2-(5-tert-Butylisoxazol-3-yl)-N'-(3-chloro-4-(trifluoromethyl)-phenyl)-2-oxoacetohydrazonoyl Cyanide

ID: ALA3593341

PubChem CID: 122181839

Max Phase: Preclinical

Molecular Formula: C17H14ClF3N4O2

Molecular Weight: 398.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C(=O)/C(C#N)=N/Nc2ccc(C(F)(F)F)c(Cl)c2)no1

Standard InChI:  InChI=1S/C17H14ClF3N4O2/c1-16(2,3)14-7-12(25-27-14)15(26)13(8-22)24-23-9-4-5-10(11(18)6-9)17(19,20)21/h4-7,23H,1-3H3/b24-13+

Standard InChI Key:  KXGWGWPOHUROGS-ZMOGYAJESA-N

Molfile:  

     RDKit          2D

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    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
   -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
    0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -6.6047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -5.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244   -8.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -9.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -9.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -8.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416  -10.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4351  -10.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532  -12.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465  -11.9692    0.0000 C   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
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0388    3.6015    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394    3.6005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0006    4.2008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  5  6  2  0
  6  1  1  0
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  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  3  0
 10 13  1  0
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 17 18  1  0
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 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  4 23  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  3 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3593341

   ---

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: 398.77

Molecular Weight (Monoisotopic): 398.0757

AlogP: 4.82

#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: 4.76

CX Basic pKa: ┄

CX LogP: 5.82

CX LogD: 4.13

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -1.60

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