:Varacin

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 399162393

| ImageFile = Varacin_structure.svg

| ImageSize =

| ImageAlt = Skeletal formula of varacin

| ImageFile1 = Varacin 3D ball.png

| ImageAlt1 = Ball-and-stick model of the varacin molecule

| ImageName = Varacin skeletal structure

| PIN = 2-(8,9-Dimethoxy-1,2,3,4,5-benzopentathiepin-6-yl)ethan-1-amine

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 134029-48-4

| PubChem = 179269

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 151233

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 156044

| SMILES = NCCc2cc(OC)c(OC)c1SSSSSc12

| InChI = 1/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3

| InChIKey = HIKCOAGMCNIBMP-UHFFFAOYAP

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = HIKCOAGMCNIBMP-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula = C₁₀H₁₃NO₂S₅

| MolarMass = 339.540 g/mol

| Appearance =

| Density =

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|Section3={{Chembox Hazards

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Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus.{{cite journal | vauthors = Makarieva TN, Stonik VA, Dmitrenok AS, Grebnev BB, Isakov VV, Rebachyk NM, Rashkes YW | title = Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp | journal = Journal of Natural Products | volume = 58 | issue = 2 | pages = 254–8 | date = February 1995 | pmid = 7769392 | doi = 10.1021/np50116a015 }} It contains an unusual pentathiepin ring which reacts with DNA, and varacin and synthetic analogues have been investigated for their antimicrobial and antitumour properties.{{cite journal | vauthors = Greer A | title = On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate | journal = Journal of the American Chemical Society | volume = 123 | issue = 42 | pages = 10379–86 | date = October 2001 | pmid = 11603989 | doi = 10.1021/ja016495p }}{{cite journal | vauthors = Brzostowska EM, Greer A | title = The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents | journal = Journal of the American Chemical Society | volume = 125 | issue = 2 | pages = 396–404 | date = January 2003 | pmid = 12517151 | doi = 10.1021/ja027416s }} Because of its potent biological activity and unusual and challenging ring system, it has been a popular target of efforts toward its total synthesis.{{cite journal| vauthors = Behar V, Danishefsky SJ |date=1993-07-01|title=Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"|journal=Journal of the American Chemical Society|volume=115|issue=15|pages=7017–7018|doi=10.1021/ja00068a087|issn=0002-7863}}{{Cite journal| vauthors = Ford PW, Narbut MR, Belli J, Davidson BS |date=1994-10-01|title=Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A|journal=The Journal of Organic Chemistry|volume=59|issue=20|pages=5955–5960|doi=10.1021/jo00099a026|issn=0022-3263}}{{Cite journal| vauthors = Toste FD, Still IW |date=1995-07-01|title=A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin |journal=Journal of the American Chemical Society |volume=117 |issue=27 |pages=7261–7262 |doi=10.1021/ja00132a033 }}

By virtue of the unsymmetrically substituted benzopentathiepin ring system, varacin and a few related polysulfane natural products exist as potentially isolable enantiomers as a result of planar chirality.{{Cite journal |last=Brzostowska |first=Edyta M. |last2=Paulynice |first2=Martine |last3=Bentley |first3=Ronald |last4=Greer |first4=Alexander |date=2007-07-01 |title=Planar Chirality due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity |url=https://pubs.acs.org/doi/epdf/10.1021/tx7000465?ref=article_openPDF& |journal=Chemical Research in Toxicology |volume=20 |issue=7 |pages=1046–1052 |doi=10.1021/tx7000465 |issn=0893-228X|url-access=subscription }}