IMPPAT Phytochemical information: 
Gardenin C

Gardenin C
Summary

SMILES: COc1c(O)cc(cc1OC)c1cc(=O)c2c(o1)c(OC)c(c(c2O)OC)OC
InChI: InChI=1S/C20H20O9/c1-24-13-7-9(6-11(22)16(13)25-2)12-8-10(21)14-15(23)18(26-3)20(28-5)19(27-4)17(14)29-12/h6-8,22-23H,1-5H3
InChIKey: FWJPIXFUGYRDQG-UHFFFAOYSA-N
DeepSMILES: COccO)cccc6OC))))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; cO; c=O; coc
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 c, Gardenin C
External chemical identifiers:
CID:CID_3084507; FDASRS:TJ3J698F99; SureChEMBL:SCHEMBL2137291
Chemical structure download


Gardenin C
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 404.37
Log P RDKit 2.91
Topological polar surface area (Å2) RDKit 116.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 9
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 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 6
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 C
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.639342


Gardenin C
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.72
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No