neosaxitoxin (CHEBI:167561)

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ChEBI Name	neosaxitoxin

ChEBI ID	CHEBI:167561

Definition	A pyrrolopurine that is saxitoxin carrying a hydroxy substituent on the nitrogen atom at position 5. It is a sodium channel blocker that is undergoing clinical trials as a prolonged-duration local anesthetic.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

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Formula

C10H17N7O5

Net Charge

Average Mass

315.290

Monoisotopic Mass

315.12912

InChI

InChI=1S/C10H17N7O5/c11-6-14-5-4(3-22-8(13)18)17(21)7(12)16-2-1-9(19,20)10(5,16)15-6/h4-5,12,19-21H,1-3H2,(H2,13,18)(H3,11,14,15)/t4-,5-,10-/m0/s1

InChIKey

PPEKGEBBBBNZKS-HGRQIUPRSA-N

SMILES

[H][C@@]12NC(N)=N[C@]11N(CCC1(O)O)C(=N)N(O)[C@H]2COC(N)=O

Metabolite of Species	Details
Aphanizomenon sp. NH-5 (NCBI:txid190592)	See: PubMed
Cylindrospermopsis raciborskii T3 (NCBI:txid398006)	GenBank: DQ787200.1 See: PubMed
Heteroscytonema crispum (NCBI:txid439476)	of strain CAWBG524 See: PubMed
Heteroscytonema crispum (NCBI:txid439476)	of strain CAWBG72 See: PubMed

Roles Classification
Biological Role(s):	voltage-gated sodium channel blocker Any sodium channel blocker that interferes with the activity of voltage-gated sodium channels. marine metabolite Any metabolite produced during a metabolic reaction in marine macro- and microorganisms. (via paralytic shellfish toxin ) neurotoxin A poison that interferes with the functions of the nervous system. (via paralytic shellfish toxin ) toxin Poisonous substance produced by a biological organism such as a microbe, animal or plant. (via paralytic shellfish toxin ) cyanotoxin Any toxin produced by cyanobacteria (blue-green algae). metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid ) sodium channel blocker An agent that inhibits sodium influx through cell membranes. (via paralytic shellfish toxin )

Application(s):	anti-inflammatory agent Any compound that has anti-inflammatory effects. local anaesthetic Any member of a group of drugs that reversibly inhibit the propagation of signals along nerves. Wide variations in potency, stability, toxicity, water-solubility and duration of action determine the route used for administration, e.g. topical, intravenous, epidural or spinal block.

ChEBI Ontology
Outgoing	neosaxitoxin (CHEBI:167561) has functional parent saxitoxin (CHEBI:34970) neosaxitoxin (CHEBI:167561) has role anti-inflammatory agent (CHEBI:67079) neosaxitoxin (CHEBI:167561) has role cyanotoxin (CHEBI:88048) neosaxitoxin (CHEBI:167561) has role local anaesthetic (CHEBI:36333) neosaxitoxin (CHEBI:167561) has role marine metabolite (CHEBI:76507) neosaxitoxin (CHEBI:167561) has role neurotoxin (CHEBI:50910) neosaxitoxin (CHEBI:167561) has role toxin (CHEBI:27026) neosaxitoxin (CHEBI:167561) has role voltage-gated sodium channel blocker (CHEBI:38634) neosaxitoxin (CHEBI:167561) is a alkaloid (CHEBI:22315) neosaxitoxin (CHEBI:167561) is a carbamate ester (CHEBI:23003) neosaxitoxin (CHEBI:167561) is a guanidines (CHEBI:24436) neosaxitoxin (CHEBI:167561) is a hydroxylamines (CHEBI:24709) neosaxitoxin (CHEBI:167561) is a ketone hydrate (CHEBI:63734) neosaxitoxin (CHEBI:167561) is a paralytic shellfish toxin (CHEBI:167564) neosaxitoxin (CHEBI:167561) is a pyrrolopurine (CHEBI:136861)

IUPAC Name

[(3aS,4R,10aS)-2-amino-5,10,10-trihydroxy-6-imino-3a,4,5,6,9,10-hexahydro-3H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate

Synonyms

Sources

[(3aS,4R,10aS)-5,10,10-Trihydroxy-2,6-diiminooctahydro-1H,8H-pyrrolo[1,2-c]purin-4-yl]methyl carbamate

ChEBI

neosaxitoxina Español

SUBMITTER

NeoSTX

ChemIDplus

NSTX

Note: (2021-02-25) Used as an abbreviation.

SUBMITTER

Registry Number	Type	Source
64296-20-4	CAS Registry Number	ChemIDplus

Last Modified

20 April 2021