2-amino-2-(hydroxymethyl)propane-1,3-diol; {[({[({[(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}phosphonic acid

• ChemBase ID: 155255
• Molecular Formular: C14H28N6O20P4
• Molecular Mass: 724.295364
• Monoisotopic Mass: 724.03088385
• 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)O)O)O)N.C(C(CO)(CO)N)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OP(=O)(O)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.OCC(CO)(CO)N
• InChI: InChI=1S/C10H17N5O17P4.C4H11NO3/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(29-9)1-28-34(22,23)31-36(26,27)32-35(24,25)30-33(19,20)21;5-4(1-6,2-7)3-8/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H,26,27)(H2,19,20,21)(H3,11,13,14,18);6-8H,1-3,5H2/t3-,5-,6-,9-;/m1./s1
• InChIKey: ZEHPDAAYQIAYON-GWTDSMLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-(hydroxymethyl)propane-1,3-diol; {[({[({[(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}phosphonic acid
• IUPAC Traditional name: [({[(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]oxyphosphonic acid; tris buffer
• Synonyms: G-tetra-P; Guanosine 5′-tetraphosphate tris salt

Database IDs

• CAS Number: 103213-27-0
• MDL Number: MFCD00058646
• PubChem SID: 162249393
• PubChem CID: 71312109

CALCULATED PROPERTIES

• Acid pKa: 1.3451104
• H Acceptors: 16
• H Donor: 9
• LogD (pH = 5.5): -13.062473
• LogD (pH = 7.4): -13.881358
• Log P: -4.02017
• Molar Refractivity: 108.1127 cm^3
• Polarizability: 43.36113 Å^3
• Polar Surface Area: 341.34 Å^2
• Rotatable Bonds: 13
• 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: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H371
• GHS Precautionary statements: P260
• Storage Temperature: -20°C

Product Information

• Purity: ~95%
• Biological Source: from Saccharomyces cerevisiae
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C10H17N5O17P4

DETAILS

Sigma Aldrich - G8378

Biochem/physiol Actions
Guanosine 5′-tetraphosphate (G-tetra-P) may be used as a substrate to study the specificity and kinetics of polyphosphatases (triphosphate tunnel metalloenzymes (TTMs)) and exopolyphosphatases. Also used as an inhibitor to study the kinetics and mechanism of various guanylate cyclases. Guanosine 5′-tetraphosphate may be used in various studies with adenosine-5′-tetraphosphate.