ITP (PAMDB120578)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120578
Identification
Name: ITP
Description:A 2-hydroxy-3-methylpentanoate in which the stereocentres at positions 2 and 3 both have R-configuration.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R,3R)-2-hydroxy-3-methylvalerate
  • (2R,3R)-isoleucate
  • (R,R)-isoleucate
  • 2-hydroxy-3-methylpentanoate
  • 2-hydroxy-3-methylvalerate
Chemical Formula: C10H11N4O14P3
Average Molecular Weight: 504.137
Monoisotopic Molecular Weight: 507.97977
InChI Key: HAEJPQIATWHALX-KQYNXXCUSA-J
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)/p-4/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:C(OP(=O)([O-])OP([O-])(=O)OP([O-])([O-])=O)C1(OC(C(O)C(O)1)N3(C=NC2(C(=O)NC=NC=23)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Pyrimidine
  • Oxolane
  • Azole
  • Vinylogous amide
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
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 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: Not Available
Reactions:
ITP + Water → Hydrogen ion + IMP + diphosphate
ATP + IDP → ITP + ADP
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:
  • 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. [11278832 ]
  • 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. [12384777 ]
  • Zachara B, Kopff M: Activity of inosine triphosphate pyrophosphohydrolase in fresh and stored human erythrocytes. Haematologia (Budap). 1981;14(3):277-83. [6120123 ]
  • 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. [11336985 ]
  • 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. [11762611 ]
  • 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. [990987 ]
  • 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. [15708 ]
  • 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. [9337071 ]
  • Zachara B, Lewandowski J: Isolation and identification of inosine triphosphate from human erythrocytes. Biochim Biophys Acta. 1974 Jun 27;353(2):253-9. [4842021 ]
  • 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. [10625215 ]
  • 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. [6147059 ]
  • 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. [1204209 ]
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
HMDBHMDB00189
BIGG33780
CHEBI133082
PUBCHEM44275035
LIGAND-CPDC00081
CAS132-06-9