Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:02 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0002670
Secondary Accession Numbers
  • HMDB02670
Metabolite Identification
Common NameNaringenin
DescriptionNaringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4', 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. 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. Naringenin is a biomarker for the consumption of citrus fruits.
Structure
Data?1585325353
Synonyms
ValueSource
(-)-(2S)-NaringeninChEBI
(2S)-NaringeninChEBI
(S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
4',5,7-TrihydroxyflavanoneChEBI
NaringetolChEBI
PelargidanonChEBI
SalipurpolChEBI
(-)-NaringeninHMDB
AsahinaHMDB
NaringenineHMDB
SalipurolHMDB
(2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-onePhytoBank
(2S)-4',5,7-TrihydroxyflavanonePhytoBank
(2S)-4’,5,7-TrihydroxyflavanonePhytoBank
(S)-NaringeninPhytoBank
S-DihydrogenisteinPhytoBank
5,7,4'-TrihydroxyflavanonePhytoBank
5,7,4’-TrihydroxyflavanonePhytoBank
Chemical FormulaC15H12O5
Average Molecular Weight272.2528
Monoisotopic Molecular Weight272.068473494
IUPAC Name(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namenaringenin
CAS Registry Number480-41-1
SMILES
OC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O
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 KeyFTVWIRXFELQLPI-ZDUSSCGKSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point251 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.52PERRISSOUD,D & TESTA,B (1986)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker167.32830932474
[M+H]+Baker167.96530932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP10(2.47) g/LALOGPS
logP10(2.84) g/LChemAxon
logS10(-3.1) g/LALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.29 m³·mol⁻¹ChemAxon
Polarizability27.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.88131661259
DarkChem[M-H]-164.15331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NaringeninOC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O3915.8Standard polar33892256
NaringeninOC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O2952.4Standard non polar33892256
NaringeninOC1=CC=C(C=C1)[C@@H]1CC(=O)C2=C(O1)C=C(O)C=C2O2843.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Naringenin,1TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C12812.2Semi standard non polar33892256
Naringenin,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C12777.2Semi standard non polar33892256
Naringenin,1TMS,isomer #3C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O22792.7Semi standard non polar33892256
Naringenin,2TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C12786.0Semi standard non polar33892256
Naringenin,2TMS,isomer #2C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C12847.9Semi standard non polar33892256
Naringenin,2TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C12746.9Semi standard non polar33892256
Naringenin,3TMS,isomer #1C[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C12821.6Semi standard non polar33892256
Naringenin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C13094.8Semi standard non polar33892256
Naringenin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O)C=C3)OC2=C13057.8Semi standard non polar33892256
Naringenin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)C[C@@H](C1=CC=C(O)C=C1)O23052.9Semi standard non polar33892256
Naringenin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C13298.3Semi standard non polar33892256
Naringenin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C13330.6Semi standard non polar33892256
Naringenin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13268.5Semi standard non polar33892256
Naringenin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C13502.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00fs-1951400000-0e93ea96a72cb2a5a8682014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a4r-2961300000-725a9d843a4286e86b062014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)splash10-00fs-1951400000-0e93ea96a72cb2a5a8682017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)splash10-0a4r-2961300000-725a9d843a4286e86b062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)splash10-00fs-1951400000-44c9c035aeffcacf4e8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)splash10-004l-1931100000-ec4d00bbd2895d4d5f9c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Naringenin GC-EI-TOF (Non-derivatized)splash10-0a4r-2961300000-6cd5d798a9dad326f7712017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-1290000000-3182db290eb43c6619192017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringenin GC-MS (3 TMS) - 70eV, Positivesplash10-01b9-2531900000-0583af94457df8aad7592017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Naringenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-00di-0190000000-ba73aef4d7cf20a2777d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-066r-3900000000-98ba56d82461a2dc7f6f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-02t9-9600000000-005d5eb55c1f6f3b893d2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOFsplash10-00di-0090000000-87dba9fe511299bf27e82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive-QTOFsplash10-00di-0090000000-52282430f89f3cfd51ff2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0g4i-1960000000-74e384d175dd4f05938c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-014i-1900000000-702ce5f0315e56bb08a02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0udi-2900000000-aeb81b324d8162537df32012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0fk9-1960000000-b4a541e5476f886245222012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOFsplash10-000i-0090000000-cfa015b97699d9b8d3a92017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 25V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 40V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 10V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 30V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 20V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOFsplash10-00di-0090000000-dae76236c5699dabc0792017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF 25V, Negative-QTOFsplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Naringenin ESI-TOF , Negative-QTOFsplash10-00di-0090010000-5e9a02398f13b71eccfb2017-09-12HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 10V, Positive-QTOFsplash10-00di-0290000000-32844ab19a143b70951b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 20V, Positive-QTOFsplash10-0fk9-0980000000-93073e4c39e23c3099c52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 40V, Positive-QTOFsplash10-0uki-4900000000-8d2daa4eb7a40b8667182017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 10V, Negative-QTOFsplash10-00di-0090000000-b29e35ecf9be0aa440c22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 20V, Negative-QTOFsplash10-00di-1390000000-e9112df7c7b29664a0112017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Naringenin 40V, Negative-QTOFsplash10-014l-6920000000-3b7e4e282dc4008e8c8e2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00815 +/- 0.0154 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.02 +/- 0.05 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0171 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0176 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0514 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0542 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0553 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.137 +/- 0.0979 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.560 +/- 1.330 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.660 +/- 1.593 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 201 details
UrineDetected and Quantified0.273 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.373 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0065 +/- 0.013 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.032 +/- 0.032 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 +/- 0.013 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 +/- 0.026 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.62 +/- 0.82 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.55 +/- 0.20 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.109 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.234 +/- 0.368 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB03467
Phenol Explorer Compound ID201
FooDB IDFDB000678
KNApSAcK IDC00000982
Chemspider ID388383
KEGG Compound IDC00509
BioCyc IDNARINGENIN-CMPD
BiGG IDNot Available
Wikipedia LinkNaringenin
METLIN ID3401
PubChem Compound439246
PDB IDNot Available
ChEBI ID17846
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000396
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Naringenin → 6-{4-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Naringenin → 3,4,5-trihydroxy-6-{[(2S)-7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
Naringenin → 3,4,5-trihydroxy-6-{[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Naringenin → {4-[(2S)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl]phenyl}oxidanesulfonic aciddetails