IPHAB Toxins

No progenitors registered

Name: Mytilus edulis
Note: AZA3 is produced by oxidative metabolism of the 22-methyl group of AZA1 (see Chem Files for atom numbering) in blue mussels, to produce the corresponding carboxylated analogue AZA17. AZA17 undergoes spontaneous decarboxylation to produce AZA3. This decarboxylation reaction is accelerated by heating, so in cooked mussels contaminated with AZAs, virtually all AZA17 will have been converted to AZA3.

Ofuji, K, 1999: First report on isolation from shellfish. AZA-3 is s shellfish metabolite of AZA-1 See: Kilcoyne, J., P. McCarron, M. J. Twiner, F. Rise, P. Hess, A. L. Wilkins and C. O. Miles (2018). "Identification of 21,22-Dehydroazaspiracids in Mussels (Mytilus edulis) and in Vitro Toxicity of Azaspiracid-26." Journal of Natural Products 81(4): 885-893.

Structure
Formula: C46H69NO12
Exact mono-isotopic mass: 827.48198
Molfile: See Chem Files
Alternative molfiles: n/a
SMILES: OC(CC/C=C/[C@@]1([H])O[C@](CC[C@@]23[C@H](C)C[C@](O[C@@]([C@H](O)[C@]4(O)O[C@@](C(C[C@]5(O[C@@]6([H])[C@]7([H])O[C@@]8(NC[C@H](C)C[C@@H]8C)C6)O[C@@H]7C[C@H](C)C5)=C)([H])[C@@H](C)CC4)([H])C9)([H])[C@]9([H])O2)(O3)CC=C1)=O
Alternative SMILES: n/a
InChi key: XGHMSEQYABFWLF-CXNMSKCESA-N
Alternative InChi keys: n/a
InChi: InChI=1S/C46H69NO12/c1-26-19-35-40-37(24-44(57-40)30(5)18-27(2)25-47-44)55-43(22-26,54-35)23-29(4)39-28(3)13-15-45(51,58-39)41(50)36-21-34-33(52-36)20-31(6)46(56-34)17-16-42(59-46)14-9-11-32(53-42)10-7-8-12-38(48)49/h7,9-11,26-28,30-37,39-41,47,50-51H,4,8,12-25H2,1-3,5-6H3,(H,48,49)/b10-7+/t26-,27+,28-,30-,31+,32+,33+,34+,35+,36-,37+,39-,40+,41-,42-,43-,44-,45+,46+/m0/s1
Alternative InChis
Spectra available: True
Chem files: chemfiles/Azaspiracid-3.cdxml chemfiles/Azaspiracid-3.mol chemfiles/Azaspiracid-3.png

Ofuji, K, 1999: First report on chemical structure. Note that the original chemical structure has been revised twice since this article.

Certified

True

Certified links

National Research Council Canada
Halifax CRM Sales Office 1411 Oxford Street Halifax, Nova Scotia B3H 3Z1 Telephone: 1-902-426-8281 Email:CRM-MRCHalifax@nrc-cnrc.gc.ca

Non certified reference material

Unknown

Azaspiracid-3