IMPPAT Phytochemical information: 
Gardenin B
Gardenin B
Summary

SMILES: COc1ccc(cc1)c1cc(=O)c2c(o1)c(OC)c(c(c2O)OC)OC
InChI: InChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3
InChIKey: LXEVSYZNYDZSOB-UHFFFAOYSA-N
DeepSMILES: COcccccc6))ccc=O)cco6)cOC))ccc6O))OC)))OC
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2ccccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CCCCC12
Functional groups: cOC; c=O; coc; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: O-methylated flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
Gardenin B, gardenin b, 5-hydroxy-6,7,8,4'-tetramethoxyflavone (gardenin b), 5-hydroxy-6,7,8,4'-tetramethoxyflavone (gardenin B)
External chemical identifiers:
CID:CID_96539; ChEMBL:CHEMBL226512; ChEBI:CHEBI:79628; ZINC:ZINC000001723552; FDASRS:313E89KN5E; SureChEMBL:SCHEMBL1764516; MolPort-003-665-805
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Gardenin B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.35
Log P RDKit 3.2
Topological polar surface area (Å2) RDKit 87.36
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Gardenin B
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 0.75
Gardenin B
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.17
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No