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^Y
ChEBI	CHEBI:80043^N
ChEMBL	ChEMBL108308^N
ChemSpider	10471625^N
Jmol 3D model	Interactive image
KEGG	C15713^Y
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^N Key: IXBQSRWSVIBXNC-HSKGSTCASA-N^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).
N verify (what is ^YN ?)
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

↑ 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.

Nodularin

References

See also