IMPPAT Phytochemical information: 
DIMBOA glucoside
DIMBOA glucoside
Summary

SMILES: OC[C@H]1O[C@@H](O[C@H]2Oc3cc(OC)ccc3N(C2=O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H19NO10/c1-23-6-2-3-7-8(4-6)24-15(13(21)16(7)22)26-14-12(20)11(19)10(18)9(5-17)25-14/h2-4,9-12,14-15,17-20,22H,5H2,1H3/t9-,10-,11+,12-,14+,15-/m1/s1
InChIKey: WTGXAWKVZMQEDA-XFWGRBSCSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@H]OcccOC))ccc6NC%10=O))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](O[C@H]1OccN(O)C1=O)C; cOC
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:
2-(2-hydroxy-4,7-dimethoxy-1-4(2h)-benzoxazin-3-one-beta-d-glucoside, (2r)-β-d-glucopyranosyloxy-4-hydroxy-7-methoxy-2h-1,4-benzoxazin-3(4h)-one, 2-(2,4-dihydroxy-7-methoxy-1-4(2h)-benzoxazin-3-(4h)on)-beta-d-glucoside, 2-(2-hydroxy-7-methoxy-1,4(2h)-benzoxazin-3(4h)-on-beta-d-glucoside, 2-(2,4-dihydroxy-1,4(2h)-benzoxazin-3(4h)-on-beta-d-glucoside
External chemical identifiers:
CID:CID_441563; ChEMBL:CHEMBL519905; ChEBI:CHEBI:37573
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
DIMBOA glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 373.31
Log P RDKit -2.05
Topological polar surface area (Å2) RDKit 158.38
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.53
Number of rotatable bonds RDKit 3
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
DIMBOA glucoside
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 1
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.37
DIMBOA glucoside
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 -9.72
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