2.0 2012-07-30 14:55:41 -0600 2015-09-13 12:56:15 -0600 ECMDB21385 M2MDB001780 Pipecolic acid Pipecolic acid is a metabolite of lysine. Recent studies suggest that pipecolic acid in mammal physiological fluids, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. (HMDB) ()-Piperidine-2-carboxylate ()-Piperidine-2-carboxylic acid (+/-)-2-Piperidinecarboxylate (+/-)-2-Piperidinecarboxylic acid (+/-)-Pipecolate (+/-)-Pipecolic acid (+/-)-Pipecolinate (+/-)-Pipecolinic acid (.+/-.)-2-piperidinecarboxylate (.+/-.)-2-Piperidinecarboxylic acid (<i>S</i>)-pipecolate (<i>S</i>)-piperidine-2-carboxylate (RS)-2-Piperidinecarboxylate (RS)-2-Piperidinecarboxylic acid (s)-Pipecolate (s)-Pipecolic acid (s)-Piperidine-2-carboxylate (s)-Piperidine-2-carboxylic acid 2-Carboxypiperidine 2-Pipecolinate 2-Pipecolinic acid 2-Piperidinecarboxylate 2-Piperidinecarboxylic acid 2-Piperidinylcarboxylate 2-Piperidinylcarboxylic acid A-Pipecolinate A-Pipecolinic acid Acide pipecolique Acide piperidine-carboxylique-2 Alpha-Pipecolinate Alpha-Pipecolinic acid 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 Homoproline Pipecolate Pipecolate free base Pipecolic acid free base Pipecolinate Pipecolinic acid Piperidine-2-carboxylate Piperidine-2-carboxylic acid Piperolinate Piperolinic acid α-Pipecolinate α-Pipecolinic 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 Solid logp -2.17 ALOGPS logs 0.09 ALOGPS solubility 1.58e+02 g/l ALOGPS melting_point 264 oC 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 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::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::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 Specdb::NmrTwoD 949 Specdb::NmrTwoD 1125 HMDB00070 849 826 C00408 17964 L-PIPECOLATE Pipecolic_acid Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. 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Epub 2003 Sep 9. 12964115 Plecko B, Stockler-Ipsiroglu S, Paschke E, Erwa W, Struys EA, Jakobs C: Pipecolic acid elevation in plasma and cerebrospinal fluid of two patients with pyridoxine-dependent epilepsy. Ann Neurol. 2000 Jul;48(1):121-5. 10894227 Kawasaki H, Hori T, Nakajima M, Takeshita K: Plasma levels of pipecolic acid in patients with chronic liver disease. Hepatology. 1988 Mar-Apr;8(2):286-9. 3356409 Chang YF: Lysine metabolism in the human and the monkey: demonstration of pipecolic acid formation in the brain and other organs. Neurochem Res. 1982 May;7(5):577-88. 6811962 van den Berg GA, Breukelman H, Elzinga H, Trijbels JM, Monnens LA, Muskiet FA: Determination of pipecolic acid in urine and plasma by isotope dilution mass fragmentography. Clin Chim Acta. 1986 Sep 30;159(3):229-37. 3769211 Danks DM, Tippett P, Adams C, Campbell P: Cerebro-hepato-renal syndrome of Zellweger. A report of eight cases with comments upon the incidence, the liver lesion, and a fault in pipecolic acid metabolism. J Pediatr. 1975 Mar;86(3):382-7. 1113225 Burton BK, Reed SP, Remy WT: Hyperpipecolic acidemia: clinical and biochemical observations in two male siblings. J Pediatr. 1981 Nov;99(5):729-34. 7299546 Trijbels JM, Monnens LA, Melis G, van den Broekvan Essen M, Bruckwilder M: Localization of pipecolic acid metabolism in rat liver peroxisomes: probable explanation for hyperpipecolataemia in Zellweger syndrome. J Inherit Metab Dis. 1987;10(2):128-34. 3116331 Thomas GH, Haslam RH, Batshaw ML, Capute AJ, Neidengard L, Ransom JL: Hyperpipecolic acidemia associated with hepatomegaly, mental retardation, optic nerve dysplasia and progressive neurological disease. Clin Genet. 1975 Nov;8(5):376-82. 1204235 Lee HF, Mak SC, Wu FW, Chi CS, Huang SC: Zellweger syndrome: report of one case. 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Clin Chim Acta. 1999 Sep;287(1-2):145-56. 10509903 http://hmdb.ca/system/metabolites/msds/000/000/051/original/HMDB00070.pdf?1358461940 Proline/betaine transporter P0C0L7 PROP_ECOLI proP http://ecmdb.ca/proteins/P0C0L7.xml 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 6.05 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 24200 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776