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Showing NP-Card for Gonyautoxin II (NP0337307)

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Record Information
Version2.0
Created at2024-09-11 10:15:42 UTC
Updated at2024-09-11 10:15:43 UTC
NP-MRD IDNP0337307
Secondary Accession NumbersNone
Natural Product Identification
Common NameGonyautoxin II
DescriptionGonyautoxin II belongs to the class of organic compounds known as saxitoxins, gonyautoxins, and derivatives. Saxitoxins, gonyautoxins, and derivatives are compounds with a structure based on a 2,6-diamino-4-methyl-pyrrolo[1,2-c]purin-10-ol skeleton. Gonyautoxin II was first documented in 2019 (PMID: 30488599). Based on a literature review very few articles have been published on Gonyautoxin II.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337307 (Gonyautoxin II)


  Mrv2104 05262312472D          

 26 28  0  0  0  0            999 V2000
   -2.0962    3.5991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    3.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6690    3.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    2.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -0.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091    0.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    0.2620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    0.6744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -2.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196   -0.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -3.5991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018   -2.8855    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168   -3.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -2.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -1.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077   -0.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 25  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
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3D MOL for NP0337307 (Gonyautoxin II)

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3D SDF for NP0337307 (Gonyautoxin II)

  Mrv2104 05262312472D          

 26 28  0  0  0  0            999 V2000
   -2.0962    3.5991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    3.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6690    3.5235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    2.3244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895    1.0869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240    0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0240   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091   -0.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091    0.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    0.2620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046    0.6744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -2.1705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018   -1.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5190   -1.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -0.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4046   -0.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196   -0.5631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1107   -3.5991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3018   -2.8855    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0168   -3.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4118   -2.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3522   -1.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077   -0.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 25  1  0  0  0  0
  9 11  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 15 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 21  2  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)OCC1NC(=N)N2CC(OS(O)(=O)=O)C(O)(O)C22NC(=N)NC12

> <INCHI_IDENTIFIER>
InChI=1/C10H17N7O8S/c11-6-15-5-3(2-24-8(13)18)14-7(12)17-1-4(25-26(21,22)23)10(19,20)9(5,17)16-6/h3-5,19-20H,1-2H2,(H2,12,14)(H2,13,18)(H3,11,15,16)(H,21,22,23)

> <INCHI_KEY>
ARSXTTJGWGCRRR-UHFFFAOYNA-N

> <FORMULA>
C10H17N7O8S

> <MOLECULAR_WEIGHT>
395.35

> <EXACT_MASS>
395.085931709

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.218585942195

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid

> <JCHEM_LOGP>
-3.8987211658229324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.873660414319652

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8608334571133467

> <JCHEM_PKA_STRONGEST_BASIC>
8.918184164901014

> <JCHEM_POLAR_SURFACE_AREA>
243.40999999999997

> <JCHEM_REFRACTIVITY>
99.9249

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0337307 (Gonyautoxin II)
Download
PDB for NP0337307 (Gonyautoxin II)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  N   UNK     0      -3.913   6.718   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.622   5.879   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.249   6.577   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.622   4.339   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.287   3.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.287   2.029   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.045   1.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.045  -0.281   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.510  -0.756   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       1.510   1.734   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.417   0.489   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.957   0.489   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -2.622   1.259   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       1.333  -4.052   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.563  -2.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.969  -2.558   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -1.287  -1.051   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.622  -0.281   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -3.957  -1.051   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      -0.207  -6.718   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       0.563  -5.386   0.000  0.00  0.00           S+0
HETATM   22  O   UNK     0       1.898  -6.156   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.769  -4.616   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.524  -2.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.189  -1.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.814  -0.784   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9   17   25                                             
CONECT    9    8   11                                                       
CONECT   10    7   11                                                       
CONECT   11    9   10   12                                                  
CONECT   12   11                                                            
CONECT   13    6   18                                                       
CONECT   14   15   21                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17    8   16   18                                                  
CONECT   18   13   17   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   14   20   22   23                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   25                                                            
CONECT   25    8   15   24   26                                             
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Download
3D PDB for NP0337307 (Gonyautoxin II)
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SMILES for NP0337307 (Gonyautoxin II)
NC(=O)OCC1NC(=N)N2CC(OS(O)(=O)=O)C(O)(O)C22NC(=N)NC12
Download
INCHI for NP0337307 (Gonyautoxin II)
InChI=1/C10H17N7O8S/c11-6-15-5-3(2-24-8(13)18)14-7(12)17-1-4(25-26(21,22)23)10(19,20)9(5,17)16-6/h3-5,19-20H,1-2H2,(H2,12,14)(H2,13,18)(H3,11,15,16)(H,21,22,23)
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SynonymsNot Available
Chemical FormulaC10H17N7O8S
Average Mass395.3500 Da
Monoisotopic Mass395.08593 Da
IUPAC Name{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-decahydropyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid
Traditional Name{4-[(carbamoyloxy)methyl]-10,10-dihydroxy-2,6-diimino-hexahydro-1H-pyrrolo[1,2-c]purin-9-yl}oxidanesulfonic acid
CAS Registry NumberNot Available
SMILES
NC(=O)OCC1NC(=N)N2CC(OS(O)(=O)=O)C(O)(O)C22NC(=N)NC12
InChI Identifier
InChI=1/C10H17N7O8S/c11-6-15-5-3(2-24-8(13)18)14-7(12)17-1-4(25-26(21,22)23)10(19,20)9(5,17)16-6/h3-5,19-20H,1-2H2,(H2,12,14)(H2,13,18)(H3,11,15,16)(H,21,22,23)
InChI KeyARSXTTJGWGCRRR-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassSaxitoxins, gonyautoxins, and derivatives  
Sub ClassNot Available
Direct ParentSaxitoxins, gonyautoxins, and derivatives  
Alternative Parents
Substituents
  • Saxitoxin-gonyautoxin skeleton
    • 

  • Imidazopyrimidine
    • 

  • Alkaloid or derivatives
    • 

  • 1,3-diazinane
    • 

  • Sulfuric acid monoester
    • 

  • Sulfate-ester
    • 

  • Alkyl sulfate
    • 

  • Sulfuric acid ester
    • 

  • Imidazolidine
    • 

  • Organic sulfuric acid or derivatives
    • 

  • Pyrrolidine
    • 

  • Guanidine
    • 

  • Azacycle
    • 

  • Carboximidic acid derivative
    • 

  • Carboximidamide
    • 

  • Carbonyl hydrate
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Imine
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.9ChemAxon
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)8.92ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area243.41 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.92 m³·mol⁻¹ChemAxon
Polarizability34.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Walker JR, Merit JE, Thomas-Tran R, Tang DTY, Du Bois J: Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid. Angew Chem Int Ed Engl. 2019 Feb 4;58(6):1689-1693. doi: 10.1002/anie.201811717.  Epub 2019 Jan 2. [PubMed:30488599  ]