IMPPAT Phytochemical information: 
Gancaonin I

Gancaonin I
Summary

SMILES: COc1c(CC=C(C)C)c(OC)cc2c1cc(o2)c1ccc(cc1O)O
InChI: InChI=1S/C21H22O5/c1-12(2)5-7-15-18(24-3)11-20-16(21(15)25-4)10-19(26-20)14-8-6-13(22)9-17(14)23/h5-6,8-11,22-23H,7H2,1-4H3
InChIKey: DKVBYQAVNNRVNN-UHFFFAOYSA-N
DeepSMILES: COccCC=CC)C))))cOC))ccc6cco5)cccccc6O)))O
Scaffold Graph/Node/Bond level: c1ccc(-c2cc3ccccc3o2)cc1
Scaffold Graph/Node level: C1CCC(C2CC3CCCCC3O2)CC1
Scaffold Graph level: C1CCC(C2CC3CCCCC3C2)CC1
Functional groups: cOC; CC=C(C)C; coc; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: 2-arylbenzofuran flavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: 2-arylbenzofurans
Synonymous chemical names:
gancaonin i
External chemical identifiers:
CID:CID_480777; ChEMBL:CHEMBL3808735; ChEBI:CHEBI:69099; ZINC:ZINC000005854532; SureChEMBL:SCHEMBL22704765; MolPort-006-668-426
Chemical structure download


Gancaonin I
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.4
Log P RDKit 5.04
Topological polar surface area (Å2) RDKit 72.06
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
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 16
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.24
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


Gancaonin I
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
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 Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.628333


Gancaonin I
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 -4.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No