[(4R,9S,10aS,10bS)-2,6-diamino-4-[(carbamoyloxy)methyl]-10,10-dihydroxy-1H,4H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-9-yl]oxidanesulfonic acid

• ChemBase ID: 169774
• Molecular Formular: C10H17N7O8S
• Molecular Mass: 395.34908
• Monoisotopic Mass: 395.08593154
• SMILES: [C@@]123N(C(=N[C@H]([C@@H]1N=C(N2)N)COC(=O)N)N)C[C@@H](C3(O)O)OS(=O)(=O)O
• Canonical SMILES: NC(=O)OC[C@@H]1N=C(N)N2[C@@]3([C@H]1N=C(N3)N)C(O)(O)[C@H](C2)OS(=O)(=O)O
• InChI: InChI=1S/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)/t3-,4-,5-,9-/m0/s1
• InChIKey: ARSXTTJGWGCRRR-LJRZAWCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R,9S,10aS,10bS)-2,6-diamino-4-[(carbamoyloxy)methyl]-10,10-dihydroxy-1H,4H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-9-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(4R,9S,10aS,10bS)-2,6-diamino-4-[(carbamoyloxy)methyl]-10,10-dihydroxy-1H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-9-yl]oxidanesulfonic acid
• Synonyms: (+)-Gonyautoxin 3; 11β-Hydroxysaxitoxin 11-sulfate; GTX III; GTX3; Gonyautoxin III; Toxin GTX3; Gonyautoxin 3; (3aS,4R,9R,10aS)-2,6-Diamino-4-[[(aminocarbonyl)oxy]methyl]-3a,4,8,9-tetrahydro-1H,10H-pyrrolo[1,2-c]purine-9,10,10-triol 9-(Hydrogen Sulfate); 11α-Hydroxysaxitoxin 11-Sulfate; GTX II; GTX2; Gonyautoxin II; Toxin GTX2; Gonyautoxin 2

Database IDs

• CAS Number: 60508-89-6; 60537-65-7
• PubChem SID: 162263906
• PubChem CID: 46217347

CALCULATED PROPERTIES

• Acid pKa: -1.8610834
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -5.6960807
• LogD (pH = 7.4): -4.208314
• Log P: -3.8766584
• Molar Refractivity: 79.3393 cm^3
• Polarizability: 32.13641 Å^3
• Polar Surface Area: 248.41 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G766750

A metabolite of Saxitoxin analog as a paralytic shellfish toxin.

Toronto Research Chemicals - G766740

A metabolite of Saxitoxin analog as a paralytic shellfish toxin.

REFERENCES

• Negri, A., et al.: Chem. Res. Toxicol., 16, 1029 (2003)
• Sayfritz, S., et al.: Toxicon, 52, 330 (2003)
• Negri, A., et al.: Chem. Res. Toxicol., 16, 1029 (2003)
• Sayfritz, S., et al.: Toxicon, 52, 330 (2003)