IMPPAT Phytochemical information: 
2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one

2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one
Summary

SMILES: O=C1C(O)Oc2c(N1O)cccc2
InChI: InChI=1S/C8H7NO4/c10-7-8(11)13-6-4-2-1-3-5(6)9(7)12/h1-4,8,11-12H
InChIKey: COVOPZQGJGUPEY-UHFFFAOYSA-N
DeepSMILES: O=CCO)OccN6O))cccc6
Scaffold Graph/Node/Bond level: O=C1COc2ccccc2N1
Scaffold Graph/Node level: OC1COC2CCCCC2N1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: O=C1C(O)OccN1O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Benzoxazines
ClassyFire Subclass: Benzoxazinones
NP Classifier Biosynthetic pathway: Alkaloids|Shikimates and Phenylpropanoids
Synonymous chemical names:
24-dihydroxy-14-benzoxazin-3-one, 2,4-dihydroxy-1,4-benzoxazin-3-one
External chemical identifiers:
CID:CID_28495; ChEMBL:CHEMBL483002; ChEBI:CHEBI:63558; FDASRS:4J4378V66G; SureChEMBL:SCHEMBL914002; MolPort-028-750-132
Chemical structure download


2,4-Dihydroxy-2H-1,4-benzoxazin-3(4H)-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 181.15
Log P RDKit 0.12
Topological polar surface area (Å2) RDKit 70
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 8
Number of heavy atoms RDKit 13
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 0.12
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


2,4-Dihydroxy-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 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
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 0.557519


2,4-Dihydroxy-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 -7.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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