# Hyperoside

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Hyperoside Names IUPAC name 3-(β-D-Galactopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one Other names Hyperozide Hyperasid Hyperosid Hyperin quercetin galactoside Quercetin-3-galactoside Quercetin-3-O-galactoside Identifiers CAS Number 482-36-0 Y 3D model (JSmol) Interactive image ChEBI CHEBI:67486 N ChEMBL ChEMBL251254 ChemSpider 4444962 N DrugBank DB16403 ECHA InfoCard 100.006.892 EC Number 207-580-6 KEGG C10073 Y PubChem CID 5281643 UNII 8O1CR18L82 Y CompTox Dashboard (EPA) DTXSID501028789 InChI InChI=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 N Key: OVSQVDMCBVZWGM-DTGCRPNFSA-N N InChI=1/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 Key: OVSQVDMCBVZWGM-DTGCRPNFBG SMILES c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O Properties Chemical formula C21H20O12 Molar mass 464.379 g·mol−1 Density 1.879 g/mL Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**Hyperoside** is a chemical compound. It is the 3-*O*-[galactoside](/source/Galactoside) of [quercetin](/source/Quercetin).

## Natural occurrences

Hyperoside has been isolated from *[Drosera rotundifolia](/source/Drosera_rotundifolia)*, from the Lamiaceae *[Stachys](/source/Stachys) sp.* and *[Prunella vulgaris](/source/Prunella_vulgaris)*, from *[Rumex acetosella](/source/Rumex_acetosella)*, *[Cuscuta chinensis](/source/Cuscuta_chinensis)* seeds, from [St John's wort](/source/Hypericum_perforatum) and from *[Camptotheca acuminata](/source/Camptotheca_acuminata)*.[1] It is one of the phenolic compounds in the invasive plant *[Carpobrotus edulis](/source/Carpobrotus_edulis)* and contributes to the antibacterial[2] properties of the plant.

In *[Rheum nobile](/source/Rheum_nobile)* and *[R. rhaponticum](/source/Rheum_rhaponticum)*, it serves as a UV blocker found in the bracts.

It is also found in *[Geranium niveum](/source/Geranium_niveum)*[3] and *[Taxillus kaempferi](/source/Taxillus_kaempferi)*.[4]

## References

1. **[^](#cite_ref-1)** Li, Shiyou; Zhang, Zhizhen; Cain, Abigail; Wang, Bo; Long, Melissa; Taylor, Josephine (2005). ["Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated from Camptotheca acuminata"](https://scholarworks.sfasu.edu/cgi/viewcontent.cgi?article=1091&context=biology). *Journal of Agricultural and Food Chemistry*. **53** (1): 32–7. [Bibcode](/source/Bibcode_(identifier)):[2005JAFC...53...32L](https://ui.adsabs.harvard.edu/abs/2005JAFC...53...32L). [doi](/source/Doi_(identifier)):[10.1021/jf0484780](https://doi.org/10.1021%2Fjf0484780). [PMID](/source/PMID_(identifier)) [15631505](https://pubmed.ncbi.nlm.nih.gov/15631505).

1. **[^](#cite_ref-2)** Van Der Watt, Elmarie; Pretorius, Johan C (2001). "Purification and identification of active antibacterial components in Carpobrotus edulis L". *Journal of Ethnopharmacology*. **76** (1): 87–91. [doi](/source/Doi_(identifier)):[10.1016/S0378-8741(01)00197-0](https://doi.org/10.1016%2FS0378-8741%2801%2900197-0). [PMID](/source/PMID_(identifier)) [11378287](https://pubmed.ncbi.nlm.nih.gov/11378287).

1. **[^](#cite_ref-3)** Calzada, F; Cerda-García-Rojas, CM; Meckes, M; Cedillo-Rivera, R; Bye, R; Mata, R (1999). "Geranins a and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum". *Journal of Natural Products*. **62** (5): 705–9. [doi](/source/Doi_(identifier)):[10.1021/np980467b](https://doi.org/10.1021%2Fnp980467b). [PMID](/source/PMID_(identifier)) [10346950](https://pubmed.ncbi.nlm.nih.gov/10346950).

1. **[^](#cite_ref-Konishi_4-0)** The constituents of Taxillus kaempferi and the host, Pinus thunbergii. I. Catechins and flavones of Taxillus kaempferi. Konishi T, Nishio T, Kiyosawa S, Fujiwara Y and Konoshima T, Yakugaku Zasshi., February 1996, volume 116, issue 2, pages 148-157 (article in Japanese)

v t e Opioid receptor modulators μ-opioid (MOR) Agonists (abridged; full list) 3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Deumitragynine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Lexanopadol Loperamide Loxicodegol LS-115509 Matrine MEB-1170 Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Naloxone benzoylhydrazone (NalBzOH) Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine Oxycodegol (NKTR-181) Oxymorphone-3-methoxynaltrexonazine (OM-3-MNZ) Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine SR-17018 Sufentanil Susineridine Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol Antagonists (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine JDTic Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin δ-opioid (DOR) Agonists 3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine Antagonists 4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine κ-opioid (KOR) Agonists 3CS-nalmefene 4-Allyl-6-oxa-noribogainalog 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuammicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH MEB-1170 Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxa-noribogaine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-54494A U-69593 Xorphanol Antagonists 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Aticaprant Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox CVL-354 Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Navacaprant Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 RU-24213 Quadazocine Taxifolin UPHIT Zyklophin Nociceptin (NOP) Agonists (Arg14,Lys15)Nociceptin ((pF)Phe4)Nociceptin(1-13)NH2 (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2 Ac-RYYRWK-NH2 Ac-RYYRIK-NH2 BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH2 Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 Sunobinop (S-117957) TH-030418 Antagonists (Nphe1)Nociceptin(1-13)NH2 AT-076 BAN-ORL-24 BTRX-246040 (LY-2940094) J-113397 JTC-801 NalBzOH Nociceptin (1-7) Nocistatin SB-612111 SR-16430 Thienorphine Trap-101 UFP-101 Others Enkephalinase inhibitors: Amastatin BL-2401 Candoxatril D-Phenylalanine Dexecadotril (retorphan) Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Opiorphan Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Pronociceptin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

v t e Flavonols and their conjugates Backbone Aglycones 3-Hydroxyflavone (synthetic) and derivatives Flavonols Aglycones Fisetin Galangin Gossypetin Herbacetin Kaempferol Morin Myricetin Quercetagetin Quercetin Robinetin Conjugates Glycosides of herbacetin Rhodionin Rhodiosin Glycosides of kaempferol Afzelin (Kaempferol 3-rhamnoside) Astragalin (kaempferol 3-O-glucoside) Kaempferitrin (kaempferol 3,7-dirhamnoside) Juglanin (Kaempferol 3-O-arabinoside) Kaempferol 3-alpha-L-arabinopyranoside Kaempferol 3-alpha-D-arabinopyranoside Kaempferol 7-alpha-L-arabinoside Kaempferol 7-O-glucoside Kaempferol 3-lathyroside Kaempferol 4'-rhamnoside Kaempferol 5-rhamnoside Kaempferol 7-rhamnoside Kaempferol 7-O-alpha-L-rhamnofuranoside Kaempferol 3-xyloside Kaempferol 7-xyloside Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside) Kaempferol 3-O-rutinoside Sophoraflavonoloside (Kaempferol 3-O-sophoroside) Trifolin (Kaempferol 3-O-beta-D-galactoside) Glycosides of myricetin Betmidin (Myricetin 3-O-arabinoside) Myricetin 3-O-rutinoside Myricetin-3-O-neohesperidoside Myricitrin (Myricetin 3-O-rhamnoside) Conjugates of quercetin Sulfates Quercetin 3-O-sulfate Quercetin 3,3'-bissulfate Quercetin 3,4'-bissulfate Glycosides Avicularin (quercetin-3-O-α-L-arabinofuranoside) CTN-986 Guaijaverin (quercetin 3-O-arabinoside) Heliosin (quercetin 3-digalactoside) Hyperoside (quercetin 3-O-galactoside) Isoquercetin (quercetin 3-O-glucoside) Miquelianin (quercetin 3-O-glucuronide) Quercetin 3,4'-diglucoside Quercetin-3-sophorodide Quercitrin (quercetin 3-O-rhamnoside) Rutin (quercetin rutinoside) Reinutrin (quercetin-3-D-xyloside) Spiraeoside (quercetin 4'-O-glucoside) Taxillusin (galloylated 3-O-glucoside of quercetin° O-Methylated flavonols Aglycones 5-O-methylmyricetin Annulatin Ayanin Axillarin Azaleatin Brickellin Centaureidin Chrysosplenetin Combretol Ermanin Eupatolitin Eupalitin Europetin Isorhamnetin Jaceidin Kaempferide Kumatakenin Laricitrin Natsudaidain Ombuin Pachypodol Patuletin Retusin Mearnsetin Rhamnazin Rhamnetin Santin Spinacetin Syringetin Tamarixetin Glycosides of isorhamnetin Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside other Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside) Derivative flavonols Aglycones Noricaritin Dihydronoricaritin Glycosides Amurensin Icariin Phelloside Dihydrophelloside Rutin S Pyranoflavonols Aglycones Karanjachromene Furanoflavonols Aglycones Karanjin Glycosides Pongamoside A, B and C Semisynthetic Glycosides Hydroxyethylrutosides Monoxerutin Troxerutin Category

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