DrugBank: Naringenin (DB03467)

targets (1) transporters (4)

Identification

Name

Naringenin

Accession Number

DB03467 (EXPT02295)

Type

small molecule

Groups

experimental

Description

Not Available

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Anti-Ulcer Agents
Estrogen Antagonists

CAS number

480-41-1

Weight

Average: 272.2528
Monoisotopic: 272.068473494

Chemical Formula

C₁₅H₁₂O₅

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Not Available

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

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

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	251 °C	PhysProp
logP	2.52	PERRISSOUD,D & TESTA,B (1986)

Predicted Properties

Property	Value	Source
water solubility	2.14e-01 g/l	ALOGPS
logP	2.47	ALOGPS
logP	2.84	ChemAxon
logS	-3.1	ALOGPS
pKa (strongest acidic)	7.91	ChemAxon
pKa (strongest basic)	-3.9	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	5	ChemAxon
hydrogen donor count	3	ChemAxon
polar surface area	86.99	ChemAxon
rotatable bond count	1	ChemAxon
refractivity	71.29	ChemAxon
polarizability	27.31	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C00509
PubChem Compound	439246
PubChem Substance	46508043
ChemSpider	388383
BindingDB	23419
ChEBI	17846
ChEMBL	17846
PharmGKB	PA151958361
HET	NAR

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1CGK

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. HTH-type transcriptional regulator ttgR Pharmacological action: unknown 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 Organism class: bacterial UniProt ID: Q9AIU0 Gene: ttgR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed

Targets

1. HTH-type transcriptional regulator ttgR

Pharmacological action: unknown

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

Organism class: bacterial
UniProt ID: Q9AIU0 Link_out

Gene: ttgR Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

Transporters
1. Solute carrier organic anion transporter family member 2B1 Actions: inhibitor Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost UniProt ID: O94956 Gene: SLCO2B1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 2. Multidrug resistance protein 1 Actions: inhibitor Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells UniProt ID: P08183 Gene: ABCB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 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 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 3. Multidrug resistance-associated protein 1 Actions: inhibitor May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics UniProt ID: P33527 Gene: ABCC1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 4. ATP-binding cassette sub-family G member 2 Actions: inhibitor Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123 UniProt ID: Q9UNQ0 Gene: ABCG2 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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. Pubmed 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

Transporters

1. Solute carrier organic anion transporter family member 2B1

Actions: inhibitor

Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost

UniProt ID: O94956 Link_out

Gene: SLCO2B1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

2. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out

Gene: ABCB1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
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
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

3. Multidrug resistance-associated protein 1

Actions: inhibitor

May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Confers resistance to anticancer drugs. Transports LTC4. May protect milk against xenobiotics

UniProt ID: P33527 Link_out

Gene: ABCC1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

4. ATP-binding cassette sub-family G member 2

Actions: inhibitor

Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123

UniProt ID: Q9UNQ0 Link_out

Gene: ABCG2 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
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

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:22