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)[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

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.

## References

1. ↑ "Calyculin A". 2015-01-02. https://media.cellsignal.com/pdf/9902.pdf.
2. ↑ "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. 1990. PMID 2160320.

[1][2]

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Original source: https://en.wikipedia.org/wiki/Calyculin. Read more

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1. ↑ Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A" (in en). Angewandte Chemie 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN 0044-8249. https://onlinelibrary.wiley.com/doi/10.1002/ange.19941060611.
2. ↑ [1]

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*[CID]: Compound ID