2-(5-tert-Butylisoxazol-3-yl)-N'-(3-nitrophenyl)-2-oxoacetohydrazonoyl Cyanide

ID: ALA3594322

PubChem CID: 71711998

Max Phase: Preclinical

Molecular Formula: C16H15N5O4

Molecular Weight: 341.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C(=O)/C(C#N)=N/Nc2cccc([N+](=O)[O-])c2)no1

Standard InChI:  InChI=1S/C16H15N5O4/c1-16(2,3)14-8-12(20-25-14)15(22)13(9-17)19-18-10-5-4-6-11(7-10)21(23)24/h4-8,18H,1-3H3/b19-13+

Standard InChI Key:  HXJCOLXKPXAVSI-CPNJWEJPSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    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
   -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
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   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
 23 24  2  0
 23 25  1  0
  4 23  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3594322

   (1E)-2-(5-tert-butyl-1,2-oxazol-3-yl)-N-(3-nitroanilino)-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: 341.33

Molecular Weight (Monoisotopic): 341.1124

AlogP: 3.05

#Rotatable Bonds: 5

Polar Surface Area: 134.42

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.66

CX Basic pKa: ┄

CX LogP: 4.27

CX LogD: 2.54

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.38

Np Likeness Score: -1.74

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