| Revision as of 12:48, 24 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit |
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{{chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 455117142 |
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| Watchedfields = changed |
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|Name=(−)-Arctigenin |
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| verifiedrevid = 457138871 |
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|ImageFile=(−)-Arctigenin.svg |
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| Name = (−)-Arctigenin |
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|ImageSize=250 |
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| ImageFile = (−)-Arctigenin.svg |
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|IUPACName=(3''R'',4''R'')-4--3- -2-tetrahydrofuranone |
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| ImageSize = 250 |
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|OtherNames= |
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| IUPACName = (3''R'',4''R'')-4--3- -2-tetrahydrofuranone |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = <!-- blanked - oldvalue: 7770-78-7 --> |
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| CASNo = 7770-78-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 435734 |
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| UNII = U76MR9VS6M |
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| PubChem=64981 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| SMILES=COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC |
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| KEGG = C10545 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 435734 |
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| PubChem = 64981 |
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| SMILES = COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 58506 |
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| ChemSpiderID = 58506 |
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| SMILES = O=C2OC(Cc1cc(OC)c(OC)cc1)2Cc3ccc(O)c(OC)c3 |
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| SMILES2 = O=C2OC(Cc1cc(OC)c(OC)cc1)2Cc3ccc(O)c(OC)c3 |
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| InChI = 1/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 |
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| InChI = 1/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 |
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| InChIKey = NQWVSMVXKMHKTF-JKSUJKDBBB |
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| InChIKey = NQWVSMVXKMHKTF-JKSUJKDBBB |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 |
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| StdInChI = 1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NQWVSMVXKMHKTF-JKSUJKDBSA-N |
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| StdInChIKey = NQWVSMVXKMHKTF-JKSUJKDBSA-N |
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| MeSHName=arctigenin |
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| MeSHName = arctigenin |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>21</sub>H<sub>24</sub>O<sub>6</sub> |
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| Formula = C<sub>21</sub>H<sub>24</sub>O<sub>6</sub> |
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| MolarMass=372.41166 |
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| MolarMass = 372.41166 |
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| Appearance = |
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| ExactMass = 372.157289 u |
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| Density = |
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| Appearance= |
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| MeltingPt = |
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| Density= |
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| BoilingPt = |
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}} |
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| Solubility= |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards = |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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}} |
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'''Arctigenin''' is a ] found in certain ] of the ], including the ] (''Arctium lappa'') and ]. It has shown ] and anticancer effects.{{cn|date=October 2011}} It is the ] of ]. |
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'''Arctigenin''' is a ] found in certain ] of the ], including the ] (''Arctium lappa'') and ]. It has shown ]<ref>{{Cite journal |
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| doi = 10.1248/bpb.33.1199 |
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| last1 = Hayashi | first1 = K. |
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| last2 = Narutaki | first2 = K. |
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| last3 = Nagaoka | first3 = Y. |
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| last4 = Hayashi | first4 = T. |
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| last5 = Uesato | first5 = S. |
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| title = Therapeutic effect of arctiin and arctigenin in immunocompetent and immunocompromised mice infected with influenza a virus |
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| journal = Biological & Pharmaceutical Bulletin |
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| volume = 33 |
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| issue = 7 |
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| pages = 1199–1205 |
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| year = 2010 |
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| pmid = 20606313 |
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| doi-access = free |
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}}</ref> and anticancer<ref>{{Cite journal |
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| last1 = Yang | first1 = S. |
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| last2 = Ma | first2 = J. |
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| last3 = Xiao | first3 = J. |
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| last4 = Lv | first4 = X. |
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| last5 = Li | first5 = X. |
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| last6 = Yang | first6 = H. |
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| last7 = Liu | first7 = Y. |
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| last8 = Feng | first8 = S. |
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| last9 = Zhang | first9 = Y. |
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| doi = 10.1002/ar.22497 |
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| title = Arctigenin Anti-Tumor Activity in Bladder Cancer T24 Cell Line Through Induction of Cell-Cycle Arrest and Apoptosis |
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| journal = The Anatomical Record |
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| volume = 295 |
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| issue = 8 |
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| pages = 1260–1266 |
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| year = 2012 |
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| pmid = 22619087 |
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| doi-access = free |
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}}</ref> effects ]. It is the ] of ]. |
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The use of arctigenin has been shown to be effective in a mouse model of ].<ref name="pmid18230688">{{cite journal |vauthors=Swarup V, Ghosh J, Mishra MK, Basu A |title=Novel strategy for treatment of Japanese encephalitis using arctigenin, a plant lignan |journal=J. Antimicrob. Chemother. |volume=61 |issue=3 |pages=679–88 |date=March 2008 |pmid=18230688 |doi=10.1093/jac/dkm503 |doi-access=free }}</ref> |
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It has been found to act as an ] of ] (AdipoR1).<ref name="pmid23691032">{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354 | bibcode = 2013PLoSO...863354S | doi-access = free }}</ref> |
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== References == |
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{{Reflist}} |
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== External links == |
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== External links == |
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* entry in the public domain NCI Dictionary of Cancer Terms |
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* entry in the public domain NCI Dictionary of Cancer Terms |
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{{NCI-cancer-dict}} |
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{{NCI-cancer-dict}} |
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{{lignan}} |
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{{Lignans}} |
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