2.0 2012-05-31 13:48:23 -0600 2015-09-13 12:56:10 -0600 ECMDB01256 M2MDB000311 Spermine Spermine is a biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure. 1,5,10,14-Tetraazatetradecane 4,9-Diaza-1,12-dodecanediamine 4,9-Diazadodecamethylenediamine 4,9-Diazadodecane-1,12-diamine Diaminopropyl-tetramethylenediamine Diaminopropyltetramethylenediamine Gerontine Musculamine N,N'-Bis(3-aminopropyl)-1,4-Butanediamine N,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamine N,N'-Bis(3-aminopropyl)butane-1,4-diamine N1,N4-bis(3-aminopropyl)-1,4-butanediamine Neuridine Spermin Spermine Spermine dihydrate Spermine dihydric acid Spermine puriss SPM C10H26N4 202.3402 202.215746852 (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine spermine 71-44-3 NCCCNCCCCNCCCN InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 PFNFFQXMRSDOHW-UHFFFAOYSA-N Solid Cytoplasm Periplasm logp -0.66 ALOGPS logs -1.97 ALOGPS solubility 2.19e+00 g/l ALOGPS melting_point 29 oC logp -1.5 ChemAxon pka_strongest_basic 10.8 ChemAxon iupac (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine ChemAxon average_mass 202.3402 ChemAxon mono_mass 202.215746852 ChemAxon smiles NCCCNCCCCNCCCN ChemAxon formula C10H26N4 ChemAxon inchi InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2 ChemAxon inchikey PFNFFQXMRSDOHW-UHFFFAOYSA-N ChemAxon polar_surface_area 76.1 ChemAxon refractivity 62.56 ChemAxon polarizability 26.69 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 4 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 Arginine and proline metabolism ec00330 beta-Alanine metabolism The Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate. Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets. PW000896 ec00410 Metabolic Specdb::CMs 713 Specdb::CMs 714 Specdb::CMs 715 Specdb::CMs 716 Specdb::CMs 717 Specdb::CMs 2057 Specdb::CMs 2082 Specdb::CMs 2104 Specdb::CMs 2216 Specdb::CMs 3229 Specdb::CMs 30404 Specdb::CMs 30405 Specdb::CMs 30694 Specdb::CMs 30932 Specdb::CMs 30933 Specdb::CMs 31299 Specdb::CMs 31300 Specdb::CMs 31301 Specdb::CMs 31302 Specdb::CMs 31889 Specdb::CMs 31890 Specdb::CMs 31891 Specdb::CMs 31892 Specdb::CMs 166578 Specdb::EiMs 918 Specdb::NmrOneD 1670 Specdb::NmrOneD 4804 Specdb::NmrOneD 4805 Specdb::NmrOneD 146970 Specdb::NmrOneD 146971 Specdb::NmrOneD 146972 Specdb::NmrOneD 146973 Specdb::NmrOneD 146974 Specdb::NmrOneD 146975 Specdb::NmrOneD 146976 Specdb::NmrOneD 146977 Specdb::NmrOneD 146978 Specdb::NmrOneD 146979 Specdb::NmrOneD 146980 Specdb::NmrOneD 146981 Specdb::NmrOneD 146982 Specdb::NmrOneD 146983 Specdb::NmrOneD 146984 Specdb::NmrOneD 146985 Specdb::NmrOneD 146986 Specdb::NmrOneD 146987 Specdb::NmrOneD 146988 Specdb::NmrOneD 146989 Specdb::MsMs 1487 Specdb::MsMs 1488 Specdb::MsMs 1489 Specdb::MsMs 5123 Specdb::MsMs 5124 Specdb::MsMs 5125 Specdb::MsMs 5126 Specdb::MsMs 5127 Specdb::MsMs 5128 Specdb::MsMs 5129 Specdb::MsMs 5130 Specdb::MsMs 5131 Specdb::MsMs 5132 Specdb::MsMs 5133 Specdb::MsMs 5134 Specdb::MsMs 5135 Specdb::MsMs 5136 Specdb::MsMs 5137 Specdb::MsMs 5138 Specdb::MsMs 21233 Specdb::MsMs 21234 Specdb::MsMs 21235 Specdb::MsMs 22784 Specdb::MsMs 22785 Specdb::MsMs 22786 Specdb::NmrTwoD 1061 Specdb::NmrTwoD 1611 HMDB01256 1103 1072 C00750 15746 SPERMINE SPM Spermine 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 Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. 18402659 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 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. 19212411 Mollica F, Li Volti S, Rapisarda A, Longo G, Pavone L, Vanella A: Increased erythrocytic spermine in Duchenne muscular dystrophy. Pediatr Res. 1980 Nov;14(11):1196-8. 7454431 Swift TA, Dias JA: Effects of the polyamine spermine on binding of follicle-stimulating hormone to membrane-bound immature bovine testis receptors. Biochim Biophys Acta. 1986 Feb 21;885(2):221-30. 3004602 Cipolla BG, Ziade J, Bansard JY, Moulinoux JP, Staerman F, Quemener V, Lobel B, Guille F: Pretherapeutic erythrocyte polyamine spermine levels discriminate high risk relapsing patients with M1 prostate carcinoma. Cancer. 1996 Sep 1;78(5):1055-65. 8780544 Venza M, Visalli M, Cicciu D, Teti D: Determination of polyamines in human saliva by high-performance liquid chromatography with fluorescence detection. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):111-7. 11419735 Uehara N, Shirakawa S, Uchino H, Saeki Y: Elevated contents of spermidine and spermine in the erythrocytes of cancer patients. Cancer. 1980 Jan 1;45(1):108-11. 7350997 Jensen PK, Therkelsen AJ: Selective inhibition of fibroblasts by spermine in primary cultures of normal human skin epithelial cells. In Vitro. 1982 Oct;18(10):867-71. 7173947 Loser C, Folsch UR, Paprotny C, Creutzfeldt W: Polyamines in colorectal cancer. Evaluation of polyamine concentrations in the colon tissue, serum, and urine of 50 patients with colorectal cancer. Cancer. 1990 Feb 15;65(4):958-66. 2297664 Proctor MS, Fletcher HV Jr, Shukla JB, Rennert OM: Elevated spermidine and spermine levels in the blood of psoriasis patients. J Invest Dermatol. 1975 Oct;65(4):409-11. 1176793 Lorenz B, Francis F, Gempel K, Boddrich A, Josten M, Schmahl W, Schmidt J, Lehrach H, Meitinger T, Strom TM: Spermine deficiency in Gy mice caused by deletion of the spermine synthase gene. Hum Mol Genet. 1998 Mar;7(3):541-7. 9467015 Hosseinkhani H, Azzam T, Tabata Y, Domb AJ: Dextran-spermine polycation: an efficient nonviral vector for in vitro and in vivo gene transfection. Gene Ther. 2004 Jan;11(2):194-203. 14712304 El Baze P, Milano G, Verrando P, Renee N, Ortonne JP: Polyamine levels in normal human skin. A comparative study of pure epidermis, pure dermis, and suction blister fluid. Arch Dermatol Res. 1983;275(4):218-21. 6625645 Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8. http://hmdb.ca/system/metabolites/msds/000/001/124/original/HMDB01256.pdf?1358462311 Spermidine synthase P09158 SPEE_ECOLI speE http://ecmdb.ca/proteins/P09158.xml S-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + Spermine R02869