Nodularin

Cayman Chemical Item Number 10007190

(CAS 118399-22-7)

Nodularin (CAS 118399-22-7)

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Description

The cyanobacterium Nodularia spumigena often contaminates the drinking water of rural communities in developing countries and accumulates in mussels, flounder, and cod from the northern Baltic Sea.1,2 Nodularin is a hepatotoxic monocylic pentapeptide produced by the N. spumigena.3 It is a potent inhibitor of protein phosphatase types 1 (PP1) and 2A (PP2A), exhibiting IC50 values of 1.8 and 0.026 nM, respectively. PP2B is inhibited to a lesser extent with an IC50 of 1.8 µM. No apparent inhibitory effect is observed with PP2C, alkaline phosphatase, acid phosphatase, insulin receptor tyrosine kinase, protein kinase A, phosphorylase kinase, or protein kinase C.4

1 Sipiä, V.O., Kankaanpää, H.T., Flinkman, J., et al. Time-dependent accumulation of cyanobacterial hepatotoxins in flounders (Platichthys flesus) and mussels (Mytilus edulis) from the northern Baltic sea. Environ Toxicol 16 330-336 (2001).

2 Sipiä, V.O., Kankaanpää, H.T., Lahti, K., et al. Detection of nodularin in flounders and cod from the Baltic Sea. Environ Toxicol 16 121-126 (2001).

3 Rinehart, K.L., Harada, K., Namikoshi, M., et al. Nodularin, microcystin, and the configuration of Adda. J Am Chem Soc 110 8557-8558 (1988).

4 Honkanen, R.E., Dukelow, M., Zwiller, J., et al. Cyanobacterial nodularin is a potent inhibitor of type 1 and type 2A protein phosphatases. Mol Pharmacol 40 577-583 (1991).

Formal Name cyclo[3S-​amino-​9S-​methoxy-​2S,​6E,​8S-​trimethyl-​10-​phenyl-​4,​6-​decadienoyl-​D-​γ-​glutamyl-​(2Z)-​2-​(methylamino)-​2-​butenoyl-​(3S)-​3-​methyl-​D-​β-​aspartyl-​L-​arginyl]
CAS Number 118399-22-7
Molecular Formula C41H60N8O10
Formula Weight 825.0
Formulation A solution in ethanol
Purity >95%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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COC(Cc1ccccc1)​C(C)​\C=C(/C)​\C=C/C1NC(=O)​C(CCCNC(=N)​N)​NC(=O)​C(C)​C(NC(=O)​\C(=C\C)​/N(C)​C(=O)​CCC(NC(=O)​C1C)​C(=O)​O)​C(=O)​O
InCHI Code
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​1S/C41H60N8O10/c1-8-31-38(54)​48-34(40(57)​58)​26(5)​36(52)​46-29(15-12-20-44-41(42)​43)​37(53)​45-28(25(4)​35(51)​47-30(39(55)​56)​18-19-33(50)​49(31)​6)​17-16-23(2)​21-24(3)​32(59-7)​22-27-13-10-9-11-14-27/h8-11,13-14,16-17,21,24-26,28-30,32,34H,12,15,18-20,22
InCHI Key
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IXBQSRWSVIBXNC-ANPQUZCZSA-N

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Size Price Quantity Subtotal
50 µg $35.00 $0.00
100 µg $67.00 $0.00
500 µg $280.00 $0.00
1 mg $490.00 $0.00
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Cart Total $0.00

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