plakoridine A

{{Chembox

| ImageFile = Plakoridine A.svg

| ImageSize = 200px

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| SystematicName = Methyl (2S,3S,4R,5E)-4-hydroxy-1-[2-(4-hydroxyphenyl)ethyl]-5-(2-oxooctadecylidene)-2-propyl-3-pyrrolidinecarboxylate

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|Section1={{Chembox Identifiers

| CASNo = 155944-28-8

| CASNo_Ref = {{Cascite|changed|{{cite web |title=KNApSAcK Metabolite Information - C00028848 |url=http://www.knapsackfamily.com/knapsack_core/information.php?word=C00028848 |website=www.knapsackfamily.com}}}}

| PubChem = 10257462

| ChemSpiderID = 8432945

| SMILES = O=C(/C=C2/N(CCc1ccc(O)cc1)[C@H]([C@H](C(=O)OC)[C@H]2O)CCC)CCCCCCCCCCCCCCCC

| InChI = 1S/C35H57NO5/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-20-30(38)27-32-34(39)33(35(40)41-3)31(19-5-2)36(32)26-25-28-21-23-29(37)24-22-28/h21-24,27,31,33-34,37,39H,4-20,25-26H2,1-3H3/b32-27+/t31-,33-,34-/m0/s1

| InChIKey = ULFKEEJTLUNSEY-CWJJWNJISA-N }}

|Section2={{Chembox Properties

| C=35 | H=57 | N=1 | O=5

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|Section3={{Chembox Hazards

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Plakoridine A is an alkaloid isolated from the marine sponge Plakortis sp.{{cite journal|title=Plakoridine A, a new tyramine-containing pyrrolidine alkaloid from the Okinawan marine sponge Plakortis sp.|year=1994|doi=10.1021/jo00092a039|last1=Takeuchi|first1=Shinji|last2=Ishibashi|first2=Masami|last3=Kobayashi|first3=Junichi|journal=The Journal of Organic Chemistry|volume=59|issue=13|pages=3712–3713}}{{cite journal|title=Total synthesis of (2S,3S,4R)-plakoridine A|year=2000|doi=10.1016/S0040-4039(00)00096-4|last1=Ma|first1=Dawei|last2=Sun|first2=Haiying|journal=Tetrahedron Letters|volume=41|issue=12|pages=1947–1950}} There are three plakoridines known, named plakoridine A, B, and C.{{cite journal |last1=Ishiguro |first1=Yuichiro |last2=Kubota |first2=Takaaki |last3=Ishiuchi |first3=Kan’ichiro |last4=Fromont |first4=Jane |last5=Kobayashi |first5=Jun’ichi |title=Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp. |journal=Tetrahedron Letters |date=July 2009 |volume=50 |issue=26 |pages=3202–3204 |doi=10.1016/j.tetlet.2009.01.135}}{{cite journal |last1=Norris |first1=Matthew D. |last2=Perkins |first2=Michael V. |title=Structural diversity and chemical synthesis of peroxide and peroxide-derived polyketide metabolites from marine sponges |journal=Natural Product Reports |date=2016 |volume=33 |issue=7 |pages=861–880 |doi=10.1039/C5NP00142K|doi-access=free |pmid=27163115 }}