2.0 2012-05-31 13:56:37 -0600 2015-09-13 12:56:12 -0600 ECMDB02322 M2MDB000457 Cadaverine Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal tissue. However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by mammals. Cadaverine is toxic in large doses. In rats it had a low acute oral toxicity of more than 2000 mg/kg body weight (Wikipedia). 1,5-Diaminopentane 1,5-Diaminopentane dihydrochloride 1,5-Pentamethylenediamine 1,5-Pentanediamine BioDex 1- Cadaverin Cadaverine dihydrochloride Diaminopentane Pentamethylenediamine Pentamethylenediamine dihydrochloride Pentane-1,5-diamine C5H14N2 102.1781 102.115698458 pentane-1,5-diamine cadaverine 462-94-2 NCCCCCN InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 VHRGRCVQAFMJIZ-UHFFFAOYSA-N Liquid Cytosol Extra-organism Periplasm logp -0.27 ALOGPS logs -0.06 ALOGPS solubility 8.91e+01 g/l ALOGPS melting_point 9 oC logp -0.4 ChemAxon pka_strongest_basic 10.51 ChemAxon iupac pentane-1,5-diamine ChemAxon average_mass 102.1781 ChemAxon mono_mass 102.115698458 ChemAxon smiles NCCCCCN ChemAxon formula C5H14N2 ChemAxon inchi InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 ChemAxon inchikey VHRGRCVQAFMJIZ-UHFFFAOYSA-N ChemAxon polar_surface_area 52.04 ChemAxon refractivity 31.98 ChemAxon polarizability 13.11 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Glutathione metabolism The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. PW000833 ec00480 Metabolic Tropane, piperidine and pyridine alkaloid biosynthesis ec00960 Lysine degradation ec00310 Metabolic pathways eco01100 Lysine Degradation I Under conditions of anaerobiosis and phosphate starvation (believed to reflect conditions in the gut), E. coli converts glucose to weak organic acids which, though they are excreted, can reenter the cell and cause bactericidal acid stress even at only moderately acidic pH. Acid resistance system 4 (AR4) is the lysine-dependent acid resistance system which allows for the survival of E. coli under these conditions when lysine is available. AR4 couples the transport activity of a lysine:cadaverine antiporter, CadB, with lysine decarboxylase, CadA. CadB functions by exchanging external lysine for internal cadaverine. Lysine is imported into the cell through CadB or generated in the cell from aspartic acid. Within the cell, lysine is decarboxylated by CadA to cadaverine, releasing CO2 and replacing it with a proton. Cadaverine is then exported through CadB. This effectively consumes protons within the cytoplasm, raising the pH. The glutamate-dependent acid resistance system (AR2) is also able to provide acid resistance to E. coli growing under conditions of anaerobiosis and phosphate starvation, but to a slightly lesser degree than AR4 possibly due to the different pH optimums of their respective decarboxylase enzymes. AR2 is more efficient than AR3 or AR4 as a mediator of acid resistance at low pH. PW000772 Metabolic inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic aminopropylcadaverine biosynthesis Polyamines are important for cell growth and are believed to be involved in many processes including DNA, RNA, and protein synthesis, as well as membrane integrity and resistance to stress, to name a few. Cadaverine and aminopropylcadaverine are alternative polyamines that can at least partially substitute for purtrescine and spermidine, the primary polyamines found in E. coli. Lysine is decarboxylated to form cadaverine which is then converted to aminopropylcadaverine by the aminopropyltransferase, SpeE. (EcoCyc) PW002039 Metabolic aminopropylcadaverine biosynthesis PWY0-1303 lysine degradation I PWY0-461 Specdb::CMs 812 Specdb::CMs 813 Specdb::CMs 814 Specdb::CMs 815 Specdb::CMs 1519 Specdb::CMs 2857 Specdb::CMs 30110 Specdb::CMs 30176 Specdb::CMs 30267 Specdb::CMs 30491 Specdb::CMs 30751 Specdb::CMs 31406 Specdb::CMs 169376 Specdb::EiMs 1871 Specdb::NmrOneD 1873 Specdb::NmrOneD 3871 Specdb::NmrOneD 4140 Specdb::NmrOneD 5097 Specdb::NmrOneD 5098 Specdb::NmrOneD 116218 Specdb::NmrOneD 116219 Specdb::NmrOneD 116220 Specdb::NmrOneD 116221 Specdb::NmrOneD 116222 Specdb::NmrOneD 116223 Specdb::NmrOneD 116224 Specdb::NmrOneD 116225 Specdb::NmrOneD 116226 Specdb::NmrOneD 116227 Specdb::NmrOneD 116228 Specdb::NmrOneD 116229 Specdb::NmrOneD 116230 Specdb::NmrOneD 116231 Specdb::NmrOneD 116232 Specdb::NmrOneD 116233 Specdb::NmrOneD 116234 Specdb::NmrOneD 116235 Specdb::NmrOneD 116236 Specdb::NmrOneD 116237 Specdb::MsMs 2055 Specdb::MsMs 2056 Specdb::MsMs 2057 Specdb::MsMs 5759 Specdb::MsMs 5760 Specdb::MsMs 5761 Specdb::MsMs 5762 Specdb::MsMs 5763 Specdb::MsMs 5768 Specdb::MsMs 20075 Specdb::MsMs 20076 Specdb::MsMs 20077 Specdb::MsMs 20516 Specdb::MsMs 20517 Specdb::MsMs 20518 Specdb::MsMs 21626 Specdb::MsMs 21627 Specdb::MsMs 21628 Specdb::MsMs 22067 Specdb::MsMs 22068 Specdb::MsMs 22069 Specdb::MsMs 445870 Specdb::MsMs 445871 Specdb::MsMs 445872 Specdb::MsMs 445873 Specdb::NmrTwoD 1810 HMDB02322 273 13866593 C01672 18127 CADAVERINE N2P Cadaverine Keseler, I. 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Clin Sci (Lond). 1993 Oct;85(4):451-4. 8222511 http://hmdb.ca/system/metabolites/msds/000/001/905/original/HMDB02322.pdf?1358461716 Spermidine synthase P09158 SPEE_ECOLI speE http://ecmdb.ca/proteins/P09158.xml Lysine decarboxylase, inducible P0A9H3 LDCI_ECOLI cadA http://ecmdb.ca/proteins/P0A9H3.xml Primary amine oxidase P46883 AMO_ECOLI tynA http://ecmdb.ca/proteins/P46883.xml Lysine decarboxylase, constitutive P52095 DCLZ_ECOLI ldcC http://ecmdb.ca/proteins/P52095.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 Probable cadaverine/lysine antiporter P0AAE8 CADB_ECOLI cadB http://ecmdb.ca/proteins/P0AAE8.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Hydrogen ion + L-Lysine <> Cadaverine + Carbon dioxide R00462 LYSDECARBOX-RXN Cadaverine + S-Adenosylmethioninamine > 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine R08359 RXN0-5217 L-Lysine <> Cadaverine + Carbon dioxide R00462 Cadaverine + Water + Oxygen <> 5-Aminopentanal + Ammonia + Hydrogen peroxide R06740 S-Adenosylmethioninamine + Cadaverine <> 5'-Methylthioadenosine + Aminopropylcadaverine R08359 Hydrogen ion + L-Lysine > Carbon dioxide + Cadaverine LYSDECARBOX-RXN L-Lysine > Cadaverine + Carbon dioxide L-Lysine + Hydrogen ion + L-Lysine > Cadaverine + Carbon dioxide PW_R002534 L-Lysine + L-Lysine > Cadaverine PW_R002535 Cadaverine + Decarboxy-SAM > Aminopropylcadaverine + 5'-Methylthioadenosine + Hydrogen ion PW_R005959 Cadaverine + S-Adenosylmethioninamine >5 5'-Methylthioadenosine + Hydrogen ion + Aminopropylcadaverine 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Shake flask 1750.0 uM 0.0 37 oC K12 HB101 Mid Log Phase 7000000 0 Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. 8742354 199 Medium with Earle’s salts –which contains 21 amino acids, 17 vitamins, 10 components of nucleic acids, sodium acetate, glucose, NaC1, KCl, CaC12, MgS04, Na2HP04, and Fe(N03)3 Shake flask 200.0 uM 0.0 37 oC K12 HB101 Stationary Phase 800000 0 Hamana, K. (1996). "Distribution of diaminopropane and acetylspermidine in Enterobacteriaceae." Can J Microbiol 42:107-114. 8742354