LIMETTIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H10O4
Molecular Weight	206.1947
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(OC)=C2C=CC(=O)OC2=C1

InChI

InChIKey=NXJCRELRQHZBQA-UHFFFAOYSA-N

InChI=1S/C11H10O4/c1-13-7-5-9(14-2)8-3-4-11(12)15-10(8)6-7/h3-6H,1-2H3

HIDE SMILES / InChI

Molecular Formula	C11H10O4
Molecular Weight	206.1947
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cell cycle 2 Target ID: map04110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18202765	Inhibitor 8504		300.0 µM [IC50]
Melanogenesis 5 Target ID: map04916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19424591\|https://www.ncbi.nlm.nih.gov/pubmed/23001511	Activator 1447

PubMed

Title	Date	PubMed
Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene.	2010-10-08	20932318
In vitro photo-induced cytotoxic activity of Citrus bergamia and C. medica L. cv. Diamante peel essential oils and identified active coumarins.	2010-09	20690896
Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.	2010-07	20606349
Limettin and furocoumarins in beverages containing citrus juices or extracts.	2010-01	19770019
[Chemical constituents of Lobelia chinensis].	2009-09	19943485
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.	2009-09	19725558
Inhibition of Mek 1/2 kinase activity and stimulation of melanogenesis by 5,7-dimethoxycoumarin treatment of melanoma cells.	2009-06	19424591
Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.	2009-03-28	19150646
The structure-activity relationship between oxycoumarin derivatives showing inhibitory effects on iNOS in mouse macrophage RAW264.7 cells.	2009-01	18607531
Characterization of Phaseolus vulgaris L. landraces cultivated in central Italy.	2008-12	18958625
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008-10-15	18692084
Cell cycle arrest and differentiation induction by 5,7-dimethoxycoumarin in melanoma cell lines.	2008-02	18202765
Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.	2007-04-04	17348674
Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland.	2006-06	16387742
Antifungal constituents of Melicope borbonica.	2004-07	15305313
Toxic effects of lemon peel constituents on Ceratitis capitata.	2004-02	15112727
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.	2003-05	12736527
Earl Grey tea intoxication.	2002-04-27	11988248
Isolation and structure elucidation of a new prenylcoumarin from Murraya paniculata var. omphalocarpa (Rutaceae).	2002-01	11824571

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:16:04 GMT 2025` Edited by `admin` on `Mon Mar 31 19:16:04 GMT 2025`
Record UNII	JWE1QQ247N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIMETTIN

Common Name

English

NSC-102793

Preferred Name

English

5,7-DIMETHOXYCOUMARIN

Systematic Name

English

5,7-DIMETHOXY-2H-CHROMEN-2-ONE

Systematic Name

English

5,7-DIMETHOXY-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

DIMETHOXYCOUMARIN, 5,7-

Systematic Name

English

LIMETTIN [MI]

Common Name

English

CITROPTEN

Common Name

English

Code System Code Type Description

MERCK INDEX

m6815