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Human Metabolome Database Version 3.5

Showing metabocard for Naringenin (HMDB02670)

• Identification
• Taxonomy
• Ontology
• Physical properties
• Spectra
• Biological properties
• Concentrations
• Links
• References

• Blood
• Urine

Record Information
Version	3.5
Creation Date	2006-05-22 09:12:02 -0600
Update Date	2013-02-08 17:12:03 -0700
HMDB ID	HMDB02670
Secondary Accession Numbers	None
Metabolite Identification
Common Name	Naringenin
Description	Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. But, one has to wonder, if given more time than 24 hours, would lower concentrations have similar effects. Wikipedia.
Structure	Download: MOL | SDF | SMILES | InChI Display: 2D Structure | 3D Structure
Synonyms	(-)-Naringenin Asahina Naringenin Naringenine Naringetol Pelargidanon Salipurol Salipurpol
Chemical Formula	C15H12O5
Average Molecular Weight	272.2528
Monoisotopic Molecular Weight	272.068473494
IUPAC Name	(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional IUPAC Name	naringenin
CAS Registry Number	480-41-1
SMILES	OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1
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
Chemical Taxonomy
Kingdom	Organic Compounds
Super Class	Aromatic Heteropolycyclic Compounds
Class	Flavonoids
Sub Class	Flavans
Other Descriptors	Aromatic Heteropolycyclic Compounds Flavanones(KEGG) Flavanones(Lipidmaps) naringenin(ChEBI)
Substituents	Alkyl Aryl Ether Benzopyran Chromane Ketone Phenol Phenol Derivative Pyran Resorcinol
Direct Parent	Flavanones
Ontology
Status	Detected and Quantified
Origin	Plant
Biofunction	anti-allergic anti-inflammatory anti-proliferative pro-oxidant
Application	Nutrient
Cellular locations	Membrane (predicted from logP)
Physical Properties
State	Solid
Experimental Properties	Property Value Reference Melting Point 251 °C Not Available Boiling Point Not Available Not Available Water Solubility Not Available Not Available LogP 2.52 PERRISSOUD,D & TESTA,B (1986)
Predicted Properties	Property Value Source Water Solubility 0.21 g/L ALOGPS LogP 2.47 ALOGPS LogP 2.84 ChemAxon LogS -3.11 ALOGPS pKa (strongest acidic) 7.91 ChemAxon pKa (strongest basic) -3.9 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 86.99 A2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 71.29 ChemAxon Polarizability 26.54 ChemAxon Formal Charge 0 ChemAxon Physiological Charge 0 ChemAxon
Spectra
	1H NMR Spectrum MS/MS Spectrum Quattro_QQQ 10 MS/MS Spectrum Quattro_QQQ 25 MS/MS Spectrum Quattro_QQQ 40 MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies ) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5 MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5 MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) [1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations	Membrane (predicted from logP)
Biofluid Locations	Blood Urine
Tissue Location	Fibroblasts Liver
Pathways	Not Available
Normal Concentrations
	Biofluid Status Value Age Sex Condition Comments Blood Detected and Quantified 0.02 +/- 0.05 uM Adult (>18 years old) Both Normal Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Blood Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Expected and not Quantified Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 201 Not Available Urine Detected and Quantified 410 umol/mmol creatinine Adult (>18 years old) Both Normal 24 hours after the 2-day diet started Urine Detected and Quantified 560 umol/mmol creatinine Adult (>18 years old) Both Normal After 2-day diet protocol Urine Detected and Quantified 0.0065 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.032 +/- 0.032 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.019 +/- 0.013 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.019 +/- 0.026 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.0 +/- 0.0065 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 1.62 +/- 0.82 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available Urine Detected and Quantified 0.55 +/- 0.20 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
	Not Available
Associated Disorders and Diseases
Disease References	None
Associated OMIM IDs	None
External Links
DrugBank ID	Not Available
Phenol Explorer Compound ID	201
Phenol Explorer Metabolite ID	201
FoodDB ID	FDB000678
KNApSAcK ID	C00000982
Chemspider ID	388383
KEGG Compound ID	C00509
BioCyc ID	CPD-3161
BiGG ID	Not Available
Wikipedia Link	Naringenin
NuGOwiki Link	HMDB02670
Metagene Link	HMDB02670
METLIN ID	3401
PubChem Compound	439246
PDB ID	NAR
ChEBI ID	17846
References
Synthesis Reference	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
General References	Walker D, Flinois JP, Monkman SC, Beloc C, Boddy AV, Cholerton S, Daly AK, Lind MJ, Pearson AD, Beaune PH, et al.: Identification of the major human hepatic cytochrome P450 involved in activation and N-dechloroethylation of ifosfamide. Biochem Pharmacol. 1994 Mar 29;47(7):1157-63. Pubmed: 8161344 Ameer B, Weintraub RA, Johnson JV, Yost RA, Rouseff RL: Flavanone absorption after naringin, hesperidin, and citrus administration. Clin Pharmacol Ther. 1996 Jul;60(1):34-40. Pubmed: 8689809 Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Mar 5;801(2):363-7. Pubmed: 14751808 Guengerich FP, Kim DH: In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis. 1990 Dec;11(12):2275-9. Pubmed: 2265479 Ishii K, Furuta T, Kasuya Y: Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Aug 30;683(2):225-9. Pubmed: 8891919 Matsuo M, Sasaki N, Saga K, Kaneko T: Cytotoxicity of flavonoids toward cultured normal human cells. Biol Pharm Bull. 2005 Feb;28(2):253-9. Pubmed: 15684479 Franke AA, Cooney RV, Henning SM, Custer LJ: Bioavailability and antioxidant effects of orange juice components in humans. J Agric Food Chem. 2005 Jun 29;53(13):5170-8. Pubmed: 15969493 Fuhr U, Kummert AL: The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther. 1995 Oct;58(4):365-73. Pubmed: 7586927 Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG: Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther. 1992 Jun;261(3):1195-9. Pubmed: 1602384 Lin YT, Hsiu SL, Hou YC, Chen HY, Chao PD: Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. Biol Pharm Bull. 2003 May;26(5):747-51. Pubmed: 12736527 Malaveille C, Hautefeuille A, Pignatelli B, Talaska G, Vineis P, Bartsch H: Dietary phenolics as anti-mutagens and inhibitors of tobacco-related DNA adduction in the urothelium of smokers. Carcinogenesis. 1996 Oct;17(10):2193-200. Pubmed: 8895488

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government.