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Human Metabolome Database Version 3.5

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Showing metabocard for Inosine triphosphate (HMDB00189)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:02 -0700
HMDB ID HMDB00189
Secondary Accession Numbers None
Metabolite Identification
Common Name Inosine triphosphate
Description Inosine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H15N4O14P3
Average Molecular Weight 508.1658
Monoisotopic Molecular Weight 507.979760744
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 Number 132-06-9
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 Key HAEJPQIATWHALX-KQYNXXCUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine Ribonucleoside Triphosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 903.5 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.78 g/L ALOGPS
LogP -0.67 ALOGPS
LogP -4.4 ChemAxon
LogS -2.03 ALOGPS
pKa (strongest acidic) 0.93 ChemAxon
pKa (strongest basic) -0.17 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 273.34 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 93.09 ChemAxon
Polarizability 38.01 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -3 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Nucleus
Biofluid Locations Not Available
Tissue Location
  • Erythrocyte
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB021902
KNApSAcK ID Not Available
Chemspider ID 8265 Link_out
KEGG Compound ID C00081 Link_out
BioCyc ID ITP Link_out
BiGG ID 33780 Link_out
Wikipedia Link ITP Link_out
NuGOwiki Link HMDB00189 Link_out
Metagene Link HMDB00189 Link_out
METLIN ID 5204 Link_out
PubChem Compound 8583 Link_out
PDB ID ITT Link_out
ChEBI ID 16039 Link_out
References
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)
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 Link_out
  2. Zachara B, Kopff M: Activity of inosine triphosphate pyrophosphohydrolase in fresh and stored human erythrocytes. Haematologia (Budap). 1981;14(3):277-83. Pubmed: 6120123 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
Enzymes
Name: Ectonucleoside triphosphate diphosphohydrolase 1
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD1
Uniprot ID: P49961 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Soluble calcium-activated nucleotidase 1
Reactions:
  • a nucleoside diphosphate + H2O = a nucleotide + phosphate [RN:R00329]
Gene Name: CANT1
Uniprot ID: Q8WVQ1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleoside triphosphate diphosphohydrolase 3
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD3
Uniprot ID: O75355 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase 1
Reactions:
  • ATP + uridine = ADP + UMP [RN:R00964]
Gene Name: UCK1
Uniprot ID: Q9HA47 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase, mitochondrial
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME4
Uniprot ID: O00746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase A
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME1
Uniprot ID: P15531 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase B
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME2
Uniprot ID: P22392 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nucleoside diphosphate kinase 6
Reactions:
  • ATP + nucleoside diphosphate = ADP + nucleoside triphosphate [RN:R00331]
Gene Name: NME6
Uniprot ID: O75414 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase
Reactions:
  • ATP + D-glucose = ADP + D-glucose 6-phosphate [RN:R00299]
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
  • ATP + D-hexose = ADP + D-hexose 6-phosphate [RN:R02848]
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inosine triphosphate pyrophosphatase
Reactions:
  • a nucleoside triphosphate + H2O = a nucleotide + diphosphate [RN:R01532]
Gene Name: ITPA
Uniprot ID: Q9BY32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase type C
Reactions:
  • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
Gene Name: PFKP
Uniprot ID: Q01813 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase, liver type
Reactions:
  • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
Gene Name: PFKL
Uniprot ID: P17858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 6-phosphofructokinase, muscle type
Reactions:
  • ATP + D-fructose 6-phosphate = ADP + D-fructose 1,6-bisphosphate [RN:R00756]
Gene Name: PFKM
Uniprot ID: P08237 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes M1/M2
Reactions:
  • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
Gene Name: PKM2
Uniprot ID: P14618 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate kinase isozymes R/L
Reactions:
  • ATP + pyruvate = ADP + phosphoenolpyruvate [RN:R00200]
Gene Name: PKLR
Uniprot ID: P30613 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [GDP-forming] subunit alpha, mitochondrial
Reactions:
  • GTP + succinate + CoA = GDP + phosphate + succinyl-CoA [RN:R00432]
Gene Name: SUCLG1
Uniprot ID: P53597 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [GDP-forming] subunit beta, mitochondrial
Reactions:
  • GTP + succinate + CoA = GDP + phosphate + succinyl-CoA [RN:R00432]
Gene Name: SUCLG2
Uniprot ID: Q96I99 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
Reactions:
  • GTP + oxaloacetate = GDP + phosphoenolpyruvate + CO2 [RN:R00431]
Gene Name: PCK1
Uniprot ID: P35558 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial
Reactions:
  • ATP + succinate + CoA = ADP + phosphate + succinyl-CoA [RN:R00405]
Gene Name: SUCLA2
Uniprot ID: Q9P2R7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase 2
Reactions:
  • ATP + uridine = ADP + UMP [RN:R00964]
Gene Name: UCK2
Uniprot ID: Q9BZX2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uridine-cytidine kinase-like 1
Reactions:
  • ATP + uridine = ADP + UMP [RN:R00964]
Gene Name: UCKL1
Uniprot ID: Q9NWZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleoside triphosphate diphosphohydrolase 8
Reactions:
  • ATP + 2 H2O = AMP + 2 phosphate [RN:R00085]
Gene Name: ENTPD8
Uniprot ID: Q5MY95 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA