2-(5-tert-Butylisoxazol-3-yl)-N'-phenyl-2-oxoacetohydrazonoylCyanide

ID: ALA3594316

PubChem CID: 6368466

Max Phase: Preclinical

Molecular Formula: C16H16N4O2

Molecular Weight: 296.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C(=O)/C(C#N)=N/Nc2ccccc2)no1

Standard InChI:  InChI=1S/C16H16N4O2/c1-16(2,3)14-9-12(20-22-14)15(21)13(10-17)19-18-11-7-5-4-6-8-11/h4-9,18H,1-3H3/b19-13+

Standard InChI Key:  ZMSCPGRZLQOTSN-CPNJWEJPSA-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
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  3  0
 10 13  1  0
 10 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 13  2  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3594316

   (1E)-N-anilino-2-(5-tert-butyl-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: 296.33

Molecular Weight (Monoisotopic): 296.1273

AlogP: 3.15

#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: 5.32

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.53

Np Likeness Score: -1.39

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]

2. Wang P, Liu Z, Chen H, Ye N, Cheng X, Zhou J..  (2017)  Exchange proteins directly activated by cAMP (EPACs): Emerging therapeutic targets.,  27  (8): [PMID:28283242] [10.1016/j.bmcl.2017.02.065]

Source

Source(1):

• Scientific Literature