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3-cyano-4-(3-hydroxyphenyl)-1,2,5-oxadiazole 2-oxide

ID: ALA571936

PubChem CID: 25269739

Max Phase: Preclinical

Molecular Formula: C9H5N3O3

Molecular Weight: 203.16

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N#Cc1c(-c2cccc(O)c2)no[n+]1[O-]

Standard InChI:  InChI=1S/C9H5N3O3/c10-5-8-9(11-15-12(8)14)6-2-1-3-7(13)4-6/h1-4,13H

Standard InChI Key:  HXBPIIAYBMAULA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
    3.2084  -13.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260  -13.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2805  -14.6718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6172  -15.1543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9581  -14.6718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9840  -15.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4266  -13.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8312  -12.4702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914  -13.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044  -12.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881  -11.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601  -11.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5501  -12.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9688  -13.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1938  -11.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  7  8  3  0
  3  4  1  0
  1  9  1  0
  4  5  1  0
  9 10  2  0
  5  1  2  0
 10 11  1  0
  1  2  1  0
 11 12  2  0
  3  6  1  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2  7  1  0
 11 15  1  0
M  CHG  2   3   1   6  -1
M  END

Alternative Forms

Associated Targets(non-human)

TGR Thioredoxin glutathione reductase (28579 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Schistosoma mansoni (6170 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 203.16Molecular Weight (Monoisotopic): 203.0331AlogP: 0.55#Rotatable Bonds: 1
Polar Surface Area: 96.99Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 8.94CX Basic pKa: CX LogP: 0.13CX LogD: 0.12
Aromatic Rings: 2Heavy Atoms: 15QED Weighted: 0.68Np Likeness Score: -0.59

References

1. Rai G, Sayed AA, Lea WA, Luecke HF, Chakrapani H, Prast-Nielsen S, Jadhav A, Leister W, Shen M, Inglese J, Austin CP, Keefer L, Arnér ES, Simeonov A, Maloney DJ, Williams DL, Thomas CJ..  (2009)  Structure mechanism insights and the role of nitric oxide donation guide the development of oxadiazole-2-oxides as therapeutic agents against schistosomiasis.,  52  (20): [PMID:19761212] [10.1021/jm901021k]

Source