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

• ChemBase ID: 155086
• Molecular Formular: C10H12Li3N5O9P2S
• Molecular Mass: 461.065902
• Monoisotopic Mass: 461.0311099
• SMILES: [Li+].[Li+].[Li+].c1nc(c2c(n1)n(cn2)[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)n1cnc2c1ncnc2N.[Li+].[Li+].[Li+]
• InChI: InChI=1S/C10H15N5O9P2S.3Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(23-10)1-22-25(18,19)24-26(20,21)27;;;/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H2,20,21,27);;;/q;3*+1/p-3/t4-,6-,7-,10-;;;/m1.../s1
• InChIKey: CPKFUAYUUSSFFZ-MSQVLRTGSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(sulfanylidene)phosphonite
• IUPAC Traditional name: trilithium(1+) ion {[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(sulfanylidene)phosphonite
• Synonyms: ADP-β-S; Adenosine-5′-0-(2-thiodiphosphate) trilithium salt; Ado-5′-PP[S]; Adenosine 5′-[β-thio]diphosphate trilithium salt

Database IDs

• CAS Number: 73536-95-5
• EC Number: 277-530-6
• MDL Number: MFCD00077314
• PubChem SID: 162249224; 24891307
• PubChem CID: 5310995

CALCULATED PROPERTIES

• Acid pKa: 1.6133308
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -6.331504
• LogD (pH = 7.4): -7.353055
• Log P: -4.188117
• Molar Refractivity: 89.5672 cm^3
• Polarizability: 36.592342 Å^3
• Polar Surface Area: 224.02 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-68/20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H371
• GHS Precautionary statements: P260
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC); ≥85% (HPLC)
• Impurities: ~10% water
• Empirical Formula (Hill Notation): C10H12Li3N5O9P2S

DETAILS

Sigma Aldrich - A8016

Biochem/physiol Actions
P2Y receptor agonist.
Other Notes
Non-hydrolyzable ADP analog
Substrates
Substrate and inhibitor for AMP dependent enzyme systems.
Application
Adenosine 5′-[β-thio]diphosphate is a substrate and inhibitor for AMP dependent enzyme systems. Adenosine 5′-[β-thio]diphosphate has been used to explore the myenteric control mechanisms of human esophageal motility and the effect of nitrergic and nonnitrergic neurotransmitters.

Sigma Aldrich - 01985

Other Notes
Substrate and inhibitor of ADP-dependent systems1