2-Hydroxy-4-oxo-4-p-tolyl-but-2-enoic acid methyl ester

ID: ALA1392694

PubChem CID: 5348939

Max Phase: Preclinical

Molecular Formula: C12H12O4

Molecular Weight: 220.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(=O)/C=C(/O)c1ccc(C)cc1

Standard InChI:  InChI=1S/C12H12O4/c1-8-3-5-9(6-4-8)10(13)7-11(14)12(15)16-2/h3-7,13H,1-2H3/b10-7+

Standard InChI Key:  KAQIFZRTEIWJID-JXMROGBWSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.9371   -2.4017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -1.9892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -1.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -3.2267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -1.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -1.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -2.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7950   -2.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -0.7517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516    0.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371    0.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661    0.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516    1.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5095   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0
  2  9  1  0
  2 16  1  0
  3  7  2  0
  4  9  2  0
  5  6  1  0
  5 10  2  0
  5 11  1  0
  6  8  2  0
  7  8  1  0
  7  9  1  0
 10 13  1  0
 11 14  2  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1392694

   methyl (E)-4-hydroxy-4-(4-methylphenyl)-2-oxobut-3-enoate

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: 220.22

Molecular Weight (Monoisotopic): 220.0736

AlogP: 1.64

#Rotatable Bonds: 3

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.21

CX Basic pKa: ┄

CX LogP: 2.56

CX LogD: 1.36

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.36

Np Likeness Score: -0.05

References

1. Drysdale MJ, Hind SL, Jansen M, Reinhard JF..  (2000)  Synthesis and SAR of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2-enoic acids and esters: potent inhibitors of kynurenine-3-hydroxylase as potential neuroprotective agents.,  43  (1): [PMID:10633043] [10.1021/jm990396t]

Source

Source(1):

• Scientific Literature