2-(5-tert-Butylisoxazol-3-yl)-N'-(4-chlorophenyl)-2-oxoacetohydrazonoyl Cyanide

ID: ALA3594318

PubChem CID: 6383743

Max Phase: Preclinical

Molecular Formula: C16H15ClN4O2

Molecular Weight: 330.78

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(C(=O)/C(C#N)=N/Nc2ccc(Cl)cc2)no1

Standard InChI:  InChI=1S/C16H15ClN4O2/c1-16(2,3)14-8-12(21-23-14)15(22)13(9-18)20-19-11-6-4-10(17)5-7-11/h4-8,19H,1-3H3/b20-13+

Standard InChI Key:  FVOOXEZIGUERJS-DEDYPNTBSA-N

Molfile:  

     RDKit          2D

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    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
   -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
    0.0031   -3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.7494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6078   -5.9988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -6.6047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6460   -5.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8244   -8.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3609   -9.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -9.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974   -8.3594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2416  -10.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4351  -10.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7532  -12.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9465  -11.9692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    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
  9 11  1  0
 11 12  3  0
 10 13  1  0
 10 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 13  2  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
  3 23  1  0
M  END

Associated Targets(Human)

HepG2-CD81 (19978 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rapgef4 Rap guanine nucleotide exchange factor 4 (114 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium berghei (192651 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 330.78Molecular Weight (Monoisotopic): 330.0884AlogP: 3.80#Rotatable Bonds: 4
Polar Surface Area: 91.28Molecular Species: ACIDHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 5.09CX Basic pKa: CX LogP: 4.94CX LogD: 3.30
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.52Np Likeness Score: -1.58

References

1. Ye N, Zhu Y, Chen H, Liu Z, Mei FC, Wild C, Chen H, Cheng X, Zhou J..  (2015)  Structure-Activity Relationship Studies of Substituted 2-(Isoxazol-3-yl)-2-oxo-N'-phenyl-acetohydrazonoyl Cyanide Analogues: Identification of Potent Exchange Proteins Directly Activated by cAMP (EPAC) Antagonists.,  58  (15): [PMID:26151319] [10.1021/acs.jmedchem.5b00635]
2. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]