AFCDB: Hesperetin (FDB002677)

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

FDB002677

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hesperetin

Description

Isolated from Mentha (peppermint) and numerous Citrussubspecies, with lemons, tangerines and oranges being especially good sources. Nutriceutical with anti-cancer props. Glycosides also widely distributed Hesperetin is a bioflavonoid and, to be more specific, a flavanone. Hesperidin (a flavonone glycoside) is water soluble due to the presence of the sugar part in its structure, so on ingestion it releases its aglycone i.e: hesperetin. Hesperidin is found in Citrus fruits.; Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions. Hesperetin is also a biomarker for the consumption of citrus fruits.

CAS Number

520-33-2

Structure

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

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.68	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.75 m³·mol⁻¹	ChemAxon
Polarizability	29.3 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H14O6

IUPAC name

(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1

InChI Key

AIONOLUJZLIMTK-AWEZNQCLSA-N

Isomeric SMILES

COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

Classification

Description

Belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
Flavanone
Hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Methoxybenzene
Phenoxy compound
Aryl alkyl ketone
Anisole
Phenol ether
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3'-hydroxyflavanones (CHEBI:28230 )
trihydroxyflavanone (CHEBI:28230 )
monomethoxyflavanone (CHEBI:28230 )
flavanones (C01709 )
Flavanones (LMPK12140003 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Foods

Fruits and vegetables:

Vegetables:

Fruity vegetables:

Tomato

Fruits:

Citrus

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 63.57%; H 4.67%; O 31.76%	DFC
Melting Point	Mp 228-230°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.60	PERRISSOUD,D & TESTA,B (1986)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]27D -37.6 (c, 1.8 in EtOH)	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	Hesperetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-0792000000-043d1ca82d4702349341	Spectrum
Predicted GC-MS	Hesperetin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udj-3860980000-a1715e067e13bbdada3e	Spectrum
Predicted GC-MS	Hesperetin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-da94c45c0a6bde515ea3	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0169000000-5d9b7fba914d229018a6	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-053i-0920000000-b6ab2fed21176a341b28	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0009000000-b833c4c244a2461530ec	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-32f8b49c4bc1df10782a	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0iki-0930000000-20176d350f94ae4a84ed	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-2910000000-54a5cf5acd3ca156389e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009000000-2a5462077f9208908972	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0139000000-0c743a741d25379011aa	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w2i-0961000000-8406f0210238c955e23e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gw0-0920000000-b833f9a80eb4ea8d3b13	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0910000000-943c442894f2e6d36fe3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0925000000-20d9733844b315a5aac1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f7c-0092000000-df166f951c1d37996e32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f79-0092000000-28f5918da43818b380bf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-fda4f743655d07e229dd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0906000000-4ff368578ae1225967b0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0900000000-aaca372b112b1730d913	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-8857224e3cadbbf71a7d	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0329000000-4364410cdc5a65b92032	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0944000000-edd7b755d11b9331e6c9	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uki-3910000000-9e449d46da8305c0b794	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0109000000-21473197ac3beced4628	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0569000000-1e4d2574c341d9d9124f	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbl-4940000000-c9a717aa36bf4402e6c7	2017-07-26	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

203

DrugBank ID

DB01094

HMDB ID

HMDB05782

CRC / DFC (Dictionary of Food Compounds) ID

CNB06-R:CNB07-S

EAFUS ID

934

Dr. Duke ID

HESPERETIN

BIGG ID

Not Available

KNApSAcK ID

C00000968

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

Hesperetin

Phenol-Explorer Metabolite ID

203

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
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti feedant			DUKE
anti lipolytic			DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
fungistat			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	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
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.	CHEBI

Enzymes

Name	Gene Name	UniProt ID
Sterol O-acyltransferase 1	SOAT1	P35610

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— 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.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Hesperetin (FDB002677)

Structure for FDB002677 (Hesperetin)