2.0 2012-05-31 14:04:04 -0600 2015-06-03 15:54:42 -0600 ECMDB04063 M2MDB000593 2'-Deoxyinosine triphosphate 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. (PMID: 11278832) 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 C10H15N4O13P3 492.1664 491.984846122 {[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 acid 16595-02-1 O[C@H]1C[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1C=NC2=C1NC=NC2=O 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 UFJPAQSLHAGEBL-RRKCRQDMSA-N Solid Cytosol logp -0.26 ALOGPS logs -1.99 ALOGPS solubility 5.04e+00 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 0.89 ChemAxon pka_strongest_basic 2.85 ChemAxon iupac {[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 ChemAxon average_mass 492.1664 ChemAxon mono_mass 491.984846122 ChemAxon 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 ChemAxon formula C10H15N4O13P3 ChemAxon 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 ChemAxon inchikey UFJPAQSLHAGEBL-RRKCRQDMSA-N ChemAxon polar_surface_area 248.56 ChemAxon refractivity 92.01 ChemAxon polarizability 36.03 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 13 ChemAxon donor_count 6 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Thiamine metabolism ec00730 Specdb::CMs 19663 Specdb::CMs 38622 Specdb::CMs 132748 Specdb::CMs 140482 Specdb::NmrOneD 28162 Specdb::NmrOneD 28163 Specdb::NmrOneD 28164 Specdb::NmrOneD 28165 Specdb::NmrOneD 28166 Specdb::NmrOneD 28167 Specdb::NmrOneD 28168 Specdb::NmrOneD 28169 Specdb::NmrOneD 28170 Specdb::NmrOneD 28171 Specdb::NmrOneD 28172 Specdb::NmrOneD 28173 Specdb::NmrOneD 28174 Specdb::NmrOneD 28175 Specdb::NmrOneD 28176 Specdb::NmrOneD 28177 Specdb::NmrOneD 28178 Specdb::NmrOneD 28179 Specdb::NmrOneD 28180 Specdb::NmrOneD 28181 Specdb::MsMs 30959 Specdb::MsMs 30960 Specdb::MsMs 30961 Specdb::MsMs 2316452 Specdb::MsMs 2316453 Specdb::MsMs 2316454 Specdb::MsMs 24401 Specdb::MsMs 24402 Specdb::MsMs 24403 Specdb::MsMs 2621699 Specdb::MsMs 2621700 Specdb::MsMs 2621701 HMDB03537 146302 129052 C01345 DITP 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. 21097882 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. 22080510 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. 17765195 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. 11278832 Nucleoside diphosphate kinase P0A763 NDK_ECOLI ndk http://ecmdb.ca/proteins/P0A763.xml Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml UPF0244 protein yjjX P39411 YJJX_ECOLI yjjX http://ecmdb.ca/proteins/P39411.xml Nucleoside diphosphate kinase P0A763 NDK_ECOLI ndk http://ecmdb.ca/proteins/P0A763.xml 2'-Deoxyinosine triphosphate + Water > DIMP + Hydrogen ion + Pyrophosphate R03531 RXN0-1602 2'-Deoxyinosine triphosphate + Water > DIDP + Hydrogen ion + Phosphate dATP + Hydrogen ion + Water > 2'-Deoxyinosine triphosphate + Ammonium Adenosine triphosphate + DIDP <> ADP + 2'-Deoxyinosine triphosphate R03530 2'-Deoxyinosine triphosphate + Water <> DIMP + Pyrophosphate R03531 Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMP R02720