Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:24:58 UTC
HMDB IDHMDB00189
Secondary Accession NumbersNone
Metabolite Identification
Common NameInosine triphosphate
DescriptionInosine triphosphate (ITP) is an intermediate in the purine metabolism pathway. Relatively high levels of ITP in red cells are found in individuals as result of deficiency of inosine triphosphatase (EC 3.1.3.56, ITPase) 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 deficiency is not associated with any defined pathology other than the characteristic and abnormal accumulation of ITP in red blood cells. Nevertheless, ITPase deficiency may have pharmacogenomic implications, and the abnormal metabolism of 6-mercaptopurine in ITPase-deficient patients may lead to thiopurine drug toxicity. 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
Synonyms
  1. 2'-Inosine-5'-triphosphate
  2. 5'-ITP
  3. 5-ITP
  4. Inosine 5
  5. Inosine 5'-(tetrahydrogen triphosphate)
  6. Inosine 5'-triphosphate
  7. Inosine 5(tetrahydrogen triphosphate)
  8. Inosine 5-triphopshate
  9. Inosine triphosphate
  10. Inosine tripolyphosphate
  11. ITP
  12. ITT
Chemical FormulaC10H15N4O14P3
Average Molecular Weight508.1658
Monoisotopic Molecular Weight507.979760744
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
CAS Registry Number132-06-9
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
InChI Identifier
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
InChI KeyHAEJPQIATWHALX-KQYNXXCUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • inosine phosphate(ChEBI)
  • purine ribonucleoside 5'-triphosphate(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Triphosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility903.5 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.78 g/LALOGPS
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 area273.34ChemAxon
rotatable bond count8ChemAxon
refractivity93.09ChemAxon
polarizability38.01ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid LocationsNot Available
Tissue Location
  • Erythrocyte
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050map00230
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021902
KNApSAcK IDNot Available
Chemspider ID8265
KEGG Compound IDC00081
BioCyc IDITP
BiGG ID33780
Wikipedia LinkITP
NuGOwiki LinkHMDB00189
Metagene LinkHMDB00189
METLIN ID5204
PubChem Compound8583
PDB IDITT
ChEBI ID16039
References
Synthesis ReferenceNakayama, Kiyoshi; Tanaka, Haruo. Fermentative preparation of inosine di- and triphosphate. Jpn. Tokkyo Koho (1972), 2 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lin S, McLennan AG, Ying K, Wang Z, Gu S, Jin H, Wu C, Liu W, Yuan Y, Tang R, Xie Y, Mao Y: Cloning, expression, and characterization of a human inosine triphosphate pyrophosphatase encoded by the itpa gene. J Biol Chem. 2001 Jun 1;276(22):18695-701. Epub 2001 Mar 13. Pubmed: 11278832
  2. 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
  3. Zachara B, Kopff M: Activity of inosine triphosphate pyrophosphohydrolase in fresh and stored human erythrocytes. Haematologia (Budap). 1981;14(3):277-83. Pubmed: 6120123
  4. 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
  5. 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
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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

Enzymes

Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Inosine triphosphate + Water unknown IDP + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Inosine triphosphate + Water unknown IDP + Phosphoric aciddetails
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Inosine triphosphate + Cytidine unknown IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine unknown IDP + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails
Gene Name:
GCK
Uniprot ID:
P35557
Gene Name:
HK3
Uniprot ID:
P52790
Gene Name:
HK2
Uniprot ID:
P52789
Gene Name:
ITPA
Uniprot ID:
Q9BY32
Reactions
Inosine triphosphate + Water unknown Inosinic acid + Pyrophosphatedetails
Gene Name:
PFKP
Uniprot ID:
Q01813
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate unknown IDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
PFKL
Uniprot ID:
P17858
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate unknown IDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
PFKM
Uniprot ID:
P08237
Reactions
Inosine triphosphate + D-Tagatose 6-phosphate unknown IDP + D-Tagatose 1,6-bisphosphatedetails
Gene Name:
PKM
Uniprot ID:
P14618
Gene Name:
PKLR
Uniprot ID:
P30613
Gene Name:
SUCLG1
Uniprot ID:
P53597
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK2
Uniprot ID:
Q16822
Reactions
Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK1
Uniprot ID:
P35558
Reactions
Inosine triphosphate + Oxalacetic acid unknown IDP + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Reactions
Inosine triphosphate + Succinic acid + Coenzyme A unknown IDP + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
UCK2
Uniprot ID:
Q9BZX2
Reactions
Inosine triphosphate + Cytidine unknown IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine unknown IDP + Uridine 5'-monophosphatedetails
Gene Name:
UCKL1
Uniprot ID:
Q9NWZ5
Reactions
Inosine triphosphate + Cytidine unknown IDP + Cytidine monophosphatedetails
Inosine triphosphate + Uridine unknown IDP + Uridine 5'-monophosphatedetails
Gene Name:
ENTPD8
Uniprot ID:
Q5MY95
Reactions
Inosine triphosphate + Water unknown IDP + Phosphoric aciddetails
Gene Name:
NME5
Uniprot ID:
P56597
Reactions
Adenosine triphosphate + IDP unknown ADP + Inosine triphosphatedetails