IMPPAT Phytochemical information: 
4H-1,4-Benzooxazine

4H-1,4-Benzooxazine
Summary

SMILES: C1=CNc2c(O1)cccc2
InChI: InChI=1S/C8H7NO/c1-2-4-8-7(3-1)9-5-6-10-8/h1-6,9H
InChIKey: QDUHQAQMOAHLRW-UHFFFAOYSA-N
DeepSMILES: C=CNccO6)cccc6
Scaffold Graph/Node/Bond level: C1=COc2ccccc2N1
Scaffold Graph/Node level: C1CCC2OCCNC2C1
Scaffold Graph level: C1CCC2CCCCC2C1
Functional groups: C1=COccN1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxazines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
Synonymous chemical names:
1,4-benzoxazine
External chemical identifiers:
CID:CID_13999802; SureChEMBL:SCHEMBL224635
Chemical structure download


4H-1,4-Benzooxazine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 133.15
Log P RDKit 1.96
Topological polar surface area (Å2) RDKit 21.26
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 10
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 2
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 2


4H-1,4-Benzooxazine
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 0.58


4H-1,4-Benzooxazine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.94
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No