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Revision as of 18:45, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444133032 of page Tautomycin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'StdInChI').  Latest revision as of 01:57, 30 June 2024 edit Zakblade2000 (talk | contribs)Extended confirmed users4,108 editsNo edit summary 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| verifiedrevid = 470477946
| ImageFile = Tautomycin.png | ImageFile = Tautomycin.png
| ImageSize = | ImageSize =
| IUPACName = -1,7-dioxaspiroundecan-2-yl]-3,7-dihydroxy-1-isopropyl-2-methoxy-6-methyl-5-oxo-undecyl] (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-3-furyl)propanoate | PIN = (3''R'',4''R'',5''R'',8''S'',9''S'',12''R'')-12-{(2''S'',3''S'',6''R'',8''S'',9''R'')-3,9-Dimethyl-8--1,7-dioxaspiroundecan-2-yl}-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3''R'')-3-hydroxy-3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoate
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| InChI = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1 | InChI = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1
| InChIKey1 = RFCWHQNNCOJYTR-IRCAEPKSSA-N | InChIKey1 = RFCWHQNNCOJYTR-IRCAEPKSSA-N
| InChI1 = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1 | InChI1 = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo =
| ChEMBL = 505512 | CASNo = 109946-35-2
| ChEBI = 9414
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 505512
| EINECS = 620-961-5
| KEGG = C05372
| PubChem = 440646 | PubChem = 440646
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 389529 | ChemSpiderID = 389529
⚫ | StdInChIKey = RFCWHQNNCOJYTR-IRCAEPKSSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = RFCWHQNNCOJYTR-IRCAEPKSSA-N
| SMILES = O=C\1OC(=O)/C(=C/1C)(O)CC(=O)O(C(C)C)(OC)(O)CC(=O)(C)(O)CC(3O2(O((C)CC2)CC(C(=O)C)C)CC3C)C | SMILES = O=C\1OC(=O)/C(=C/1C)(O)CC(=O)O(C(C)C)(OC)(O)CC(=O)(C)(O)CC(3O2(O((C)CC2)CC(C(=O)C)C)CC3C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1 | StdInChI = 1S/C41H66O13/c1-21(2)36(51-34(47)20-31(45)35-27(8)39(48)52-40(35)49)38(50-10)32(46)19-30(44)26(7)29(43)13-11-24(5)37-25(6)16-18-41(54-37)17-15-23(4)33(53-41)14-12-22(3)28(9)42/h21-26,29,31-33,36-38,43,45-46H,11-20H2,1-10H3/t22-,23+,24+,25-,26-,29-,31+,32+,33-,36+,37-,38+,41+/m0/s1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C41H66O13
| MolarMass = 766.95 | C=41 | H=66 | O=13
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Tautomycin''' is a chemical that occurs naturally in ] and is produced by the bacterium '']''. It is a ]-based structure characterized by a three ] groups, two ]s, a dialkylmaleic anhydride, an ] linkage (connecting anhydride unit to polyketide chain), a spiroketal and one ] ] among others.

==Pharmacology==
It is a very potent inhibitor of the protein ]s PP1 and PP2A.<ref>{{cite journal | doi = 10.1007/bf01197780 | pmid = 7559747 | title = Tautomycin: An inhibitor of protein phosphatases 1 and 2A but not a tumor promoter on mouse skin and in rat glandular stomach | journal = Journal of Cancer Research and Clinical Oncology | volume = 121 | issue = 9–10 | pages = 621–627 | year = 1995 | last1 = Suganuma | first1 = Masami | last2 = Okabe | first2 = Sachiko | last3 = Sueoka | first3 = Eisaburo | last4 = Nishiwaki | first4 = Rie | last5 = Komori | first5 = Atsumasa | last6 = Uda | first6 = Naoto | last7 = Isono | first7 = Kiyoshi | last8 = Fujiki | first8 = Hirota | s2cid = 739519 }}</ref> Tautomycin demonstrates a slight preference for PP1 inhibition relative to PP2A inhibition. Tautomycin is closely related to another anhydride containing polyketide PP inhibitor called ] which, in addition to being useful as a lead for ] drug discovery, also is a very potent immunosuppressor. The mechanism of immunosuppression by Tautomycetin differs from that of more classical immunosuppressors such as ] and ].

==References==
{{reflist}}

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