Showing Compound Hyperin (FDB002711)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:29 UTC

Update date

2019-11-26 02:57:51 UTC

Primary ID

FDB002711

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hyperin

Description

Quercetin 3-galactoside, also known as hyperin or hyperoside, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Quercetin 3-galactoside is found, on average, in the highest concentration within a few different foods, such as common walnuts (Juglans regia), black chokeberries (Photinia melanocarpa), and sorrels (Rumex acetosa) and in a lower concentration in red raspberries (Rubus idaeus), summer grapes (Vitis aestivalis), and almonds (Prunus dulcis). Quercetin 3-galactoside has also been detected, but not quantified in, several different foods, such as pepper (spice), red tea, loquats (Eriobotrya japonica), common buckwheats (Fagopyrum esculentum), and herbs and spices. This could make quercetin 3-galactoside a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Quercetin 3-galactoside.

CAS Number

482-36-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2-(3,4-Dihydroxyphenyl)-3-(beta-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	ChEBI
Hyperin	ChEBI
Hyperoside	ChEBI
Quercetin 3-O-galactoside	ChEBI
2-(3,4-Dihydroxyphenyl)-3-(b-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
2-(3,4-Dihydroxyphenyl)-3-(β-D-galactopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one	Generator
Quercetin galactoside	MeSH
Quercetin-3-O-galactoside	MeSH
3-O-b-D-Galactopyranosyloxy-3',4',5,7-tetrahydroxyflavone	HMDB
Hyperozide	HMDB
Jyperin	HMDB
Quercetin 3-beta-D-galactopyranoside	HMDB
Quercetin 3-D-galactoside	HMDB
Quercetin 3-O-beta-D-galactopyranoside	HMDB
Quercetin 3-O-beta-D-galactoside	HMDB
Quercetin 3-galactoside	ChEBI
Quercetin 3-O-b-D-galactopyranoside	Generator
Quercetin 3-O-β-D-galactopyranoside	Generator
3,3',4',5,7-Pentahydroxyflavone 3-O-beta-D-galactopyranoside	PhytoBank
3,3',4',5,7-Pentahydroxyflavone 3-O-β-D-galactopyranoside	PhytoBank
3,3’,4’,5,7-Pentahydroxyflavone 3-O-β-D-galactopyranoside	PhytoBank
3-D-Galactosylquercetin	PhytoBank
3-O-beta-D-Galactopyranosyl quercetin	PhytoBank
3-O-β-D-Galactopyranosyl quercetin	PhytoBank
3-O-beta-D-Galactopyranosylquercetin	PhytoBank
3-O-β-D-Galactopyranosylquercetin	PhytoBank
Hyperosid	PhytoBank
Quercetin 3-O-galactopyranoside	PhytoBank
Quercetin 3-O-β-D-galactoside	PhytoBank
Quercetin 3-O-beta-galactopyranoside	PhytoBank
Quercetin 3-O-β-galactopyranoside	PhytoBank
Quercetin 3-O-beta-galactoside	PhytoBank
Quercetin 3-O-β-galactoside	PhytoBank
Quercetin 3-beta-D-galactoside	PhytoBank
Quercetin 3-β-D-galactoside	PhytoBank
Quercetin 3-beta-galactoside	PhytoBank
Quercetin 3-β-galactoside	PhytoBank
Quercetin 3-O-β-D-galactopyranoside	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.95 g/L	ALOGPS
logP	0.47	ALOGPS
logP	-0.14	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.37	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.28 m³·mol⁻¹	ChemAxon
Polarizability	43.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H20O12

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-chromen-4-one

InChI Identifier

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

InChI Key

OVSQVDMCBVZWGM-DTGCRPNFSA-N

Isomeric SMILES

OC[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 Weight

464.3763

Monoisotopic Molecular Weight

464.095476104

Classification

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hexose monosaccharide
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Catechol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Monosaccharide
Oxane
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monosaccharide derivative (CHEBI:67486 )
beta-D-galactoside (CHEBI:67486 )
tetrahydroxyflavone (CHEBI:67486 )
quercetin O-glycoside (CHEBI:67486 )
flavonols (C10073 )
Flavones and Flavonols (C10073 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 54.32%; H 4.34%; O 41.34%	DFC
Melting Point	Mp 232-233° dec.	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -83 (c, 0.2 in Py)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Hyperin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0uea-8903800000-499ac85a438f6221151e	Spectrum
Predicted GC-MS	Hyperin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014r-3620009000-aa92fb234d45c04fb4a1	Spectrum
Predicted GC-MS	Hyperin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-0119000000-7653e3fde6f08a1f608e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0000900000-d60d8b7b555f72b770e8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0001900000-f2659f2ecc8cfe825e94	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009200000-fb8341fdb16a9e23a75e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0019000000-1a226fba24f56b619964	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uk9-0097000000-5067646f23e49b711552	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w29-0179700000-5040715c1b88dc41ba6a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0003900002-b3b20b949d3387148921	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0059000000-901297fb44ccb903acfa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0000900000-84736db1d76deb6da60c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w29-0179400000-aa2a652149ab343a1341	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w29-0189500000-7ff049ba7cc9caedea63	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0udi-0139300000-b99c9ec27bda7ca0248a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009300000-c1c93b32f056b141b26a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-24376004571f89c29c26	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-5cc0caf744b94b4e08cf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-d83176614063aaa00578	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-5d64182b6ec0f035e317	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-e4f36aa3a2f59746a2de	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uxr-0238900000-84d67141521459a118c0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0269100000-855726a927e888161d78	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-2962000000-bc39b0d9e5586054d85f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-1306900000-12c0a6f0c9db05e8c9bd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-2439200000-fc56cb8d8bcb486e96a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zfr-6963000000-3bde95e6420d1d4a73e4	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

292

DrugBank ID

Not Available

HMDB ID

HMDB30775

CRC / DFC (Dictionary of Food Compounds) ID

CNF10-I:CNF10-I

EAFUS ID

Not Available

Dr. Duke ID

HYPERIN|HYPEROSIDE|QUERCETIN-3-O-GALACTOSIDE|3-O-(BETA-D-GALACTOPYRANOSYL)-QUERCETIN

BIGG ID

Not Available

KNApSAcK ID

C00005372

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Hyperoside

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Analgesic	35480	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-aging	52217	An agent that slows or reverses cellular aging, promoting youthful function. Its biological role involves protecting against oxidative stress and DNA damage. Therapeutically, it has applications in dermatology, gerontology, and regenerative medicine, with key medical uses including skin rejuvenation, reducing age-related diseases, and improving overall healthspan.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti capillary-fragility		An 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 dermatitic	50177	An agent that reduces skin inflammation and irritation, commonly used to treat dermatitis, eczema, and other skin disorders, providing relief from itching, redness, and swelling.	DUKE
Anti elastase	23924	An agent that inhibits elastase activity, reducing tissue damage and inflammation. It plays a biological role in protecting tissues from enzymatic degradation. Therapeutically, it is used to manage conditions such as chronic obstructive pulmonary disease (COPD), cystic fibrosis, and acute respiratory distress syndrome (ARDS), where excessive elastase activity contributes to disease progression.	DUKE
Anti-flu	22587	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 hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti-inflammatory	35472	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-ischemic	52217	An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.	DUKE
Anti nociceptive	35470	An agent that reduces the sensitivity to painful stimuli, blocking the transmission of pain signals. Its biological role is to modulate pain perception, with therapeutic applications in managing acute and chronic pain. Key medical uses include treating headaches, arthritis, and post-surgical pain, as well as providing relief for cancer and neuropathic pain.	DUKE
Anti-oxidant	22586	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 radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti-tussive	52217	An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.	DUKE
Anti-viral	22587	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
Anti-wrinkle		An agent that prevents or diminishes wrinkle formation, often a factor of aging, used therapeutically to reduce fine lines and skin folds, with key medical applications in cosmetic dermatology and facial rejuvenation.	DUKE
Calcium antagonist	48706	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
cAMP inhibitor	35222	An agent that blocks the activity of cyclic adenosine monophosphate (cAMP), a key signaling molecule. It reduces intracellular cAMP levels, modulating various biological processes. Therapeutically, cAMP inhibitors are used to treat conditions like asthma, cancer, and cardiovascular diseases by regulating cell signaling pathways and inflammation.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Capillarifortificant		An agent that strengthens blood capillaries, enhancing their integrity and reducing permeability. It plays a biological role in maintaining vascular health, and has therapeutic applications in treating conditions like fragile capillaries, easy bruising, and edema. Key medical uses include managing vascular fragility, improving circulation, and reducing inflammation.	DUKE
Capillarigenic		An agent that promotes formation or proliferation of capillaries, enhancing blood flow and tissue oxygenation. It has therapeutic applications in wound healing, cardiovascular health, and tissue repair, with key medical uses in treating ischemic conditions, promoting angiogenesis, and supporting tissue regeneration.	DUKE
Cyclooxygenase activator		An agent that stimulates cyclooxygenase, enhancing prostanoid formation, including prostaglandins. It has therapeutic applications in cardiovascular health and may be used to manage conditions like atherosclerosis and thrombosis, promoting blood flow and preventing clotting.	DUKE
Diuretic	35498	An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Pesticide	25944	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
Tissue thromboplastin inhibitor	50427	An agent that blocks tissue thromboplastin, reducing blood clot formation. It has therapeutic applications in preventing thrombosis and is commonly used in managing cardiovascular disorders, such as deep vein thrombosis and pulmonary embolism.	DUKE
Xanthine oxidase inhibitor	35634	An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.	DUKE