Nodularin

Nodularin

Names
Other names Cyclo[(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl-(2Z)-2-(methylamino)-2-butenoyl-(3S)-3-methyl-D-β-aspartyl-L-arginyl]
Identifiers
CAS Number	118399-22-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:80043
ChEMBL	ChEMBL108308
ChemSpider	10471625
ECHA InfoCard	100.150.290
KEGG	C15713
InChI InChI=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,12,15,18-20,22H2,1-7H3,(H,45,53)(H,46,52)(H,47,51)(H,48,54)(H,55,56)(H,57,58)(H4,42,43,44)/b17-16+,23-21+,31-8-/t24-,25-,26-,28-,29-,30+,32-,34+/m0/s1 Key: IXBQSRWSVIBXNC-HSKGSTCASA-N
SMILES C/C=C\1/C(=O)N[C@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@H](CCC(=O)N1C)C(=O)O)C)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C)CCCNC(=N)N)C)C(=O)O
Properties
Chemical formula	C41H60N8O10
Molar mass	824.98 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nodularin-R is a cyclic nonribosomal peptide produced by the cyanobacterium Nodularia spumigena.^[1] This cyanobacterium forms blooms in brackish water bodies throughout the world. The late summer blooms of Nodularia spumigena are among the largest cyanobacterial mass occurrences in the world. Nodularin-R is a cyclic pentapeptide and contains several unusual non-proteinogenic amino acids such as N-methyl-didehydroaminobutyric acid and the β-amino acid ADDA. Nodularin-R is a potent hepatotoxin and may cause serious damage to the liver of humans and other animals.

References

1. Sivonen K, Kononen K, Carmichael WW, Dahlem AM, Rinehart KL, Kiviranta J, Niemela SI (1989). "Occurrence of the hepatotoxic cyanobacterium Nodularia spumigena in the Baltic Sea and structure of the toxin". Appl. Environ. Microbiol. 55 (8): 1990–5. PMC 202992. PMID 2506812.

See also

• Microcystins
• Nonribosomal peptides
• Cyclic peptides