2.0 2012-05-31 13:59:45 -0600 2015-09-13 12:56:13 -0600 ECMDB03551 M2MDB000513 Carbamic acid Carbamic acid products of several amines, such as beta-N-methylamino-L-alanine (BMAA), ethylenediamine, and L-cysteine have been implicated in toxicity. Studies suggested that a significant portion of amino-compounds in biological samples (that naturally contain CO2/bicarbonate) can be present as a carbamic acid. There has been no obvious species specificity for their formation and no preference for 1 or 2 degree amines. Many biological reactions have also been described in the literature that involve the reaction of CO2 with amino groups of biomolecules. For example, CO2 generated from cellular respiration is expired in part through the reversible formation of a carbamate between CO2 and the -amino groups of the alpha and beta-chains of hemoglobin. The carbamic acid is also a substrate for glucuronidation and results in a stable carbamate glucuronide metabolite. The detection and characterization of these products has been facilitated greatly by the advent of soft ionization mass spectrometry techniques and high field NMR instrumentation. (PMID: 16268118, 17168688, 12929145) Aminoformate Aminoformic acid Carbamate Carbamate ion Carbamic acid Carbamic acid ion Chlorphenesin carbamate Chlorphenesin carbamic acid Maolate Maolic acid CH3NO2 61.04 61.016378345 carbamic acid carbamic acid 463-77-4 NC(O)=O InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) KXDHJXZQYSOELW-UHFFFAOYSA-N Solid Cytosol logp -1.10 ALOGPS logs 0.79 ALOGPS solubility 3.79e+02 g/l ALOGPS logp -0.56 ChemAxon pka_strongest_acidic 3.92 ChemAxon iupac carbamic acid ChemAxon average_mass 61.04 ChemAxon mono_mass 61.016378345 ChemAxon smiles NC(O)=O ChemAxon formula CH3NO2 ChemAxon inchi InChI=1S/CH3NO2/c2-1(3)4/h2H2,(H,3,4) ChemAxon inchikey KXDHJXZQYSOELW-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 11.32 ChemAxon polarizability 4.68 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Alanine, aspartate and glutamate metabolism ec00250 Nitrogen metabolism The biological process of the nitrogen cycle is a complex interplay among many microorganisms catalyzing different reactions, where nitrogen is found in various oxidation states ranging from +5 in nitrate to -3 in ammonia. The ability of fixing atmospheric nitrogen by the nitrogenase enzyme complex is present in restricted prokaryotes (diazotrophs). The other reduction pathways are assimilatory nitrate reduction and dissimilatory nitrate reduction both for conversion to ammonia, and denitrification. Denitrification is a respiration in which nitrate or nitrite is reduced as a terminal electron acceptor under low oxygen or anoxic conditions, producing gaseous nitrogen compounds (N2, NO and N2O) to the atmosphere. Nitrate can be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK or a nitrate / nitrite transporter NarU. Nitrate is then reduced by a Nitrate Reductase resulting in the release of water, an acceptor and a Nitrite. Nitrite can also be introduced into the cytoplasm through a nitrate:nitrite antiporter NarK Nitrite can be reduced a NADPH dependent nitrite reductase resulting in water and NAD and Ammonia. Nitrite can interact with hydrogen ion, ferrocytochrome c through a cytochrome c-552 ferricytochrome resulting in the release of ferricytochrome c, water and ammonia Another process by which ammonia is produced is by a reversible reaction of hydroxylamine with a reduced acceptor through a hydroxylamine reductase resulting in an acceptor, water and ammonia. Water and carbon dioxide react through a carbonate dehydratase resulting in carbamic acid. This compound reacts spontaneously with hydrogen ion resulting in the release of carbon dioxide and ammonia. Carbon dioxide can interact with water through a carbonic anhydrase resulting in hydrogen carbonate. This compound interacts with cyanate and hydrogen ion through a cyanate hydratase resulting in a carbamic acid. Ammonia can be metabolized by reacting with L-glutamine and ATP driven glutamine synthetase resulting in ADP, phosphate and L-glutamine. The latter compound reacts with oxoglutaric acid and hydrogen ion through a NADPH dependent glutamate synthase resulting in the release of NADP and L-glutamic acid. L-glutamic acid reacts with water through a NADP-specific glutamate dehydrogenase resulting in the release of oxoglutaric acid, NADPH, hydrogen ion and ammonia. PW000755 ec00910 Metabolic Pyrimidine metabolism The metabolism of pyrimidines begins with L-glutamine interacting with water molecule and a hydrogen carbonate through an ATP driven carbamoyl phosphate synthetase resulting in a hydrogen ion, an ADP, a phosphate, an L-glutamic acid and a carbamoyl phosphate. The latter compound interacts with an L-aspartic acid through a aspartate transcarbamylase resulting in a phosphate, a hydrogen ion and a N-carbamoyl-L-aspartate. The latter compound interacts with a hydrogen ion through a dihydroorotase resulting in the release of a water molecule and a 4,5-dihydroorotic acid. This compound interacts with an ubiquinone-1 through a dihydroorotate dehydrogenase, type 2 resulting in a release of an ubiquinol-1 and an orotic acid. The orotic acid then interacts with a phosphoribosyl pyrophosphate through a orotate phosphoribosyltransferase resulting in a pyrophosphate and an orotidylic acid. The latter compound then interacts with a hydrogen ion through an orotidine-5 '-phosphate decarboxylase, resulting in an release of carbon dioxide and an Uridine 5' monophosphate. The Uridine 5' monophosphate process to get phosphorylated by an ATP driven UMP kinase resulting in the release of an ADP and an Uridine 5--diphosphate. Uridine 5-diphosphate can be metabolized in multiple ways in order to produce a Deoxyuridine triphosphate. 1.-Uridine 5-diphosphate interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in the release of a water molecule and an oxidized thioredoxin and an dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 2.-Uridine 5-diphosphate interacts with a reduced NrdH glutaredoxin-like protein through a Ribonucleoside-diphosphate reductase 1 resulting in a release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dUDP. The dUDP is then phosphorylated by an ATP through a nucleoside diphosphate kinase resulting in the release of an ADP and a DeoxyUridine triphosphate. 3.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate. The latter compound interacts with a reduced flavodoxin through ribonucleoside-triphosphate reductase resulting in the release of an oxidized flavodoxin, a water molecule and a Deoxyuridine triphosphate 4.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate interacts with a reduced flavodoxin through a ribonucleoside-triphosphate reductase resulting in the release of a water molecule, an oxidized flavodoxin and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 5.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP then interacts with a reduced NrdH glutaredoxin-like protein through a ribonucleoside-diphosphate reductase 2 resulting in the release of a water molecule, an oxidized NrdH glutaredoxin-like protein and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. 6.-Uridine 5-diphosphate is phosphorylated by an ATP-driven nucleoside diphosphate kinase resulting in an ADP and an Uridinetriphosphate The uridine triphosphate interacts with a L-glutamine and a water molecule through an ATP driven CTP synthase resulting in an ADP, a phosphate, a hydrogen ion, an L-glutamic acid and a cytidine triphosphate. The cytidine triphosphate then interacts spontaneously with a water molecule resulting in the release of a phosphate, a hydrogen ion and a CDP. The CDP interacts with a reduced thioredoxin through a ribonucleoside diphosphate reductase 1 resulting in a release of a water molecule, an oxidized thioredoxin and a dCDP. The dCDP is then phosphorylated through an ATP driven nucleoside diphosphate kinase resulting in an ADP and a dCTP. The dCTP interacts with a water molecule and a hydrogen ion through a dCTP deaminase resulting in a release of an ammonium molecule and a Deoxyuridine triphosphate. The deoxyuridine triphosphate then interacts with a water molecule through a nucleoside triphosphate pyrophosphohydrolase resulting in a release of a hydrogen ion, a phosphate and a dUMP. The dUMP then interacts with a methenyltetrahydrofolate through a thymidylate synthase resulting in a dihydrofolic acid and a 5-thymidylic acid. Then 5-thymidylic acid is then phosphorylated through a nucleoside diphosphate kinase resulting in the release of an ADP and thymidine 5'-triphosphate. PW000942 ec00240 Metabolic Metabolic pathways eco01100 Uracil degradation III PW002026 Metabolic cyanate degradation The cyanate degradation pathway begins with the transportation of cyanate into the cytosol through a cynX transporter. Once inside the cytosol cyanate reacts with hydrogen carbonate and a hydrogen ion through a cyanase resulting in the release of carbon dioxide and carbamate. Carbamate reacts spontaneously with hydrogen resulting in the release of ammonium and carbon dioxide. Carbon dioxide reacts with water through carbonic anhydrase resulting in the release of hydrogen ion and hydrogen carbonate. PW002099 Metabolic uracil degradation III PWY0-1471 cyanate degradation CYANCAT-PWY Specdb::CMs 24121 Specdb::CMs 38628 Specdb::CMs 154700 Specdb::NmrOneD 283509 Specdb::NmrOneD 283510 Specdb::NmrOneD 283511 Specdb::NmrOneD 283512 Specdb::NmrOneD 283513 Specdb::NmrOneD 283514 Specdb::NmrOneD 283515 Specdb::NmrOneD 283516 Specdb::NmrOneD 283517 Specdb::NmrOneD 283518 Specdb::NmrOneD 283519 Specdb::NmrOneD 283520 Specdb::NmrOneD 283521 Specdb::NmrOneD 283522 Specdb::NmrOneD 283523 Specdb::NmrOneD 283524 Specdb::NmrOneD 283525 Specdb::NmrOneD 283526 Specdb::NmrOneD 283527 Specdb::NmrOneD 283528 Specdb::MsMs 20651 Specdb::MsMs 20652 Specdb::MsMs 20653 Specdb::MsMs 22202 Specdb::MsMs 22203 Specdb::MsMs 22204 Specdb::MsMs 3035489 Specdb::MsMs 3035490 Specdb::MsMs 3035491 Specdb::MsMs 3105239 Specdb::MsMs 3105240 Specdb::MsMs 3105241 HMDB03551 277 271 C01563 28616 CARBAMATE OUT Carbamic acid 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Rendon von Osten, J., Epomex, C., Tinoco-Ojanguren, R., Soares, A. M., Guilhermino, L. (2004). "Effect of pesticide exposure on acetylcholinesterase activity in subsistence farmers from Campeche, Mexico." Arch Environ Health 59:418-425. 16268118 Schaefer WH: Reaction of primary and secondary amines to form carbamic acid glucuronides. Curr Drug Metab. 2006 Dec;7(8):873-81. 17168688 Smit LA, van-Wendel-de-Joode BN, Heederik D, Peiris-John RJ, van der Hoek W: Neurological symptoms among Sri Lankan farmers occupationally exposed to acetylcholinesterase-inhibiting insecticides. Am J Ind Med. 2003 Sep;44(3):254-64. 12929145 http://hmdb.ca/system/metabolites/msds/000/003/132/original/HMDB03551.pdf?1358462089 Cyanate hydratase P00816 CYNS_ECOLI cynS http://ecmdb.ca/proteins/P00816.xml Carbamate kinase P37306 ARCC_ECOLI arcC http://ecmdb.ca/proteins/P37306.xml Carbamate kinase-like protein yahI P77624 ARCM_ECOLI yahI http://ecmdb.ca/proteins/P77624.xml Carbamate kinase-like protein yqeA Q46807 ARCL_ECOLI yqeA http://ecmdb.ca/proteins/Q46807.xml Putative isochorismatase family protein rutB P75897 RUTB_ECOLI rutB http://ecmdb.ca/proteins/P75897.xml Water + Ureidoacrylate peracid > Carbamic acid + Hydrogen ion + Peroxyaminoacrylate R09947 RXN0-6460 Carbamic acid + 2 Hydrogen ion > Carbon dioxide + Ammonium Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate R01395 Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid R03546 R524-RXN Ureidoacrylate peracid + Water <> Peroxyaminoacrylate + Carbamic acid R09947 Ureidoacrylate + Water <> 3-Aminoacrylate + Carbamic acid R09980 Carbamic acid + Hydrogen ion > Ammonia + Carbon dioxide RXN0-5222 3-ureidoacrylate + Water > Hydrogen ion + Carbamic acid + 3-Aminoacrylate RXN0-6451 Cyanate + Hydrogen carbonate + Hydrogen ion > Carbamic acid + Carbon dioxide R524-RXN (<i>Z</i>)-2-methylureidoacrylate peracid + Water > (<i>Z</i>)-2-methyl-peroxyaminoacrylate + Carbamic acid + Hydrogen ion RXN-12896 2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate R00575 Cyanate + Hydrogen carbonate + 2 Hydrogen ion + Carbamic acid <> Ammonia +2 Carbon dioxide R10079 Ureidoacrylate peracid + Water + Carbamic acid + (Z)-2-Methyl-ureidoacrylate peracid <> Peroxyaminoacrylate + Carbon dioxide + Ammonia + (Z)-2-Methyl-peroxyaminoacrylate R09948 Hydrogen carbonate + Cyanate + Hydrogen ion + Cyanate > Carbamic acid PW_R002431 Carbon dioxide + Water > Carbamic acid PW_R002432 Ureidoacrylate peracid + Water > Peroxyaminoacrylate + Carbamic acid + Hydrogen ion + 3-Aminoacrylate PW_R005906 Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate Cyanate + Hydrogen ion + Hydrogen carbonate <> Carbon dioxide + Carbamic acid