1.0 2010-04-08 22:04:36 UTC 2024-11-29 22:25:44 UTC FDB000509 NG,N'G-Dimethyl-L-arginine Isolated from broad bean (Vicia faba) seed proteins Symmetric dimethylarginine (SDMA) is an endogenously produced inhibitor of nitric oxide synthase (EC-Number 1.14.13.39). However, elevated levels of SDMA occur in patients with vascular disease, especially suffering end-stage renal disease. (PMID 12401860). NG,N'G-Dimethyl-L-arginine is found in pulses. (2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoate (2S)-2-amino-5-(N',n''-dimethylcarbamimidamido)pentanoic acid (S)-2-amino-5-(N',n''-dimethylguanidino)pentanoate (S)-2-amino-5-(N',N''-dimethylguanidino)pentanoic acid Guanidino-N(1),N(2)-dimethylarginine L-Ornithine, N5-((methylamino)(methylimino)methyl)- N,N'-dimethylarginine N(3),N(4)-Dimethyl-L-arginine N(3),N(4)-Dimethylarginine N(5)-(N,N'-dimethylamidino)-L-ornithine N(5)-(N,N'-dimethylcarbamimidoyl)-L-ornithine N(5)-[Bis(methylamino)methylene]-L-ornithine N(g),N'(g)-dimethyl-L-arginine N(g),N'(g)-dimethylarginine N(G1),N(G2)-Dimethylarginine N5-((methylamino)(methylimino)methyl)-L-Ornithine N5-(N,N'-dimethylamidino)-L-Ornithine N5-[bis(methylamino)methylene]-L-Ornithine NG,N'G-Dimethyl-L-arginine NG,n'g-dimethylarginine NG,N'G-Dimethylarginine; L-form NG,ng'-dimethylarginine SDMA Symmetric dimethylarginine C8H18N4O2 202.2541 202.14297584 (2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid N3, N4-dimethylarginine 30344-00-4 CN\C(NCCC[C@H](N)C(O)=O)=N/C InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1 HVPFXCBJHIIJGS-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. Arginine and derivatives Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds 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 Propargyl-type 1,3-dipolar organic 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 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound L-arginine derivative dimethylarginine guanidines non-proteinogenic L-alpha-amino acid Solid logp -2.94 ALOGPS logs -2.11 ALOGPS solubility 1.56e+00 g/l ALOGPS melting_point Mp 237-239° (diflavianate) logp -2.7 ChemAxon pka_strongest_acidic 2.54 ChemAxon pka_strongest_basic 12.4 ChemAxon iupac (2S)-2-amino-5-[(E)-N',N''-dimethylcarbamimidamido]pentanoic acid ChemAxon average_mass 202.2541 ChemAxon mono_mass 202.14297584 ChemAxon smiles CN\C(NCCC[C@H](N)C(O)=O)=N/C ChemAxon formula C8H18N4O2 ChemAxon inchi InChI=1S/C8H18N4O2/c1-10-8(11-2)12-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H,13,14)(H2,10,11,12)/t6-/m0/s1 ChemAxon inchikey HVPFXCBJHIIJGS-LURJTMIESA-N ChemAxon polar_surface_area 99.74 ChemAxon refractivity 53.18 ChemAxon polarizability 22.22 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Metabolism and Physiological Effects of Symmetric dimethylarginine (SDMA) SMP0124764 Specdb::CMs 12637 Specdb::CMs 38573 Specdb::CMs 132059 Specdb::CMs 139793 Specdb::MsIr 1927 Specdb::MsIr 1928 Specdb::MsIr 1929 Specdb::MsMs 57705 Specdb::MsMs 57706 Specdb::MsMs 57707 Specdb::MsMs 113466 Specdb::MsMs 113467 Specdb::MsMs 113468 Specdb::MsMs 2235735 Specdb::MsMs 2237625 Specdb::MsMs 2239762 Specdb::MsMs 2787508 Specdb::MsMs 2787509 Specdb::MsMs 2787510 Specdb::MsMs 2917607 Specdb::MsMs 2917608 Specdb::MsMs 2917609 Specdb::NmrOneD 1952 Specdb::NmrOneD 135590 Specdb::NmrOneD 135591 Specdb::NmrOneD 135592 Specdb::NmrOneD 135593 Specdb::NmrOneD 135594 Specdb::NmrOneD 135595 Specdb::NmrOneD 135596 Specdb::NmrOneD 135597 Specdb::NmrOneD 135598 Specdb::NmrOneD 135599 Specdb::NmrOneD 135600 Specdb::NmrOneD 135601 Specdb::NmrOneD 135602 Specdb::NmrOneD 135603 Specdb::NmrOneD 135604 Specdb::NmrOneD 135605 Specdb::NmrOneD 135606 Specdb::NmrOneD 135607 Specdb::NmrOneD 135608 Specdb::NmrOneD 135609 HMDB03334 25682 2MR #<Reference:0x000055ce302c4648> #<Reference:0x000055ce302c4468> #<Reference:0x000055ce302c4288> #<Reference:0x000055ce302c40a8> #<Reference:0x000055ce302c7410> #<Reference:0x000055ce302c7c58> #<Reference:0x000055ce302c3dd8> #<Reference:0x000055ce302c3b58> #<Reference:0x000055ce302c3950> #<Reference:0x000055ce302c3798> #<Reference:0x000055ce302c35e0> #<Reference:0x000055ce302c3310> #<Reference:0x000055ce302c30b8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Pulses Unknown generic Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823