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Hesperidin (FDB002680)

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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
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 capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
anti LDL35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti allergenic50857 A drug used to treat allergic reactions.DUKE
anti bradykinicDUKE
anti capillary-fragilityDUKE
anti-DNADUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti-RNADUKE
anti stomatiticDUKE
anti triglyceride35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
anti vaccinia22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anxiolytic35474 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
capillariprotectiveDUKE
catabolicDUKE
cholereticDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
hypolipidemicDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pro HLDLDUKE
vasopressorDUKE
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.