IMPPAT Phytochemical information: 
Cynaroside
Cynaroside
Summary

SMILES: OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)oc(cc3=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
InChIKey: PEFNSGRTCBGNAN-QNDFHXLGSA-N
DeepSMILES: OC[C@H]O[C@@H]OcccO)ccc6)occc6=O)))cccccc6)O))O)))))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1cc(-c2ccccc2)oc2cc(OC3CCCCO3)ccc12
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3CCCCO3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCCC3)CCC12
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavones
Synonymous chemical names:
Luteolin-7-glucoside, luteolin-7-glucoside, luteolin and its 7 glucoside, Glucoluteolin, luteolin-7-o-glucopyranoside, luteolin-7-β-glucoside, luteolin-7-glucosides, cynaroside, Gluco Luteolin, Luteolin-7-O-glucoside, cinaroside, galuteolin, luteolin-7-mono-beta-d-glucopyranoside, luteolin-7-β-d-glucoside, Cynaroside, luteolin-7-o-glucoside, luteoloside, luteolin 7-o-glucoside, luteolin-7-glucosylglucuronide, luteolin-7-o-beta-glucoside, glucoluteolin, 7-glucoside of luteolin, luteolin 7-glucoside, luteolin -7- glucoside
External chemical identifiers:
CID:CID_5280637; ChEMBL:CHEMBL233929; ChEBI:CHEBI:27994; ZINC:ZINC000004096258; FDASRS:98J6XDS46I; SureChEMBL:SCHEMBL149118; MolPort-001-740-780
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Cynaroside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 448.38
Log P RDKit -0.24
Topological polar surface area (Å2) RDKit 190.28
Number of hydrogen bond acceptors RDKit 11
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 32
Number of heteroatoms RDKit 11
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4
Cynaroside
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.260645
Cynaroside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.00
Number of PAINS structural alerts SwissADME 1
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 Yes
Cynaroside
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_001676ENSG00000165392WRN7486NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001616ENSG00000228321TNF7124BindingDB, ChEMBL, NPASS
TAR_EXP_001557ENSG00000012048BRCA1672NPASS
TAR_EXP_001545ENSG00000130413STK3365975BindingDB
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001151ENSG00000170734POLH5429ChEMBL, NPASS
TAR_EXP_001145ENSG00000175535PNLIP5406ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000222ENSG00000112062MAPK141432BindingDB
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_001137ENSG00000122194PLG5340ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000635ENSG00000167701GPT2875ChEMBL, NPASS
TAR_EXP_000881ENSG00000087085ACHE43BindingDB
TAR_EXP_000756ENSG00000109471IL23558ChEMBL, NPASS
TAR_EXP_000559ENSG00000185513L3MBTL126013ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_001238ENSG00000109339MAPK105602BindingDB