2-(Benzo[d]isoxazol-3-yl)-N-(4-chloro-3-(trifluoromethyl)phenyl)-2-oxoacetohydrazonoyl cyanide

ID: ALA4099528

PubChem CID: 137662326

Max Phase: Preclinical

Molecular Formula: C17H8ClF3N4O2

Molecular Weight: 392.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#C/C(=N\Nc1ccc(Cl)c(C(F)(F)F)c1)C(=O)c1noc2ccccc12

Standard InChI:  InChI=1S/C17H8ClF3N4O2/c18-12-6-5-9(7-11(12)17(19,20)21)23-24-13(8-22)16(26)15-10-3-1-2-4-14(10)27-25-15/h1-7,23H/b24-13+

Standard InChI Key:  LVQHZXLSPXWLOW-ZMOGYAJESA-N

Molfile:  

     RDKit          2D

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    2.3263   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3252   -6.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0374   -6.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -6.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7483   -5.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0356   -4.8162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331   -3.9949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -3.5842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7413   -2.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4519   -2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4495   -1.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1650   -2.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4603   -3.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9075   -2.4223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3120   -1.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0538   -3.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2515   -3.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7031   -4.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9560   -4.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622   -5.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3070   -4.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4636   -6.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4649   -7.2812    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1748   -6.0501    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1714   -6.8718    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372   -7.2790    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 18  1  0
 17 13  1  0
 13 14  1  0
 14 12  2  0
 15 16  3  0
  9 15  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  4 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  3 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099528

   ---

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: 392.72

Molecular Weight (Monoisotopic): 392.0288

AlogP: 4.67

#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: 4.71

CX Basic pKa: ┄

CX LogP: 5.37

CX LogD: 3.67

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -1.75

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