Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H20O7 |
Molecular Weight | 372.3686 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(C=C1OC)C2=CC(=O)C3=C(O2)C=C(OC)C(OC)=C3OC
InChI
InChIKey=LKMNXYDUQXAUCZ-UHFFFAOYSA-N
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(27-14)10-17(24-3)19(25-4)20(18)26-5/h6-10H,1-5H3
Sinensetin is a methylated flavone found in certain citrus fruits. pocess potent antiangiogenesis and anti-inflammatory, sinensetin enhances adipogenesis and lipolysis. Sinensetin is a selective inhibitor of α-glucosidase with IC50 value of 0.66 mg/ml. Alpha-glucosidase and α-amylase inhibition could the mechanisms through which sinensetin exert its antidiabetic activity, indicating that it could have potential use in the management of non-insulin-dependent diabetes. Sinensetin inhibits inflammatory gene expression and STAT1 activation. It has meaningful anti-inflammatory properties which may be utilized in the development of novel anti-inflammatory treatments.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25442272 |
40.2 µM [IC50] | ||
Target ID: GO:0090599 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079 |
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Target ID: GO:0004556 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23039079 |
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Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11087521 |
74.0 µM [IC50] | ||
Target ID: CHEMBL4321 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Immunotoxicity of a standardized citrus polymethoxylated flavone extract. | 2001 Nov |
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Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones. | 2002 May |
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Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels. | 2002 May 8 |
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Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora. | 2004 Apr 7 |
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ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal. | 2005 Oct 4 |
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Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques. | 2007 May 9 |
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Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts. | 2008 Jan |
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UPLC/Q-TOFMS/MS as a powerful technique for rapid identification of polymethoxylated flavones in Fructus aurantii. | 2009 Aug 15 |
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Evaluation of the anti-pyretic potential of Orthosiphon stamineus Benth standardized extract. | 2009 Feb |
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Methylation of dietary flavones increases their metabolic stability and chemopreventive effects. | 2009 Nov 18 |
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Induction of apoptosis in human cervical carcinoma HeLa cells by polymethoxylated flavone-rich Citrus grandis Osbeck (Dangyuja) leaf extract. | 2010 Aug-Sep |
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Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook. | 2010 Feb 26 |
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Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong. | 2010 Sep 8 |
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In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent. | 2012 Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22516932
Sinensetin (50 mg/kg i. p.) inhibited carrageenan-induced paw inflammation in mice.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19666078
Sinensetin inhibited proliferation of MDA-MB-468 and
MCF-10A cells with IC50 values of 0.2 and 65 uM respectively.
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2306-27-6
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SINENSETIN
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145659
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DTXSID60177626
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SUBSTANCE RECORD