2.02012-07-30 14:55:41 -06002015-09-13 12:56:15 -0600ECMDB21385M2MDB001780Pipecolic acidPipecolic 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 acid2-Carboxypiperidine2-Pipecolinate2-Pipecolinic acid2-Piperidinecarboxylate2-Piperidinecarboxylic acid2-Piperidinylcarboxylate2-Piperidinylcarboxylic acidA-PipecolinateA-Pipecolinic acidAcide pipecoliqueAcide piperidine-carboxylique-2Alpha-PipecolinateAlpha-Pipecolinic acidAlpha.-pipecolinateAlpha.-Pipecolinic acidDihydrobaikianeDL-2-PiperidinecarboxylateDL-2-Piperidinecarboxylic acidDL-HomoprolineDL-PipecolateDL-Pipecolic acidDL-PipecolinateDL-Pipecolinic acidHexahydro-2-picolinateHexahydro-2-picolinic acidHexahydropicolinateHexahydropicolinic acidHomoprolinePipecolatePipecolate free basePipecolic acid free basePipecolinatePipecolinic acidPiperidine-2-carboxylatePiperidine-2-carboxylic acidPiperolinatePiperolinic acidα-Pipecolinateα-Pipecolinic acidC6H11NO2129.157129.078978601piperidine-2-carboxylic acid(+,-)-pipecolic acid535-75-1OC(=O)C1CCCCN1InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)HXEACLLIILLPRG-UHFFFAOYSA-NSolidlogp-2.17logs0.09solubility1.58e+02 g/lmelting_point264 oClogp-2.1pka_strongest_acidic2.06pka_strongest_basic10.39iupacpiperidine-2-carboxylic acidaverage_mass129.157mono_mass129.078978601smilesOC(=O)C1CCCCN1formulaC6H11NO2inchiInChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)inchikeyHXEACLLIILLPRG-UHFFFAOYSA-Npolar_surface_area49.33refractivity32.67polarizability13.47rotatable_bond_count1acceptor_count3donor_count2physiological_charge0formal_charge0Specdb::CMs3026Specdb::CMs32094Specdb::CMs37279Specdb::CMs99532Specdb::CMs102574Specdb::CMs102575Specdb::CMs172158Specdb::CMs1049579Specdb::CMs1049580Specdb::CMs1049582Specdb::NmrOneD1067Specdb::NmrOneD5552Specdb::NmrOneD5553Specdb::NmrOneD5554Specdb::NmrOneD5555Specdb::NmrOneD5556Specdb::NmrOneD5557Specdb::NmrOneD5558Specdb::NmrOneD5559Specdb::NmrOneD5560Specdb::NmrOneD5561Specdb::NmrOneD5562Specdb::NmrOneD5563Specdb::NmrOneD5564Specdb::NmrOneD5565Specdb::NmrOneD5566Specdb::NmrOneD5567Specdb::NmrOneD5568Specdb::NmrOneD5569Specdb::NmrOneD5570Specdb::NmrOneD5571Specdb::MsMs111Specdb::MsMs112Specdb::MsMs113Specdb::MsMs2755Specdb::MsMs2756Specdb::MsMs2757Specdb::MsMs20741Specdb::MsMs20742Specdb::MsMs20743Specdb::MsMs22292Specdb::MsMs22293Specdb::MsMs22294Specdb::MsMs439263Specdb::MsMs440083Specdb::MsMs448203Specdb::MsMs448204Specdb::MsMs451913Specdb::MsMs2258398Specdb::MsMs2260169Specdb::MsMs2447847Specdb::MsMs2447848Specdb::MsMs2447849Specdb::MsMs2517708Specdb::MsMs2517709Specdb::MsMs2517710Specdb::NmrTwoD949Specdb::NmrTwoD1125HMDB00070849826C0040817964L-PIPECOLATEPipecolic_acidIshii, 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 316:593-597.17379776Sreekumar 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. Nature. 2009 Feb 12;457(7231):910-4.19212411Medana IM, Hien TT, Day NP, Phu NH, Mai NT, Chu'ong LV, Chau TT, Taylor A, Salahifar H, Stocker R, Smythe G, Turner GD, Farrar J, White NJ, Hunt NH: The clinical significance of cerebrospinal fluid levels of kynurenine pathway metabolites and lactate in severe malaria. J Infect Dis. 2002 Mar 1;185(5):650-6. Epub 2002 Feb 14.11865422Smythe GA, Poljak A, Bustamante S, Braga O, Maxwell A, Grant R, Sachdev P: ECNI GC-MS analysis of picolinic and quinolinic acids and their amides in human plasma, CSF, and brain tissue. Adv Exp Med Biol. 2003;527:705-12.15206793Medana IM, Day NP, Salahifar-Sabet H, Stocker R, Smythe G, Bwanaisa L, Njobvu A, Kayira K, Turner GD, Taylor TE, Hunt NH: Metabolites of the kynurenine pathway of tryptophan metabolism in the cerebrospinal fluid of Malawian children with malaria. J Infect Dis. 2003 Sep 15;188(6):844-9. Epub 2003 Sep 9.12964115Plecko 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):121-5.10894227Kawasaki H, Hori T, Nakajima M, Takeshita K: Plasma levels of pipecolic acid in patients with chronic liver disease. Hepatology. 1988 Mar-Apr;8(2):286-9.3356409Chang 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):577-88.6811962van 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):229-37.3769211Danks 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):382-7.1113225Burton BK, Reed SP, Remy WT: Hyperpipecolic acidemia: clinical and biochemical observations in two male siblings. J Pediatr. 1981 Nov;99(5):729-34.7299546Trijbels 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):128-34.3116331Thomas 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):376-82.1204235Lee HF, Mak SC, Wu FW, Chi CS, Huang SC: Zellweger syndrome: report of one case. Acta Paediatr Taiwan. 2001 Jan-Feb;42(1):53-6.11270189Kok RM, Kaster L, de Jong AP, Poll-The B, Saudubray JM, Jakobs C: Stable isotope dilution analysis of pipecolic acid in cerebrospinal fluid, plasma, urine and amniotic fluid using electron capture negative ion mass fragmentography. Clin Chim Acta. 1987 Sep 30;168(2):143-52.3315316Baas JC, van de Laar R, Dorland L, Duran M, Berger R, Poll-The BT, de Koning TJ: Plasma pipecolic acid is frequently elevated in non-peroxisomal disease. J Inherit Metab Dis. 2002 Dec;25(8):699-701.12705501Dancis J, Hutzler J: Comparative rates of metabolism of pipecolic acid in several animal species. Comp Biochem Physiol B. 1982;73(4):1011-2.6817963Fujita T, Hada T, Higashino K: Origin of D- and L-pipecolic acid in human physiological fluids: a study of the catabolic mechanism to pipecolic acid using the lysine loading test. Clin Chim Acta. 1999 Sep;287(1-2):145-56.10509903http://hmdb.ca/system/metabolites/msds/000/000/051/original/HMDB00070.pdf?1358461940Proline/betaine transporterP0C0L7PROP_ECOLIproPhttp://ecmdb.ca/proteins/P0C0L7.xml48 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 GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h6.05uM0.037 oCBW25113Stationary Phase, glucose limited242000Ishii, 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