Drug General Information
Drug ID
D02ABO
Former ID
DNC007019
Drug Name
NARINGENIN
Drug Type
Small molecular drug
Indication Discovery agent Phase 1 [522980]
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 [529300]
Estrogen receptor beta Target Info Inhibitor [528557]
Cytochrome P450 1B1 Target Info Inhibitor [531094]
Cytochrome P450 19 Target Info Inhibitor [530867]
Estradiol 17 beta-dehydrogenase 1 Target Info Inhibitor [529519]
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
Benzo(a)pyrene metabolism
Tamoxifen metabolism
Tryptophan metabolism
Oxidation by Cytochrome P450
Nuclear Receptors Meta-Pathway
Estrogen Receptor Pathway
Sulindac Metabolic Pathway
Arylhydrocarbon receptor (AhR) signaling pathway
miR-targeted genes in muscle cell - TarBase
miR-targeted genes in lymphocytes - TarBase
miR-targeted genes in epithelium - TarBase
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 522980ClinicalTrials.gov (NCT01091077) A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection. U.S. National Institutes of Health.
Ref 528557J 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 529300Bioorg 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 529519J 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.
Ref 530867Bioorg 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 531094Bioorg 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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