Nodularin

Nodularin-R

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80043 Y
ChEMBL	ChEMBL108308 Y
ChemSpider	10471625 Y
EC Number	621-437-9
KEGG	C15713 Y
PubChem CID	14217092
UNII	0979BIK2QU Y
CompTox Dashboard (EPA)	DTXSID60880022
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	824.977 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H315, H317, H319, H330, H335
Precautionary statements	P260, P261, P262, P264, P270, P271, P272, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
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

Nodularins are potent toxins produced by the cyanobacterium Nodularia spumigena,^[1] among others.^[2] This aquatic, photosynthetic cyanobacterium forms visible colonies that present as algal blooms in brackish water bodies throughout the world.^[3] The late summer blooms of Nodularia spumigena are among the largest cyanobacterial mass occurrences in the world. Cyanobacteria are composed of many toxic substances, most notably of microcystins and nodularins: the two are not easily differentiated. A significant homology of structure and function exists between the two, and microcystins have been studied in greater detail. Because of this, facts from microcystins are often extended to nodularins.^[4]

Nodularin-R is the predominant toxin variant, though 10 variants of nodularin have been discovered to date. Nodularins are cyclic nonribosomal pentapeptides and contain several unusual non-proteinogenic amino acids such as N-methyl-didehydroaminobutyric acid and the β-amino acid ADDA. These compounds are relatively stable compounds: light, temperature, and microwaves do little to degrade the compounds.^[5]

Nodularins are often attributed to gastroenteritis, allergic irritation reactions, and liver diseases.^[6] Nodularin-R is most notorious as a potent hepatotoxin that may cause serious damage to the liver of humans and other animals. The WHO drinking water concentration limit for nodularins (extended from microcystins-LR) is 1.5 ug /L.^[7]