2-Amino-4-(3,4-dichloro-phenyl)-4-oxo-butyric acid

ID: ALA139909

PubChem CID: 9926281

Max Phase: Preclinical

Molecular Formula: C10H9Cl2NO3

Molecular Weight: 262.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CC(=O)c1ccc(Cl)c(Cl)c1)C(=O)O

Standard InChI:  InChI=1S/C10H9Cl2NO3/c11-6-2-1-5(3-7(6)12)9(14)4-8(13)10(15)16/h1-3,8H,4,13H2,(H,15,16)

Standard InChI Key:  MXBKZYGNMKXYQE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  4  6  1  0
  5  6  2  0
  2  7  1  0
  3  7  1  0
  5  8  1  0
  3  9  2  0
  1 10  2  0
  4 11  2  0
  8 12  2  0
 11 12  1  0
  5 13  1  0
  7 14  1  0
  3 15  1  0
  8 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA139909

   2-Amino-4-(3,4-dichloro-phenyl)-4-oxo-butyric acid

2. Alternative Forms:

   

   ALA139909

   2-Amino-4-(3,4-dichlorophenyl)-4-oxobutanoic acid;hydrochloride

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: 262.09

Molecular Weight (Monoisotopic): 260.9959

AlogP: 1.98

#Rotatable Bonds: 4

Polar Surface Area: 80.39

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.26

CX Basic pKa: 8.96

CX LogP: -0.52

CX LogD: -0.53

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.81

Np Likeness Score: -0.27

References

1. Röver S, Cesura AM, Huguenin P, Kettler R, Szente A..  (1997)  Synthesis and biochemical evaluation of N-(4-phenylthiazol-2-yl)benzenesulfonamides as high-affinity inhibitors of kynurenine 3-hydroxylase.,  40  (26): [PMID:9435907] [10.1021/jm970467t]

2. Toledo-Sherman LM, Prime ME, Mrzljak L, Beconi MG, Beresford A, Brookfield FA, Brown CJ, Cardaun I, Courtney SM, Dijkman U, Hamelin-Flegg E, Johnson PD, Kempf V, Lyons K, Matthews K, Mitchell WL, O'Connell C, Pena P, Powell K, Rassoulpour A, Reed L, Reindl W, Selvaratnam S, Friley WW, Weddell DA, Went NE, Wheelan P, Winkler C, Winkler D, Wityak J, Yarnold CJ, Yates D, Munoz-Sanjuan I, Dominguez C..  (2015)  Development of a series of aryl pyrimidine kynurenine monooxygenase inhibitors as potential therapeutic agents for the treatment of Huntington's disease.,  58  (3): [PMID:25590515] [10.1021/jm501350y]

3. Ahamad S, Bhat SA..  (2022)  The Emerging Landscape of Small-Molecule Therapeutics for the Treatment of Huntington's Disease.,  65  (24.0): [PMID:36490325] [10.1021/acs.jmedchem.2c00799]

Source

Source(1):

• Scientific Literature