2.02012-05-31 14:04:04 -06002015-06-03 15:54:42 -0600ECMDB04063M2MDB0005932'-Deoxyinosine triphosphate2'-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. (PMID: 11278832)2'-Deoxy-Inosine 5'-(tetrahydrogen triphosphate)2'-Deoxy-inosine 5'-(tetrahydrogen triphosphoric acid)2'-Deoxyinosine triphosphoric acid2'-Deoxyinosine-5'-triphosphate2'-Deoxyinosine-5'-triphosphoric acid2'-DitpDeoxyinosine 5'-triphosphateDeoxyinosine 5'-triphosphoric acidDeoxyinosine triphosphateDeoxyinosine triphosphoric acidDITPC10H15N4O13P3492.1664491.984846122{[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[hydroxy({hydroxy[(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphoryl}oxy)phosphoryl]oxyphosphonic acid16595-02-1O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=OInChI=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/s1UFJPAQSLHAGEBL-RRKCRQDMSA-NSolidCytosollogp-0.26logs-1.99solubility5.04e+00 g/llogp-3.8pka_strongest_acidic0.89pka_strongest_basic2.85iupac{[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 acidaverage_mass492.1664mono_mass491.984846122smilesO[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=OformulaC10H15N4O13P3inchiInChI=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/s1inchikeyUFJPAQSLHAGEBL-RRKCRQDMSA-Npolar_surface_area248.56refractivity92.01polarizability36.03rotatable_bond_count8acceptor_count13donor_count6physiological_charge-4formal_charge0Purine metabolismec00230Thiamine metabolismec00730Specdb::CMs19663Specdb::CMs38622Specdb::CMs132748Specdb::CMs140482Specdb::NmrOneD28162Specdb::NmrOneD28163Specdb::NmrOneD28164Specdb::NmrOneD28165Specdb::NmrOneD28166Specdb::NmrOneD28167Specdb::NmrOneD28168Specdb::NmrOneD28169Specdb::NmrOneD28170Specdb::NmrOneD28171Specdb::NmrOneD28172Specdb::NmrOneD28173Specdb::NmrOneD28174Specdb::NmrOneD28175Specdb::NmrOneD28176Specdb::NmrOneD28177Specdb::NmrOneD28178Specdb::NmrOneD28179Specdb::NmrOneD28180Specdb::NmrOneD28181Specdb::MsMs30959Specdb::MsMs30960Specdb::MsMs30961Specdb::MsMs2316452Specdb::MsMs2316453Specdb::MsMs2316454Specdb::MsMs24401Specdb::MsMs24402Specdb::MsMs24403Specdb::MsMs2621699Specdb::MsMs2621700Specdb::MsMs2621701HMDB03537146302129052C01345DITPKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Lin, 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 276:18695-18701.11278832Nucleoside diphosphate kinaseP0A763NDK_ECOLIndkhttp://ecmdb.ca/proteins/P0A763.xmlNucleoside-triphosphatase rdgBP52061RDGB_ECOLIrdgBhttp://ecmdb.ca/proteins/P52061.xmlUPF0244 protein yjjXP39411YJJX_ECOLIyjjXhttp://ecmdb.ca/proteins/P39411.xmlNucleoside diphosphate kinaseP0A763NDK_ECOLIndkhttp://ecmdb.ca/proteins/P0A763.xml2'-Deoxyinosine triphosphate + Water > DIMP + Hydrogen ion + PyrophosphateR03531RXN0-16022'-Deoxyinosine triphosphate + Water > DIDP + Hydrogen ion + PhosphatedATP + Hydrogen ion + Water > 2'-Deoxyinosine triphosphate + AmmoniumAdenosine triphosphate + DIDP <> ADP + 2'-Deoxyinosine triphosphateR035302'-Deoxyinosine triphosphate + Water <> DIMP + PyrophosphateR03531Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMPR02720