Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2018-05-29 00:36:10 UTC
Primary IDFDB002711
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHyperin
DescriptionOccurs widely in plants, e.g. in apple peel and Hypericum perforatum (St John's wort) Hyperoside is the 3-O-galactoside of quercetin. It is a medicinally active compound that can be isolated from Drosera rotundifolia, from the Stachys plant, from Prunella vulgaris, from Rumex acetosella and from St John's wort. Hyperin is found in many foods, some of which are apricot, pear, guava, and common buckwheat.
CAS Number482-36-0
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3-(beta-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneChEBI
HyperinChEBI
HyperosideChEBI
Quercetin 3-O-galactosideChEBI
2-(3,4-Dihydroxyphenyl)-3-(b-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
2-(3,4-Dihydroxyphenyl)-3-(β-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-oneGenerator
3-O-b-D-Galactopyranosyloxy-3',4',5,7-tetrahydroxyflavoneHMDB
HyperozideHMDB
JyperinHMDB
Quercetin 3-beta-D-galactopyranosideHMDB
Quercetin 3-D-galactosideHMDB
Quercetin 3-O-beta-D-galactopyranosideHMDB
Quercetin 3-O-beta-D-galactosideHMDB
Quercetin galactosideHMDB
Quercetin-3-O-galactosideHMDB
Quercetin 3-galactosideChEBI
Quercetin 3-O-b-D-galactopyranosideGenerator
Quercetin 3-O-β-D-galactopyranosideGenerator
Quercetin 3-O-β-D-galactopyranosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility1.95 g/LALOGPS
logP0.47ALOGPS
logP-0.14ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.28 m³·mol⁻¹ChemAxon
Polarizability43.34 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O12
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1
InChI KeyOVSQVDMCBVZWGM-DTGCRPNFSA-N
Isomeric SMILESOC[C@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight464.3763
Monoisotopic Molecular Weight464.095476104
Classification
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Oplopane sesquiterpenoid
  • Fatty acid ester
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.32%; H 4.34%; O 41.34%DFC
Melting PointMp 232-233° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -83 (c, 0.2 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uea-8903800000-499ac85a438f6221151eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014r-3620009000-aa92fb234d45c04fb4a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0119000000-7653e3fde6f08a1f608eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0000900000-d60d8b7b555f72b770e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0001900000-f2659f2ecc8cfe825e94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0009200000-fb8341fdb16a9e23a75eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0019000000-1a226fba24f56b619964View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uk9-0097000000-5067646f23e49b711552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0179700000-5040715c1b88dc41ba6aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0003900002-b3b20b949d3387148921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0059000000-901297fb44ccb903acfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0000900000-84736db1d76deb6da60cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0179400000-aa2a652149ab343a1341View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0w29-0189500000-7ff049ba7cc9caedea63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0139300000-b99c9ec27bda7ca0248aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009300000-c1c93b32f056b141b26aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-24376004571f89c29c26View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-5cc0caf744b94b4e08cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-d83176614063aaa00578View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-5d64182b6ec0f035e317View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0009000000-e4f36aa3a2f59746a2deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0238900000-84d67141521459a118c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0269100000-855726a927e888161d78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2962000000-bc39b0d9e5586054d85fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1306900000-12c0a6f0c9db05e8c9bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2439200000-fc56cb8d8bcb486e96a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-6963000000-3bde95e6420d1d4a73e4View in MoNA
ChemSpider ID4444962
ChEMBL IDCHEMBL251254
KEGG Compound IDC10073
Pubchem Compound ID5281643
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID292
DrugBank IDNot Available
HMDB IDHMDB30775
CRC / DFC (Dictionary of Food Compounds) IDCNF10-I:CNF10-I
EAFUS IDNot Available
Dr. Duke IDHYPERIN|HYPEROSIDE|QUERCETIN-3-O-GALACTOSIDE|3-O-(BETA-D-GALACTOPYRANOSYL)-QUERCETIN
BIGG IDNot Available
KNApSAcK IDC00005372
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHyperoside
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
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 aging52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti capillary-fragilityDUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti elastase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti ischemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti nociceptive35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.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 radicularDUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti wrinkleDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cAMP inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
capillarifortificantDUKE
capillarigenicDUKE
cyclooxygenase activatorDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
hypotensiveDUKE
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
tissue thromboplastin inhibitor50427 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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.