N-(3-chlorophenyl)-2-(5-(4-(tert-butyl)phenyl)isoxazol-3-yl)-2-oxoacetohydrazonoyl cyanide

ID: ALA4092801

PubChem CID: 137654439

Max Phase: Preclinical

Molecular Formula: C22H19ClN4O2

Molecular Weight: 406.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(-c2cc(C(=O)/C(C#N)=N/Nc3cccc(Cl)c3)no2)cc1

Standard InChI:  InChI=1S/C22H19ClN4O2/c1-22(2,3)15-9-7-14(8-10-15)20-12-18(27-29-20)21(28)19(13-24)26-25-17-6-4-5-16(23)11-17/h4-12,25H,1-3H3/b26-19+

Standard InChI Key:  UCZLCCZFNICGRG-LGUFXXKBSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    8.5502   -4.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5491   -5.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2612   -5.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9709   -5.3714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9681   -4.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2594   -4.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2570   -3.3139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9635   -2.9032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9610   -2.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6717   -1.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6692   -0.8457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3847   -2.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4696   -2.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2736   -3.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6842   -2.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1314   -1.7372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2448   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -1.2678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6117   -3.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1275   -4.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4615   -5.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2794   -5.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7622   -4.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4256   -3.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6191   -6.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1375   -6.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4363   -6.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0202   -6.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8369   -5.7799    0.0000 Cl  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
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 17 18  3  0
  9 17  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 14 19  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092801

   ---

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: 406.87

Molecular Weight (Monoisotopic): 406.1197

AlogP: 5.47

#Rotatable Bonds: 5

Polar Surface Area: 91.28

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.86

CX Basic pKa: ┄

CX LogP: 6.59

CX LogD: 4.91

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.76

References

1. Ye N, Zhu Y, Liu Z, Mei FC, Chen H, Wang P, Cheng X, Zhou J..  (2017)  Identification of novel 2-(benzo[d]isoxazol-3-yl)-2-oxo-N-phenylacetohydrazonoyl cyanide analoguesas potent EPAC antagonists.,  134  [PMID:28399451] [10.1016/j.ejmech.2017.04.001]

Source

Source(1):

• Scientific Literature