disodium dihydrate {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatooxy)phosphonate

• ChemBase ID: 155862
• Molecular Formular: C10H18N5Na2O16P3
• Molecular Mass: 603.174643
• Monoisotopic Mass: 602.97567797
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)([O-])OP(=O)(O)[O-])O)O)N.O.O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)[O-])[O-])O)O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.O.O.[Na+].[Na+]
• InChI: InChI=1S/C10H16N5O14P3.2Na.2H2O/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;;/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18);;;2*1H2/q;2*+1;;/p-2/t3-,5-,6-,9-;;;;/m1..../s1
• InChIKey: HPLNHYUZFVUXFJ-ZVQJTLEUSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium dihydrate {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (hydrogen phosphonatooxy)phosphonate
• IUPAC Traditional name: disodium dihydrate [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl hydrogen phosphonatooxyphosphonate
• Synonyms: 5′-GTP-Na2; Guanosine 5′-triphosphate sodium salt hydrate

Database IDs

• CAS Number: 36051-31-7
• EC Number: 252-847-2
• MDL Number: MFCD00149227
• Beilstein Number: 4113439
• PubChem SID: 24873428; 162250000
• PubChem CID: 16213707

CALCULATED PROPERTIES

• Acid pKa: 0.802243
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -10.325367
• LogD (pH = 7.4): -11.083946
• Log P: -3.633383
• Molar Refractivity: 94.9964 cm^3
• Polarizability: 38.29559 Å^3
• Polar Surface Area: 300.47 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -24±2°, c = 1% in 0.5 M Na2HPO4

Safety Information

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

Product Information

• Purity: ≥90% (HPLC)
• Impurities: ≤3 mol/mol water (NMR)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C10H16N5O14P3 · xNa+ · yH2O

DETAILS

Sigma Aldrich - 51120

Application
Guanosine 5′-triphosphate (GTP), a purine trinucleotide, is a substrate for RNA polymerases and a wide range of GTPase including G-protein coupled receptor (GPCR) GTPases and cell signaling and cycling associated guanine nucleotide exhange factors (GEF).