Calyculin

Calyculins
	; Calyculins A and C
Names
	IUPAC name ((2R,3R,5R,7R,8S,9S)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((E)-3-(2-((2S)-4-(((2S,3S,4S)-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)
Identifiers
CAS Number	101932-71-2 (Calyculin A) ;
ChEMBL	ChEMBL384277 ;
ChemSpider	9084513 (Calyculin A) ;
PubChem CID	10909255 (Calyculin A);
UNII	7D07U14TK3 (Calyculin A) ;
	InChI InChI=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 Key: FKAWLXNLHHIHLA-LIKMAGLISA-N ;
Properties
Chemical formula	C51H83N4O15P (Calyculin C)
Molar mass	1023.2 g/mol (Calyculin C)
Properties
Chemical formula	C50H81N4O15P (Calyculin A)
Molar mass	1009.17 g/mol (Calyculin A)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Calyculins are natural products originally isolated from the marine sponge Discodermia calyx.^[2] 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.^[3]

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.^[4]

References

^ "Calyculin A" (PDF). Cell Signaling Technology. 2015-01-02.
^ Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990). "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. PMID 2160320.
^ Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A". Angewandte Chemie. 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN 0044-8249.
^ Jomori, Takahiro; Matsuda, Kenichi; Egami, Yoko; Abe, Ikuro; Takai, Akira; Wakimoto, Toshiyuki (2021). "Insights into phosphatase-activated chemical defense in a marine sponge holobiont". RSC Chemical Biology. 2 (6): 1600–1607. doi:10.1039/D1CB00163A. ISSN 2633-0679. PMC 8637855. PMID 34977575.

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[1] "Calyculin A" (PDF). Cell Signaling Technology. 2015-01-02.

[2] Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990). "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. PMID 2160320.

[3] Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A". Angewandte Chemie. 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN 0044-8249.

[r125-4] Jomori, Takahiro; Matsuda, Kenichi; Egami, Yoko; Abe, Ikuro; Takai, Akira; Wakimoto, Toshiyuki (2021). "Insights into phosphatase-activated chemical defense in a marine sponge holobiont". RSC Chemical Biology. 2 (6): 1600–1607. doi:10.1039/D1CB00163A. ISSN 2633-0679. PMC 8637855. PMID 34977575.

[2]

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[3]

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Names
Calyculins A and C
IUPAC name ((2R,3R,5R,7R,8S,9S)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((E)-3-(2-((2S)-4-(((2S,3S,4S)-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)^[1]
Identifiers
CAS Number	101932-71-2 (Calyculin A)^Y
ChEMBL	ChEMBL384277^N
ChemSpider	9084513 (Calyculin A)^Y
PubChem CID	10909255 (Calyculin A)
UNII	7D07U14TK3 (Calyculin A)^Y
InChI InChI=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^Y Key: FKAWLXNLHHIHLA-LIKMAGLISA-N^Y
Properties
Chemical formula	C₅₁H₈₃N₄O₁₅P (Calyculin C)
Molar mass	1023.2 g/mol (Calyculin C)
Properties
Chemical formula	C₅₀H₈₁N₄O₁₅P (Calyculin A)
Molar mass	1009.17 g/mol (Calyculin A)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references