IMPPAT Phytochemical information: 
2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Summary

SMILES: O=C1Nc2ccccc2OC1O
InChI: InChI=1S/C8H7NO3/c10-7-8(11)12-6-4-2-1-3-5(6)9-7/h1-4,8,11H,(H,9,10)
InChIKey: VMQBFYRBJKDACN-UHFFFAOYSA-N
DeepSMILES: O=CNcccccc6OC%10O
Scaffold Graph/Node/Bond level: O=C1COc2ccccc2N1
Scaffold Graph/Node level: OC1COC2CCCCC2N1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: O=C1NccOC1O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxazines
ClassyFire Subclass: Benzoxazinones
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
Synonymous chemical names:
2-hydroxy-2h-14-benzoxazin-3(4h)-one, blepharigenin
External chemical identifiers:
CID:CID_322636; ChEMBL:CHEMBL457386; ChEBI:CHEBI:63559; SureChEMBL:SCHEMBL912962; MolPort-028-750-271
Chemical structure download


2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 165.15
Log P RDKit 0.34
Topological polar surface area (Å2) RDKit 58.56
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 12
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.12
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.12
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


2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.582245


2-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one
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 -7.08
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