2.0 2012-05-31 13:01:59 -0600 2015-09-13 12:56:09 -0600 ECMDB00905 M2MDB000199 Deoxyadenosine monophosphate Adenosine is a nucleoside comprised of adenine attached to a ribose (ribofuranose) moiety via a -N9-glycosidic bond. 2'-dAMP 2'-Deoxy-5'-adenylate 2'-Deoxy-5'-adenylic acid 2'-Deoxy-adenosine 5'-phosphate 2'-Deoxy-Adenosine 5'-phosphorate 2'-Deoxy-Adenosine 5'-phosphoric acid 2'-Deoxy-AMP 2'-Deoxyadenosine 5'-monophosphate 2'-Deoxyadenosine 5'-monophosphoric acid 2'-Deoxyadenosine 5'-phosphate 2'-Deoxyadenosine 5'-phosphoric acid 2'-Deoxyadenosine monophosphate 2'-Deoxyadenosine monophosphoric acid 2'-Deoxyadenosine-5'-monophosphate 2'-Deoxyadenosine-5'-monophosphoric acid 2'-Deoxyadenosine-5'-phosphate 2'-Deoxyadenosine-5'-phosphoric acid 2'-Deoxyadenylate 2'-Deoxyadenylic acid DAMP Deoxy-5'-adenylate Deoxy-5'-adenylic acid Deoxy-AMP Deoxyadenosine 5'-monophosphate Deoxyadenosine 5'-monophosphoric acid Deoxyadenosine 5'-phosphate Deoxyadenosine 5'-phosphoric acid Deoxyadenosine monophosphate Deoxyadenosine monophosphoric acid Deoxyadenosine-phosphate Deoxyadenosine-phosphoric acid Deoxyadenylate Deoxyadenylic acid PdA C10H14N5O6P 331.2218 331.068169717 {[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid DAMP 653-63-4 NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 KHWCHTKSEGGWEX-RRKCRQDMSA-N Solid Cytosol Extra-organism Periplasm logp -2.44 ALOGPS logs -2.09 ALOGPS solubility 2.71e+00 g/l ALOGPS melting_point 148 oC logp -3.8 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic 3.94 ChemAxon iupac {[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 331.2218 ChemAxon mono_mass 331.068169717 ChemAxon smiles NC1=NC=NC2=C1N=CN2[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 ChemAxon formula C10H14N5O6P ChemAxon inchi InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1 ChemAxon inchikey KHWCHTKSEGGWEX-RRKCRQDMSA-N ChemAxon polar_surface_area 165.84 ChemAxon refractivity 72.56 ChemAxon polarizability 28.98 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 9 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Purine metabolism ec00230 Specdb::CMs 672 Specdb::CMs 11895 Specdb::CMs 30844 Specdb::CMs 37835 Specdb::CMs 137640 Specdb::CMs 145374 Specdb::CMs 1081347 Specdb::CMs 1081349 Specdb::CMs 1081351 Specdb::CMs 1081353 Specdb::CMs 1081355 Specdb::NmrOneD 1282 Specdb::NmrOneD 1597 Specdb::NmrOneD 4709 Specdb::NmrOneD 4894 Specdb::NmrOneD 21002 Specdb::NmrOneD 21003 Specdb::NmrOneD 21004 Specdb::NmrOneD 21005 Specdb::NmrOneD 21006 Specdb::NmrOneD 21007 Specdb::NmrOneD 21008 Specdb::NmrOneD 21009 Specdb::NmrOneD 21010 Specdb::NmrOneD 21011 Specdb::NmrOneD 21012 Specdb::NmrOneD 21013 Specdb::NmrOneD 21014 Specdb::NmrOneD 21015 Specdb::NmrOneD 21016 Specdb::NmrOneD 21017 Specdb::NmrOneD 21018 Specdb::NmrOneD 21019 Specdb::NmrOneD 21020 Specdb::NmrOneD 21021 Specdb::NmrOneD 166510 Specdb::MsMs 1289 Specdb::MsMs 1290 Specdb::MsMs 1291 Specdb::MsMs 4869 Specdb::MsMs 4870 Specdb::MsMs 4871 Specdb::MsMs 178050 Specdb::MsMs 178051 Specdb::MsMs 178052 Specdb::MsMs 180363 Specdb::MsMs 180364 Specdb::MsMs 180365 Specdb::MsMs 439042 Specdb::MsMs 447970 Specdb::MsMs 447971 Specdb::MsMs 2236518 Specdb::MsMs 2236880 Specdb::MsMs 2238651 Specdb::MsMs 2238906 Specdb::MsMs 2240654 Specdb::MsMs 2241061 Specdb::MsMs 2242684 Specdb::MsMs 2243139 Specdb::MsMs 2244715 Specdb::MsMs 2244833 Specdb::NmrTwoD 1045 Specdb::NmrTwoD 1538 HMDB00905 621 12079 C00360 17713 DAMP DA Deoxyadenosine monophosphate 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 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Hohenester E, Hutchinson WL, Pepys MB, Wood SP: Crystal structure of a decameric complex of human serum amyloid P component with bound dAMP. J Mol Biol. 1997 Jun 20;269(4):570-8. 9217261 Avkin S, Adar S, Blander G, Livneh Z: Quantitative measurement of translesion replication in human cells: evidence for bypass of abasic sites by a replicative DNA polymerase. Proc Natl Acad Sci U S A. 2002 Mar 19;99(6):3764-9. Epub 2002 Mar 12. 11891323 Duarte V, Muller JG, Burrows CJ: Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 1999 Jan 15;27(2):496-502. 9862971 Chen XR, Li GM, Wang JR, Chen JJ: [Portal hemodynamics in patients with different syndromes of cirrhosis] Zhong Xi Yi Jie He Xue Bao. 2004 May;2(3):178-81. 15339437 Zhong H, Zang KT: Therapeutic approaches for chronic gastralgia based on differentiation of symptoms and signs. Di Yi Jun Yi Da Xue Xue Bao. 2002 Jul;22(7):639-40. 12376299 Hashimoto K, Tominaga Y, Nakabeppu Y, Moriya M: Futile short-patch DNA base excision repair of adenine:8-oxoguanine mispair. Nucleic Acids Res. 2004 Nov 5;32(19):5928-34. Print 2004. 15531653 Zhang Q, Zhang WT, Wei JJ, Wang XB, Liu P: [Combined use of factor analysis and cluster analysis in classification of traditional Chinese medical syndromes in patients with posthepatitic cirrhosis] Zhong Xi Yi Jie He Xue Bao. 2005 Jan;3(1):14-8. 15644152 Levine RL, Yang IY, Hossain M, Pandya GA, Grollman AP, Moriya M: Mutagenesis induced by a single 1,N6-ethenodeoxyadenosine adduct in human cells. Cancer Res. 2000 Aug 1;60(15):4098-104. 10945616 Scarano, E. Incorporation of adenine-C14 into deoxyadenylic acid. Bollettino - Societa Italiana di Biologia Sperimentale (1958), 34 1620-1. http://hmdb.ca/system/metabolites/msds/000/000/817/original/HMDB00905.pdf?1358461499 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 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml Class B acid phosphatase P0AE22 APHA_ECOLI aphA http://ecmdb.ca/proteins/P0AE22.xml Protein mazG P0AEY3 MAZG_ECOLI mazG http://ecmdb.ca/proteins/P0AEY3.xml Dihydroneopterin triphosphate pyrophosphatase P0AFC0 NUDB_ECOLI nudB http://ecmdb.ca/proteins/P0AFC0.xml Adenylate kinase P69441 KAD_ECOLI adk http://ecmdb.ca/proteins/P69441.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 Deoxyadenosine monophosphate + Water > Deoxyadenosine + Phosphate dATP + Water > Deoxyadenosine monophosphate + Hydrogen ion + Pyrophosphate RXN0-384 Adenosine triphosphate + Deoxyadenosine monophosphate <> ADP + dADP R01547 Deoxyadenosine monophosphate + Water <> Deoxyadenosine + Phosphate R02088 Deoxyadenosine monophosphate + Water > Deoxyadenosine + Phosphate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 8.84 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 35360 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 14.5 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 58000 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776