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Record Information
Creation Date2006-05-22 15:12:45 UTC
Update Date2016-02-11 01:06:08 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameHesperidin
DescriptionHesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit. Hesperidin is an abundant and inexpensive by-product of Citrus cultivation and is the major flavonoid in sweet orange and lemon. In young immature oranges it can account for up to 14% of the fresh weight of the fruit due to vitamin C deficiency such as bruising due to capillary fragility were found in early studies to be relieved by crude vitamin C extract but not by purified vitamin C. The bioflavonoids, formerly called "vitamin P", were found to be the essential components in correcting this bruising tendency and improving the permeability and integrity of the capillary lining. These bioflavonoids include hesperidin, citrin, rutin, flavones, flavonols, catechin and quercetin. Of historical importance is the observation that "citrin", a mixture of two flavonoids, eriodictyol and hesperidin, was considered to possess a vitamin-like activity, as early as in 1949. Hesperidin deficiency has since been linked with abnormal capillary leakiness as well as pain in the extremities causing aches, weakness and night leg cramps. Supplemental hesperidin also helps in reducing oedema or excess swelling in the legs due to fluid accumulation. As with other bioflavonoids, hesperidin works best when administered concomitantly with vitamin C. No signs of toxicity have been observed with normal intake of hesperidin. Hesperidin was first discovered in 1827, by Lebreton, but not in a pure state and has been under continuous investigation since then (PMID: 11746857 ).
Atripliside bHMDB
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
Chemical FormulaC28H34O15
Average Molecular Weight610.5606
Monoisotopic Molecular Weight610.189770418
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
CAS Registry Number520-26-3
InChI Identifier
Chemical Taxonomy
DescriptionThis compound 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
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
  • Flavonoid-7-o-glycoside
  • Methoxyflavonoid skeleton
  • 4p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavanone
  • Fatty acyl glycoside
  • 5-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Chromane
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Anisole
  • Phenol
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Saccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
StatusExpected but not Quantified
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility2.69 mg/mLALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity140.77 m3·mol-1ChemAxon
Polarizability59.76 Å3ChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Intestine
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04703
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID207
FoodDB IDFDB002680
KNApSAcK IDC00000970
Chemspider IDNot Available
KEGG Compound IDC09755
BioCyc IDCPD-7075
BiGG IDNot Available
Wikipedia LinkHesperidin
NuGOwiki LinkHMDB03265
Metagene LinkHMDB03265
PubChem Compound53477767
PDB IDNot Available
ChEBI ID28775
Synthesis ReferenceKometani 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [15351063 ]
  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. [16424119 ]
  3. 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. [15339471 ]
  4. 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. [15240993 ]
  5. Garg A, Garg S, Zaneveld LJ, Singla AK: Chemistry and pharmacology of the Citrus bioflavonoid hesperidin. Phytother Res. 2001 Dec;15(8):655-69. [11746857 ]


General function:
Involved in protein kinase activity
Specific function:
May be directly involved in regulating the cleavage of polar spindle microtubules and is a key regulator for the onset of cytokinesis during mitosis. Component of the chromosomal passenger complex (CPC), a complex that acts as a key regulator of mitosis. The CPC complex has essential functions at the centromere in ensuring correct chromosome alignment and segregation and is required for chromatin-induced microtubule stabilization and spindle assembly. Phosphorylates 'Ser-10' and 'Ser-28' of histone H3 during mitosis. Required for kinetochore localization of BUB1 and SGOL1
Gene Name:
Uniprot ID:
Molecular weight:
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]