| Common Name |
Saxitoxin
| Description |
Saxitoxin is a paralytic poison from Alaska butter clams (Saxidomus giganteus), toxic mussels (Mytilus californianus), the plankton Gonyaliax cantenella and Protogonyaliax tamarensis. Causal agent of paralytic shellfish poisoning. Saxitoxin (STX) is a neurotoxin naturally produced by certain species of marine dinoflagellates (Alexandrium sp., Gymnodinium sp., Pyrodinium sp.) and cyanobacteria (Anabaena sp., some Aphanizomenon species, Cylindrospermopsis sp., Lyngbya sp., Planktothrix sp.). Ingestion of saxitoxin (usually through shellfish contaminated by toxic algal blooms) is responsible for the human illness known as paralytic shellfish poisoning (PSP). (Wikipedia) Saxitoxin has been shown to exhibit emetic function (PMID 17482032 ).Saxitoxin belongs to the family of Saxitoxins, Gonyautoxins, and Derivatives. These are compounds whose structure is based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29368 (Saxitoxin)
| Synonyms |
| Value |
Source |
Gonyaliax catenella poisonHMDB
Mytilus californianus poisonHMDB
Saxidomus giganteus poisonHMDB
Saxitoxin (8ci)HMDB
| Chemical Formlia |
C10H17N7O4
| Average Molecliar Weight |
299.2865
| Monoisotopic Molecliar Weight |
299.134202067
| IUPAC Name |
[(4R,10aS,10bS)-2-amino-10,10-dihydroxy-6-imino-3H,4H,5H,6H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
| Traditional Name |
[(4R,10aS,10bS)-2-amino-10,10-dihydroxy-6-imino-3H,4H,5H,8H,9H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
| CAS Registry Number |
35523-89-8
| SMILES |
NC(=O)OC[C@@H]1NC(=N)N2CCC(O)(O)[C@@]22N=C(N)N[C@@H]12
| InChI Identifier |
InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4-,5-,10-/m0/s1
| InChI Key |
RPQXVSUAYFXFJA-HGRQIUPRSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as saxitoxins, gonyautoxins, and derivatives. These are compounds with a structure based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Saxitoxins, gonyautoxins, and derivatives
| Sub Class |
Not Available
| Direct Parent |
Saxitoxins, gonyautoxins, and derivatives
| Alternative Parents |
Imidazopyrimidines
Alkaloids and derivatives
Hydropyrimidines
Pyrrolidines
Imidazolines
Tertiary amines
Guanidines
Propargyl-type 1,3-dipolar organic compounds
Monocarboxylic acids and derivatives
Carboximidamides
Carbonyl hydrates
Azacyclic compounds
1,1-diols
Imines
Hydrocarbon derivatives
| Substituents |
Saxitoxin-gonyautoxin skeleton
Alkaloid or derivatives
Imidazopyrimidine
1,3-diazinane
Pyrrolidine
2-imidazoline
Tertiary amine
Guanidine
Azacycle
Organoheterocyclic compound
1,1-diol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Monocarboxylic acid or derivatives
Carbonyl hydrate
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Amine
Aliphatic heteropolycyclic compound
| Molecliar Framework |
Aliphatic heteropolycyclic compounds
| External Descriptors |
carbamate ester (CHEBI:34970 )
organic heterotricyclic compound (CHEBI:34970 )
guanidines (CHEBI:34970 )
alkaloid (CHEBI:34970 )
Alkaloids (C13757 )
Carbamate derivatives (C13757 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
emetic
| Application |
Toxic Substance
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility4.12 mg/mLALOGPS
logP-2.7ALOGPS
logP-2.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.74ChemAxon
pKa (Strongest Basic)9.89ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area182.31 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity78.13 m3·mol-1ChemAxon
Polarizability28.07 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000437
| KNApSAcK ID |
Not Available
| Chemspider ID |
34106
| KEGG Compound ID |
C13757
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Saxitoxin
| NuGOwiki Link |
HMDB29368
| Metagene Link |
HMDB29368
| METLIN ID |
Not Available
| PubChem Compound |
37165
| PDB ID |
Not Available
| ChEBI ID |
610951
Product: Tyrphostin AG 879
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Holstege CP, Bechtel LK, Reilly TH, Wispelwey BP, Dobmeier SG: Unusual but potential agents of terrorists. Emerg Med Clin North Am. 2007 May;25(2):549-66; abstract xi. [PubMed:17482032 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 17625499
