2.02012-05-31 13:48:23 -06002015-09-13 12:56:10 -0600ECMDB01256M2MDB000311SpermineSpermine 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-Tetraazatetradecane4,9-Diaza-1,12-dodecanediamine4,9-Diazadodecamethylenediamine4,9-Diazadodecane-1,12-diamineDiaminopropyl-tetramethylenediamineDiaminopropyltetramethylenediamineGerontineMusculamineN,N'-Bis(3-aminopropyl)-1,4-ButanediamineN,N'-Bis(3-aminopropyl)-1,4-tetramethylenediamineN,N'-Bis(3-aminopropyl)butane-1,4-diamineN1,N4-bis(3-aminopropyl)-1,4-butanediamineNeuridineSperminSpermineSpermine dihydrateSpermine dihydric acidSpermine purissSPMC10H26N4202.3402202.215746852(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})aminespermine71-44-3NCCCNCCCCNCCCNInChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2PFNFFQXMRSDOHW-UHFFFAOYSA-NSolidCytoplasmPeriplasmlogp-0.66logs-1.97solubility2.19e+00 g/lmelting_point29 oClogp-1.5pka_strongest_basic10.8iupac(3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amineaverage_mass202.3402mono_mass202.215746852smilesNCCCNCCCCNCCCNformulaC10H26N4inchiInChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2inchikeyPFNFFQXMRSDOHW-UHFFFAOYSA-Npolar_surface_area76.1refractivity62.56polarizability26.69rotatable_bond_count11acceptor_count4donor_count4physiological_charge4formal_charge0Glutathione metabolismThe 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.
PW000833ec00480MetabolicArginine and proline metabolismec00330beta-Alanine metabolismThe 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.PW000896ec00410MetabolicSpecdb::CMs713Specdb::CMs714Specdb::CMs715Specdb::CMs716Specdb::CMs717Specdb::CMs2057Specdb::CMs2082Specdb::CMs2104Specdb::CMs2216Specdb::CMs3229Specdb::CMs30404Specdb::CMs30405Specdb::CMs30694Specdb::CMs30932Specdb::CMs30933Specdb::CMs31299Specdb::CMs31300Specdb::CMs31301Specdb::CMs31302Specdb::CMs31889Specdb::CMs31890Specdb::CMs31891Specdb::CMs31892Specdb::CMs166578Specdb::EiMs918Specdb::NmrOneD1670Specdb::NmrOneD4804Specdb::NmrOneD4805Specdb::NmrOneD146970Specdb::NmrOneD146971Specdb::NmrOneD146972Specdb::NmrOneD146973Specdb::NmrOneD146974Specdb::NmrOneD146975Specdb::NmrOneD146976Specdb::NmrOneD146977Specdb::NmrOneD146978Specdb::NmrOneD146979Specdb::NmrOneD146980Specdb::NmrOneD146981Specdb::NmrOneD146982Specdb::NmrOneD146983Specdb::NmrOneD146984Specdb::NmrOneD146985Specdb::NmrOneD146986Specdb::NmrOneD146987Specdb::NmrOneD146988Specdb::NmrOneD146989Specdb::MsMs1487Specdb::MsMs1488Specdb::MsMs1489Specdb::MsMs5123Specdb::MsMs5124Specdb::MsMs5125Specdb::MsMs5126Specdb::MsMs5127Specdb::MsMs5128Specdb::MsMs5129Specdb::MsMs5130Specdb::MsMs5131Specdb::MsMs5132Specdb::MsMs5133Specdb::MsMs5134Specdb::MsMs5135Specdb::MsMs5136Specdb::MsMs5137Specdb::MsMs5138Specdb::MsMs21233Specdb::MsMs21234Specdb::MsMs21235Specdb::MsMs22784Specdb::MsMs22785Specdb::MsMs22786Specdb::NmrTwoD1061Specdb::NmrTwoD1611HMDB0125611031072C0075015746SPERMINESPMSpermineKeseler, 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-D114.22080510Vijayendran, 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:R72.18402659van 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Sreekumar 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):910-4.19212411Mollica 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):1196-8.7454431Swift 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):221-30.3004602Cipolla 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):1055-65.8780544Venza 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):111-7.11419735Uehara 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):108-11.7350997Jensen PK, Therkelsen AJ: Selective inhibition of fibroblasts by spermine in primary cultures of normal human skin epithelial cells. In Vitro. 1982 Oct;18(10):867-71.7173947Loser 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):958-66.2297664Proctor 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):409-11.1176793Lorenz 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):541-7.9467015Hosseinkhani 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):194-203.14712304El 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):218-21.6625645Wrede, 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?1358462311Spermidine synthaseP09158SPEE_ECOLIspeEhttp://ecmdb.ca/proteins/P09158.xmlS-Adenosylmethioninamine + Spermidine <> 5'-Methylthioadenosine + SpermineR02869