IMPPAT Phytochemical information: 
Tiliroside
Tiliroside
Summary

SMILES: O=C(OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O
InChI: InChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+/t21-,24-,26+,27-,30+/m1/s1
InChIKey: DVGGLGXQSFURLP-VWMSDXGPSA-N
DeepSMILES: O=COC[C@H]O[C@@H]Occoccc6=O))cO)ccc6)O)))))))cccccc6))O))))))))[C@@H][C@H][C@@H]6O))O))O)))))))/C=C/cccccc6))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OCC1CCCC(Oc2c(-c3ccccc3)oc3ccccc3c2=O)O1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OCC1CCCC(OC2C(O)C3CCCCC3OC2C2CCCCC2)O1
Scaffold Graph level: CC(CCC1CCCCC1)CCC1CCCC(CC2C(C)C3CCCCC3CC2C2CCCCC2)C1
Functional groups: c/C=C/C(=O)OC; CO; cO[C@@H](C)OC; coc; cO; 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: Flavonols
Synonymous chemical names:
"kaempferol-3-o-α-l-(2""-e-p-coumaroyl)-glucopyranoside(tiliroside), tiliroside, tribuloside, Tribuloside, Tiliroside"
External chemical identifiers:
CID:CID_5320686; ChEMBL:CHEMBL266564; ChEBI:CHEBI:80944; ZINC:ZINC000017654711; FDASRS:15M04TXR9M; SureChEMBL:SCHEMBL23597; MolPort-001-740-347
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tiliroside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 594.53
Log P RDKit 1.73
Topological polar surface area (Å2) RDKit 216.58
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Tiliroside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
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 0.119957
Tiliroside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.17
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
Tiliroside
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000341785ADIPOR1800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.