(E)-N'-(3,5-dichlorophenyl)-2-(5-methylisoxazol-3-yl)-2-oxoacetohydrazonoyl cyanide

ID: ALA3593480

PubChem CID: 71712136

Max Phase: Preclinical

Molecular Formula: C13H8Cl2N4O2

Molecular Weight: 323.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)/C(C#N)=N/Nc2cc(Cl)cc(Cl)c2)no1

Standard InChI:  InChI=1S/C13H8Cl2N4O2/c1-7-2-11(19-21-7)13(20)12(6-16)18-17-10-4-8(14)3-9(15)5-10/h2-5,17H,1H3/b18-12+

Standard InChI Key:  MRQAHBHMDCPCKT-LDADJPATSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7945   -7.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 N   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
   -6.2346   -2.4107    0.0000 N   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
    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
   -6.5408   -5.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3272   -7.4918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1944   -3.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5445   -6.5046    0.0000 C   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
   -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
   -3.8933   -3.7570    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
   -8.7379   -6.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 18 16  1  0
  3 11  1  0
  5  1  1  0
 17  8  2  0
 10 14  2  0
  9  5  2  0
 13  6  3  0
 20  2  1  0
  8  7  1  0
  8  9  1  0
 11 12  2  0
 14  3  1  0
 20 17  1  0
 16 12  1  0
  4 18  2  0
 16 15  2  0
 12 10  1  0
  5 19  1  0
  2  4  1  0
 19 20  2  0
 18 13  1  0
 14 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3593480

   (1E)-N-(3,5-dichloroanilino)-2-(5-methyl-1,2-oxazol-3-yl)-2-oxoethanimidoyl cyanide

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: 323.14

Molecular Weight (Monoisotopic): 322.0024

AlogP: 3.46

#Rotatable Bonds: 4

Polar Surface Area: 91.28

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.41

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 2.56

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.53

Np Likeness Score: -1.92

References

1. Ye N, Zhu Y, Chen H, Liu Z, Mei FC, Wild C, Chen H, Cheng X, Zhou J..  (2015)  Structure-Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N'-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists.,  58  (15): [PMID:26151319] [10.1021/acs.jmedchem.5b00635]

Source

Source(1):

• Scientific Literature