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 8297		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 1430

PubMed

Title	Date	PubMed
Earl Grey tea intoxication.	2002 Apr 27	11988248
Isolation and structure elucidation of a new prenylcoumarin from Murraya paniculata var. omphalocarpa (Rutaceae).	2002 Jan	11824571
Degradation of flavonoid aglycones by rabbit, rat and human fecal flora.	2003 May	12736527
Toxic effects of lemon peel constituents on Ceratitis capitata.	2004 Feb	15112727
Antifungal constituents of Melicope borbonica.	2004 Jul	15305313
Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland.	2006 Jun	16387742
Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.	2007 Apr 4	17348674
Characterization of Phaseolus vulgaris L. landraces cultivated in central Italy.	2008 Dec	18958625
Cell cycle arrest and differentiation induction by 5,7-dimethoxycoumarin in melanoma cell lines.	2008 Feb	18202765
Effects of naturally occurring coumarins on hepatic drug-metabolizing enzymes in mice.	2008 Oct 15	18692084
The structure-activity relationship between oxycoumarin derivatives showing inhibitory effects on iNOS in mouse macrophage RAW264.7 cells.	2009 Jan	18607531
Inhibition of Mek 1/2 kinase activity and stimulation of melanogenesis by 5,7-dimethoxycoumarin treatment of melanoma cells.	2009 Jun	19424591
Comparison of citrus coumarins on carcinogen-detoxifying enzymes in Nrf2 knockout mice.	2009 Mar 28	19150646
[Chemical constituents of Lobelia chinensis].	2009 Sep	19943485
Relative photomutagenicity of furocoumarins and limettin in the hypoxanthine phosphoribosyl transferase assay in V79 cells.	2009 Sep	19725558
Limettin and furocoumarins in beverages containing citrus juices or extracts.	2010 Jan	19770019
Anti-human immunodeficiency virus-1 constituents of the bark of Poncirus trifoliata.	2010 Jul	20606349
Aggressive mammary carcinoma progression in Nrf2 knockout mice treated with 7,12-dimethylbenz[a]anthracene.	2010 Oct 8	20932318
In vitro photo-induced cytotoxic activity of Citrus bergamia and C. medica L. cv. Diamante peel essential oils and identified active coumarins.	2010 Sep	20690896

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:35:40 GMT 2023` Edited by `admin` on `Fri Dec 15 18:35:40 GMT 2023`
Record UNII	JWE1QQ247N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LIMETTIN

Common 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

NSC-102793

Code

English

Code System Code Type Description

MERCK INDEX

m6815