2'-Deoxyinosine triphosphate (PAMDB000593)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000593
Identification
Name: 2'-Deoxyinosine triphosphate
Description:2'-Deoxyinosine triphosphate (dITP) is a deoxyribonucleotide that may be generated from dATP by slow, non-enzymatic hydrolysis or by reduction of ITP. Normally, the cellular dITP concentration is very low. The inability to demonstrate the synthesis of dITP in cellular preparations has been attributed to the presence in the cytoplasm of an inosine triphosphatase pyrophosphatase (ITPase, EC 3.6.1.19), an enzyme that does not permit accumulation of these nucleotides. dITP can be incorporated into DNA by polymerases. The deoxyribonucleotide dITP behaves as a dGTP analogue and is incorporated opposite cytosine with about 50% efficiency. Both isolated nuclei and purified DNA polymerases rapidly incorporated dITP into DNA. In the presence of ATP, dITP is stabilized in extracts of nuclei. dITP exist in all cells and is potentially mutagenic, and the levels of these nucleotides are controlled by ITPase. The function of this ubiquitous protein family is proposed to be the elimination of minor potentially mutagenic or clastogenic purine nucleoside triphosphates from the cell.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2'-Deoxy-Inosine 5'-(tetrahydrogen triphosphate)
  • 2'-Deoxy-inosine 5'-(tetrahydrogen triphosphoric acid)
  • 2'-Deoxyinosine triphosphoric acid
  • 2'-Deoxyinosine-5'-triphosphate
  • 2'-Deoxyinosine-5'-triphosphoric acid
  • 2'-Ditp
  • Deoxyinosine 5'-triphosphate
  • Deoxyinosine 5'-triphosphoric acid
  • Deoxyinosine triphosphate
  • Deoxyinosine triphosphoric acid
  • DITP
Chemical Formula: C10H15N4O13P3
Average Molecular Weight: 492.1664
Monoisotopic Molecular Weight: 491.984846122
InChI Key: UFJPAQSLHAGEBL-RRKCRQDMSA-N
InChI:InChI=1S/C10H15N4O13P3/c15-5-1-7(14-4-13-8-9(14)11-3-12-10(8)16)25-6(5)2-24-29(20,21)27-30(22,23)26-28(17,18)19/h3-7,15H,1-2H2,(H,20,21)(H,22,23)(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1
CAS number: 16595-02-1
IUPAC Name:{[hydroxy({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name: [hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid
SMILES:O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine 2'-deoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at position 2.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine deoxyribonucleotides
Direct Parent Purine 2'-deoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2'-deoxyribonucleoside triphosphate
  • Organic pyrophosphate
  • Hypoxanthine
  • 6-oxopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 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:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-3.355PhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.04 mg/mLALOGPS
logP-0.26ALOGPS
logP-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)2.85ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area248.56 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity92.01 m3·mol-1ChemAxon
Polarizability36.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2'-Deoxyinosine triphosphate + Water > DIMP + Hydrogen ion + Pyrophosphate
2'-Deoxyinosine triphosphate + Water > DIDP + Hydrogen ion + Phosphate
dATP + Hydrogen ion + Water > 2'-Deoxyinosine triphosphate + Ammonium
Adenosine triphosphate + DIDP <> ADP + 2'-Deoxyinosine triphosphate
2'-Deoxyinosine triphosphate + Water <> DIMP + Pyrophosphate
Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0901200000-094550daf6257cf48e86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-7da6dbb92e894a102adaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1910000000-297ae75d9d85a395a019View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0220900000-05764a0399ea663bda0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-7940100000-7be6289aa2147474bbc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9710000000-4a8af53537c11f3268feView in MoNA
References
References:
  • 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
  • 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
  • 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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28807
HMDB IDHMDB03537
Pubchem Compound ID146302
Kegg IDC01345
ChemSpider ID129052
Wikipedia IDNot Available
BioCyc IDDITP
EcoCyc IDDITP