1.0 2016-09-30 22:47:23 UTC 2020-06-04 19:39:56 UTC BMDB0001539 BMDB01539 Dimethyl-L-arginine Asymmetric dimethylarginine, also known as N(g),N(g)-dimethylarginine or guanidino-N,N-dimethylarginine, belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Asymmetric dimethylarginine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Asymmetric dimethylarginine exists in all eukaryotes, ranging from yeast to humans. Asymmetric dimethylarginine is a potentially toxic compound. ADMA Guanidino-N,N-dimethylarginine N,N-Dimethylarginine N(5)-((Dimethylamino)iminomethyl)-L-ornithine NG,NG-Dimethyl-L-arginine N(g),N(g)-Dimethylarginine N(g)-Dimethylarginine N(g1),N(g1)-Dimethylarginine Nomega,nomega-dimethyl-L-arginine 2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoate 2-Amino-5-(amino-dimethylamino-methylidene)amino-pentanoic acid Dimethyl-L-arginine N(Omega),N(omega)-dimethyl-L-arginine NG,NG-Dimethylarginine NG-Dimethylarginine Nomega,nomega'-dimethyl-L-arginine Asymmetric dimethylarginine C8H18N4O2 202.2541 202.14297584 (2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid asymmetric dimethylarginine 30315-93-6 N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1 YDGMGEXADBMOMJ-LURJTMIESA-N belongs to the class of organic compounds known as arginine and derivatives. Arginine and derivatives are compounds containing arginine or a derivative thereof resulting from reaction of arginine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Arginine and derivatives Amino acids Carbonyl compounds Carboximidamides Carboxylic acids Fatty acids and conjugates Guanidines Hydrocarbon derivatives Imines L-alpha-amino acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Arginine or derivatives Carbonyl group Carboximidamide Carboxylic acid Fatty acid Guanidine Hydrocarbon derivative Imine L-alpha-amino acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds L-arginine derivative dimethylarginine guanidines non-proteinogenic L-alpha-amino acid Solid logp -3.13 ALOGPS logs -1.48 ALOGPS logp -2.7 ChemAxon pka_strongest_acidic 2.54 ChemAxon pka_strongest_basic 12.34 ChemAxon iupac (2S)-2-amino-5-[(E)-[amino(dimethylamino)methylidene]amino]pentanoic acid ChemAxon average_mass 202.2541 ChemAxon mono_mass 202.14297584 ChemAxon smiles N[C@@H](CCC\N=C(/N)N(C)C)C(O)=O ChemAxon formula C8H18N4O2 ChemAxon inchi InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1 ChemAxon inchikey YDGMGEXADBMOMJ-LURJTMIESA-N ChemAxon polar_surface_area 104.94 ChemAxon refractivity 53.7 ChemAxon polarizability 22.19 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 3 ChemAxon physiological_charge 1 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 Specdb::NmrOneD 96378 Specdb::NmrOneD 96379 Specdb::NmrOneD 96380 Specdb::NmrOneD 96381 Specdb::NmrOneD 96382 Specdb::NmrOneD 96383 Specdb::NmrOneD 96384 Specdb::NmrOneD 96385 Specdb::NmrOneD 96386 Specdb::NmrOneD 96387 Specdb::NmrOneD 96388 Specdb::NmrOneD 96389 Specdb::NmrOneD 96390 Specdb::NmrOneD 96391 Specdb::NmrOneD 96392 Specdb::NmrOneD 96393 Specdb::NmrOneD 96394 Specdb::NmrOneD 96395 Specdb::NmrOneD 96396 Specdb::NmrOneD 96397 Specdb::CMs 2615 Specdb::CMs 31806 Specdb::CMs 38114 Specdb::CMs 99697 Specdb::CMs 132003 Specdb::CMs 139737 Specdb::MsMs 85719 Specdb::MsMs 85720 Specdb::MsMs 85721 Specdb::MsMs 147858 Specdb::MsMs 147859 Specdb::MsMs 147860 Specdb::MsMs 2257621 Specdb::MsMs 2258931 Specdb::MsMs 2259651 Specdb::MsMs 2446819 Specdb::MsMs 2446820 Specdb::MsMs 2446821 Specdb::MsMs 2516454 Specdb::MsMs 2516455 Specdb::MsMs 2516456 Specdb::MsIr 1326 Specdb::MsIr 1327 Specdb::MsIr 1328 Blood 1.1 +/- 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 Blood 1.3-2.1 uM By HPLC Chan JR, Boger RH, Bode-Boger SM, Tangphao O, Tsao PS, Blaschke TF, Cooke JP: Asymmetric dimethylarginine increases mononuclear cell adhesiveness in hypercholesterolemic humans. Arterioscler Thromb Vasc Biol. 2000 Apr;20(4):1040-6. doi: 10.1161/01.atv.20.4.1040. 10764670 Kidney 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 1 +/- 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 Longissimus Thoracis Muscle 0.8 +/- 0.2 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 0.08 +/- 0.01 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.09 +/- 0.01 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.1 +/- 0.01 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.10 +/- 0.01 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Placenta 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 4 +/- 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 Ruminal Fluid 0.33 +/- 0.14 uM Samples have been collected from 8 healthy primiparous Holstein cow, no barley grains in diet. Metabolite measured DFI-MS/MS. Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Semimembranosus Muscle 0.9 +/- 0.2 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 0.8 +/- 0.2 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 FDB000508 C03626 DB01686 110375 123831 17929 Asymmetric dimethylarginine 6309 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)