Showing Metabocard for XTP (BASm0004083)

Common NameXtp
DescriptionXanthosine 5-triphosphate (XTP) is a Guanosine triphosphate (GTP) analogue. The base of XTP, xanthine, bears a keto group instead of an amino group at C2 of the purine rings. XTP can substitute for GTP in supporting receptor-mediated adenylyl cyclase activation. XTP competitively inhibits the binding of GTP to the guanine nucleotide-binding site of retinal G-protein, transducin (TD). These suggests that GTP, ITP, and XTP are differential signal sorters and signal amplifiers at the G-protein level. G-proteins mediate signal transfer from receptors to effector systems. (PMID: 9337071 ). Xanthosine 5-triphosphate is an intermediate of the Purine metabolism pathway, a substrate of the enzymes dinucleoside tetraphosphatase (EC 3.6.1.17) and nucleoside-triphosphate pyrophosphatase (EC 3.6.1.19). (KEGG).
Structure
Molecular FormulaC10H15N4O15P3
Average Mass524.16520
Monoisotopic Mass523.97468
IUPAC Name({[({[(2R,3S,4R,5R)-5-(2,6-dihydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name({[(2r,3s,4r,5r)-5-(2,6-dihydroxypurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry Number6253-56-1
SMILESO=c1[nH]c(=O)c2ncn([C@@H]3O[C@H](COP(=O)([O-])OP(=O)([O-])OP(=O)([O-])[O-])[C@@H](O)[C@H]3O)c2[nH]1
InChI IdentifierInChI=1S/C10H15N4O15P3/c15-5-3(1-26-31(22,23)29-32(24,25)28-30(19,20)21)27-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6-,9-/m1/s1
InChI KeyCAEFEWVYEZABLA-UUOKFMHZSA-N
CHEBI IDCHEBI:61314
HMDB IDHMDB0000293
StateSolid
Water Solubility4.04e+00 g/l
logP-0.45
logS-2.11
pKa (Strongest Acidic)0.96
pKa (Strongest Basic)0.02
Hydrogen Acceptor Count15
Hydrogen Donor Count8
Polar Surface Area293.57 Ų
Rotatable Bond Count8
Physiological Charge-3
Formal Charge0
Refractivity95.02 m³·mol⁻¹
Polarizability39.11

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