2.0 2012-05-31 14:08:56 -0600 2015-06-03 15:54:53 -0600 ECMDB06555 M2MDB000681 DIMP dIMP is a deoxyribonucleoside and is considered a derivative of the nucleoside inosine, differing from the latter by the replacement of a hydroxyl group (-OH) by hydrogen (-H) at the 2' position of its ribose sugar moiety. The hydrolytic deamination of dAMP residues in DNA yields dIMP residues. The deamination of adenine residues in DNA generates hypoxanthine, which is mutagenic since it can pair not only with thymine but also with cytosine and therefore would result in A-T to G-C transitions after DNA replication. Hypoxanthine DNA glycosylase (EC 3.2.2.15) excises hypoxanthine from DNA containing dIMP residues in cells. (PMID: 10684927, 8016081) 2'-Deoxy-5'-inosinate 2'-Deoxy-5'-inosinic acid 2'-Deoxy-IMP 2'-Deoxyinosine 5'-monophosphate 2'-Deoxyinosine 5'-monophosphoric acid 2'-Deoxyinosine 5'-phosphate 2'-Deoxyinosine 5'-phosphoric acid 9-(2-deoxy-5-O-phosphono-&beta;-D-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-b-D-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-b-delta-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-b-δ-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-beta-delta-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol 9-(2-Deoxy-5-O-phosphono-β-δ-erythro-pentofuranosyl)-9H-purin-6-ol Deoxyinosine monophosphate Deoxyinosine monophosphoric acid DIMP Hypoxanthine deoxyriboside [(2R,3S,4R,5R)-3-hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphate [(2R,3S,4R,5R)-3-Hydroxy-5-(6-hydroxy-9H-purin-9-yl)tetrahydrofuran-2-yl]methyl dihydrogen phosphoric acid C10H13N4O7P 332.2066 332.052185302 {[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid [(2R,3S,5R)-3-hydroxy-5-(6-oxo-3H-purin-9-yl)oxolan-2-yl]methoxyphosphonic acid 3393-18-8 O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1 PHNGFPPXDJJADG-RRKCRQDMSA-N Solid Cytosol Extra-organism Periplasm logp -1.58 ALOGPS logs -2.20 ALOGPS solubility 2.10e+00 g/l ALOGPS logp -2.6 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 2.77 ChemAxon iupac {[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 332.2066 ChemAxon mono_mass 332.052185302 ChemAxon smiles O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=O ChemAxon formula C10H13N4O7P ChemAxon inchi InChI=1S/C10H13N4O7P/c15-5-1-7(21-6(5)2-20-22(17,18)19)14-4-13-8-9(14)11-3-12-10(8)16/h3-7,15H,1-2H2,(H,11,12,16)(H2,17,18,19)/t5-,6+,7+/m0/s1 ChemAxon inchikey PHNGFPPXDJJADG-RRKCRQDMSA-N ChemAxon polar_surface_area 155.5 ChemAxon refractivity 70.26 ChemAxon polarizability 27.21 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 4 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Thiamine metabolism ec00730 Specdb::CMs 883 Specdb::CMs 14679 Specdb::CMs 30896 Specdb::CMs 39038 Specdb::CMs 163105 Specdb::NmrOneD 74772 Specdb::NmrOneD 74773 Specdb::NmrOneD 74774 Specdb::NmrOneD 74775 Specdb::NmrOneD 74776 Specdb::NmrOneD 74777 Specdb::NmrOneD 74778 Specdb::NmrOneD 74779 Specdb::NmrOneD 74780 Specdb::NmrOneD 74781 Specdb::NmrOneD 74782 Specdb::NmrOneD 74783 Specdb::NmrOneD 74784 Specdb::NmrOneD 74785 Specdb::NmrOneD 74786 Specdb::NmrOneD 74787 Specdb::NmrOneD 74788 Specdb::NmrOneD 74789 Specdb::NmrOneD 74790 Specdb::NmrOneD 74791 Specdb::MsMs 6472 Specdb::MsMs 6473 Specdb::MsMs 6474 Specdb::MsMs 298444 Specdb::MsMs 298445 Specdb::MsMs 298446 Specdb::MsMs 340210 Specdb::MsMs 340211 Specdb::MsMs 340212 Specdb::MsMs 439045 Specdb::MsMs 447976 Specdb::MsMs 447977 Specdb::MsMs 2233365 Specdb::MsMs 2675602 Specdb::MsMs 2675603 Specdb::MsMs 2675604 Specdb::MsMs 3033587 Specdb::MsMs 3033588 Specdb::MsMs 3033589 HMDB06555 91531 82650 C06196 28806 DIMP OIP 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 Saparbaev, M., Mani, J. C., Laval, J. (2000). "Interactions of the human, rat, Saccharomyces cerevisiae and Escherichia coli 3-methyladenine-DNA glycosylases with DNA containing dIMP residues." Nucleic Acids Res 28:1332-1339. 10684927 Saparbaev M, Laval J: Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proc Natl Acad Sci U S A. 1994 Jun 21;91(13):5873-7. 8016081 Ogilvie, Kelvin K.; Slotin, Lewis A. Anhydronucleosides. XI. Synthesis of nucleotides from 8,2'-thioanhydropurine nucleosides. Canadian Journal of Chemistry (1973), 51(14), 2397-405. Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Nucleoside-triphosphatase rdgB P52061 RDGB_ECOLI rdgB http://ecmdb.ca/proteins/P52061.xml 5'-nucleotidase yfbR P76491 YFBR_ECOLI yfbR http://ecmdb.ca/proteins/P76491.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml DIMP + Water > Deoxyinosine + Phosphate 2'-Deoxyinosine triphosphate + Water > DIMP + Hydrogen ion + Pyrophosphate R03531 RXN0-1602 2'-Deoxyinosine triphosphate + Water <> DIMP + Pyrophosphate R03531 Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMP R02720