2.02012-05-31 14:08:56 -06002015-06-03 15:54:53 -0600ECMDB06555M2MDB000681DIMPdIMP 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'-inosinate2'-Deoxy-5'-inosinic acid2'-Deoxy-IMP2'-Deoxyinosine 5'-monophosphate2'-Deoxyinosine 5'-monophosphoric acid2'-Deoxyinosine 5'-phosphate2'-Deoxyinosine 5'-phosphoric acid9-(2-deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-b-D-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-b-delta-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-b-δ-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-beta-delta-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-9H-purin-6-ol9-(2-Deoxy-5-O-phosphono-β-δ-erythro-pentofuranosyl)-9H-purin-6-olDeoxyinosine monophosphateDeoxyinosine monophosphoric acidDIMPHypoxanthine 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 acidC10H13N4O7P332.2066332.052185302{[(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 acid3393-18-8O[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=OInChI=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/s1PHNGFPPXDJJADG-RRKCRQDMSA-NSolidCytosolExtra-organismPeriplasmlogp-1.58logs-2.20solubility2.10e+00 g/llogp-2.6pka_strongest_acidic1.22pka_strongest_basic2.77iupac{[(2R,3S,5R)-3-hydroxy-5-(6-oxo-6,9-dihydro-3H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acidaverage_mass332.2066mono_mass332.052185302smilesO[C@H]1C[C@@H](O[C@@H]1COP(O)(O)=O)N1C=NC2=C1NC=NC2=OformulaC10H13N4O7PinchiInChI=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/s1inchikeyPHNGFPPXDJJADG-RRKCRQDMSA-Npolar_surface_area155.5refractivity70.26polarizability27.21rotatable_bond_count4acceptor_count9donor_count4physiological_charge-3formal_charge0Purine metabolismec00230Thiamine metabolismec00730Specdb::CMs883Specdb::CMs14679Specdb::CMs30896Specdb::CMs39038Specdb::CMs163105Specdb::NmrOneD74772Specdb::NmrOneD74773Specdb::NmrOneD74774Specdb::NmrOneD74775Specdb::NmrOneD74776Specdb::NmrOneD74777Specdb::NmrOneD74778Specdb::NmrOneD74779Specdb::NmrOneD74780Specdb::NmrOneD74781Specdb::NmrOneD74782Specdb::NmrOneD74783Specdb::NmrOneD74784Specdb::NmrOneD74785Specdb::NmrOneD74786Specdb::NmrOneD74787Specdb::NmrOneD74788Specdb::NmrOneD74789Specdb::NmrOneD74790Specdb::NmrOneD74791Specdb::MsMs6472Specdb::MsMs6473Specdb::MsMs6474Specdb::MsMs298444Specdb::MsMs298445Specdb::MsMs298446Specdb::MsMs340210Specdb::MsMs340211Specdb::MsMs340212Specdb::MsMs439045Specdb::MsMs447976Specdb::MsMs447977Specdb::MsMs2233365Specdb::MsMs2675602Specdb::MsMs2675603Specdb::MsMs2675604Specdb::MsMs3033587Specdb::MsMs3033588Specdb::MsMs3033589HMDB065559153182650C0619628806DIMPOIPKeseler, 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 370:17-25.17765195Saparbaev, 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 28:1332-1339.10684927Saparbaev 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):5873-7.8016081Ogilvie, 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 ushAP07024USHA_ECOLIushAhttp://ecmdb.ca/proteins/P07024.xmlMultifunctional protein surEP0A840SURE_ECOLIsurEhttp://ecmdb.ca/proteins/P0A840.xmlClass B acid phosphataseP0AE22APHA_ECOLIaphAhttp://ecmdb.ca/proteins/P0AE22.xmlNucleoside-triphosphatase rdgBP52061RDGB_ECOLIrdgBhttp://ecmdb.ca/proteins/P52061.xml5'-nucleotidase yfbRP76491YFBR_ECOLIyfbRhttp://ecmdb.ca/proteins/P76491.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlDIMP + Water > Deoxyinosine + Phosphate2'-Deoxyinosine triphosphate + Water > DIMP + Hydrogen ion + PyrophosphateR03531RXN0-16022'-Deoxyinosine triphosphate + Water <> DIMP + PyrophosphateR03531Xanthosine 5-triphosphate + Water + 2'-Deoxyinosine triphosphate <> Xanthylic acid + Pyrophosphate + DIMPR02720