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Calyculin A

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Formula: C50H81 N4 O15 P
CAS: 101932-71-2
search Element: calyculin

Identification

Structural Formula
Calyculin A
CAS:
101932-71-2
EINECS:
Molecular Formula:
C50H81 N4 O15 P
MDL:
MFCD06795864
SMILES:
C[C@H]1[C@@H](C[C@@]2(C([C@H]([C@H](O2)[C@H](C[C@@H]([C@H](C)[C@@H]([C@H](C)/C=C(C)/C(=C/C=C/C(=CC#N)/C)/C)O)O)OC)OP(=O)(O)O)(C)C)O[C@H]1C/C=C/C3=COC(=N3)[C@@H](C)CCNC(=O)[C@H]([C@H]([C@H](COC)N(C)C)O)O)O
Synonym:
c05370 ; calyculin a ; n-[(3s)-[4-(1e)-3-[(2r,3r,4r,7s,8s,9r)-2-[(1s,3s,4s,5r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-o ; n-[(3s)-[4-(1e)-3-[(2r,3r,4r,7s,8s,9r)-2-[(1s,3s,4s,5r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentam ; l-ribonamide,n-[(3s)-3-[4-[(1e)-3-[(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraen-1-yl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propen-1-yl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-o-methyl- ; calyculin a from discodermia calyx, 10 u g ; calyculin a from discodermia calyx ; calyculin a, discodermia calyx ; l-ribonamide,n-[(3s)-3-[4-[(1e)-3-[(2r,3r,5r,7s,8s,9r)-2-[(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-o-methyl-(9ci) ; (-)-calyculin a ; 1,6-dioxaspiro[4.5]decane, l-ribonamide deriv. ; l-ribonamide,n-[3-[4-[3-[2-(14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl)-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-oxazolyl]butyl]-4-deoxy-4-(dimethylamino)-5-o-methyl-,[5r-[5a[2r*(1s*,3s*,4s*,5r*,6r*,7e,9e,11e,13z),3r*],7b[e(s*)],8b,9a]]- ; n-[(3s)-[4-(1e)-3-[(2r,3r,4r,7s,8s,9r)-2-[(1s,3s,4s,5r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl]-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro[4.5]dec-7-yl]-1-propenyl]-2-oxazoly]butyl]-4-deoxy-4-(dimethylamino)-5-o-methyl-l-ribonamide ; l-ribonamide, n-(3s)-3-4-(1e)-3-(2r,3r,5r,7s,8s,9r)-2-(1s,3s,4s,5r,6r,7e,9e,11e,13z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyl-7,9,11,13-tetradecatetraenyl-9-hydroxy-4,4,8-trimethyl-3-(phosphonooxy)-1,6-dioxaspiro4.5dec-7-yl-1-propenyl-2-oxa


Description

Calyculin A, a marine toxin isolated from Disodermia calyx, is a structurally distinct inhibitor of protein phosphatase 1 (PP1) and protein phosphatase 2A (PP2A-C). It has been shown that calyculin A displays inhibitory properties towards the endogenous phosphatase of smooth muscle myosin B and induces contraction in the muscle fibers. Contraction induced by calyculin A was accompanied by an increase in the cytosolic free Ca2+ concentration. Additionally it has been reported that this compound can bind to protein phosphatases in mouse skin, which serve as okadaic acid receptors. Consequentially, calyculin A induces ornithine decarboxylase in the mouse skin and is believed to promote tumor growth.


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Santa Cruz Biotechnology, Inc.
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Properties for Calyculin A

Molecular Weight:
1009.17 g·mol−1
Density:
1.26 g/cm3
Melting point:
247-249 °C
Solubility:
DMSO: soluble
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Safety & Transport Information

Risk Codes:
R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed
R38 - Irritating to skin
Safety Codes:
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection
S45 - In case of accident or if you feel unwell seek medical advice immediately (show the label where possible)
Hazard Classes:
6.1(a)
Hazard Symbols:
T
Hazard symbol T
Storage temperature :
-20°C
RID/ADR certification :
UN 3462 6.1 / PG 3
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Alternative Distributors of [Calyculin A]

Producers or manufacturers change the product range from time to time. The following companies
have appeared as suppliers in the past / currently not verified

Cfm Oskar Tropitzsch GmbH

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