IMPPAT Phytochemical information: 
Hesperidin
Hesperidin
Summary

SMILES: COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O[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
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)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey: QUQPHWDTPGMPEX-QJBIFVCTSA-N
DeepSMILES: COcccccc6O)))[C@@H]CC=O)ccO6)cccc6O)))O[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
Scaffold Graph/Node/Bond level: O=C1CC(c2ccccc2)Oc2cc(OC3CCCC(COC4CCCCO4)O3)ccc21
Scaffold Graph/Node level: OC1CC(C2CCCCC2)OC2CC(OC3CCCC(COC4CCCCO4)O3)CCC12
Scaffold Graph level: CC1CC(C2CCCCC2)CC2CC(CC3CCCC(CCC4CCCCC4)C3)CCC12
Functional groups: cOC; CO; cO; cC(=O)C; cO[C@@H](C)OC; CO[C@@H](C)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: Flavanones
Synonymous chemical names:
cirantin, hesperetin-7-rutinoside, hesperidine, hesperidoside, 7-rutinoside of hesperetin, hesperidin, hesperidin (hesperetin-7-o-rutinoside)
External chemical identifiers:
CID:CID_10621; ChEMBL:CHEMBL449317; ChEBI:CHEBI:28775; ZINC:ZINC000008143568; FDASRS:E750O06Y6O; SureChEMBL:SCHEMBL94586; MolPort-001-794-015
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Hesperidin
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
Hesperidin
Drug-likeness
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
Hesperidin
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 -10.12
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
Hesperidin
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_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_001150ENSG00000070501POLB5423NPASS
TAR_EXP_000491ENSG00000186318BACE123621ChEMBL, NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB, ChEMBL, NPASS
TAR_EXP_000660ENSG00000082701GSK3B2932BindingDB, ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000086ENSG00000173083HPSE10855BindingDB, ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_001693ENSG00000148408CACNA1B774ChEMBL
TAR_EXP_001328ENSG00000144579CTDSP158190BindingDB, ChEMBL, NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_000414ENSG00000170323FABP42167ChEMBL
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_000700ENSG00000276497APBA1320ChEMBL, NPASS
TAR_EXP_000674ENSG00000123636BAZ2B29994ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_001736ENSG00000143933CALM2805ChEMBL