Identification
- Generic Name
- Naringenin
- DrugBank Accession Number
- DB03467
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Naringenin (DB03467)
- Weight
- Average: 272.2528
Monoisotopic: 272.068473494 - Chemical Formula
- C15H12O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHTH-type transcriptional regulator TtgR Not Available Pseudomonas putida (strain DOT-T1E) UEstrogen receptor alpha Not Available Humans UAldo-keto reductase family 1 member C1 antagonistHumans UCytochrome P450 1B1 Not Available Humans UKAT8 regulatory NSL complex subunit 3 Not Available Humans USex hormone-binding globulin Not Available Humans UCytochrome P450 19A1 inhibitorHumans UEstrogen receptor beta partial agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib Naringenin may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Afatinib Naringenin may decrease the excretion rate of Afatinib which could result in a higher serum level. Allopurinol Naringenin may decrease the excretion rate of Allopurinol which could result in a higher serum level. Alpelisib The serum concentration of Alpelisib can be increased when it is combined with Naringenin. Apixaban Naringenin may decrease the excretion rate of Apixaban which could result in a higher serum level. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Flavans
- Direct Parent
- Flavanones
- Alternative Parents
- 7-hydroxyflavonoids / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / Chromones / Aryl alkyl ketones / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Vinylogous acids show 3 more
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- naringenin (CHEBI:17846) / flavanones (C00509) / Flavanones (LMPK12140001)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- HN5425SBF2
- CAS number
- 480-41-1
- InChI Key
- 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
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 References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002670
- KEGG Compound
- C00509
- PubChem Compound
- 439246
- PubChem Substance
- 46508043
- ChemSpider
- 388383
- BindingDB
- 23419
- 1368173
- ChEBI
- 17846
- ChEMBL
- CHEMBL9352
- ZINC
- ZINC000000156701
- PharmGKB
- PA151958361
- PDBe Ligand
- NAR
- Wikipedia
- Naringenin
- PDB Entries
- 1cgk / 1eyq / 2brt / 2uxu / 4a87 / 4d06 / 4deu / 4eh3 / 5wkr / 5wks … show 12 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 251 °C PhysProp logP 2.52 PERRISSOUD,D & TESTA,B (1986) - Predicted Properties
Property Value Source Water Solubility 0.214 mg/mL 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 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.967 Blood Brain Barrier + 0.6794 Caco-2 permeable + 0.7533 P-glycoprotein substrate Substrate 0.5458 P-glycoprotein inhibitor I Non-inhibitor 0.9638 P-glycoprotein inhibitor II Non-inhibitor 0.8859 Renal organic cation transporter Non-inhibitor 0.8949 CYP450 2C9 substrate Non-substrate 0.7425 CYP450 2D6 substrate Non-substrate 0.8691 CYP450 3A4 substrate Non-substrate 0.6294 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.7463 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Inhibitor 0.8988 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7121 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.9364 Biodegradation Not ready biodegradable 0.7934 Rat acute toxicity 3.5110 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.964 hERG inhibition (predictor II) Non-inhibitor 0.8832
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 175.383828 predictedDarkChem Lite v0.1.0 [M-H]- 175.667728 predictedDarkChem Lite v0.1.0 [M-H]- 175.391828 predictedDarkChem Lite v0.1.0 [M-H]- 175.553428 predictedDarkChem Lite v0.1.0 [M-H]- 161.70134 predictedDeepCCS 1.0 (2019) [M+H]+ 177.009428 predictedDarkChem Lite v0.1.0 [M+H]+ 177.089628 predictedDarkChem Lite v0.1.0 [M+H]+ 177.425828 predictedDarkChem Lite v0.1.0 [M+H]+ 177.181728 predictedDarkChem Lite v0.1.0 [M+H]+ 164.05934 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.718528 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.862028 predictedDarkChem Lite v0.1.0 [M+Na]+ 176.552828 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.035728 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.96957 predictedDeepCCS 1.0 (2019)
Targets
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- 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 chloram...
- Gene Name
- ttgR
- Uniprot ID
- Q9AIU0
- Uniprot Name
- HTH-type transcriptional regulator TtgR
- Molecular Weight
- 23854.075 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Hunter DS, Hodges LC, Vonier PM, Fuchs-Young R, Gottardis MM, Walker CL: Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium. Cancer Res. 1999 Jul 1;59(13):3090-9. [Article]
- Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
- Gene Name
- AKR1C1
- Uniprot ID
- Q04828
- Uniprot Name
- Aldo-keto reductase family 1 member C1
- Molecular Weight
- 36788.02 Da
References
- Brozic P, Smuc T, Gobec S, Rizner TL: Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1. Mol Cell Endocrinol. 2006 Oct 19;259(1-2):30-42. Epub 2006 Sep 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- Shimada T, Tanaka K, Takenaka S, Murayama N, Martin MV, Foroozesh MK, Yamazaki H, Guengerich FP, Komori M: Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives. Chem Res Toxicol. 2010 Dec 20;23(12):1921-35. doi: 10.1021/tx100286d. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- As part of the NSL complex it is involved in acetylation of nucleosomal histone H4 on several lysine residues and therefore may be involved in the regulation of transcription.
- Specific Function
- Not Available
- Gene Name
- KANSL3
- Uniprot ID
- Q9P2N6
- Uniprot Name
- KAT8 regulatory NSL complex subunit 3
- Molecular Weight
- 95990.725 Da
References
- Priscilla DH, Roy D, Suresh A, Kumar V, Thirumurugan K: Naringenin inhibits alpha-glucosidase activity: a promising strategy for the regulation of postprandial hyperglycemia in high fat diet fed streptozotocin induced diabetic rats. Chem Biol Interact. 2014 Mar 5;210:77-85. doi: 10.1016/j.cbi.2013.12.014. Epub 2014 Jan 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Kao YC, Zhou C, Sherman M, Laughton CA, Chen S: Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study. Environ Health Perspect. 1998 Feb;106(2):85-92. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Kuiper GG, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg B, Gustafsson JA: Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology. 1998 Oct;139(10):4252-63. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Downregulator
- 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
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Abdallah HM, Al-Abd AM, El-Dine RS, El-Halawany AM: P-glycoprotein inhibitors of natural origin as potential tumor chemo-sensitizers: A review. J Adv Res. 2015 Jan;6(1):45-62. doi: 10.1016/j.jare.2014.11.008. Epub 2014 Dec 1. [Article]
- Kind
- Protein
- Organism
- Humans
- 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, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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 fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52