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Saving copy of the {{chembox}} taken from revid 444133032 of page Tautomycin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'StdInChI').
 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:Tautomycin|oldid=444133032}} 444133032] of page [[Tautomycin]] with values updated to verified values.}}
{{Chembox
{{Chembox
| verifiedrevid = 470477946
| ImageFile = Tautomycin.png
| ImageFile = Tautomycin.png
| ImageSize =
| ImageSize =
| IUPACName = [(1R,2R,3R,6S,7S,10R)-10-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxo-pentyl]-1,7-dioxaspiro[5.5]undecan-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-[(3''S'')-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-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)[C@H](O)CC(=O)O[C@H](C(C)C)[C@H](OC)[C@H](O)CC(=O)[C@@H](C)[C@@H](O)CC[C@H]([C@@H]3O[C@@]2(O[C@H]([C@H](C)CC2)CC[C@@H](C(=O)C)C)CC[C@@H]3C)C
| SMILES = O=C\1OC(=O)/C(=C/1C)[C@H](O)CC(=O)O[C@H](C(C)C)[C@H](OC)[C@H](O)CC(=O)[C@@H](C)[C@@H](O)CC[C@H]([C@@H]3O[C@@]2(O[C@H]([C@H](C)CC2)CC[C@@H](C(=O)C)C)CC[C@@H]3C)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 [[shellfish]] and is produced by the bacterium ''[[Streptomyces spiroverticillatus]]''. It is a [[polyketide]]-based structure characterized by a three [[hydroxyl]] groups, two [[ketone]]s, a dialkylmaleic anhydride, an [[ester]] linkage (connecting anhydride unit to polyketide chain), a spiroketal and one [[methyl group|methyl]] [[ether]] among others.

==Pharmacology==
It is a very potent inhibitor of the protein [[phosphatase]]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 [[tautomycetin]] which, in addition to being useful as a lead for [[cancer]] drug discovery, also is a very potent immunosuppressor. The mechanism of immunosuppression by Tautomycetin differs from that of more classical immunosuppressors such as [[rapamycin]] and [[tacrolimus]].

==References==
{{reflist}}

[[Category:Phosphatase inhibitors]]
[[Category:Polyketides]]
[[Category:Spiro compounds]]
[[Category:Carboxylic anhydrides]]
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