trisodium hydrate [(2R,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl (phosphonatooxy)phosphonate

• ChemBase ID: 133570
• Molecular Formular: C11H16N5Na3O11P2S
• Molecular Mass: 557.253472
• Monoisotopic Mass: 556.97353346
• SMILES: CSc1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])[O-])O)O)N.O.[Na+].[Na+].[Na+]
• Canonical SMILES: CSc1nc(N)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(OP(=O)([O-])[O-])[O-].O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C11H17N5O10P2S.3Na.H2O/c1-29-11-14-8(12)5-9(15-11)16(3-13-5)10-7(18)6(17)4(25-10)2-24-28(22,23)26-27(19,20)21;;;;/h3-4,6-7,10,17-18H,2H2,1H3,(H,22,23)(H2,12,14,15)(H2,19,20,21);;;;1H2/q;3*+1;/p-3/t4-,6-,7-,10-;;;;/m1..../s1
• InChIKey: JPTPEMXICPAWKJ-KWIZKVQNSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium hydrate [(2R,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)-9H-purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl (phosphonatooxy)phosphonate
• IUPAC Traditional name: trisodium hydrate [(2R,3S,4R,5R)-5-[6-amino-2-(methylsulfanyl)purin-9-yl]-3,4-dihydroxyoxolan-2-yl]methyl phosphonatooxyphosphonate
• Synonyms: 2-(Methylthio)adenosine 5′-trihydrogen diphosphate trisodium salt hydrate; 2-Methylthio-ADP trisodium salt hydrate; 2-(Methylthio)adenosine 5′-diphosphate trisodium salt hydrate

Database IDs

• CAS Number: 475193-31-8(anhydrous)
• MDL Number: MFCD11044463
• PubChem SID: 162227847; 24278816
• PubChem CID: 71308687

CALCULATED PROPERTIES

• Acid pKa: 1.7434459
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): -5.733315
• LogD (pH = 7.4): -6.3633413
• Log P: -2.6991715
• Molar Refractivity: 94.2812 cm^3
• Polarizability: 38.336517 Å^3
• Polar Surface Area: 241.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥89% (HPLC)

DETAILS

Sigma Aldrich - M152

Caution
Hygroscopic, air sensitive
Biochem/physiol Actions
2-Methylthio-ADP (2-ME-SADP) is a P2 purinoceptor agonist, which induces platelet aggregation and shape change and inhibits cyclic AMP accumulation in platelets exposed to prostaglandin E1. Compared with ADP, 2-methylthio-ADP was 3-5 times as active as an aggregating agent and 150-200 times as active as an inhibitor of cyclic AMP accumulation. Purinergic signaling may be an important factor in TSP-1-mediated cell-matrix and cell-cell interactions such as those occurring during development and repair.