1.0 2016-09-30 22:43:09 UTC 2020-06-04 20:46:15 UTC BMDB0001256 BMDB01256 Spermine Spermine, also known as gerontine or musculamine, belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Spermine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. Spermine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Spermine exists in all living species, ranging from bacteria to humans. 5'-Methylthioadenosine and spermine can be biosynthesized from S-adenosylmethioninamine and spermidine through the action of the enzyme spermine synthase. In cattle, spermine is involved in the metabolic pathway called spermidine and spermine biosynthesis pathway. Spermine is a potentially toxic compound. 4,9-Diaza-1,12-dodecanediamine 4,9-Diazadodecane-1,12-diamine N,N'-bis(3-aminopropyl)-1,4-butanediamine 1,5,10,14-Tetraazatetradecane 4,9-Diazadodecamethylenediamine Diaminopropyl-tetramethylenediamine Diaminopropyltetramethylenediamine Gerontine Musculamine 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 dihydrate 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 belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. Organic compounds Organic nitrogen compounds Organonitrogen compounds Amines Dialkylamines Hydrocarbon derivatives Monoalkylamines Organopnictogen compounds Aliphatic acyclic compound Hydrocarbon derivative Organopnictogen compound Primary aliphatic amine Primary amine Secondary aliphatic amine Aliphatic acyclic compounds polyazaalkane tetraamine Solid melting_point 29 °C logp -0.66 ALOGPS logs -1.97 ALOGPS 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 number_of_rings 0 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Spermidine and Spermine Biosynthesis SMP0087213 Specdb::EiMs 918 Specdb::NmrTwoD 1061 Specdb::NmrTwoD 1611 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::MsIr 1159 Specdb::MsIr 1160 Specdb::MsIr 1161 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 Blood 0.2 +/- 0.2 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Epidermis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Erythrocyte Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Intestine Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Liver 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Longissimus Thoracis Muscle 0.2 +/- 0.1 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Milk 1.0700 - 7.560 uM colostrum Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33. 7613766 Milk 3.2 uM Whole milk Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33. 7613766 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Pancreas Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Platelet Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 3 +/- 3 uM By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Semimembranosus Muscle 0.11 +/- 0.03 nmol/g of tissue By LC-MS/MS Aidin Foroutan, Carolyn Fitzsimmons, Rupasri Mandal, Hamed Piri‐Moghadam, Jiamin Zheng, AnChi Guo, Carin Li, Le Luo Guan and David S. Wishart. The Bovine Metabolome. Metabolites 2020, 10, 233; doi:10.3390/metabo10060233 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C00750 DB00127 FDB003225 1072 1103 15746 SPERMINE C00001432 35875 Spermine 255 Wrede, Fritz; Strack, Erich; Hettche, Otto. Spermine. VII. Z. physiol. Chem. (1928), 173 61-8. Motyl T, Ploszaj T, Wojtasik A, Kukulska W, Podgurniak M: Polyamines in cow's and sow's milk. Comp Biochem Physiol B Biochem Mol Biol. 1995 Jul;111(3):427-33. 7613766 BMDBP00126 Spermine synthase Q3SZA5 SMS Enzyme BMDBP01355 Solute carrier family 22 member 1 A7MBE0 SLC22A1 Enzyme