Pinnatoxin C

Pinnatoxin

Last updated at: Oct. 28, 2025

Recommended name
Pinnatoxin C
Synonyms
Pinnatoxin-C, Pinnatoxin C (34R isomer)
Recommended acronym
PnTX-C
Abbreviation

Progenitors

Name
Vulcanodinium rugosum
Note
Pinnatoxin C (like B) is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally purified by Takada et al., 2001, from Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-C (like B) likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum.

Vector Species

Name
Pinna muricata
Note
Pinnatoxin C (like B) is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally purified by Takada et al., 2001, from Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-C (like B) likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum.

References

Takada et al.,, 2001
Takada, N., Umemura, N., Suenaga, K., Chou, T., Nagatsu, A., Haino, T., Yamada, K., Uemura, D., 2001. Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 42(20), 3491-3494.
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
C42H64N2O9
Exact mono-isotopic mass
740.46118
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@@H](N)C(O)=O)CC6
Alternative SMILES
n/a
InChi key
HSMXADLEHIWNJP-CINYWUSPSA-N
Alternative InChi keys
n/a
InChi
InChI=1S/C42H64N2O9/c1-24-8-6-10-32-39(20-25(2)27(4)23-44-32)15-11-28(33(43)37(46)47)19-31(39)35-36-34(45)26(3)21-41(51-35,52-36)22-30-9-7-13-40(49-30)16-17-42(53-40)38(5,48)14-12-29(18-24)50-42/h19,25-27,29-31,33-36,45,48H,1,6-18,20-23,43H2,2-5H3,(H,46,47)/t25-,26+,27-,29-,30+,31+,33+,34+,35-,36+,38+,39+,40+,41+,42+/m0/s1
Alternative InChis
Spectra available
Unknown
Chem files
chemfiles/PnTX-G_ZAixC2a.cdxml chemfiles/PnTX-C.mol

References

Takada et al.,, 2001
Takada, N., Umemura, N., Suenaga, K., Chou, T., Nagatsu, A., Haino, T., Yamada, K., Uemura, D., 2001. Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 42(20), 3491-3494.
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.
Certified
False
Certified links
    n/a
Non certified reference material
Unknown

Chemical analysis

Research
True
Standardized
Unknown
Validated
Unknown
Official
n/a

Structure recognition assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Functional assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a

Animal assays

Research
Unknown
Standardized
Unknown
Validated
Unknown
Official
n/a
Regulatory status
False
Human toxic syndrome(s)
n/a
Organ system toxicity
n/a
Risk assessment
Unknown
Molecular targets known
True
Molecular targets
Nicotinic acetylcholine receptors
Toxic to aquatic animals
Unknown
TEF available
False
Notes
Pinnatoxin B and - C were not originally separated as stereoisomers and were obtained as a 1:1 mixture (Takada et al., 2001). Pinnatoxin C is not produced by Vulcanodinium rugosum (or other microalgae) but is a shellfish metabolite originally purified by Takada et al., 2001, from Pinna muricata. For metabolism hypotheses see Selwood et al., 2010. PnTX-C likely derives from metabolism of PnTX-G, which in turn is produced by V. rugosum. Pinnatoxin C (34R isomer) is a stereoisomer of Pinnatoxin B (34S isomer).

References

Takada et al.,, 2001
Takada, N., Umemura, N., Suenaga, K., Chou, T., Nagatsu, A., Haino, T., Yamada, K., Uemura, D., 2001. Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 42(20), 3491-3494.
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.
Philipp Hess
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