{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid amine

• ChemBase ID: 133415
• Molecular Formular: C20H32N11O24P5
• Molecular Mass: 965.396185
• Monoisotopic Mass: 965.03097411
• 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)OP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1nc([nH]c2=O)N)O)O)O)O)N.N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2nc(N)[nH]c3=O)O)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.N
• InChI: InChI=1S/C20H29N10O24P5.H3N/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(49-17)1-47-55(37,38)51-57(41,42)53-59(45,46)54-58(43,44)52-56(39,40)48-2-6-10(32)12(34)18(50-6)30-4-24-8-14(30)26-20(22)28-16(8)36;/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H3,21,25,27,35)(H3,22,26,28,36);1H3/t5-,6-,9-,10-,11-,12-,17-,18-;/m1./s1
• InChIKey: JYGFCNUGRSNROE-AORRWANRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid amine
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid amine
• Synonyms: Diguanosine pentaphosphate; G(5′]P5(5′)G; P1,P5-Di(guanosine-5′) pentaphosphate ammonium salt

Database IDs

• CAS Number: 102783-42-6
• MDL Number: MFCD11045927
• PubChem SID: 24893537; 162227692
• PubChem CID: 71308665

CALCULATED PROPERTIES

• Acid pKa: 0.3751234
• H Acceptors: 24
• H Donor: 13
• LogD (pH = 5.5): -17.556147
• LogD (pH = 7.4): -18.198729
• Log P: -6.3373017
• Molar Refractivity: 179.8277 cm^3
• Polarizability: 71.21094 Å^3
• Polar Surface Area: 511.86 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - D1762

Biochem/physiol Actions
Naturally occurring dinucleoside polyphosphate, approx. 10 nM in normal human plasma. At physiological concentrations, potentiates angiotensin-induced vasoconstriction, possibly via activation of rho kinase through P2Y receptors, and increases blood pressure.1