Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2019-11-26 02:57:48 UTC
Primary IDFDB002680
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHesperidin
DescriptionHesperidin, also known as ciratin or hesperidoside, 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. Hesperidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Hesperidin is found, on average, in the highest concentration within a few different foods, such as hyssops, peppermints, and sweet oranges and in a lower concentration in grapefruits, mandarin orange (clementine, tangerine), and limes. Hesperidin has also been detected, but not quantified in, several different foods, such as rosemaries, lindens, red bell peppers, cornmints, and yellow bell peppers. This could make hesperidin a potential biomarker for the consumption of these foods.
CAS Number520-26-3
Structure
Thumb
Synonyms
SynonymSource
(S)-(-)-HesperidinChEBI
CirantinChEBI
CiratinChEBI
Hesperetin 7-O-rutinosideChEBI
HesperidosideChEBI
Hesperetin 7 rhamnoglucosideMeSH
7-Rhamnoglucoside, hesperetinMeSH
Hesperetin 7-rhamnoglucosideMeSH
Hesperetin-7-rutinosideMeSH
Hesperetin 7 rutinosideMeSH
(2S)-Hesperidinbiospider
4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-manual
Atripliside Bbiospider
Cirontindb_source
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-rhamnoglucosidebiospider
Hesperetin 7-rutinosidedb_source
Hesperetin-rutinosideHMDB
Hesperidindb_source
Hesperidin, (2S)-biospider
Hesperidin, (S)-(-)-biospider
HesperidineHMDB
Hesperitin-7-rhamnoglucosideHMDB
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
Polarizability58.87 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H34O15
IUPAC name(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
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
Isomeric 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
Average Molecular Weight610.5606
Monoisotopic Molecular Weight610.189770418
Classification
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 Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 55.08%; H 5.61%; O 39.31%DFC
Melting PointMp 258-262° (softens at 250°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -47.3 (Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0a4i-0960000000-19057cfec7c79b016a552017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0009000000-283330c229581467aa8c2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0a4i-0002009000-ef46dd12935025cc99f32017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0009002000-4750b2aa846256abc7dc2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0a4i-0010009000-7d463589853787a4d83a2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0029000000-5abbbe61f9472ac9f4462017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0009000000-865b6028ed5cc1fd73d82017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-2924000000-2288595ee1b67877de4b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000009000-8c42f8adffac7d78b94c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-0006009000-1f68460ef007fbd1cfa92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009002000-26d653ee690ce5c6cd202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009000000-a4d68b31e046fbf057d62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0019000000-e9135e61d5aa11f401352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0119003000-80c5f918f82d46fc11312017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-0349353000-321b597839a676166b982016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0679200000-a1b174ec1d2feacb1e052016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0933000000-e77d04d786da1eae235e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r00-5659348000-127002c9964ea54f38db2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-4759120000-f28ca408fe1f550a3a8a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-3698000000-6678009a010a429a4ce12016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09755
Pubchem Compound ID53477767
Pubchem Substance IDNot Available
ChEBI ID28775
Phenol-Explorer ID207
DrugBank IDDB04703
HMDB IDHMDB03265
CRC / DFC (Dictionary of Food Compounds) IDCNB06-R:CNB12-Q
EAFUS ID1608
Dr. Duke IDHESPERIDOSIDE|HESPERIDIN
BIGG IDNot Available
KNApSAcK IDC00000970
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHesperidin
Phenol-Explorer Metabolite ID207
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Analgesic35480 An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.DUKE
Anti LDL35222 An agent that reduces low-density lipoprotein (LDL) cholesterol levels, playing a crucial role in preventing cardiovascular disease. Therapeutically, it inhibits LDL uptake, promoting cardiovascular health. Key medical uses include managing hyperlipidemia, reducing atherosclerosis risk, and preventing heart attacks and strokes.DUKE
Anti-allergenic50857 An agent that reduces or blocks allergic reactions, commonly used to treat conditions such as hay fever, asthma, and skin allergies, by inhibiting the release of histamine and other inflammatory mediators, providing relief from symptoms like itching, sneezing, and congestion.DUKE
Anti bradykinicAn agent that inhibits the action of bradykinin, a peptide causing blood vessels to dilate and leading to increased permeability, pain, and inflammation. Therapeutically, anti-bradykinics are used to treat conditions like hereditary angioedema, reducing swelling and pain, and may also have applications in managing other inflammatory disorders.DUKE
Anti capillary-fragilityAn agent that strengthens capillary walls to prevent rupture, reducing bruising and bleeding. It plays a biological role in maintaining vascular integrity, and has therapeutic applications in treating conditions like purpura and hemorrhoids, with key medical uses in preventing and managing microvascular damage.DUKE
Anti-DNAAn antibody that binds to DNA, used for diagnostic purposes, particularly in detecting autoimmune diseases like systemic lupus erythematosus (SLE), and has potential therapeutic applications in treating these conditions.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti histaminic37956 An agent that blocks histamine receptors, reducing allergic symptoms. Therapeutically, it alleviates itching, sneezing, and runny nose, commonly used in managing allergies, itching, and hives, as well as treating conditions like anaphylaxis and allergic rhinitis.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti leukotriene35222 An agent that blocks the action of leukotrienes, reducing inflammation and bronchoconstriction. Therapeutically, it is used to treat asthma, allergic rhinitis, and other respiratory disorders by inhibiting the biological role of leukotrienes in mediating inflammatory responses.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti-RNAAn agent that binds to RNA, inhibiting its function and replication. It plays a biological role in regulating gene expression and has therapeutic applications in treating viral infections and cancer. Key medical uses include antiviral therapy and gene silencing, making it a potential treatment for diseases such as hepatitis and HIV.DUKE
Anti-stomatiticAn agent that relieves inflammation of the mucous membrane of the mouth, reducing oral discomfort and pain. Its biological role is to soothe and protect the mucosa, with therapeutic applications in managing mouth ulcers, oral thrush, and other stomatitis-related conditions. Key medical uses include treating oral inflammation, irritation, and infections.DUKE
Anti triglyceride35222 An agent that reduces triglyceride levels, lowering cardiovascular disease risk. It inhibits triglyceride synthesis or increases clearance, commonly used in managing hypertriglyceridemia, preventing pancreatitis, and reducing cardiovascular events.DUKE
Anti ulcer49201 An agent that reduces stomach acid and protects the mucous lining, preventing ulcer formation. It is used to treat conditions like gastroesophageal reflux disease (GERD), peptic ulcers, and Zollinger-Ellison syndrome, promoting healing and relieving symptoms.DUKE
Anti-vaccinia22587 An antibody that neutralizes the vaccinia virus, used to treat complications from smallpox vaccination, such as eczema vaccinatum and progressive vaccinia, by reducing viral replication and promoting healing.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Anxiolytic35474 An agent that reduces anxiety symptoms, commonly used in managing anxiety disorders, such as generalized anxiety disorder and panic disorder, by modulating neurotransmitters like GABA, promoting relaxation and calming effects.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
CapillariprotectiveAn agent that protects and strengthens capillaries, alleviating conditions such as fragility and permeability. Therapeutically, it helps manage disorders like hemorrhoids and varicose veins, and has applications in reducing inflammation and improving microcirculation, commonly used in vascular health and wound healing.DUKE
CatabolicA biological process that breaks down molecules, releasing energy used to fuel anabolic reactions. Therapeutically, catabolic agents are used to manage weight loss, treat metabolic disorders, and enhance athletic performance. Key medical uses includeDUKE
CholereticAn agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.DUKE
Central nervous system depressant35470 An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
HypolipidemicAn agent that lowers lipid levels, treating hyperlipidemias by reducing cholesterol and triglyceride production, with therapeutic applications in managing cardiovascular disease, atherosclerosis, and stroke, commonly used to prevent heart attacks and improve overall cardiovascular health.DUKE
Lipoxygenase inhibitor35856 An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Pro HLDLAn agent that enhances the activity of HDL (High Density Lipoprotein), facilitating the removal of excess cholesterol from the bloodstream, thereby reducing the risk of cardiovascular disease and promoting overall heart health.DUKE
VasopressorAn agent that causes constriction of blood vessels, increasing blood pressure. It plays a biological role in regulating blood pressure and fluid balance. Therapeutically, vasopressors are used to treat hypotension, shock, and bleeding, and have key medical applications in surgery, trauma, and critical care.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.