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