(3-Benzyloxyphenylamino)-acetic acid [1-pyridin-4-yl-eth-(E)-ylidene]-hydrazide

ID: ALA3731262

PubChem CID: 58897655

Max Phase: Preclinical

Molecular Formula: C22H22N4O2

Molecular Weight: 374.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\NC(=O)CNc1cccc(OCc2ccccc2)c1)c1ccncc1

Standard InChI:  InChI=1S/C22H22N4O2/c1-17(19-10-12-23-13-11-19)25-26-22(27)15-24-20-8-5-9-21(14-20)28-16-18-6-3-2-4-7-18/h2-14,24H,15-16H2,1H3,(H,26,27)/b25-17+

Standard InChI Key:  DCJIPWKGABWYAG-KOEQRZSOSA-N

Molfile:  

     RDKit          2D

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    1.2990    0.7500    0.0000 N   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
   -2.5972   -1.5031    0.0000 C   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
   -3.8933   -3.7570    0.0000 N   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
   -5.1894   -6.0109    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
   -5.1872   -7.5117    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4854   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4855   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7845  -10.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0836   -8.2649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7846   -7.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7875  -12.0157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0883  -12.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0914  -14.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3904  -15.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3904  -16.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0914  -17.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7923  -16.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7923  -15.0152    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
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
  7 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3731262

   2-(3-phenylmethoxyanilino)-N-[(E)-1-pyridin-4-ylethylideneamino]acetamide

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: 374.44

Molecular Weight (Monoisotopic): 374.1743

AlogP: 3.61

#Rotatable Bonds: 8

Polar Surface Area: 75.61

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.65

CX Basic pKa: 4.18

CX LogP: 2.45

CX LogD: 2.45

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.71

References

1.  (2007)  Hydrazide compounds, 

2. Cho, Sung Yun SY and 9 more authors.  2013-12-15  Design and synthesis of novel 3-(benzo[d]oxazol-2-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine derivatives as selective G-protein-coupled receptor kinase-2 and -5 inhibitors.  [PMID:24210504]

Source

Source(1):

• Patent Bioactivity Data