1.0 2016-09-30 22:30:56 UTC 2020-05-11 20:36:58 UTC BMDB0000450 BMDB00450 5-Hydroxylysine 5-Hydroxylysine, also known as lysine, 5 hydroxy, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 5-Hydroxylysine is possibly soluble (in water) and a very strong basic compound (based on its pKa). 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. In cattle, 5-hydroxylysine is involved in the metabolic pathway called the lysine degradation pathway. (2S,5R)-5-Hydroxylysine (5R)-5-Hydroxy-L-lysine alpha,epsilon-Diamino-delta-hydroxycaproic acid L-Erythro-5-hydroxylysine L-Normal-5-hydroxylysine 5-Hydroxy-L-lysine a,epsilon-Diamino-delta-hydroxycaproate a,epsilon-Diamino-delta-hydroxycaproic acid alpha,epsilon-Diamino-delta-hydroxycaproate Α,epsilon-diamino-δ-hydroxycaproate Α,epsilon-diamino-δ-hydroxycaproic acid Lysine, 5 hydroxy 2,6-Diamino-5-hydroxyhexanoic acid 5 Hydroxylysine Hydroxylysine (2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid 2,6 Diamino 5 hydroxyhexanoic acid a,epsilon-diamino-δ-hydroxycaproate a,epsilon-diamino-δ-hydroxycaproic acid (2S,5R)-2,6-diamino-5-Hydroxyhexanoate 5-Hydroxy-lysine D-Hydroxy-L-lysine D-Hydroxylysine delta-DL-Hydroxylysine delta-Hydroxy-L-lysine delta-Hydroxylysine erythro-5-Hydroxy-L-lysine Hydroxy-lysine L-D-Hydroxylysine L-delta-Hydroxylysine Procollagen 5-hydroxy-L-lysine Procollagen L-erythro-5-hydroxy-L-lysine 5-HYDROXYLYSINE C6H14N2O3 162.187 162.100442324 (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid L-hydroxylysine 1190-94-9 NC[C@H](O)CC[C@H](N)C(O)=O InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1 YSMODUONRAFBET-UHNVWZDZSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues L-alpha-amino acids 1,2-aminoalcohols Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Hydroxy fatty acids Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Secondary alcohols 1,2-aminoalcohol Alcohol Aliphatic acyclic compound Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Fatty acid Fatty acyl Hydrocarbon derivative Hydroxy fatty acid L-alpha-amino acid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary alcohol Aliphatic acyclic compounds 5-hydroxylysine hydroxy-L-lysine Solid water_solubility 23 mg/mL logp -3.77 ALOGPS logs -0.12 ALOGPS logp -4.4 ChemAxon pka_strongest_acidic 2.45 ChemAxon pka_strongest_basic 9.75 ChemAxon iupac (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid ChemAxon average_mass 162.187 ChemAxon mono_mass 162.100442324 ChemAxon smiles NC[C@H](O)CC[C@H](N)C(O)=O ChemAxon formula C6H14N2O3 ChemAxon inchi InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)/t4-,5+/m1/s1 ChemAxon inchikey YSMODUONRAFBET-UHNVWZDZSA-N ChemAxon polar_surface_area 109.57 ChemAxon refractivity 39.17 ChemAxon polarizability 16.55 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 4 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::MsIr 529 Specdb::MsIr 530 Specdb::MsIr 531 Specdb::NmrTwoD 1319 Specdb::CMs 3376 Specdb::CMs 37544 Specdb::CMs 169900 Specdb::CMs 1062908 Specdb::CMs 1062910 Specdb::CMs 1062912 Specdb::CMs 1062914 Specdb::CMs 1062915 Specdb::CMs 1062917 Specdb::CMs 1062919 Specdb::CMs 1062921 Specdb::CMs 1062923 Specdb::CMs 1062925 Specdb::CMs 1062926 Specdb::CMs 1062928 Specdb::CMs 1062930 Specdb::CMs 1062932 Specdb::CMs 1062934 Specdb::CMs 1062936 Specdb::CMs 1062938 Specdb::CMs 1062940 Specdb::CMs 1062941 Specdb::CMs 1062943 Specdb::CMs 1062945 Specdb::CMs 1062946 Specdb::NmrOneD 1375 Specdb::NmrOneD 6782 Specdb::NmrOneD 6783 Specdb::NmrOneD 6784 Specdb::NmrOneD 6785 Specdb::NmrOneD 6786 Specdb::NmrOneD 6787 Specdb::NmrOneD 6788 Specdb::NmrOneD 6789 Specdb::NmrOneD 6790 Specdb::NmrOneD 6791 Specdb::NmrOneD 6792 Specdb::NmrOneD 6793 Specdb::NmrOneD 6794 Specdb::NmrOneD 6795 Specdb::NmrOneD 6796 Specdb::NmrOneD 6797 Specdb::NmrOneD 6798 Specdb::NmrOneD 6799 Specdb::NmrOneD 6800 Specdb::NmrOneD 6801 Specdb::MsMs 656 Specdb::MsMs 657 Specdb::MsMs 658 Specdb::MsMs 180051 Specdb::MsMs 180052 Specdb::MsMs 180053 Specdb::MsMs 182385 Specdb::MsMs 182386 Specdb::MsMs 182387 Specdb::MsMs 2226475 Specdb::MsMs 2228255 Specdb::MsMs 2228875 Specdb::MsMs 2230547 Specdb::MsMs 2231343 Specdb::MsMs 2232877 Specdb::MsMs 2233690 Specdb::MsMs 2235235 Specdb::MsMs 2252215 Specdb::MsMs 2252584 Specdb::MsMs 2253889 Specdb::MsMs 2254260 Specdb::MsMs 2254326 Specdb::MsMs 2474765 Specdb::MsMs 2474766 Specdb::MsMs 2474767 Milk Commercial whole milk with 3.25% fat Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809 Milk Commercial milk, by CIL LC-MS Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 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 FDB012682 2297721 3032849 C16741 18040 CPD-14226 53055 Hydroxylysine 5439 Allevi, P.; Anastasia, M. Synthesis of all four possible stereoisomers of 5-hydroxylysine. Tetrahedron: Asymmetry (2000), 11(15), 3151-3160. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. 28306241 Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. 29291809