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

• ChemBase ID: 133795
• Molecular Formular: C20H32N11O21P4+
• Molecular Mass: 886.424224
• Monoisotopic Mass: 886.07246862
• SMILES: c1nc2c(n1C1C(C(C(O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)n1cnc3c1[nH]c(nc3=O)N)O)O)O)O)[nH]c(nc2=O)N.[NH4+]
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(OP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2[nH]c(N)nc3=O)O)O)O)O)OC(C1O)n1cnc2c1[nH]c(N)nc2=O.[NH4+]
• InChI: InChI=1S/C20H28N10O21P4.H3N/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)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)(H3,21,25,27,35)(H3,22,26,28,36);1H3/p+1
• InChIKey: WDOHMQPAFMGSPZ-UHFFFAOYSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: ammonium {[5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid
• IUPAC Traditional name: ammonium [5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[({[5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphinic acid
• Synonyms: Diguanosine tetraphosphate; G(5′)P4(5′)G; GP4G; P1,P4-Di(guanosine-5′) tetraphosphate ammonium salt

Database IDs

• CAS Number: 102783-33-5
• MDL Number: MFCD00058645
• PubChem SID: 162228072; 24893328
• PubChem CID: 16219205

CALCULATED PROPERTIES

• Acid pKa: 0.588686
• H Acceptors: 24
• H Donor: 12
• LogD (pH = 5.5): -13.810322
• LogD (pH = 7.4): -14.556331
• Log P: -4.8696384
• Molar Refractivity: 168.088 cm^3
• Polarizability: 66.75482 Å^3
• Polar Surface Area: 465.33 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• 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: ~95% (HPLC)

DETAILS

Sigma Aldrich - D1028

Application
P1,P4-Di(guanosine-5′) tetraphosphate (Diguanosine tetraphosphate) (GP4G) is a dinucleoside polyphosphate which may be used to study potential pathological effects of dinucleoside polyphosphtes in vivo. GP4G is an acceptor molecule for cytidine-3′, 5′-bisphosphate from the adenylylated donor 5′-adenylylated cytidine 5′,3′-bisphosphate in the T4 RNA ligase catalyzed reactions. GP4G is a used as an inhibitor of DNA apurinic/apyrimidinic endonuclease (APE1).