1.0 2016-09-30 22:27:45 UTC 2020-05-19 22:01:07 UTC BMDB0000279 BMDB00279 Saccharopine Saccharopinee belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Saccharopinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Saccharopinee exists in all living species, ranging from bacteria to humans. Saccharopinee participates in a number of enzymatic reactions, within cattle. In particular, Saccharopinee can be biosynthesized from L-lysine and oxoglutaric acid; which is catalyzed by the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In addition, Saccharopinee can be converted into allysine and L-glutamic acid through the action of the enzyme Alpha-aminoadipic semialdehyde synthase, mitochondrial. In cattle, saccharopinee is involved in the metabolic pathway called the lysine degradation pathway. Saccharopinee is a potentially toxic compound. epsilon-N-(L-Glutar-2-yl)-L-lysine N-[(S)-5-Amino-5-carboxypentyl]-L-glutamic acid N6-(L-1,3-Dicarboxypropyl)-L-lysine L-Saccharopine N-[(S)-5-Amino-5-carboxypentyl]-L-glutamate (S)-N-(5-Amino-5-carboxypentyl)-L-glutamic acid L-N-(5-Amino-5-carboxypentyl)-glutamic acid L-Saccharopin N(6)-(L-1,3-Dicarboxypropyl)-L-lysine N-(5-Amino-5-carboxypentyl)-glutamic acid N-(5-Amino-5-carboxypentyl)-L-glutamic acid N-[(5S)-5-Amino-5-carboxypentyl]-L-glutamic acid Saccharopin C11H20N2O6 276.2863 276.132136382 (2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid saccharopine 997-68-2 N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 ZDGJAHTZVHVLOT-YUMQZZPRSA-N belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid 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 Glutamic acid and derivatives Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Dialkylamines Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines Organic oxides Organopnictogen compounds Tricarboxylic acids and derivatives Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Fatty acyl Glutamic acid or derivatives Hydrocarbon derivative L-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary aliphatic amine Secondary amine Tricarboxylic acid or derivatives Aliphatic acyclic compounds L-lysine derivative amino acid opine Solid melting_point 247 - 250 °C logp -2.77 ALOGPS logs -1.72 ALOGPS logp -5.4 ChemAxon pka_strongest_acidic 1.44 ChemAxon pka_strongest_basic 10.89 ChemAxon iupac (2S)-2-{[(5S)-5-amino-5-carboxypentyl]amino}pentanedioic acid ChemAxon average_mass 276.2863 ChemAxon mono_mass 276.132136382 ChemAxon smiles N[C@@H](CCCCN[C@@H](CCC(O)=O)C(O)=O)C(O)=O ChemAxon formula C11H20N2O6 ChemAxon inchi InChI=1S/C11H20N2O6/c12-7(10(16)17)3-1-2-6-13-8(11(18)19)4-5-9(14)15/h7-8,13H,1-6,12H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 ChemAxon inchikey ZDGJAHTZVHVLOT-YUMQZZPRSA-N ChemAxon polar_surface_area 149.95 ChemAxon refractivity 63.95 ChemAxon polarizability 28.14 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 8 ChemAxon donor_count 5 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 Lysine Degradation SMP0087203 Specdb::CMs 862 Specdb::CMs 863 Specdb::CMs 2336 Specdb::CMs 30609 Specdb::CMs 30610 Specdb::CMs 37399 Specdb::CMs 156617 Specdb::CMs 1056540 Specdb::CMs 1056542 Specdb::CMs 1056543 Specdb::CMs 1056545 Specdb::CMs 1056547 Specdb::CMs 1056549 Specdb::CMs 1056550 Specdb::CMs 1056552 Specdb::CMs 1056554 Specdb::CMs 1056556 Specdb::CMs 1056557 Specdb::CMs 1056559 Specdb::CMs 1056561 Specdb::CMs 1056563 Specdb::CMs 1056565 Specdb::CMs 1056567 Specdb::CMs 1056569 Specdb::CMs 1056570 Specdb::MsMs 6240 Specdb::MsMs 6241 Specdb::MsMs 177951 Specdb::MsMs 177952 Specdb::MsMs 177953 Specdb::MsMs 180264 Specdb::MsMs 180265 Specdb::MsMs 180266 Specdb::MsMs 439167 Specdb::MsMs 448117 Specdb::MsMs 2409556 Specdb::MsMs 2409557 Specdb::MsMs 2409558 Specdb::MsMs 2553592 Specdb::MsMs 2553593 Specdb::MsMs 2553594 Specdb::NmrTwoD 1253 Specdb::NmrOneD 1310 Specdb::NmrOneD 143270 Specdb::NmrOneD 143271 Specdb::NmrOneD 143272 Specdb::NmrOneD 143273 Specdb::NmrOneD 143274 Specdb::NmrOneD 143275 Specdb::NmrOneD 143276 Specdb::NmrOneD 143277 Specdb::NmrOneD 143278 Specdb::NmrOneD 143279 Specdb::NmrOneD 143280 Specdb::NmrOneD 143281 Specdb::NmrOneD 143282 Specdb::NmrOneD 143283 Specdb::NmrOneD 143284 Specdb::NmrOneD 143285 Specdb::NmrOneD 143286 Specdb::NmrOneD 143287 Specdb::NmrOneD 143288 Specdb::NmrOneD 143289 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 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 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 C00449 DB04207 FDB000461 141086 160556 16927 C00007227 SACCHAROPINE Saccharopine 1484994 383 Burkard, Ulrike; Walther, Ingrid; Effenberger, Franz. Amino acids. 6. Investigations on the synthesis of L-saccharopin. Liebigs Annalen der Chemie (1986), (6), 1030-43. BMDBP00631 Alpha-aminoadipic semialdehyde synthase, mitochondrial A8E657 AASS Enzyme BMDBP00632 Saccharopine dehydrogenase-like oxidoreductase Q3T067 SCCPDH Enzyme