创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 15:38:59 UTC
名称
Xanthosine 5-triphosphate
描述
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).
同义词
1:O(5')-(Tetrahydroxytriphosphoryl)xanthosine
2:Triphopsphoric acid 1-xanthosin-5'-yl ester
3:Xanthosine 5'-triphosphate
4:Xanthosine triphosphate
5:Triphopsphate 1-xanthosin-5'-yl ester
6:Triphopsphic acid 1-xanthosin-5'-yl ester
7:Xanthosine 5'-triphosphoric acid
8:Xanthosine triphosphoric acid
9:Xanthosine 5-triphosphoric acid
10:5'-XTP
11:Xanthosine mono(tetrahydrogen triphosphate)
12:XTP
13:Xanthosine 5'-triphosphate 2Sodium salt
化学名称
({[({[(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
传统名称
xanthosine 5-triphosphate
代谢物结构字符串
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标识符
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
印记键
CAEFEWVYEZABLA-UUOKFMHZSA-N
分类学
description: 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.
description:Purine ribonucleoside triphosphates
kingdom:Organic compounds
super_class:Nucleosides, nucleotides, and analogues
class:Purine nucleotides
sub_class:Purine ribonucleotides
molecular_framework:Aromatic heteropolycyclic compounds
1:1,2-diols
2:Alkaloids and derivatives
3:Azacyclic compounds
4:Glycosylamines
5:Heteroaromatic compounds
6:Hydrocarbon derivatives
7:Hydroxypyrimidines
8:Monoalkyl phosphates
9:Monosaccharide phosphates
10:N-substituted imidazoles
11:Organic oxides
12:Organonitrogen compounds
13:Organopnictogen compounds
14:Oxacyclic compounds
15:Pentose phosphates
16:Purine ribonucleoside monophosphates
17:Secondary alcohols
18:Tetrahydrofurans
19:Xanthines
20:1,2-diol
21:Alcohol
22:Alkaloid or derivatives
23:Alkyl phosphate
24:Aromatic heteropolycyclic compound
25:Azacycle
26:Azole
27:Glycosyl compound
28:Heteroaromatic compound
29:Hydrocarbon derivative
30:Hydroxypyrimidine
31:Imidazole
32:Imidazopyrimidine
33:Monoalkyl phosphate
34:Monosaccharide
35:Monosaccharide phosphate
36:N-glycosyl compound
37:N-substituted imidazole
38:Organic nitrogen compound
39:Organic oxide
40:Organic oxygen compound
41:Organic phosphoric acid derivative
42:Organoheterocyclic compound
43:Organonitrogen compound
44:Organooxygen compound
45:Organopnictogen compound
46:Oxacycle
47:Pentose monosaccharide
48:Pentose phosphate
49:Pentose-5-phosphate
50:Phosphoric acid ester
51:Purine
52:Purine ribonucleoside monophosphate
53:Purine ribonucleoside triphosphate
54:Pyrimidine
55:Secondary alcohol
56:Tetrahydrofuran
57:Xanthine
58:purine ribonucleoside 5'-triphosphate
59:xanthosine 5'-phosphate
本体论
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Endogenous
definition:
parent_id:7735
**level:3
type:child
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Subcellular
definition:An anatomical organizational level including a component within a biological cell .
parent_id:7725
**level:3
type:parent
term:Cytoplasm
definition:The portion of the cell contained within the plasma membrane but excluding the nucleus.
parent_id:7730
***level:4
type:child
synonym:Cytoplasma
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Prostate
definition:The male reproductive accessory gland that produces prostatic fluid and is located adjacent to or around the urethra distal to the urinary bladder in mammals. (nci).
parent_id:7727
***level:4
type:child
synonym:Prostate gland
预测性质
1:
kind:logp
value:-0.45
source:ALOGPS
2:
kind:logs
value:-2.11
source:ALOGPS
3:
kind:solubility
value:4.04 g/L
source:ALOGPS
4:
kind:logp
value:-4.1
source:ChemAxon
5:
kind:pka_strongest_acidic
value:0.96
source:ChemAxon
6:
kind:pka_strongest_basic
value:0.016
source:ChemAxon
7:
kind:iupac
value:({[({[(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
source:ChemAxon
8:
kind:average_mass
value:524.1652
source:ChemAxon
9:
kind:mono_mass
value:523.974675366
source:ChemAxon
10:
kind:smiles
value: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
source:ChemAxon
11:
kind:formula
value:C10H15N4O15P3
source:ChemAxon
12:
kind:inchi
value: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
source:ChemAxon
13:
kind:inchikey
value:CAEFEWVYEZABLA-UUOKFMHZSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:293.57
source:ChemAxon
15:
kind:refractivity
value:95.02
source:ChemAxon
16:
kind:polarizability
value:39.11
source:ChemAxon
17:
kind:rotatable_bond_count
value:8
source:ChemAxon
18:
kind:acceptor_count
value:15
source:ChemAxon
19:
kind:donor_count
value:8
source:ChemAxon
20:
kind:physiological_charge
value:-3
source:ChemAxon
21:
kind:formal_charge
value:0
source:ChemAxon
22:
kind:number_of_rings
value:3
source:ChemAxon
23:
kind:bioavailability
value:No
source:ChemAxon
24:
kind:rule_of_five
value:No
source:ChemAxon
25:
kind:ghose_filter
value:No
source:ChemAxon
26:
kind:veber_rule
value:No
source:ChemAxon
27:
kind:mddr_like_rule
value:Yes
source:ChemAxon
生物学性质
1:
cellular:(1):Cytoplasm
2:
3:
tissue:(1):Prostate
4:
综合参考
anachkov I; Pan J Y; Wessling-Resnick M; Wright G E Synthesis and effect of nonhydrolyzable xanthosine triphosphate derivatives on prenylation of Rab5D136N. Molecular pharmacology (1997), 51(1), 47-51.
一般参考
1:
protein_accession:HMDBP00431
name:Inosine triphosphate pyrophosphatase
uniprot_id:Q9BY32
gene_name:ITPA
protein_type:Unknown
2:
protein_accession:HMDBP00621
name:Bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]
uniprot_id:P50583
gene_name:NUDT2
protein_type:Unknown
蛋白质结合
1:
reference_text:Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
pubmed_id:19212411
2:
reference_text:Klinker JF, Seifert R: Functionally nonequivalent interactions of guanosine 5'-triphosphate, inosine 5'-triphosphate, and xanthosine 5'-triphosphate with the retinal G-protein, transducin, and with Gi-proteins in HL-60 leukemia cell membranes. Biochem Pharmacol. 1997 Sep 1;54(5):551-62.
pubmed_id:9337071