Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Allopumiliotoxin 267A: Difference between pages
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Allopumiliotoxin_267A|oldid=445026678}} 445026678] of page [[Allopumiliotoxin_267A]] with values updated to verified values.}} |
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| verifiedrevid = |
| verifiedrevid = 477314460 |
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|ImageFile=Allopumiliotoxin267A.png |
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|ImageFile=Allopumiliotoxin 267A.svg |
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|ImageSize=240 |
|ImageSize=240 |
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|PIN=(6''E'',7''R'',8''R'',8a''S'')-8-Methyl-6-[(2''R'')-2-methylhexylidene]octahydroindolizine-7,8-diol |
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|OtherNames= |
|OtherNames= |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4580699 |
| ChemSpiderID = 4580699 |
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| InChI = 1/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1 |
| InChI = 1/C16H29NO2/c1-4-5-7-12(2)10-13-11-17-9-6-8-14(17)16(3,19)15(13)18/h10,12,14-15,18-19H,4-9,11H2,1-3H3/b13-10+/t12-,14+,15-,16-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = LWXKAVPXEDNHLL-VRUXTKGDSA-N |
| StdInChIKey = LWXKAVPXEDNHLL-VRUXTKGDSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 73376-38-2 --> |
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| CASNo= 73376-38-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = TEP57TLJ38 |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| C=16 | H=29 | N=1 | O=2 |
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|Section3={{Chembox Hazards |
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| MainHazards=Highly toxic |
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'''Allopumiliotoxin 267A''' is a toxin found in the skin of several [[poison frog]]s of the family ''[[Dendrobates]]''.<ref>{{Cite journal | pmid = 3236011| year = 1988| last1 = Edwards| first1 = M. W.| title = Alkaloids from a Panamanian poison frog, Dendrobates speciosus: Identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine| journal = Journal of Natural Products| volume = 51| issue = 6| pages = 1188–97| last2 = Daly| first2 = J. W.| last3 = Myers| first3 = C. W.| doi = 10.1021/np50060a023}}</ref> It is a member of the class of compounds known as [[allopumiliotoxin]]s. The frogs produce the toxin by modifying the original version, [[pumiliotoxin 251D]].<ref>{{Cite journal | pmid = 12960405| pmc = 196932| year = 2003| last1 = Daly| first1 = J. W.| title = Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates| journal = Proceedings of the National Academy of Sciences of the United States of America| volume = 100| issue = 19| pages = 11092–7| last2 = Garraffo| first2 = H. M.| last3 = Spande| first3 = T. F.| last4 = Clark| first4 = V. C.| last5 = Ma| first5 = J.| last6 = Ziffer| first6 = H.| last7 = Cover Jr| first7 = J. F.| doi = 10.1073/pnas.1834430100| bibcode = 2003PNAS..10011092D| doi-access = free}}</ref> It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.<ref>{{Cite journal | pmid = 11428041| year = 2001| last1 = Comins| first1 = D. L.| title = Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A| journal = Organic Letters| volume = 3| issue = 3| pages = 469–71| last2 = Huang| first2 = S.| last3 = McArdle| first3 = C. L.| last4 = Ingalls| first4 = C. L.| doi = 10.1021/ol0069709}}</ref><ref>{{cite journal | doi = 10.1021/cr950021p | pmid = 11848762 | title = Total Syntheses of Pumiliotoxin a and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies | journal = Chemical Reviews | volume = 96 | issue = 1 | pages = 505–522 | year = 1996 | last1 = Franklin | first1 = Alison S. | last2 = Overman | first2 = Larry E. }}</ref><ref>{{cite journal | doi =10.1021/ja001440t | title =Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B | journal =Journal of the American Chemical Society | volume =122 | issue =29 | pages =6950–6954 | year =2000 | last1 =Tang | first1 =Xiao-Qing | last2 =Montgomery | first2 =John | url =https://figshare.com/articles/Nickel-Catalyzed_Preparation_of_Bicyclic_Heterocycles_Total_Synthesis_of_-Allopumiliotoxin_267A_-Allopumiliotoxin_339A_and_-Allopumiliotoxin_339B/3629484 }}</ref><ref>{{cite journal | doi =10.1021/ja00077a044 | title =Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/Chromium(II)-mediated cyclization | journal =Journal of the American Chemical Society | volume =115 | issue =24 | pages =11393–11409 | year =1993 | last1 =Aoyagi | first1 =Sakae | last2 =Wang | first2 =Tzu Chueh | last3 =Kibayashi | first3 =Chihiro }}</ref> |
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== See also == |
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* [[Pumiliotoxin]] |
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* [[Allopumiliotoxin]] |
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== References == |
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{{reflist}} |
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{{Poison frog alkaloids}} |
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[[Category:Amphibian toxins]] |
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[[Category:Alkaloids]] |
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[[Category:Ion channel toxins]] |
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[[Category:Vicinal diols]] |