IMPPAT Phytochemical information: 
2-beta-d-Glucopyranosyloxy-1,4-benzoxazin-3-one
2-beta-d-Glucopyranosyloxy-1,4-benzoxazin-3-one
Summary

SMILES: OC[C@H]1O[C@@H](OC2Oc3ccccc3NC2=O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C14H17NO8/c16-5-8-9(17)10(18)11(19)13(22-8)23-14-12(20)15-6-3-1-2-4-7(6)21-14/h1-4,8-11,13-14,16-19H,5H2,(H,15,20)/t8-,9-,10+,11-,13+,14?/m1/s1
InChIKey: PYQSUTLVBSTCSK-BJPDSMLBSA-N
DeepSMILES: OC[C@H]O[C@@H]OCOcccccc6NC%10=O))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2OC1OC1CCCCO1
Scaffold Graph/Node level: OC1NC2CCCCC2OC1OC1CCCCO1
Scaffold Graph level: CC1CC2CCCCC2CC1CC1CCCCC1
Functional groups: CO; CO[C@@H](OC1OccNC1=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
Synonymous chemical names:
blepharin (benzoxazine glucoside), blepharin
External chemical identifiers:
CID:CID_14605137
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
2-beta-d-Glucopyranosyloxy-1,4-benzoxazin-3-one
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 327.29
Log P RDKit -1.84
Topological polar surface area (Å2) RDKit 137.71
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
2-beta-d-Glucopyranosyloxy-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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.436596
2-beta-d-Glucopyranosyloxy-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 Low
Log Kp (Skin permeation, cm/s) SwissADME -9.20
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