AFCDB: (S)-Naringenin (FDB000678)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-09-17 15:39:05 UTC

Primary ID

FDB000678

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(S)-Naringenin

Description

Naringenin, also known as (2S)-naringenin or naringetol, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, naringenin is considered to be a flavonoid lipid molecule. The (S)-enantiomer of naringenin. Naringenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Naringenin exists in all living organisms, ranging from bacteria to humans. Naringenin is a bitter tasting compound. Outside of the human body, Naringenin is found, on average, in the highest concentration within a few different foods, such as sweet oranges, common oregano, and mexican oregano and in a lower concentration in sorghums, grape wines, and mandarin orange (clementine, tangerine). Naringenin has also been detected, but not quantified in, several different foods, such as saffrons, white lupines, alpine sweetvetchs, dates, and elderberries. This could make naringenin a potential biomarker for the consumption of these foods.

CAS Number

480-41-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.29 m³·mol⁻¹	ChemAxon
Polarizability	27.31 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

C15H12O5

IUPAC name

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

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

Isomeric SMILES

[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

Classification

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

naringenin (CHEBI:17846 )
flavanones (C00509 )
Flavanones (LMPK12140001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Animal

Plant:

Biological location:

Organ and components:

Liver

Cell and elements:

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Biological role:

Pro-oxidant

Foods

Fruits and vegetables:

Vegetables:

Fruity vegetables:

Tomato

Fruits:

Citrus

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 66.17%; H 4.44%; O 29.38%	DFC
Melting Point	Mp 250-251° (227-228°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	2.52	PERRISSOUD,D & TESTA,B (1986)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]27D -22.5 (MeOH)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-0a4r-2961300000-725a9d843a4286e86b06	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-00fs-1951400000-0e93ea96a72cb2a5a868	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-0a4r-2961300000-725a9d843a4286e86b06	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-00fs-1951400000-44c9c035aeffcacf4e8c	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-004l-1931100000-ec4d00bbd2895d4d5f9c	Spectrum
GC-MS	(S)-Naringenin, non-derivatized, GC-MS Spectrum	splash10-0a4r-2961300000-6cd5d798a9dad326f771	Spectrum
Predicted GC-MS	(S)-Naringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-006x-1290000000-3182db290eb43c661919	Spectrum
Predicted GC-MS	(S)-Naringenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-2531900000-0583af94457df8aad759	Spectrum
Predicted GC-MS	(S)-Naringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(S)-Naringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-00di-0190000000-ba73aef4d7cf20a2777d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-066r-3900000000-98ba56d82461a2dc7f6f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-9600000000-005d5eb55c1f6f3b893d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-87dba9fe511299bf27e8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-00di-0090000000-52282430f89f3cfd51ff	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0g4i-1960000000-74e384d175dd4f05938c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-014i-1900000000-702ce5f0315e56bb08a0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-2900000000-aeb81b324d8162537df3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0fk9-1960000000-b4a541e5476f88624522	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-cfa015b97699d9b8d3a9	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0090000000-dae76236c5699dabc079	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-0gb9-0900000000-5295f7ce31d20a80235c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0090010000-5e9a02398f13b71eccfb	2017-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0290000000-32844ab19a143b70951b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0980000000-93073e4c39e23c3099c5	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uki-4900000000-8d2daa4eb7a40b866718	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-b29e35ecf9be0aa440c2	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1390000000-e9112df7c7b29664a011	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-6920000000-3b7e4e282dc4008e8c8e	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

BFM77-B:BFM78-C

EAFUS ID

Not Available

Dr. Duke ID

NARINGENIN

BIGG ID

Not Available

KNApSAcK ID

C00000982

HET ID

NAR

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Naringenin

Phenol-Explorer Metabolite ID

201

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
11beta-hydroxysteroid-dehydrogenase inhibitor	23924	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
aldose reductase inhibitor	48550	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
anti acetylcholinesterase	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE
anti aflatoxin	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti aggregant			DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti amnesic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti amyloid-beta			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti escherichic			DUKE
anti estrogenic	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
anti fibrotic			DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukemic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti mutagenic			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 peristaltic			DUKE
anti peroxidative			DUKE
anti radicular			DUKE
anti sindhis			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor promoter	35610	A substance that inhibits or prevents the proliferation of neoplasms.	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 viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
aphidifuge	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
aromatase inhibitor	50790	An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones.	DUKE
cAMP-phosphodiesterase inhibitor	23924	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
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
choleretic			DUKE
cytochrome-P450 inhibitor	50183	An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.	DUKE
decarboxylase inhibitor	23924	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
embryotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
estrogenic			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
fungistat			DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
neuroprotective	63726	Any compound that can be used for the treatment of neurodegenerative disorders.	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
serotonin inhibitor	48279	Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.	DUKE
teratogenic	50905	A role played by a chemical compound in biological systems with adverse consequences in embryo developments, leading to birth defects, embryo death or altered development, growth retardation and functional defect.	DUKE
TNF-alpha inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
utero trophic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Enzymes

Not Available

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

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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.

(S)-Naringenin (FDB000678)

Structure for FDB000678 ((S)-Naringenin)