Pinnatoxin A

Pinnatoxin

Last updated at: Oct. 28, 2025

Recommended name
Pinnatoxin A
Synonyms
Pinnatoxin-A, (+)-pinnatoxin-A
Recommended acronym
PnTX-A
Abbreviation

Progenitors

Name
Vulcanodinium rugosum
Note
Pinnatoxin A is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally identified by Uemura et al., 1995, in Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-A likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum.

Vector Species

Name
Pinna muricata
Note
Pinnatoxin A is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally identified by Uemura et al., 1995, in Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-A likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum.

References

Uemura et al.,, 1995
Uemura, D., Chou, T., Haino, T., Nagatsu, A., Fukuzawa, S., Zheng, S.-Z., Chen, H.-S., 1995. Pinnatoxin A: a toxic amphoteric macroycle from the Okinawan bivalve Pinna muricata. J. Am. Chem. Soc. 117, 1155-1156.
Nézan & Chomérat,, 2011
Nézan, E., Chomérat, N., 2011. Vulcanodinium rugosum gen. et sp. nov. (Dinophyceae), un nouveau dinoflagellé marin de la côte méditerraneenne française. Cryptogamie, Algologie 32(1), 3-18.
Structure
Formula
C41H61NO9
Exact mono-isotopic mass
711.434633
Molfile
see chemfiles
Alternative molfiles
n/a
SMILES
C[C@@H](CN=C1CCCC(C[C@@H]2CC[C@](O)(C)[C@](O2)(O3)CC[C@@]3(O4)CCC[C@@H]4C5)=C)[C@@H](C)C[C@@]61[C@]([C@@H]7O[C@]85C[C@@H](C)[C@@H](O)[C@H]7O8)([H])C=C(C(O)=O)CC6
Alternative SMILES
n/a
InChi key
ZYFHPTPXLHNGQK-OICTYLSBSA-N
Alternative InChi keys
n/a
InChi
InChI=1S/C41H61NO9/c1-24-8-6-10-32-38(20-25(2)27(4)23-42-32)15-11-28(36(44)45)19-31(38)34-35-33(43)26(3)21-40(49-34,50-35)22-30-9-7-13-39(47-30)16-17-41(51-39)37(5,46)14-12-29(18-24)48-41/h19,25-27,29-31,33-35,43,46H,1,6-18,20-23H2,2-5H3,(H,44,45)/t25-,26+,27-,29-,30+,31+,33+,34-,35+,37+,38+,39+,40+,41+/m0/s1
Alternative InChis
Spectra available
True
Chem files
chemfiles/PnTX-A.cdxml chemfiles/PnTX-A.mol

References

Selwood et al.,, 2010
Selwood, A.I., Miles, C.O., Wilkins, A.L., van Ginkel, R., Munday, R., Rise, F., McNabb, P., 2010. Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. J. Agric. Food Chem. 58(10), 6532-6542.
Araoz et al.,, 2011
Araoz, R., Servent, D., Molgó, J., Iorga, B.I., Fruchart-Gaillard, C., Benoit, E., Gu, Z., Stivala, C.E., Zakarian, A., 2011. Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A. J. Am. Chem. Soc. 133(27), 10499-10511.
Uemura et al.,, 1995
Uemura, D., Chou, T., Haino, T., Nagatsu, A., Fukuzawa, S., Zheng, S.-Z., Chen, H.-S., 1995. Pinnatoxin A: a toxic amphoteric macroycle from the Okinawan bivalve Pinna muricata. J. Am. Chem. Soc. 117, 1155-1156.
Certified
Unknown
Certified links
    n/a
Non certified reference material
Unknown

Chemical analysis

Research
True
Standardized
False
Validated
False
Official
n/a

Structure recognition assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Functional assays

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a

Animal assays

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a
Regulatory status
False
Human toxic syndrome(s)
n/a
Organ system toxicity
n/a
Risk assessment
True
Molecular targets known
True
Molecular targets
Nicotinic acetylcholine receptors
Toxic to aquatic animals
Unknown
TEF available
False
Notes
Pinnatoxin A is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally identified by Uemura et al., 1995, in Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-A likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum.

References

Uemura et al.,, 1995
Uemura, D., Chou, T., Haino, T., Nagatsu, A., Fukuzawa, S., Zheng, S.-Z., Chen, H.-S., 1995. Pinnatoxin A: a toxic amphoteric macroycle from the Okinawan bivalve Pinna muricata. J. Am. Chem. Soc. 117, 1155-1156.
Selwood et al.,, 2010
Selwood, A.I., Miles, C.O., Wilkins, A.L., van Ginkel, R., Munday, R., Rise, F., McNabb, P., 2010. Isolation, Structural Determination and Acute Toxicity of Pinnatoxins E, F and G. J. Agric. Food Chem. 58(10), 6532-6542.
Araoz et al.,, 2011
Araoz, R., Servent, D., Molgó, J., Iorga, B.I., Fruchart-Gaillard, C., Benoit, E., Gu, Z., Stivala, C.E., Zakarian, A., 2011. Total Synthesis of Pinnatoxins A and G and Revision of the Mode of Action of Pinnatoxin A. J. Am. Chem. Soc. 133(27), 10499-10511.
Philipp Hess
Contact