Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2018-05-29 00:36:05 UTC
Primary IDFDB002680
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHesperidin
DescriptionFound in most citrus fruits and other members of the Rutaceae, also in Mentha longifolia Hesperidin is a flavanone glycoside (flavonoid) (C28H34O15) found abundantly in citrus fruits. Its aglycone form is called hesperetin.
CAS Number520-26-3
Structure
Thumb
Synonyms
SynonymSource
(S)-(-)-HesperidinChEBI
CirantinChEBI
CiratinChEBI
Hesperetin 7-O-rutinosideChEBI
HesperidosideChEBI
(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-rhamnoglucosidebiospider
Hesperetin 7-rutinosidedb_source
Hesperetin-7-rutinosideHMDB
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 triazoles. Triazoles are compounds containing a five-member aromatic ring of two carbon atoms and three nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTriazoles
Direct ParentTriazoles
Alternative Parents
Substituents
  • Heteroaromatic compound
  • 1,2,4-triazole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
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
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.