Misplaced Pages

Calyculin: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively
Page 1
Page 2
← Previous editContent deleted Content addedVisualWikitext
Revision as of 19:46, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit Latest revision as of 22:54, 18 November 2024 edit undoPhotocyte (talk | contribs)Extended confirmed users1,787 edits Add biosynthesis details 
(29 intermediate revisions by 23 users not shown)
Line 1: Line 1:
{{Chembox {{Chembox
⚫ | Section7 = {{Chembox Properties
⚫ | ImageFile = Calyculin.png|Calyculin A and C
⚫ | Formula = C<sub>50</sub>H<sub>81</sub>N<sub>4</sub>O<sub>15</sub>P (Calyculin A)
⚫ | ImageSize =
⚫ | MolarMass = 1009.17 g/mol (Calyculin A)
| ImageAlt =
| IUPACName = | Appearance =
| OtherNames = | Density =
⚫ | MeltingPt =
⚫ | Section1 = {{Chembox Identifiers
| BoilingPt =
⚫ | ChemSpiderID = 9084513
⚫ | Solubility = }}
| Verifiedfields = changed
| Watchedfields = changed
| Name = Calyculins
| verifiedrevid = 460015289
⚫ | ImageFile = Calyculin A and C Structure.svg
⚫ | ImageSize =
| ImageCaption = Calyculins A and C
| IUPACName = ((2''R'',3''R'',5''R'',7''R'',8''S'',9''S'')-2-((1''S'',3''S'',4''S'',5''R'',6''R'',7''E'',9''E'',11''E'',13''Z'')-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((''E'')-3-(2-((2''S'')-4-(((2''S'',3''S'',4''S'')-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanoyl)amino)butan-2-yl)-1,3-oxazol-4-yl)prop-2-enyl)-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro(4.5)decan-3-yl) dihydrogen phosphate (Calyculin A)<ref>{{cite web| title=Calyculin A| date=2015-01-02| website=Cell Signaling Technology| url=https://media.cellsignal.com/pdf/9902.pdf}}</ref>
| OtherNames =
⚫ | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 9084513
| ChemSpiderID_Comment = (Calyculin A)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Comment = (Calyculin A)
| StdInChI = 1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m1/s1 | StdInChI = 1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FKAWLXNLHHIHLA-LIKMAGLISA-N | StdInChIKey = FKAWLXNLHHIHLA-LIKMAGLISA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =
| PubChem = 10909255 | CASNo = 101932-71-2
| CASNo_Comment = (Calyculin A)
| ChEMBL = <!-- blanked - oldvalue: 384277 -->
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES = }}
| UNII = 7D07U14TK3
⚫ | Section2 = {{Chembox Properties
| UNII_Comment = (Calyculin A)
⚫ | Formula = C<sub>51</sub>H<sub>83</sub>N<sub>4</sub>O<sub>15</sub>P
| PubChem = 10909255
⚫ | MolarMass = 1023.2 g/mol
| PubChem_Comment = (Calyculin A)
| Appearance =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | Density =
| ChEMBL = 384277
⚫ | MeltingPt =
| BoilingPt = | SMILES = }}
| Section2 = {{Chembox Properties
⚫ | Solubility = }}
| Formula = C<sub>51</sub>H<sub>83</sub>N<sub>4</sub>O<sub>15</sub>P (Calyculin C)
⚫ | Section3 = {{Chembox Hazards
| MolarMass = 1023.2 g/mol (Calyculin C)
⚫ | MainHazards =
| FlashPt = | Appearance =
⚫ | Density =
| Autoignition = }}
| MeltingPt =
| BoilingPt =
⚫ | Solubility = }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
| FlashPt =
| AutoignitionPt = }}
}} }}
'''Calyculins''' are natural products originally isolated from the marine sponge ''].''<ref>{{cite journal| title = Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin| author = Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T.| journal = Cancer Res.| year = 1990| volume = 50| issue =12| pages = 3521–3525}}</ref> Calyculins have proven to be strong serine/threonine protein phosphatase inhibitors and based on this property, calyculins might be potential ]. '''Calyculins''' are natural products originally isolated from the marine sponge ''].''<ref>{{cite journal| title = Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin| vauthors = Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T| journal = Cancer Res.| year = 1990| volume = 50| issue =12| pages = 3521–3525| pmid = 2160320}}</ref> Calyculins have proven to be strong serine/threonine protein phosphatase inhibitors and based on this property, calyculins might be potential tumor-promoting agents.


A laboratory synthesis of calyculin A has been reported.<ref>{{Cite journal |last=Tanimoto |first=Norihiko |last2=Gerritz |first2=Samuel W. |last3=Sawabe |first3=Akiyoshi |last4=Noda |first4=Takeshi |last5=Filla |first5=Sandra A. |last6=Masamune |first6=Satoru |date=1994-03-17 |title=Synthese von natürlich vorkommendem (−)‐Calyculin A |url=https://onlinelibrary.wiley.com/doi/10.1002/ange.19941060611 |journal=Angewandte Chemie |language=en |volume=106 |issue=6 |pages=674–677 |doi=10.1002/ange.19941060611 |issn=0044-8249}}</ref>
⚫ ==References==
⚫ {{reflist}}


==Biosynthesis==
]
Calyculin A is biosynthesized as a pyrophosphate containing phosphocalyculin A protoxins by a hybrid PKS-NRPS pathway within the sponge bacterial symbiont, "''Candidatus'' Entotheonella" sp.<ref name="r125">{{cite journal | last=Jomori | first=Takahiro | last2=Matsuda | first2=Kenichi | last3=Egami | first3=Yoko | last4=Abe | first4=Ikuro | last5=Takai | first5=Akira | last6=Wakimoto | first6=Toshiyuki | title=Insights into phosphatase-activated chemical defense in a marine sponge holobiont | journal=RSC Chemical Biology | volume=2 | issue=6 | date=2021 | issn=2633-0679 | pmid=34977575 | pmc=8637855 | doi=10.1039/D1CB00163A | doi-access=free | pages=1600–1607}}</ref>

⚫ == References ==
⚫ {{reflist}}


]
]
]


{{organic-compound-stub}} {{organic-compound-stub}}