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Record Information
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:45 UTC
Update Date2020-02-26 21:24:28 UTC
Secondary Accession Numbers
  • HMDB03265
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 ).
7-Rhamnoglucoside, hesperetinHMDB
Hesperetin 7-rhamnoglucosideHMDB
Atripliside bHMDB
Hesperetin 7 rhamnoglucosideHMDB
Hesperetin 7 rutinosideHMDB
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
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
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
  • 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

Route of exposure:


Biological location:

Physical Properties
Experimental Properties
Melting Point262 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility2.69 g/LALOGPS
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
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-7432290000-b2e363b3a4573c409d87Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-066r-7330019000-b63391bb7f1e41c9f778Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0009000000-283330c229581467aa8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0002009000-ef46dd12935025cc99f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009002000-4750b2aa846256abc7dcSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0010009000-7d463589853787a4d83aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0029000000-5abbbe61f9472ac9f446Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-865b6028ed5cc1fd73d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-2924000000-2288595ee1b67877de4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-8c42f8adffac7d78b94cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0006009000-1f68460ef007fbd1cfa9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009002000-26d653ee690ce5c6cd20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-a4d68b31e046fbf057d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0019000000-e9135e61d5aa11f40135Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0119003000-80c5f918f82d46fc1131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-0449354000-fbc98e9137414ef7f9d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0798110000-16e3084699e73d1ab59dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-0922000000-3a62c905fced57caf060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r00-5649448000-9cac05e933663578912dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-3759130000-62395a3dbb85c7dd9d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3698000000-d4e4fc069a84c3e6d9e0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Intestine
Normal Concentrations
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002680
KNApSAcK IDC00000970
Chemspider ID35013051
KEGG Compound IDC09755
BioCyc IDCPD-7075
BiGG IDNot Available
Wikipedia LinkHesperidin
PubChem Compound53477767
PDB IDNot Available
ChEBI ID28775
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. 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. [PubMed:16424119 ]
  2. 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. [PubMed:15351063 ]
  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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10592235 ]