HESPERIDIN (CED0002510)

Record Information
Version1.0
Creation Date2016-05-19 02:08:14 UTC
Update Date2026-05-14 18:09:56 UTC
Accession NumberCHEM005941
Identification
Common NameHESPERIDIN
ClassSmall Molecule
Description
HESPERIDIN belongs to the flavonoid glycosides, a subclass of flavonoids within the organic compounds. With an average molecular weight of 610.56 g/mol, HESPERIDIN is a heavy molecule with the chemical formula C28H34O15. It is categorized within the superclass of phenylpropanoids and polyketides. Biologically, the compound acts as an antioxidant (PMC10812391, PMC11548494, PMC11643819, PMC13207936, PMC13360740, PMC8819208) and a drug (PMC7895681). Industrially, it is utilized as a softener, conditioner, flavouring, and nutrient (PMC10812391, PMC11548494, PMC11643819, PMC13207936, PMC13360740, PMC8819208). The compound is found in 19 recorded sources, including drinking water and building and construction materials such as ceilings and fencing. It is also present in household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is associated with electrical and electronic equipment, such as video games, electrodes, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. It is also found in food, food processing and cookware, including food preservation, fermentation processes for beer, the preparation of vinegar, the preparation of wine or sparkling wine, and the processing of fish. The recorded exposure route is oral. HESPERIDIN targets two proteins: the voltage-dependent N-type calcium channel subunit alpha-1B (CACNA1B) and the Aurora kinase B (AURKB), of which it is an inhibitor or regulator. Regarding health effects, it is associated with inflammation (PMC10812391) but also provides a therapeutic effect on inflammation (PMC13480764) and hyperglycemia (PMC8398118). Furthermore, it is used as a treatment for diabetes mellitus (PMC10646315).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
7-Rhamnoglucoside, hesperetinHMDB
Hesperetin 7-rhamnoglucosideHMDB
Hesperetin-7-rutinosideHMDB
Atripliside bHMDB
Hesperetin 7 rhamnoglucosideHMDB
Hesperetin 7 rutinosideHMDB
(2S)-HesperidinHMDB
(S)-(-)-HesperidinHMDB
CirantinHMDB
CiratinHMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-a-L-rhamnosyl-D-glucoside) (7ci)HMDB
Flavanone, 3',5,7-trihydroxy-4'-methoxy-, 7-(6-O-alpha-L-rhamnosyl-delta-glucoside) (7ci)HMDB
Hesper bitabsHMDB
Hesperetin 7-O-rutinosideHMDB
Hesperetin-rutinosideHMDB
HesperidineHMDB
HesperidosideHMDB
Hesperitin-7-rhamnoglucosideHMDB
2S, HesperidinMeSH
Hesperidin 2SMeSH
HesperidinMeSH
Chemical FormulaC28H34O15
Average Molecular Mass610.561 g/mol
Monoisotopic Mass610.190 g/mol
CAS Registry Number520-26-3
IUPAC Name(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namehesperidine
SMILESCOC1=CC=C(C=C1O)[C@@H]1CC(=O)C2=C(O1)C=C(O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C=C2O
InChI IdentifierInChI=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
InChI KeyQUQPHWDTPGMPEX-QJBIFVCTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Polyol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.69 g/LALOGPS
logP-0.27ALOGPS
logP-0.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.61ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity140.77 m³·mol⁻¹ChemAxon
Polarizability59.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0960000000-19057cfec7c79b016a55Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-283330c229581467aa8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0002009000-ef46dd12935025cc99f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009002000-4750b2aa846256abc7dcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0010009000-7d463589853787a4d83aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0029000000-5abbbe61f9472ac9f446Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-865b6028ed5cc1fd73d8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2924000000-2288595ee1b67877de4bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0000009000-8c42f8adffac7d78b94cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0zfr-0006009000-1f68460ef007fbd1cfa9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009002000-26d653ee690ce5c6cd20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-a4d68b31e046fbf057d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0019000000-e9135e61d5aa11f40135Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0119003000-80c5f918f82d46fc1131Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0029000000-15e7bff1df4ba788d095Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ika-0003906000-8e92397c3ef59083d90bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109500000-d16e1ccb83edc18c2285Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0109000000-44829065079eda0599e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0209000000-edd02887a04b421dbb39Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0819000000-3ad8fb39515b5eaa0fd2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3719300000-f2635b73560ddfd8533fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-2924000000-2288595ee1b67877de4bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-0349353000-321b597839a676166b98Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-0679200000-a1b174ec1d2feacb1e05Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-0933000000-e77d04d786da1eae235eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0r00-5659348000-127002c9964ea54f38dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-4759120000-f28ca408fe1f550a3a8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-3698000000-6678009a010a429a4ce1Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
8699.0Log mg/kg[4900:15000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
inflammationassociated_withNot AvailablePMC10812391
inflammationhas_therapeutic_effect_onNot AvailablePMC13480764
diabetes mellitusis_treatment_forNot AvailablePMC10646315
hyperglycemiahas_therapeutic_effect_onNot AvailablePMC8398118
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)1.71268
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)44.1405
Cytochrome P450 1B1 structureClick to view 3D structureCytochrome P450 1B1Q16678HumansPredicted (SEA)15.2584
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)30.0498
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)57.5306
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)77.3043
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)27.5586
Xanthine dehydrogenase/oxidase structureClick to view 3D structureXanthine dehydrogenase/oxidaseP47989HumansPredicted (SEA)6.38364
Click to view 3D structureTaste receptor type 2 member 31P59538HumansPredicted (SEA)0.622794
Cytochrome P450 1A1 structureClick to view 3D structureCytochrome P450 1A1P04798HumansPredicted (SEA)29.8941
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)754.437
Dipeptidyl peptidase 4 structureClick to view 3D structureDipeptidyl peptidase 4P27487HumansPredicted (SEA)45.7753
Lysine-specific histone demethylase 1A structureClick to view 3D structureLysine-specific histone demethylase 1AO60341HumansPredicted (SEA)63.2136
Click to view 3D structureSolute carrier organic anion transporter family member 2B1O94956HumansPredicted (SEA)15.1027
Click to view 3D structureMonocarboxylate transporter 8P36021HumansPredicted (SEA)1.08989
Beta-secretase 1 structureClick to view 3D structureBeta-secretase 1P56817HumansPredicted (SEA)162.316
Click to view 3D structureTrehalose-phosphataseA8NS89Brugia malayiPredicted (SEA)6.38364
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)30.6726
Aldo-keto reductase family 1 member B1 structureClick to view 3D structureAldo-keto reductase family 1 member B1P15121HumansPredicted (SEA)79.8733
Click to view 3D structureTyrosinaseO42713Agaricus bisporusPredicted (SEA)22.8877
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)170.801
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)1073.31
Click to view 3D structureNonstructural protein 5V5TFZ2Dengue virusPredicted (SEA)15.5698
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)32.6188
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)790.948
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0003265
FooDB IDFDB002680
Phenol Explorer IDNot Available
KNApSAcK IDC00000970
BiGG IDNot Available
BioCyc IDCPD-7075
METLIN ID3678
PDB IDNot Available
Wikipedia LinkHesperidin
Chemspider ID35013051
ChEBI ID28775
PubChem Compound ID53477767
Kegg Compound IDC09755
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kometani T; Nishimura T; Nakae T; Takii H; Okada S Synthesis of neohesperidin glycosides and naringin glycosides by cyclodextrin glucanotransferase from an alkalophilic Bacillus species. Bioscience, biotechnology, and biochemistry (1996), 60(4), 645-9.
2. Nielsen IL, Chee WS, Poulsen L, Offord-Cavin E, Rasmussen SE, Frederiksen H, Enslen M, Barron D, Horcajada MN, Williamson G: Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: a randomized, double-blind, crossover trial. J Nutr. 2006 Feb;136(2):404-8.
3. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81.
4. Li QS, Lou GY, Qian MZ: [Effect of hesperidin and rutin on oxidative modification of high density lipoprotein in vitro]. Zhong Xi Yi Jie He Xue Bao. 2004 Mar;2(2):115-6, 119.
5. Lee NK, Choi SH, Park SH, Park EK, Kim DH: Antiallergic activity of hesperidin is activated by intestinal microflora. Pharmacology. 2004 Aug;71(4):174-80.
6. Garg A, Garg S, Zaneveld LJ, Singla AK: Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Phytother Res. 2001 Dec;15(8):655-69.