lithium(1+) ion 2-amino-9-[(2R,3R,4S,5R)-5-{[({[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 133625
• Molecular Formular: C10H15LiN5O14P3
• Molecular Mass: 529.113483
• Monoisotopic Mass: 528.99883963
• SMILES: [Li+].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
• 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.[Li+]
• InChI: InChI=1S/C10H16N5O14P3.Li/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);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1
• InChIKey: WDCLDKGIVWUKSE-GWTDSMLYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: lithium(1+) ion 2-amino-9-[(2R,3R,4S,5R)-5-{[({[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: lithium(1+) ion 2-amino-9-[(2R,3R,4S,5R)-5-[({[hydrogen phosphonatooxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-1H-purin-6-one
• Synonyms: GTP lithium salt; Guanosine 5′-triphosphate lithium salt

Database IDs

• CAS Number: 85737-04-8
• MDL Number: MFCD00070012
• PubChem SID: 24895236; 162227902
• PubChem CID: 71308693

CALCULATED PROPERTIES

• Acid pKa: 0.802243
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -10.325367
• LogD (pH = 7.4): -11.083946
• Log P: -3.633383
• Molar Refractivity: 96.1181 cm^3
• Polarizability: 38.41571 Å^3
• Polar Surface Area: 297.64 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC)
• Shipped in: dry ice

DETAILS

Sigma Aldrich - G5884

Caution
Stability is much better than sodium salt.
Preparation Note
Prepared by enzymatic phosphorylation of 5′-GMP.
Biochem/physiol Actions
GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.