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Onchidal

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Chemical compound

Pharmaceutical compound

Onchidal
Clinical data

ATC code	none
Identifiers
IUPAC name (1E,3E)-5-(2,2-Dimethyl-6-methylenecyclohexyl)-3-formylpenta-1,3-dien-1-yl acetate
CAS Number	67656-42-2
PubChemCID	6441116
ChemSpider	4945331^Y
CompTox Dashboard(EPA)	DTXSID90897204
Chemical and physical data
Formula	C₁₇H₂₄O₃
Molar mass	276.376 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)O\C=C\C(=C/CC1C(=C)CCCC1(C)C)\C=O
InChI InChI=1S/C17H24O3/c1-13-6-5-10-17(3,4)16(13)8-7-15(12-18)9-11-20-14(2)19/h7,9,11-12,16H,1,5-6,8,10H2,2-4H3/b11-9+,15-7+^Y Key:BEKQPDFPPJFVJP-AHSQCEKMSA-N^Y
(verify)

Onchidal is a naturally occurringneurotoxin produced as a defensive secretion by themolluscOnchidella binneyi and several other related species inOnchidella, a genus of small, air-breathing sea slugs. It acts as an irreversibleacetylcholinesterase inhibitor, the same mechanism of action as that of the deadlynerve agents, however onchidal is not anorganophosphorus orcarbamate compound and bears little resemblance to other compounds of this nature.^[1]

References

[edit]

^Abramson SN, Radic Z, Manker D, Faulkner DJ, Taylor P (September 1989). "Onchidal: a naturally occurring irreversible inhibitor of acetylcholinesterase with a novel mechanism of action".Molecular Pharmacology.36 (3):349–54.doi:10.1016/S0026-895X(25)09328-9.PMID 2779521.

Toxins

Clostridium:	tetani Tetanospasmin Tetanolysin perfringens Alpha toxin Enterotoxin difficile A B botulinum Botox
Other:	Anthrax toxin Listeriolysin O

Cocci

Streptolysin Leukocidin Panton–Valentine leukocidin
Staphylococcus	Staphylococcus aureus alpha/beta/delta Exfoliatin Toxic shock syndrome toxin Staphylococcal Enterotoxin B (SEB)

Lipopolysaccharide
- Lipid A
Bacillus thuringiensis delta endotoxin
- Cry1Ac
- Cry3Bb1
OtherB. thuringiensis toxins
- Cry6Aa
- Cry34Ab1

Virulence
factor

Mycotoxins

Plant toxins

Invertebrate
toxins

Scorpion:	Androctonus australis hector insect toxin Charybdotoxin Maurotoxin Agitoxin Margatoxin Slotoxin Scyllatoxin Hefutoxin HgeTx1 HsTx1 Kaliotoxin Lq2 Birtoxin Bestoxin BmKAEP Phaiodotoxin Imperatoxin Pi3
Spider:	Latrotoxin Alpha-latrotoxin CSTX Cupiennins PhTx3 Stromatoxin Vanillotoxin Huwentoxin
Mollusca:	Conotoxin Eledoisin Onchidal Saxitoxin Tetrodotoxin

Vertebrate
toxins

Fish:	Ciguatoxin Tetrodotoxin
Amphibian:	(+)-Allopumiliotoxin 267A Batrachotoxin Bufotoxins Arenobufagin Bufotalin Bufotenin Cinobufagin Marinobufagin Epibatidine Histrionicotoxin Pumiliotoxin 251D Samandarin Samandaridine Tarichatoxin Zetekitoxin AB
Reptile/ Snake venom:	Bungarotoxin α-Bungarotoxin β-Bungarotoxin Calciseptine Taicatoxin Calcicludine Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species

Category

Acetylcholine metabolism andtransport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase	Inhibitors:1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase	Inhibitors:Reversible: Carbamates:Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines:Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others:Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huperzine B Huprine W Huprine X Huprine Y Huprine Z Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Velnacrine Zanapezil Irreversible: Organophosphates:2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others:Demecarium Fasciculins (green mamba toxins) (1,2,3,4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted:α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators:Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChETooltip Butyrylcholinesterase	Inhibitors:Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter	Inhibitors:Hemicholinium-3 (hemicholine) Triethylcholine Enhancers:Coluracetam
VAChTTooltip Vesicular acetylcholine transporter	Inhibitors:Vesamicol

Release
(modulators)

Inhibitors	SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators:Botulinum toxin (A,C,E) VAMPTooltip Vesicle-associated membrane protein inactivators:Botulinum toxin (B,D,F,G) Others:Bungarotoxins (β-bungarotoxin,γ-bungarotoxin)
Enhancers	LPHNTooltip Latrophilin agonists:α-Latrotoxin Others: Atracotoxins (e.g.,robustoxin,versutoxin) Crotoxin

See also: Receptor/signaling modulators; Muscarinic acetylcholine receptor modulators; Nicotinic acetylcholine receptor modulators

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