(E)-4-(3-((2-(4-hydroxybenzoyl)hydrazono)methyl)phenoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide

ID: ALA4063158

PubChem CID: 137634843

Max Phase: Preclinical

Molecular Formula: C22H16N4O7S

Molecular Weight: 480.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N/N=C/c1cccc(Oc2no[n+]([O-])c2S(=O)(=O)c2ccccc2)c1)c1ccc(O)cc1

Standard InChI:  InChI=1S/C22H16N4O7S/c27-17-11-9-16(10-12-17)20(28)24-23-14-15-5-4-6-18(13-15)32-21-22(26(29)33-25-21)34(30,31)19-7-2-1-3-8-19/h1-14,27H,(H,24,28)/b23-14+

Standard InChI Key:  BOIGRUPBBUJXQV-OEAKJJBVSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    9.3688  -17.4540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2025  -16.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991  -16.7235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7846  -15.9258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2418  -17.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2366  -18.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6567  -17.8661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9496  -17.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0763  -17.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1659  -18.6828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3786  -18.1424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8284  -17.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5320  -17.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8182  -17.8558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1083  -17.4397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945  -17.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6888  -17.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906  -18.6703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6945  -16.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9855  -16.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707  -16.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2694  -17.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790  -17.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1956  -18.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603  -16.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  9  1  1  0
  1 11  1  0
 11 12  2  0
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 15  3  1  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  5 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 26  1  0
 14 33  1  0
 30 34  1  0
M  CHG  2  14   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4063158

   ---

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: 480.46

Molecular Weight (Monoisotopic): 480.0740

AlogP: 2.40

#Rotatable Bonds: 7

Polar Surface Area: 158.03

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.33

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.52

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.23

Np Likeness Score: -1.30

References

1. Dutra LA, Guanaes JFO, Johmann N, Lopes Pires ME, Chin CM, Marcondes S, Dos Santos JL..  (2017)  Synthesis, antiplatelet and antithrombotic activities of resveratrol derivatives with NO-donor properties.,  27  (11): [PMID:28400236] [10.1016/j.bmcl.2017.04.007]

Source

Source(1):

• Scientific Literature