calyculin

{{Chembox

| Section7 = {{Chembox Properties

| Formula = C₅₀H₈₁N₄O₁₅P (Calyculin A)

| MolarMass = 1009.17 g/mol (Calyculin A)

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

| Verifiedfields = changed

| Watchedfields = changed

| Name = Calyculins

| verifiedrevid = 460015289

| ImageFile = Calyculin A and C Structure.svg

| ImageSize =

| ImageCaption = Calyculins A and C

| IUPACName = ((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){{cite web| title=Calyculin A| date=2015-01-02| website=Cell Signaling Technology| url=https://media.cellsignal.com/pdf/9902.pdf}}

| 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FKAWLXNLHHIHLA-LIKMAGLISA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 101932-71-2

| CASNo_Comment = (Calyculin A)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7D07U14TK3

| UNII_Comment = (Calyculin A)

| PubChem = 10909255

| PubChem_Comment = (Calyculin A)

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 384277

| ChEBI = 41791

| ChEBI_Comment = (Calyculin A)

| SMILES = }}

| Section2 = {{Chembox Properties

| Formula = C₅₁H₈₃N₄O₁₅P (Calyculin C)

| MolarMass = 1023.2 g/mol (Calyculin C)

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Calyculins are natural products originally isolated from the marine sponge Discodermia calyx.{{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}} 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.{{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}}