1.0 2016-09-30 22:19:15 UTC 2020-05-11 20:46:18 UTC BMDB0000070 BMDB00070 Pipecolic acid DL-Pipecolic acid, also known as pipecolinate or homoproline, 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). DL-Pipecolic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. DL-Pipecolic acid exists in all living species, ranging from bacteria to humans. DL-Pipecolic acid has been found to be associated with several diseases known as malaria, schizophrenia, rhizomelic chondrodysplasia punctata, and perillyl alcohol administration for cancer treatment; also dl-pipecolic acid has been linked to the inborn metabolic disorders including adrenoleukodystrophy. 2-Piperidinecarboxylic acid Homoproline Pipecolinic acid 2-Piperidinecarboxylate Pipecolinate Pipecolate ()-Piperidine-2-carboxylic acid (+/-)-2-piperidinecarboxylate (+/-)-2-piperidinecarboxylic acid (+/-)-pipecolate (+/-)-pipecolic acid (+/-)-pipecolinate (+/-)-pipecolinic acid (.+/-.)-2-piperidinecarboxylic acid (RS)-2-Piperidinecarboxylate (RS)-2-Piperidinecarboxylic acid .alpha.-pipecolinic acid 2-Carboxypiperidine 2-Pipecolinic acid 2-Piperidinylcarboxylic acid a-Pipecolinate a-Pipecolinic acid Acide pipecolique Acide piperidine-carboxylique-2 alpha-Pipecolinate alpha-Pipecolinic acid Dihydrobaikiane DL-2-Piperidinecarboxylate DL-2-Piperidinecarboxylic acid DL-Homoproline DL-Pipecolate DL-Pipecolic acid DL-Pipecolinate DL-Pipecolinic acid hexahydro-2-Picolinate hexahydro-2-Picolinic acid Hexahydropicolinate Hexahydropicolinic acid Pipecolic acid free base Piperidine-2-carboxylic acid Piperolinate Piperolinic acid L-Pipecolic acid Pipecolic acid, (R)-isomer Pipecolic acid, ion (1-) Pipecolic acid, monopotassium salt Pipecolic acid hydrochloride, (+-)-isomer Pipecolic acid, (S)-isomer Pipecolic acid, 14C-labeled CPD, (+,-)-isomer Homopipecolic acid Pipecolic acid, (+,-)-isomer Pipecolic acid, ion(1-), (+,-)-isomer Pipecolic acid, ion(1-), (S)-isomer Piperidine-2-carboxylate Pipecolic acid C6H11NO2 129.157 129.078978601 piperidine-2-carboxylic acid (+,-)-pipecolic acid 535-75-1 OC(=O)C1CCCCN1 InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) HXEACLLIILLPRG-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 Azacyclic compounds Carbonyl compounds Carboxylic acids Dialkylamines Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Piperidinecarboxylic acids Aliphatic heteromonocyclic compound Alpha-amino acid Amine Amino acid Azacycle Carbonyl group Carboxylic acid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Piperidine Piperidinecarboxylic acid Secondary aliphatic amine Secondary amine Aliphatic heteromonocyclic compounds piperidinemonocarboxylic acid Solid melting_point 264 °C water_solubility 314 mg/mL logp -2.31 TSAI,RS ET AL. (1991) logp -2.17 ALOGPS logs 0.09 ALOGPS logp -2.1 ChemAxon pka_strongest_acidic 2.06 ChemAxon pka_strongest_basic 10.39 ChemAxon iupac piperidine-2-carboxylic acid ChemAxon average_mass 129.157 ChemAxon mono_mass 129.078978601 ChemAxon smiles OC(=O)C1CCCCN1 ChemAxon formula C6H11NO2 ChemAxon inchi InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9) ChemAxon inchikey HXEACLLIILLPRG-UHFFFAOYSA-N ChemAxon polar_surface_area 49.33 ChemAxon refractivity 32.67 ChemAxon polarizability 13.47 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrOneD 1067 Specdb::NmrOneD 5552 Specdb::NmrOneD 5553 Specdb::NmrOneD 5554 Specdb::NmrOneD 5555 Specdb::NmrOneD 5556 Specdb::NmrOneD 5557 Specdb::NmrOneD 5558 Specdb::NmrOneD 5559 Specdb::NmrOneD 5560 Specdb::NmrOneD 5561 Specdb::NmrOneD 5562 Specdb::NmrOneD 5563 Specdb::NmrOneD 5564 Specdb::NmrOneD 5565 Specdb::NmrOneD 5566 Specdb::NmrOneD 5567 Specdb::NmrOneD 5568 Specdb::NmrOneD 5569 Specdb::NmrOneD 5570 Specdb::NmrOneD 5571 Specdb::MsIr 32 Specdb::MsIr 144 Specdb::MsIr 145 Specdb::MsIr 146 Specdb::CMs 3026 Specdb::CMs 32094 Specdb::CMs 37279 Specdb::CMs 99532 Specdb::CMs 102574 Specdb::CMs 102575 Specdb::CMs 172158 Specdb::CMs 1049579 Specdb::CMs 1049580 Specdb::CMs 1049582 Specdb::NmrTwoD 949 Specdb::NmrTwoD 1125 Specdb::MsMs 111 Specdb::MsMs 112 Specdb::MsMs 113 Specdb::MsMs 2755 Specdb::MsMs 2756 Specdb::MsMs 2757 Specdb::MsMs 20741 Specdb::MsMs 20742 Specdb::MsMs 20743 Specdb::MsMs 22292 Specdb::MsMs 22293 Specdb::MsMs 22294 Specdb::MsMs 439263 Specdb::MsMs 440083 Specdb::MsMs 448203 Specdb::MsMs 448204 Specdb::MsMs 451913 Specdb::MsMs 2258398 Specdb::MsMs 2260169 Specdb::MsMs 2447847 Specdb::MsMs 2447848 Specdb::MsMs 2447849 Specdb::MsMs 2517708 Specdb::MsMs 2517709 Specdb::MsMs 2517710 Intestine 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 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 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 Milk 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 C00408 FDB000545 849 C00001387 826 17964 Pipecolic_acid 50 Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland. New synthesis of pipecolic acid and analogs. Tetrahedron Letters (1981), 22(2), 141-4. 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