IMPPAT Phytochemical information: 
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Summary

SMILES: COc1ccc2c(c1)OC(C(=O)N2)O
InChI: InChI=1S/C9H9NO4/c1-13-5-2-3-6-7(4-5)14-9(12)8(11)10-6/h2-4,9,12H,1H3,(H,10,11)
InChIKey: NDEPTLCFICMYLH-UHFFFAOYSA-N
DeepSMILES: COcccccc6)OCC=O)N6))O
Scaffold Graph/Node/Bond level: O=C1COc2ccccc2N1
Scaffold Graph/Node level: OC1COC2CCCCC2N1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cOC; 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-7-methoxy-2h-1,4-benzoxazin-3-one
External chemical identifiers:
CID:CID_152213; ChEMBL:CHEMBL451316; SureChEMBL:SCHEMBL914279
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 195.17
Log P RDKit 0.34
Topological polar surface area (Å2) RDKit 67.79
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 14
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.22
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-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
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 0
Ghose rule RDKit Passed
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 0.68
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-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 -7.28
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