3

Molecular Weight: 283.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C)C(=Nc2cccc(C(=O)O)c2)C(C)=C(C)C1=O

Standard InChI:  InChI=1S/C17H17NO3/c1-9-11(3)16(19)12(4)10(2)15(9)18-14-7-5-6-13(8-14)17(20)21/h5-8H,1-4H3,(H,20,21)

Standard InChI Key:  ISFKGBVARWDHQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   24.0832   -7.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0820   -8.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8004   -8.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5163   -8.2909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5134   -7.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7986   -7.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2298   -7.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2268   -6.2136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3692   -7.0485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9448   -7.4524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6554   -7.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9434   -7.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2318   -7.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2277   -8.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9416   -8.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6594   -8.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3735   -8.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9390   -9.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5194   -7.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9469   -6.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5124   -8.6872    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 12  1  0
 11 16  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 15 18  1  0
 13 19  1  0
 12 20  1  0
 14 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2283228

   3-[(2,3,5,6-Tetramethyl-4-oxocyclohexa-2,5-dien-1-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: 283.33

Molecular Weight (Monoisotopic): 283.1208

AlogP: 3.71

#Rotatable Bonds: 2

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: 4.70

CX Basic pKa: 3.75

CX LogP: 4.08

CX LogD: 1.70

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -0.26

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