Inosine triphosphate (PAMDB000078)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000078
Identification
Name: Inosine triphosphate
Description:Inosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. ITPase is a cytosolic nucleoside triphosphate pyrophosphohydrolase specific for ITP catalysis to inosine monophosphate (IMP) and deoxy-inosine triphosphate (dITP) to deoxy-inosine monophosphate. ITPase's function is not clearly understood but possible roles for ITPase could be to prevent the accumulation of rogue nucleotides which would be otherwise incorporated into DNA and RNA, or compete with nucleotides such as GTP in signalling processes. (PMID : 170291, 1204209, 17113761, 17924837)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2'-Inosine-5'-triphosphate
  • 2'-Inosine-5'-triphosphoric acid
  • 5'-ITP
  • 5-ITP
  • Inosine 5
  • Inosine 5'-(tetrahydrogen triphosphate)
  • Inosine 5'-(tetrahydrogen triphosphoric acid)
  • Inosine 5'-triphosphate
  • Inosine 5'-triphosphoric acid
  • Inosine 5(tetrahydrogen triphosphate)
  • Inosine 5(tetrahydrogen triphosphoric acid)
  • Inosine 5-triphopshate
  • Inosine 5-triphopshic acid
  • Inosine triphosphate
  • Inosine triphosphoric acid
  • Inosine tripolyphosphate
  • Inosine tripolyphosphoric acid
  • ITP
  • ITT
Chemical Formula: C10H15N4O14P3
Average Molecular Weight: 508.1658
Monoisotopic Molecular Weight: 507.979760744
InChI Key: HAEJPQIATWHALX-KQYNXXCUSA-N
InChI:InChI=1S/C10H15N4O14P3/c15-6-4(1-25-30(21,22)28-31(23,24)27-29(18,19)20)26-10(7(6)16)14-3-13-5-8(14)11-2-12-9(5)17/h2-4,6-7,10,15-16H,1H2,(H,21,22)(H,23,24)(H,11,12,17)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
CAS number: 132-06-9
IUPAC Name:({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name: ({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxypurin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
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=CN=C2O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Hypoxanthine
  • Purine
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:903.5 mg/mL [sodium salt, HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.78 mg/mLALOGPS
logP-0.67ALOGPS
logP-4.4ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.93ChemAxon
pKa (Strongest Basic)-0.17ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area273.34 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity93.09 m3·mol-1ChemAxon
Polarizability38.01 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Inosine triphosphate > Hydrogen ion + IDP + Phosphate
Adenosine monophosphate + Inosine triphosphate <> ADP + IDP
Water + Inosine triphosphate > Hydrogen ion + Inosinic acid + Pyrophosphate
Adenosine triphosphate + Hydrogen ion + Water > Inosine triphosphate + Ammonium
Inosine triphosphate + Water <> Inosinic acid + Pyrophosphate
Adenosine triphosphate + IDP <> ADP + Inosine triphosphate
Inosine triphosphate + Cytidine <> IDP + Cytidine monophosphate
Inosine triphosphate + Uridine <> IDP + Uridine 5'-monophosphate
Inosine triphosphate + D-Tagatose 6-phosphate <> IDP + D-Tagatose 1,6-bisphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0510090000-c39217a77098a2ef6d34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-3900000000-24a790aa14cc5baf5627View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-3900000000-29bad6cebedb5d34080aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Dutta TK, Goel A, Ghotekar LH, Hamide A, Badhe BA, Basu D: Dapsone in treatment of chronic idiopathic thrombocytopenic purpura in adults. J Assoc Physicians India. 2001 Apr;49:421-5. Pubmed: 11762611
  • Fraser JH, Meyers H, Henderson JF, Brox LW, McCoy EE: Individual variation in inosine triphosphate accumulation in human erythrocytes. Clin Biochem. 1975 Dec;8(6):353-64. Pubmed: 1204209
  • Henderson JF, Zombor G, Fraser JH, McCoy EE, Verhoef V, Morris AJ: Factors affecting inosinate synthesis and inosine triphosphate accumulation in human erythrocytes. Can J Biochem. 1977 Apr;55(4):359-64. Pubmed: 15708
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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: 9337071
  • Kopff M, Zachara B, Klem J, Zakrzewska I: [Accumulation of inosine triphosphate in human erythrocytes as a function of ITP-pyrophosphohydrolase activity] Acta Haematol Pol. 1983 Jul-Dec;14(3-4):165-71. Pubmed: 6147059
  • Lin, S., McLennan, A. G., Ying, K., Wang, Z., Gu, S., Jin, H., Wu, C., Liu, W., Yuan, Y., Tang, R., Xie, Y., Mao, Y. (2001). "Cloning, expression, and characterization of a human inosine triphosphate pyrophosphatase encoded by the itpa gene." J Biol Chem 276:18695-18701. Pubmed: 11278832
  • Mikami T, Yoshino Y, Ito A: Does a relationship exist between the urate pool in the body and lipid peroxidation during exercise? Free Radic Res. 2000 Jan;32(1):31-9. Pubmed: 10625215
  • Soder C, Henderson JF, Zombor G, McCoy EE, Verhoef V, Morris AJ: Relationships between nucleoside triphosphate pyrophosphohydrolase activity and inosine triphosphate accumulation in human erythrocytes. Can J Biochem. 1976 Oct;54(10):843-7. Pubmed: 990987
  • Sumi S, Marinaki AM, Arenas M, Fairbanks L, Shobowale-Bakre M, Rees DC, Thein SL, Ansari A, Sanderson J, De Abreu RA, Simmonds HA, Duley JA: Genetic basis of inosine triphosphate pyrophosphohydrolase deficiency. Hum Genet. 2002 Oct;111(4-5):360-7. Epub 2002 Aug 15. Pubmed: 12384777
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vormittag W, Brannath W: As to the clastogenic-, sister-chromatid exchange inducing-and cytotoxic activity of inosine triphosphate in cultures of human peripheral lymphocytes. Mutat Res. 2001 May 9;476(1-2):71-81. Pubmed: 11336985
  • Zachara B, Kopff M: Activity of inosine triphosphate pyrophosphohydrolase in fresh and stored human erythrocytes. Haematologia (Budap). 1981;14(3):277-83. Pubmed: 6120123
  • Zachara B, Lewandowski J: Isolation and identification of inosine triphosphate from human erythrocytes. Biochim Biophys Acta. 1974 Jun 27;353(2):253-9. Pubmed: 4842021
Synthesis Reference: Nakayama, Kiyoshi; Tanaka, Haruo. Fermentative preparation of inosine di- and triphosphate. Jpn. Tokkyo Koho (1972), 2 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID16039
HMDB IDHMDB00189
Pubchem Compound ID8583
Kegg IDC00081
ChemSpider ID8265
WikipediaITP
BioCyc IDITP
EcoCyc IDITP
Ligand ExpoITT