Showing Compound Card for Naringenin (CDB004939)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:52:35 UTC
Updated at2022-12-13 19:31:28 UTC
CannabisDB IDCDB004939
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNaringenin
DescriptionNaringenin, 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. Naringenin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight272.25
Monoisotopic Molecular Weight272.0685
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point251 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility475 mg/LWikipedia
logP2.52PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
logP2.47ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-00fs-1951400000-0e93ea96a72cb2a5a868Spectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-0a4r-2961300000-725a9d843a4286e86b06Spectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-00fs-1951400000-0e93ea96a72cb2a5a868Spectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-0a4r-2961300000-725a9d843a4286e86b06Spectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-00fs-1951400000-44c9c035aeffcacf4e8cSpectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-004l-1931100000-ec4d00bbd2895d4d5f9cSpectrum
GC-MSNaringenin, non-derivatized, GC-MS Spectrumsplash10-0a4r-2961300000-6cd5d798a9dad326f771Spectrum
Predicted GC-MSNaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-1290000000-3182db290eb43c661919Spectrum
Predicted GC-MSNaringenin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-2531900000-0583af94457df8aad759Spectrum
Predicted GC-MSNaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSNaringenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0190000000-ba73aef4d7cf20a2777d2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-066r-3900000000-98ba56d82461a2dc7f6f2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-9600000000-005d5eb55c1f6f3b893d2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-00di-0090000000-87dba9fe511299bf27e82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-00di-0090000000-52282430f89f3cfd51ff2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0g4i-1960000000-74e384d175dd4f05938c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-1900000000-702ce5f0315e56bb08a02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-aeb81b324d8162537df32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fk9-1960000000-b4a541e5476f886245222012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-000i-0090000000-cfa015b97699d9b8d3a92017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0090000000-dae76236c5699dabc0792017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 25V, Negativesplash10-0gb9-0900000000-5295f7ce31d20a80235c2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00di-0090010000-5e9a02398f13b71eccfb2017-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0290000000-32844ab19a143b70951b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fk9-0980000000-93073e4c39e23c3099c52017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uki-4900000000-8d2daa4eb7a40b8667182017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-b29e35ecf9be0aa440c22017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1390000000-e9112df7c7b29664a0112017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-6920000000-3b7e4e282dc4008e8c8e2017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
QuadraDetected and Quantified0.000617 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.000839 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0002670
DrugBank IDDB03467
Phenol Explorer Compound ID201
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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
Enzyme Details
2. Sulfotransferase 1A3
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