| Common Name |
Neosaxitoxin
| Description |
Neosaxitoxin is produced by Protogonyaliax and found in shellfishNeosaxitoxin has been shown to exhibit anesthetic function (PMID 19636660 ).Neosaxitoxin 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 |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29369 (Neosaxitoxin)
| Synonyms |
| Value |
Source |
NeoSTXKegg
| Chemical Formlia |
C10H17N7O5
| Average Molecliar Weight |
315.2859
| Monoisotopic Molecliar Weight |
315.129116689
| IUPAC Name |
[(4R,10aS,10bS)-2-amino-5,10,10-trihydroxy-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-5,10,10-trihydroxy-6-imino-3H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
| CAS Registry Number |
64296-20-4
| SMILES |
NC(=O)OC[C@H]1[C@@H]2NC(N)=N[C@]22N(CCC2(O)O)C(=N)N1O
| InChI Identifier |
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
| InChI Key |
PPEKGEBBBBNZKS-HGRQIUPRSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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 |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Saxitoxins, gonyautoxins, and derivatives
| Direct Parent |
Saxitoxins, gonyautoxins, and derivatives
| Alternative Parents |
Alkaloids and derivatives
Imidazopyrimidines
Diazinanes
N-hydroxyguanidines
Pyrrolidines
Carbamate esters
Imidazolines
Organic carbonic acids and derivatives
Propargyl-type 1,3-dipolar organic compounds
Azacyclic compounds
Polyols
Carbonyl hydrates
Carboximidamides
Carbonyl compounds
Organopnictogen compounds
Hydrocarbon derivatives
Organic oxides
Imines
| Substituents |
Saxitoxin-gonyautoxin skeleton
Imidazopyrimidine
Alkaloid or derivatives
1,3-diazinane
N-hydroxyguanidine
2-imidazoline
Pyrrolidine
Carbamic acid ester
Guanidine
Carbonic acid derivative
Carbonyl hydrate
Azacycle
Polyol
Organoheterocyclic compound
Organic 1,3-dipolar compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Carbonyl group
Imine
Organooxygen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aliphatic heteropolycyclic compound
| Molecliar Framework |
Aliphatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anesthetic
| 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 Solubility4.19 mg/mLALOGPS
logP-2ALOGPS
logP-2.6ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)10.6ChemAxon
pKa (Strongest Basic)9.14ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area193.75 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.89 m3·mol-1ChemAxon
Polarizability28.82 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot 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 |
FDB000438
| KNApSAcK ID |
Not Available
| Chemspider ID |
19975931
| KEGG Compound ID |
C17208
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29369
| Metagene Link |
HMDB29369
| METLIN ID |
Not Available
| PubChem Compound |
104753
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: BEC (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Rodriguez-Navarro AJ, Lagos M, Figueroa C, Garcia C, Recabal P, Silva P, Iglesias V, Lagos N: Potentiation of local anesthetic activity of neosaxitoxin with bupivacaine or epinephrine: development of a long-acting pain blocker. Neurotox Res. 2009 Nov;16(4):408-15. doi: 10.1007/s12640-009-9092-3. Epub 2009 Jul 28. [PubMed:19636660 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 16298400