1.0 2016-09-30 22:31:53 UTC 2020-06-04 20:23:43 UTC BMDB0000510 BMDB00510 Aminoadipic acid Aminoadipic acid, also known as aminoadipic acid or Aminoadipic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Aminoadipic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Aminoadipic acid exists in all eukaryotes, ranging from yeast to humans. Aminoadipic acid participates in a number of enzymatic reactions, within cattle. In particular, Aminoadipic acid can be biosynthesized from allysine through the action of the enzyme Alpha-aminoadipic semialdehyde dehydrogenase. In addition, Aminoadipic acid and oxoglutaric acid can be converted into oxoadipic acid and L-glutamic acid through its interaction with the enzyme kynurenine/alphaminoadipic acid aminotransferase, mitochondrial. In cattle, aminoadipic acid is involved in the metabolic pathway called the lysine degradation pathway. Aminoadipic acid is a potentially toxic compound. (+/-)-2-aminoadipic acid Aad alpha-Aminoadipic acid DL-2-Aminoadipic acid DL-2-Aminohexanedioic acid DL-alpha-Aminoadipic acid (+/-)-2-aminoadipate a-Aminoadipate a-Aminoadipic acid alpha-Aminoadipate Α-aminoadipate Α-aminoadipic acid DL-2-Aminoadipate DL-2-Aminohexanedioate DL-a-Aminoadipate DL-a-Aminoadipic acid DL-alpha-Aminoadipate DL-Α-aminoadipate DL-Α-aminoadipic acid Aminoadipate 2 Aminoadipic acid 2 Aminohexanedioic acid 2-Aminoadipic acid Acid, 2 aminoadipic Acid, 2-aminoadipic Acid, 2-aminohexanedioic Acid, alpha-aminoadipic Aminoadipic acid, 2 alpha Aminoadipic acid 2-Aminoadipate alpha-amino-Adipic acid L-2-Aminoadipate L-2-Aminoadipic acid L-2-Aminohexanedioate L-2-Aminohexanedioic acid L-alpha-Aminoadipate L-alpha-Aminoadipic acid 2-Aminohexanedioic acid C6H11NO4 161.1558 161.068807845 2-aminohexanedioic acid aminoadipic acid 542-32-5 NC(CCCC(O)=O)C(O)=O InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) OYIFNHCXNCRBQI-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Alpha amino acids Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Organic oxides Organopnictogen compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Aliphatic acyclic compounds Dicarboxylic acids amino dicarboxylic acid non-proteinogenic alpha-amino acid Solid melting_point 196 - 198 °C water_solubility 2.2 mg/mL logp -3.43 ALOGPS logs -0.69 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 2.01 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac 2-aminohexanedioic acid ChemAxon average_mass 161.1558 ChemAxon mono_mass 161.068807845 ChemAxon smiles NC(CCCC(O)=O)C(O)=O ChemAxon formula C6H11NO4 ChemAxon inchi InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11) ChemAxon inchikey OYIFNHCXNCRBQI-UHFFFAOYSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 35.89 ChemAxon polarizability 15.53 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 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 Lysine Degradation SMP0087203 Specdb::CMs 16997 Specdb::CMs 32002 Specdb::CMs 37582 Specdb::CMs 99576 Specdb::NmrOneD 1401 Specdb::NmrOneD 4832 Specdb::NmrOneD 4833 Specdb::NmrTwoD 1345 Specdb::MsMs 731 Specdb::MsMs 732 Specdb::MsMs 733 Specdb::MsMs 12053 Specdb::MsMs 12054 Specdb::MsMs 12055 Specdb::MsMs 18725 Specdb::MsMs 18726 Specdb::MsMs 18727 Specdb::MsMs 447303 Specdb::MsMs 1471149 Specdb::MsMs 1471324 Specdb::MsMs 1472449 Specdb::MsMs 1472450 Specdb::MsMs 1472451 Specdb::MsMs 1472452 Specdb::MsMs 1472453 Specdb::MsMs 1472454 Specdb::MsMs 1472455 Specdb::MsMs 1472456 Specdb::MsMs 1472457 Specdb::MsMs 1472458 Specdb::MsMs 3602486 Specdb::MsMs 3602487 Specdb::MsMs 3602488 Blood 1.28 +/- 0.52 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 7.3-8.1 uM By HPLC Zhou Z, Vailati-Riboni M, Luchini DN, Loor JJ: Methionine and Choline Supply during the Periparturient Period Alter Plasma Amino Acid and One-Carbon Metabolism Profiles to Various Extents: Potential Role in Hepatic Metabolism and Antioxidant Status. Nutrients. 2016 Dec 29;9(1). pii: nu9010010. doi: 10.3390/nu9010010. 28036059 Liver 68 +/- 27 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 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 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Longissimus Thoracis Muscle 7 +/- 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 Mammary Gland 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 Mammary Gland 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 Milk 4.3 +/- 0.1 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 6.1 +/- 0.1 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 5.4 +/- 0.1 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 5.0 +/- 0.1 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 Milk 195 - 427 uM Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 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 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 1 +/- 1 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 10 +/- 4 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 98 +/- 39 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 FDB007648 456 469 37024 Alpha-Aminoadipic_acid C00007393 Khan, Naseem H.; Ali, Mohd.; Panda, H.; Rakhshinda. Synthesis of a-aminoadipic acid. Journal of the Indian Chemical Society (1982), 59(9), 1077-8. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. 20338431 Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 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 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00239 Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q5E9N4 AADAT Enzyme BMDBP00954 Alpha-aminoadipic semialdehyde dehydrogenase Q2KJC9 ALDH7A1 Enzyme