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

• ChemBase ID: 177697
• Molecular Formular: C10H17N7O4
• Molecular Mass: 299.28648
• Monoisotopic Mass: 299.13420206
• SMILES: [C@@]123N(C(=NC([C@@H]1N=C(N2)N)COC(=O)N)N)CCC3(O)O
• Canonical SMILES: NC(=O)OCC1N=C(N)N2[C@@]3([C@H]1N=C(N3)N)C(O)(O)CC2
• InChI: InChI=1S/C10H17N7O4/c11-6-15-5-4(3-21-8(13)18)14-7(12)17-2-1-9(19,20)10(5,17)16-6/h4-5,19-20H,1-3H2,(H2,12,14)(H2,13,18)(H3,11,15,16)/t4?,5-,10-/m0/s1
• InChIKey: RPQXVSUAYFXFJA-AOPOZUIUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(10aS,10bS)-2,6-diamino-10,10-dihydroxy-1H,4H,8H,9H,10H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• IUPAC Traditional name: [(10aS,10bS)-2,6-diamino-10,10-dihydroxy-1H,4H,8H,9H,10bH-pyrrolo[1,2-c]purin-4-yl]methyl carbamate
• Synonyms: STX; Saxitoxin Hydrate; Saxitoxin; (3aS,4R,10aS)-2,6-Diamino-4-[[(aminocarbonyl)oxy]methyl]-3a,4,8,9-tetrahydro-1H,10H-pyrrolo[1,2-c]purine-10,10-diol; [3aS-(3aα,4α,10aR*)]-2,6-Diamino-4-[[(aminocarbonyl)oxy]methyl]-3a,4,8,9-tetrahydro-1H,10H-pyrrolo[1,2-c]purine-10,10-diol; (+)-Saxitoxin

Database IDs

• CAS Number: 35523-89-8
• PubChem SID: 164233607
• PubChem CID: 71752159

CALCULATED PROPERTIES

• Acid pKa: 10.760259
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -6.9040685
• LogD (pH = 7.4): -4.8416314
• Log P: -2.5058892
• Molar Refractivity: 67.8368 cm^3
• Polarizability: 26.428762 Å^3
• Polar Surface Area: 184.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S143730

Mussel poison; clam poison; paralytic shellfish poison; gonyaulax toxin. These poisonous shellfish have been connected to instances of toxic”red-tides” where the high concentration of algae discoloring the water were of the Gonyaulax genus. Used as a tool

REFERENCES

• Kao, et al.: Pharmacol. Rev., 18, 997 (1966)
• Evans, et al.: Br. Med. Bull., 25, 263 (1966)