Tautomycin: Difference between revisions

Browse history interactively ← Previous editContent deleted Content addedVisual WikitextInline

Revision as of 11:48, 3 June 2011 editHarbinary (talk \| contribs)1,113 edits cat← Previous edit		Latest revision as of 01:57, 30 June 2024 edit undoZakblade2000 (talk \| contribs)Extended confirmed users4,108 editsNo edit summary
(20 intermediate revisions by 13 users not shown)
Line 1:		Line 1:
	{{Unreferenced\|date=December 2009}}

	{{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~~ =
	\| ~~PubChem~~ = ~~440646~~		\| CASNo = 109946-35-2
	\| ~~ChemSpiderID~~ = ~~389529~~		\| ChEBI = 9414
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
⚫	\| 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
			\| ChEMBL = 505512
⚫	\| StdInChI = ~~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
			\| EINECS = 620-961-5
⚫	}}
			\| KEGG = C05372
⚫	\| Section2 = {{Chembox Properties
	\| ~~Formula~~ = ~~C41H66O13~~		\| PubChem = 440646
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| MolarMass = 766.95
	\| ~~Appearance~~ =		\| ChemSpiderID = 389529
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| Density =
			\| StdInChIKey = RFCWHQNNCOJYTR-IRCAEPKSSA-N
⚫	\| MeltingPt =
		⚫	\| 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
⚫	\| BoilingPt =
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| Solubility =
		⚫	\| 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
⚫	}}
		⚫	}}
⚫	\| Section3 = {{Chembox Hazards
		⚫	\|Section2={{Chembox Properties
⚫	\| MainHazards =
	\| ~~FlashPt~~ =		\| C=41 \| H=66 \| O=13
	\| ~~Autoignition~~ =		\| Appearance =
		⚫	\| Density =
⚫	}}
		⚫	\| MeltingPt =
		⚫	\| BoilingPt =
		⚫	\| Solubility =
		⚫	}}
		⚫	\|Section3={{Chembox Hazards
		⚫	\| MainHazards =
			\| FlashPt =
			\| AutoignitionPt =
		⚫	}}
	}}		}}
	'''Tautomycin''' is a chemical that occurs naturally in ] and is produced by the bacterium ''Streptomyces spiroverticillatus''. It is a polyketide-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.		'''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==		==Pharmacology==
	It is a very potent inhibitor of the protein ]s PP1 and PP2A. 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 ].		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}}

	]		]
			]

			]
	{{Pharma-stub}}
			]

Latest revision as of 01:57, 30 June 2024

Tautomycin
Names

Preferred IUPAC name (3R,4R,5R,8S,9S,12R)-12-{(2S,3S,6R,8S,9R)-3,9-Dimethyl-8--1,7-dioxaspiroundecan-2-yl}-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl (3R)-3-hydroxy-3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoate
Identifiers
CAS Number	109946-35-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:9414
ChEMBL	ChEMBL505512
ChemSpider	389529
ECHA InfoCard	100.149.857
EC Number	620-961-5
KEGG	C05372
PubChem CID	440646
CompTox Dashboard (EPA)	DTXSID10894179
InChI 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/s1Key: RFCWHQNNCOJYTR-IRCAEPKSSA-N 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/s1Key: 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
Properties
Chemical formula	C₄₁H₆₆O₁₃
Molar mass	766.966 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

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 ketones, a dialkylmaleic anhydride, an ester linkage (connecting anhydride unit to polyketide chain), a spiroketal and one methyl ether among others.

Pharmacology

It is a very potent inhibitor of the protein phosphatases PP1 and PP2A. 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

Suganuma, Masami; Okabe, Sachiko; Sueoka, Eisaburo; Nishiwaki, Rie; Komori, Atsumasa; Uda, Naoto; Isono, Kiyoshi; Fujiki, Hirota (1995). "Tautomycin: An inhibitor of protein phosphatases 1 and 2A but not a tumor promoter on mouse skin and in rat glandular stomach". Journal of Cancer Research and Clinical Oncology. 121 (9–10): 621–627. doi:10.1007/bf01197780. PMID 7559747. S2CID 739519.

Categories: