IMPPAT Phytochemical information: 
5-Oxo-2(5H)-isoxazolepropanenitrile

5-Oxo-2(5H)-isoxazolepropanenitrile
Summary

SMILES: C(n1ccc(=O)o1)CC#N
InChI: InChI=1S/C6H6N2O2/c7-3-1-4-8-5-2-6(9)10-8/h2,5H,1,4H2
InChIKey: DNSSEQBYSHSUGR-UHFFFAOYSA-N
DeepSMILES: Cnccc=O)o5)))))CC#N
Scaffold Graph/Node/Bond level: O=c1cc[nH]o1
Scaffold Graph/Node level: OC1CCNO1
Scaffold Graph level: CC1CCCC1
Functional groups: con(C)c; c=O; CC#N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Azoles
ClassyFire Subclass: Isoxazoles
Synonymous chemical names:
5-oxo-2(5h)-isoxazolepropanenitrile
External chemical identifiers:
CID:CID_171055; ChEBI:CHEBI:173579
Chemical structure download


5-Oxo-2(5H)-isoxazolepropanenitrile
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 138.13
Log P RDKit 0.35
Topological polar surface area (Å2) RDKit 58.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 6
Number of heavy atoms RDKit 10
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 3
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1


5-Oxo-2(5H)-isoxazolepropanenitrile
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.59


5-Oxo-2(5H)-isoxazolepropanenitrile
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.04
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No