4-(4-hydroxy-3-methoxybenzylidene)-1-(3-chlorophenyl)pyrazolidine-3,5-dione

ID: ALA211756

PubChem CID: 825523

Max Phase: Preclinical

Molecular Formula: C17H13ClN2O4

Molecular Weight: 344.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\C(=O)NN(c3cccc(Cl)c3)C2=O)ccc1O

Standard InChI:  InChI=1S/C17H13ClN2O4/c1-24-15-8-10(5-6-14(15)21)7-13-16(22)19-20(17(13)23)12-4-2-3-11(18)9-12/h2-9,21H,1H3,(H,19,22)/b13-7+

Standard InChI Key:  JYRNUSZDFUPATQ-NTUHNPAUSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -4.5056   -0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5068   -1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7919   -1.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0755   -1.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0784   -0.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7937    0.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -1.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6466   -1.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8960   -1.3787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3448   -0.7646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7586   -0.0508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7235   -2.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    0.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4802   -0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8834   -1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -0.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7140   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8911   -0.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1289    0.6519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7962    1.0170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830    1.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2202    0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12  8  1  0
  6  1  2  0
  9 13  2  0
  1  2  1  0
 12 14  2  0
  4  7  1  0
 10 15  1  0
  3  4  1  0
 15 16  2  0
  7  8  2  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
 18 19  1  0
  4  5  2  0
 19 20  2  0
 20 15  1  0
  2  3  2  0
 19 21  1  0
  5  6  1  0
  6 22  1  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
  1 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA211756

   4-(4-Hydroxy-3-methoxybenzylidene)-1-(3-chlorophenyl)pyrazolidine-3,5-dione

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: 344.75

Molecular Weight (Monoisotopic): 344.0564

AlogP: 2.52

#Rotatable Bonds: 3

Polar Surface Area: 78.87

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.87

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.07

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.66

Np Likeness Score: -0.93

References

1. Kim ND, Yoon J, Kim JH, Lee JT, Chon YS, Hwang MK, Ha I, Song WJ..  (2006)  Putative therapeutic agents for the learning and memory deficits of people with Down syndrome.,  16  (14): [PMID:16698266] [10.1016/j.bmcl.2006.04.042]

Source

Source(1):

• Scientific Literature