Neosaxitoxin

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
    1. 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 ]
    2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

    PMID: 16298400

    Neosaxitoxin

    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
    1. 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 ]
    2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

    PMID: 16298400