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Identification
NameNaringenin
Accession NumberDB03467  (EXPT02295)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIHN5425SBF2
CAS number480-41-1
WeightAverage: 272.2528
Monoisotopic: 272.068473494
Chemical FormulaC15H12O5
InChI KeyInChIKey=FTVWIRXFELQLPI-ZDUSSCGKSA-N
InChI
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
IUPAC Name
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
SMILES
[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavanones. These 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
  • Hydroxyflavonoid
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.967
Blood Brain Barrier+0.6794
Caco-2 permeable+0.7533
P-glycoprotein substrateSubstrate0.5458
P-glycoprotein inhibitor INon-inhibitor0.9638
P-glycoprotein inhibitor IINon-inhibitor0.8859
Renal organic cation transporterNon-inhibitor0.8949
CYP450 2C9 substrateNon-substrate0.7425
CYP450 2D6 substrateNon-substrate0.8691
CYP450 3A4 substrateNon-substrate0.6294
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.7463
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.8988
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7121
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9364
BiodegradationNot ready biodegradable0.7934
Rat acute toxicity3.5110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.964
hERG inhibition (predictor II)Non-inhibitor0.8832
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point251 °CPhysProp
logP2.52PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.214 mg/mLALOGPS
logP2.47ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.91ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.29 m3·mol-1ChemAxon
Polarizability27.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00fs-1951400000-0e93ea96a72cb2a5a868View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4r-2961300000-725a9d843a4286e86b06View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-0190000000-ba73aef4d7cf20a2777dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-066r-3900000000-98ba56d82461a2dc7f6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-9600000000-005d5eb55c1f6f3b893dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-00di-0090000000-87dba9fe511299bf27e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-00di-0090000000-52282430f89f3cfd51ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0g4i-1960000000-74e384d175dd4f05938cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-1900000000-702ce5f0315e56bb08a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-2900000000-aeb81b324d8162537df3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0fk9-1960000000-b4a541e5476f88624522View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Heike Wilhelm, Ludger A. Wessojohann, Martin Biendl, “METHOD FOR PRODUCING NARINGENIN DERIVATIVES FROM XANTHOHUMOL.” U.S. Patent US20090227806, issued September 10, 2009.

US20090227806
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Naringenin.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Naringenin.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Naringenin.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Naringenin.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Naringenin.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Naringenin.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Naringenin.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Naringenin.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Naringenin.
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Naringenin.
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Naringenin.
AtenololThe serum concentration of Atenolol can be increased when it is combined with Naringenin.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Naringenin.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Naringenin.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Naringenin.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Naringenin.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Naringenin.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Naringenin.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Naringenin.
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Naringenin.
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Naringenin.
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Naringenin.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Naringenin.
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Naringenin.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Naringenin.
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Naringenin.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Naringenin.
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Naringenin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Naringenin.
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Naringenin.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Naringenin.
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Naringenin.
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Naringenin.
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Naringenin.
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Naringenin.
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Naringenin.
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Naringenin.
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Naringenin.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Naringenin.
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Naringenin.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Naringenin.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Naringenin.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Naringenin.
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Naringenin.
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Naringenin.
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Naringenin.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Naringenin.
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Naringenin.
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Naringenin.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Naringenin.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Naringenin.
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Naringenin.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Naringenin.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Naringenin.
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Naringenin.
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Naringenin.
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Naringenin.
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Naringenin.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Naringenin.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Naringenin.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Naringenin.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Naringenin.
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Naringenin.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Naringenin.
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Naringenin.
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Naringenin.
EstriolThe serum concentration of Estriol can be increased when it is combined with Naringenin.
EstroneThe serum concentration of Estrone can be increased when it is combined with Naringenin.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Naringenin.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Naringenin.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Naringenin.
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Naringenin.
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Naringenin.
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Naringenin.
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Naringenin.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Naringenin.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Naringenin.
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Naringenin.
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Naringenin.
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Naringenin.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Naringenin.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Naringenin.
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Naringenin.
IdelalisibThe serum concentration of Idelalisib can be increased when it is combined with Naringenin.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Naringenin.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Naringenin.
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Naringenin.
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Naringenin.
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Naringenin.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Naringenin.
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Naringenin.
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Naringenin.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Naringenin.
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Naringenin.
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Naringenin.
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Naringenin.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Naringenin.
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Naringenin.
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Naringenin.
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Naringenin.
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Naringenin.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Naringenin.
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Naringenin.
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Naringenin.
LosartanThe serum concentration of Losartan can be increased when it is combined with Naringenin.
MannitolThe serum concentration of Mannitol can be increased when it is combined with Naringenin.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Naringenin.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Naringenin.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Naringenin.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Naringenin.
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Naringenin.
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Naringenin.
MorphineThe serum concentration of Morphine can be increased when it is combined with Naringenin.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Naringenin.
NadololThe serum concentration of Nadolol can be increased when it is combined with Naringenin.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Naringenin.
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Naringenin.
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Naringenin.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Naringenin.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Naringenin.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Naringenin.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Naringenin.
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Naringenin.
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Naringenin.
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Naringenin.
OsimertinibThe serum concentration of Osimertinib can be increased when it is combined with Naringenin.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Naringenin.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Naringenin.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Naringenin.
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Naringenin.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Naringenin.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Naringenin.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Naringenin.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Naringenin.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Naringenin.
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Naringenin.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Naringenin.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Naringenin.
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Naringenin.
PropranololThe serum concentration of Propranolol can be increased when it is combined with Naringenin.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Naringenin.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Naringenin.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Naringenin.
QuinineThe serum concentration of Quinine can be increased when it is combined with Naringenin.
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Naringenin.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Naringenin.
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Naringenin.
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Naringenin.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Naringenin.
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Naringenin.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Naringenin.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Naringenin.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Naringenin.
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Naringenin.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Naringenin.
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Naringenin.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Naringenin.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Naringenin.
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Naringenin.
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Naringenin.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Naringenin.
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Naringenin.
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Naringenin.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Naringenin.
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Naringenin.
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Naringenin.
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Naringenin.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Naringenin.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Naringenin.
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Naringenin.
TimololThe serum concentration of Timolol can be increased when it is combined with Naringenin.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Naringenin.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Naringenin.
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Naringenin.
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Naringenin.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Naringenin.
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Naringenin.
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Naringenin.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Naringenin.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Naringenin.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Naringenin.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Naringenin.
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Naringenin.
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Naringenin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Pseudomonas putida (strain DOT-T1E)
Pharmacological action
unknown
General Function:
Dna binding
Specific Function:
Represses expression from the ttgABC operon promoter and its own expression. Binds to a promoter region between the divergently transcribed ttgR and ttgABC genes/operons; in the presence of chloramphenicol or tetracycline this binding no longer occurs and ttgR and ttgABC are derepressed. This suggests that TtgR binds these antibiotics.
Gene Name:
ttgR
Uniprot ID:
Q9AIU0
Molecular Weight:
23854.075 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
References
  1. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y: Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B. Drug Metab Dispos. 2005 Apr;33(4):518-23. Epub 2005 Jan 7. [PubMed:15640378 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Takanaga H, Ohnishi A, Matsuo H, Sawada Y: Inhibition of vinblastine efflux mediated by P-glycoprotein by grapefruit juice components in caco-2 cells. Biol Pharm Bull. 1998 Oct;21(10):1062-6. [PubMed:9821810 ]
  2. Eagling VA, Profit L, Back DJ: Inhibition of the CYP3A4-mediated metabolism and P-glycoprotein-mediated transport of the HIV-1 protease inhibitor saquinavir by grapefruit juice components. Br J Clin Pharmacol. 1999 Oct;48(4):543-52. [PubMed:10583025 ]
  3. Youdim KA, Qaiser MZ, Begley DJ, Rice-Evans CA, Abbott NJ: Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604. [PubMed:14980703 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency.
Gene Name:
ABCC1
Uniprot ID:
P33527
Molecular Weight:
171589.5 Da
References
  1. Leslie EM, Mao Q, Oleschuk CJ, Deeley RG, Cole SP: Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Mol Pharmacol. 2001 May;59(5):1171-80. [PubMed:11306701 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. Zhang S, Yang X, Morris ME: Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol Pharmacol. 2004 May;65(5):1208-16. [PubMed:15102949 ]
  2. Imai Y, Tsukahara S, Asada S, Sugimoto Y: Phytoestrogens/flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance. Cancer Res. 2004 Jun 15;64(12):4346-52. [PubMed:15205350 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23