| Drug General Information |
| Drug ID |
D02ABO
|
| Former ID |
DNC007019
|
| Drug Name |
NARINGENIN
|
| Drug Type |
Small molecular drug
|
| Indication |
Discovery agent
|
Phase 1 |
[1]
|
|---|
| Structure |
|
Download
2D MOL
3D MOL
|
| Formula |
C15H12O5
|
| Canonical SMILES |
C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
|
| 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
|
| InChIKey |
FTVWIRXFELQLPI-ZDUSSCGKSA-N
|
| CAS Number |
CAS 480-41-1
|
| PubChem Compound ID |
|
| Target and Pathway |
| Target(s) |
Lactoylglutathione lyase |
Target Info |
Inhibitor |
[2]
|
|---|
| Estrogen receptor beta |
Target Info |
Inhibitor |
[3]
|
| Cytochrome P450 1B1 |
Target Info |
Inhibitor |
[4]
|
| Cytochrome P450 19 |
Target Info |
Inhibitor |
[5]
|
| Estradiol 17 beta-dehydrogenase 1 |
Target Info |
Inhibitor |
[6]
|
|
BioCyc Pathway
|
Methylglyoxal degradation IPWY66-401:Superpathway of tryptophan utilization
|
|
Superpathway of melatonin degradation
|
|
Melatonin degradation IPWY-7305:Superpathway of steroid hormone biosynthesis
|
|
Estradiol biosynthesis II
|
|
Estradiol biosynthesis IPWY-7305:Superpathway of steroid hormone biosynthesis
|
|
Estradiol biosynthesis I
|
|
KEGG Pathway
|
Pyruvate metabolismhsa04915:Estrogen signaling pathway
|
|
Prolactin signaling pathwayhsa00140:Steroid hormone biosynthesis
|
|
Tryptophan metabolism
|
|
Metabolism of xenobiotics by cytochrome P450
|
|
Ovarian steroidogenesis
|
|
Chemical carcinogenesis
|
|
MicroRNAs in cancerhsa00140:Steroid hormone biosynthesis
|
|
Metabolic pathways
|
|
Ovarian steroidogenesishsa00140:Steroid hormone biosynthesis
|
|
NetPath Pathway
|
TCR Signaling PathwayNetPath_23:TSH Signaling Pathway
|
|
IL4 Signaling Pathway
|
|
TGF_beta_Receptor Signaling PathwayNetPath_25:FSH Signaling PathwayNetPath_25:FSH Signaling Pathway
|
|
PANTHER Pathway
|
Androgen/estrogene/progesterone biosynthesisP02727:Androgen/estrogene/progesterone biosynthesis
|
|
Pathway Interaction Database
|
Plasma membrane estrogen receptor signaling
|
|
Validated nuclear estrogen receptor beta network
|
|
Validated nuclear estrogen receptor alpha network
|
|
PathWhiz Pathway
|
Pyruvaldehyde Degradation
|
|
Pyruvate MetabolismPW000045:Androgen and Estrogen MetabolismPW000045:Androgen and Estrogen Metabolism
|
|
Reactome
|
Pyruvate metabolismR-HSA-383280:Nuclear Receptor transcription pathwayR-HSA-211976:Endogenous sterolsR-HSA-211976:Endogenous sterolsR-HSA-2453902:The canonical retinoid cycle in rods (twilight vision)
|
|
WikiPathways
|
SIDS Susceptibility Pathways
|
|
Ovarian Infertility Genes
|
|
Integrated Pancreatic Cancer Pathway
|
|
Nuclear ReceptorsWP702:Metapathway biotransformation
|
|
Estrogen metabolism
|
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Benzo(a)pyrene metabolism
|
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Tamoxifen metabolism
|
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Tryptophan metabolism
|
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Oxidation by Cytochrome P450
|
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Nuclear Receptors Meta-Pathway
|
|
Estrogen Receptor Pathway
|
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Sulindac Metabolic Pathway
|
|
Arylhydrocarbon receptor (AhR) signaling pathway
|
|
miR-targeted genes in muscle cell - TarBase
|
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miR-targeted genes in lymphocytes - TarBase
|
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miR-targeted genes in epithelium - TarBase
|
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miR-targeted genes in adipocytes - TarBase
|
|
Phase 1 - Functionalization of compoundsWP702:Metapathway biotransformation
|
|
Metabolism of steroid hormones and vitamin D
|
|
FSH signaling pathway
|
|
Integrated Breast Cancer Pathway
|
|
Phase 1 - Functionalization of compoundsWP496:Steroid Biosynthesis
|
|
Prostate Cancer
|
| References |
| REF 1 | ClinicalTrials.gov (NCT01091077) A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection. U.S. National Institutes of Health. |
|---|
| REF 2 | Bioorg Med Chem. 2008 Apr 1;16(7):3969-75. Epub 2008 Jan 24.Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects. |
|---|
| REF 3 | J Med Chem. 2006 Dec 14;49(25):7357-65.Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen receptors alphaand beta. |
|---|
| REF 4 | Bioorg Med Chem. 2010 Sep 1;18(17):6310-5. Epub 2010 Jul 13.Selective inhibition of methoxyflavonoids on human CYP1B1 activity. |
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| REF 5 | Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64. Epub 2010 Apr 8.Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). |
|---|
| REF 6 | J Med Chem. 2008 Jul 24;51(14):4188-99. Epub 2008 Jun 6.Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. |
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