trilithium(1+) ion ({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(sulfanylidene)phosphonite

• ChemBase ID: 132315
• Molecular Formular: C10H12Li3N5O10P2S
• Molecular Mass: 477.065302
• Monoisotopic Mass: 477.02602452
• SMILES: [Li+].[Li+].[Li+].c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=S)([O-])[O-])O)O)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=S)([O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.[Li+].[Li+].[Li+]
• InChI: InChI=1S/C10H15N5O10P2S.3Li/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(24-9)1-23-26(19,20)25-27(21,22)28;;;/h2-3,5-6,9,16-17H,1H2,(H,19,20)(H2,21,22,28)(H3,11,13,14,18);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1
• InChIKey: LMCWQGPJYZRMKU-CYCLDIHTSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion ({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(sulfanylidene)phosphonite
• IUPAC Traditional name: trilithium(1+) ion {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(sulfanylidene)phosphonite
• Synonyms: GDPβS trilithium salt; GDP-β-S-Li3; GDP-β-S; Guanosine 5′-[β-thio]diphosphate trilithium salt

Database IDs

• CAS Number: 97952-36-8
• EC Number: 308-328-9
• MDL Number: MFCD00057735
• Beilstein Number: 8181243
• PubChem SID: 162226592
• PubChem CID: 71300853

CALCULATED PROPERTIES

• Acid pKa: 1.8169125
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -6.848288
• LogD (pH = 7.4): -8.087706
• Log P: -2.5937517
• Molar Refractivity: 90.9927 cm^3
• Polarizability: 36.422047 Å^3
• Polar Surface Area: 239.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble20 mg/mL (Solutions are very unstable; prepare immediately prior to use.)
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC); 90-95% (HPLC)
• Impurities: ~14% water
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C10H12Li3N5O10P2S

DETAILS

Sigma Aldrich - G7637

Linkage
Non-hydrolyzable GDP analog

Sigma Aldrich - 51113

Other Notes
Competitively inhibits the stimulation of adenylate cyclase activity by GTP and fluoride1