AFCDB: Hesperidin (FDB002680)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:28 UTC

Update date

2019-11-26 02:57:48 UTC

Primary ID

FDB002680

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hesperidin

Description

Hesperidin, 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 Number

520-26-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.69 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.31	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.61	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	234.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.77 m³·mol⁻¹	ChemAxon
Polarizability	58.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C28H34O15

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 Identifier

InChI=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 Key

QUQPHWDTPGMPEX-QJBIFVCTSA-N

Isomeric SMILES

COC1=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 Weight

610.5606

Monoisotopic Molecular Weight

610.189770418

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

rutinoside (CHEBI:28775 )
disaccharide derivative (CHEBI:28775 )
3'-hydroxyflavanones (CHEBI:28775 )
monomethoxyflavanone (CHEBI:28775 )
flavanone glycoside (CHEBI:28775 )
dihydroxyflavanone (CHEBI:28775 )
flavanones (C09755 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 55.08%; H 5.61%; O 39.31%	DFC
Melting Point	Mp 258-262° (softens at 250°)	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 -47.3 (Py)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0a4i-0960000000-19057cfec7c79b016a55	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0udi-0009000000-283330c229581467aa8c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0002009000-ef46dd12935025cc99f3	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0009002000-4750b2aa846256abc7dc	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0010009000-7d463589853787a4d83a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-0udi-0029000000-5abbbe61f9472ac9f446	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0udi-0009000000-865b6028ed5cc1fd73d8	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-2924000000-2288595ee1b67877de4b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0000009000-8c42f8adffac7d78b94c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0006009000-1f68460ef007fbd1cfa9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009002000-26d653ee690ce5c6cd20	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009000000-a4d68b31e046fbf057d6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0019000000-e9135e61d5aa11f40135	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0119003000-80c5f918f82d46fc1131	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udl-0349353000-321b597839a676166b98	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0679200000-a1b174ec1d2feacb1e05	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-0933000000-e77d04d786da1eae235e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0r00-5659348000-127002c9964ea54f38db	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-4759120000-f28ca408fe1f550a3a8a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-3698000000-6678009a010a429a4ce1	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C09755

Pubchem Compound ID

53477767

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

CNB06-R:CNB12-Q

EAFUS ID

1608

Dr. Duke ID

HESPERIDOSIDE|HESPERIDIN

BIGG ID

Not Available

KNApSAcK ID

C00000970

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

Hesperidin

Phenol-Explorer Metabolite ID

207

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
analgesic	35480	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 LDL	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti allergenic	50857	A drug used to treat allergic reactions.	DUKE
anti bradykinic			DUKE
anti capillary-fragility			DUKE
anti-DNA			DUKE
anti flu	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti histaminic	37956	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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukotriene	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antioxidant	22586	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 prostaglandin	49020	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-RNA			DUKE
anti stomatitic			DUKE
anti triglyceride	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti ulcer	49201	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 vaccinia	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anxiolytic	35474	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 antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
capillariprotective			DUKE
catabolic			DUKE
choleretic			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
cyclooxygenase inhibitor	35544	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
hypolipidemic			DUKE
lipoxygenase inhibitor	35856	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
pesticide	25944	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 HLDL			DUKE
vasopressor			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not 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.

Hesperidin (FDB002680)

Structure for FDB002680 (Hesperidin)