1.0
2011-09-21 00:05:26 UTC
2015-07-21 06:56:53 UTC
FDB021932
Xanthosine 5-triphosphate
Xanthosine 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) [HMDB]
5'-XTP
O(5')-(Tetrahydroxytrioryl)xanthosine
Triphopsphate 1-xanthosin-5'-yl ester
Triphopsphic acid 1-xanthosin-5'-yl ester
Triphopsphoric acid 1-xanthosin-5'-yl ester
Xanthosine 5'-triate
Xanthosine 5'-triic acid
Xanthosine 5'-triphosphate
Xanthosine 5'-triphosphic acid
Xanthosine mono(tetrahydrogen triate)
Xanthosine mono(tetrahydrogen triphosphate)
Xanthosine triate
Xanthosine triic acid
Xanthosine triphosphate
XTP
C10H15N4O15P3
524.1652
523.974675366
({[({[(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
xanthosine 5-triphosphate
6253-56-1
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
InChI=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
CAEFEWVYEZABLA-UUOKFMHZSA-N
belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Purine ribonucleoside triphosphates
Organic compounds
Nucleosides, nucleotides, and analogues
Purine nucleotides
Purine ribonucleotides
Aromatic heteropolycyclic compounds
1,2-diols
Alkaloids and derivatives
Azacyclic compounds
Glycosylamines
Heteroaromatic compounds
Hydrocarbon derivatives
Hydroxypyrimidines
Monoalkyl phosphates
Monosaccharide phosphates
N-substituted imidazoles
Organic oxides
Organonitrogen compounds
Organopnictogen compounds
Oxacyclic compounds
Pentose phosphates
Purine ribonucleoside monophosphates
Secondary alcohols
Tetrahydrofurans
Xanthines
1,2-diol
Alcohol
Alkaloid or derivatives
Alkyl phosphate
Aromatic heteropolycyclic compound
Azacycle
Azole
Glycosyl compound
Heteroaromatic compound
Hydrocarbon derivative
Hydroxypyrimidine
Imidazole
Imidazopyrimidine
Monoalkyl phosphate
Monosaccharide
Monosaccharide phosphate
N-glycosyl compound
N-substituted imidazole
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organic phosphoric acid derivative
Organoheterocyclic compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Oxacycle
Pentose monosaccharide
Pentose phosphate
Pentose-5-phosphate
Phosphoric acid ester
Purine
Purine ribonucleoside monophosphate
Purine ribonucleoside triphosphate
Pyrimidine
Secondary alcohol
Tetrahydrofuran
Xanthine
purine ribonucleoside 5'-triphosphate
xanthosine 5'-phosphate
Solid
logp
-0.45
logs
-2.11
solubility
4.04e+00 g/l
logp
-4.1
pka_strongest_acidic
0.96
pka_strongest_basic
0.016
iupac
({[({[(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
average_mass
524.1652
mono_mass
523.974675366
smiles
O[C@@H]1[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=C(O)N=C2O
formula
C10H15N4O15P3
inchi
InChI=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
inchikey
CAEFEWVYEZABLA-UUOKFMHZSA-N
polar_surface_area
293.57
refractivity
95.02
polarizability
39.11
rotatable_bond_count
8
acceptor_count
15
donor_count
8
physiological_charge
-3
formal_charge
0
Specdb::NmrOneD
143370
Specdb::NmrOneD
143371
Specdb::NmrOneD
143372
Specdb::NmrOneD
143373
Specdb::NmrOneD
143374
Specdb::NmrOneD
143375
Specdb::NmrOneD
143376
Specdb::NmrOneD
143377
Specdb::NmrOneD
143378
Specdb::NmrOneD
143379
Specdb::NmrOneD
143380
Specdb::NmrOneD
143381
Specdb::NmrOneD
143382
Specdb::NmrOneD
143383
Specdb::NmrOneD
143384
Specdb::NmrOneD
143385
Specdb::NmrOneD
143386
Specdb::NmrOneD
143387
Specdb::NmrOneD
143388
Specdb::NmrOneD
143389
Specdb::CMs
15558
Specdb::CMs
37407
Specdb::CMs
1056912
Specdb::CMs
1056913
Specdb::CMs
1056915
Specdb::CMs
1056917
Specdb::CMs
1056919
Specdb::CMs
1056921
Specdb::CMs
1056923
Specdb::CMs
1056925
Specdb::CMs
1056926
Specdb::CMs
1056929
Specdb::CMs
1056931
Specdb::CMs
1056933
Specdb::CMs
1056935
Specdb::CMs
1056937
Specdb::CMs
1056939
Specdb::CMs
1056941
Specdb::CMs
1056943
Specdb::CMs
1056944
Specdb::CMs
1056945
Specdb::CMs
1056947
Specdb::CMs
1056949
Specdb::CMs
1056951
Specdb::CMs
1056953
Specdb::MsMs
27920
Specdb::MsMs
27921
Specdb::MsMs
27922
Specdb::MsMs
34478
Specdb::MsMs
34479
Specdb::MsMs
34480
Specdb::MsMs
2758455
Specdb::MsMs
2758456
Specdb::MsMs
2758457
Specdb::MsMs
2950332
Specdb::MsMs
2950333
Specdb::MsMs
2950334
HMDB00293
#<Reference:0x0000555675e931a0>
#<Reference:0x0000555675e92f70>
Anatidae
Type 1
specific
Anatidae
8830
Beefalo
Type 1
specific
Bos taurus X Bison bison
297284
Bison
Type 1
specific
Bison bison
9901
Buffalo
Type 1
specific
Bubalus bubalis
89462
Cattle (Beef, Veal)
Type 1
specific
Bos taurus
9913
Chicken
Type 1
specific
Gallus gallus
9031
Columbidae (Dove, Pigeon)
Type 1
specific
Columbidae
8930
Deer
Type 1
specific
Cervidae
9850
Domestic goat
Type 1
specific
Capra aegagrus hircus
9925
Domestic pig
Type 1
specific
Sus scrofa domestica
9825
Elk
Type 1
specific
Cervus canadensis
1574408
Emu
Type 1
specific
Dromaius novaehollandiae
8790
European rabbit
Type 1
specific
Oryctolagus
9984
Greylag goose
Type 1
specific
Anser anser
8843
Guinea hen
Type 1
specific
Numida meleagris
8996
Horse
Type 1
specific
Equus caballus
9796
Mallard duck
Type 1
specific
Anas platyrhynchos
8839
Mountain hare
Type 1
specific
Lepus timidus
62621
Mule deer
Type 1
specific
Odocoileus
9871
Ostrich
Type 1
specific
Struthio camelus
8801
Pheasant
Type 1
specific
Phasianus colchicus
9054
Quail
Type 1
specific
Phasianidae
9005
Rabbit
Type 1
specific
Leporidae
9979
Rock ptarmigan
Type 1
specific
Lagopus muta
64668
Sheep (Mutton, Lamb)
Type 1
specific
Ovis aries
9940
Squab
Type 1
specific
Columba
8931
Turkey
Type 1
specific
Meleagris gallopavo
9103
Velvet duck
Type 1
specific
Melanitta fusca
371864
Wild boar
Type 1
specific
Sus scrofa
9823