:Raucaffrinoline

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{{Chembox

| ImageFile = Raucaffrinoline.svg

| ImageSize =

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| IUPACName = [(1R,10S,12S,13R,14S,16S,18R)-13-(hydroxymethyl)-14-methyl-8,15-diazahexacyclo[14.2.1.0^1,9.0^2,7.0^10,15.0^12,17]nonadeca-2,4,6,8-tetraen-18-yl] acetate

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|Section1={{Chembox Identifiers

| CASNo = 36285-11-7

| CASNo_Ref = {{Cascite|changed|ChemSpider}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3DFF5QDK46

| ChEBI = 63167

| KEGG = C19931

| PubChem = 56927714

| ChemSpiderID = 26332998

| StdInChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20+,21+/m0/s1

| StdInChIKey = XIMPCXFLDSKALH-FXRWJBKJSA-N

| SMILES = C[C@H]1[C@@H]([C@@H]2C[C@@H]3N1[C@@H]4C2[C@H]([C@@]5(C4)C3=NC6=CC=CC=C56)OC(=O)C)CO

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|Section2={{Chembox Properties

| C=21 | H=24 | N=2 | O=3

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|Section3={{Chembox Hazards

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Raucaffrinoline is an indole alkaloid isolated from the leaves of various plants in the Rauvolfia family, such as Rauvolfia yunnanensis.{{cite journal | vauthors = Khan MA, Siddiqui S | title = Isolation and structure of raucaffrinoline--a new alkaloid from Rauwolfia caffra sonder | journal = Experientia | volume = 28 | issue = 2 | pages = 127–128 | date = February 1972 | pmid = 5020328 | doi = 10.1007/BF01935708 }}{{cite journal | vauthors = Rosenthal C, Mueller U, Panjikar S, Sun L, Ruppert M, Zhao Y, Stöckigt J | title = Expression, purification, crystallization and preliminary X-ray analysis of perakine reductase, a new member of the aldo-keto reductase enzyme superfamily from higher plants | journal = Acta Crystallographica. Section F, Structural Biology and Crystallization Communications | volume = 62 | issue = Pt 12 | pages = 1286–1289 | date = December 2006 | pmid = 17142919 | doi = 10.1107/S174430910605041X | pmc = 2225361 }}{{cite journal | vauthors = Cao P, Liang Y, Gao X, Li XM, Song ZQ, Liang G | title = Monoterpenoid indole alkaloids from Alstonia yunnanensis and their cytotoxic and anti-inflammatory activities | journal = Molecules | volume = 17 | issue = 11 | pages = 13631–13641 | date = November 2012 | pmid = 23159924 | doi = 10.3390/molecules171113631 | doi-access = free | pmc = 6268798 }}{{cite journal | vauthors = Geng CA, Liu XK | title = Five new indole alkaloids from the leaves of Rauvolfia yunnanensis | journal = Fitoterapia | volume = 89 | pages = 42–47 | date = September 2013 | pmid = 23707746 | doi = 10.1016/j.fitote.2013.05.017 }}