IMPPAT Phytochemical information: 
isorhamnetin 3-O-(6'-O-p-coumaroyl)-glucoside
isorhamnetin 3-O-(6'-O-p-coumaroyl)-glucoside
Summary

SMILES: COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O)O
InChI: InChI=1S/C31H28O14/c1-41-20-10-15(5-8-18(20)34)29-30(26(38)24-19(35)11-17(33)12-21(24)43-29)45-31-28(40)27(39)25(37)22(44-31)13-42-23(36)9-4-14-2-6-16(32)7-3-14/h2-12,22,25,27-28,31-35,37,39-40H,13H2,1H3/b9-4+/t22-,25-,27+,28-,31+/m1/s1
InChIKey: TVMGLJJYKIHJNJ-SETHOQODSA-N
DeepSMILES: COcccccc6O))))cocccO)ccc6c=O)c%10O[C@@H]O[C@H]COC=O)/C=C/cccccc6))O))))))))))[C@H][C@@H][C@H]6O))O))O)))))))))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: cOC; cO; CO; coc; c=O; cO[C@@H](C)OC; c/C=C/C(=O)OC
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:
isorhamnetin-3-0-glucopyranoside
External chemical identifiers:
CID:CID_44429737; ChEMBL:CHEMBL233903; ZINC:ZINC000028816567
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
isorhamnetin 3-O-(6'-O-p-coumaroyl)-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 624.55
Log P RDKit 1.73
Topological polar surface area (Å2) RDKit 225.81
Number of hydrogen bond acceptors RDKit 14
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 45
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 24
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.23
Number of rotatable bonds RDKit 9
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
isorhamnetin 3-O-(6'-O-p-coumaroyl)-glucoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.11
isorhamnetin 3-O-(6'-O-p-coumaroyl)-glucoside
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 -8.38
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