IMPPAT Phytochemical information: 
Isohesperidin
Isohesperidin
Summary

SMILES: COc1ccc(cc1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O
InChI: InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)42-17-5-11(3-4-15(17)38-2)16-8-14(31)20-13(30)6-12(29)7-18(20)41-16/h3-7,10,16,19,21-30,32-37H,8-9H2,1-2H3/t10-,16-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey: KGLNDYQQXNMWCQ-GBWQQRHQSA-N
DeepSMILES: COcccccc6O[C@@H]O[C@H]CO[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))[C@H][C@@H][C@H]6O))O))O))))))))[C@@H]CC=O)ccO6)cccc6O)))O
Scaffold Graph/Node/Bond level: O=C1CC(c2cccc(OC3CCCC(COC4CCCCO4)O3)c2)Oc2ccccc21
Scaffold Graph/Node level: OC1CC(C2CCCC(OC3CCCC(COC4CCCCO4)O3)C2)OC2CCCCC12
Scaffold Graph level: CC1CC(C2CCCC(CC3CCCC(CCC4CCCCC4)C3)C2)CC2CCCCC12
Functional groups: cC(=O)C; cOC; cO[C@@H](C)OC; cO; CO[C@@H](C)OC; CO
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: Flavanones
Synonymous chemical names:
isohesperidin
External chemical identifiers:
CID:CID_70688501; ChEMBL:CHEMBL2058850; ZINC:ZINC000084689141
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isohesperidin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 610.57
Log P RDKit -1.16
Topological polar surface area (Å2) RDKit 234.29
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 28
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 11
Stereochemical complexity RDKit 0.39
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.54
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Isohesperidin
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 4
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 0.184717
Isohesperidin
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 -10.75
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes