Pyrrolidonecarboxylic acid (ECMDB00805) (M2MDB000187)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-05-31 13:01:16 -0600
Update Date2015-10-15 16:13:37 -0600
Secondary Accession Numbers
  • ECMDB00805
Identification
Name:Pyrrolidonecarboxylic acid
DescriptionPyrrolidonecarboxylic acid is a member of the chemical class known as Pyrrolidine Carboxylic Acids and Derivatives. These are compounds containing a pyrrolidine ring which bears a carboxylic acid or a derivative thereof. 2-Pyrrolidone-5-carboxylic acid (PCA) is a cyclic derivative of glutamic acid, and has been found in E. coli beta-galactosidase. It is produced by gamma-glutamyl phosphate reductase (glutamate semialdehyde dehydrogenase) via glutamic acid 5-semidaldehyde [PMID: 7034716].
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (+)-2-Pyrrolidone-5-carboxylate
  • (+)-2-Pyrrolidone-5-carboxylic acid
  • (+)-Pyroglutamate
  • (+)-Pyroglutamic acid
  • (2R)-2-Carboxy-5-pyrrolidinone
  • (R)-(+)-2-Pyrrolidone-5-carboxylate
  • (R)-(+)-2-Pyrrolidone-5-carboxylic acid
  • (R)-2-Pyrrolidone-5-carboxylate
  • (R)-2-Pyrrolidone-5-carboxylic acid
  • (R)-5-Oxopyrrolidine-2-carboxylate
  • (R)-5-Oxopyrrolidine-2-carboxylic acid
  • 5-Oxo-D-proline
  • D-2-Pyrrolidone-5-carboxylic
  • D-5-Pyrrolidone-2-carboxylate
  • D-5-Pyrrolidone-2-carboxylic acid
  • D-Pyroglutamate
  • D-Pyroglutamic acid
  • Pyrrolidonecarboxylate
Chemical Formula:C5H7NO3
Weight:Average: 129.114
Monoisotopic: 129.042593095
InChI Key:ODHCTXKNWHHXJC-VKHMYHEASA-N
InChI:InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
CAS number:4042-36-8
IUPAC Name:(2R)-5-oxopyrrolidine-2-carboxylic acid
Traditional IUPAC Name:5-oxo-D-proline
SMILES:OC(=O)[C@@H]1CCC(=O)N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Oxoproline
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidone
  • 2-pyrrolidone
  • Pyrrolidine
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:155 - 162 °C
Experimental Properties:
PropertyValueSource
Water Solubility:SolublePhysProp
LogP:-0.809PhysProp
Predicted Properties
PropertyValueSource
Water Solubility151 g/LALOGPS
logP-1ALOGPS
logP-0.89ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m³·mol⁻¹ChemAxon
Polarizability11.42 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
D-Glutamine and D-glutamate metabolismPW000769 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • D-Glutamine and D-glutamate metabolism ec00471
EcoCyc Pathways:Not Available
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
197± 0 uMBW2511348 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 GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-c811841958c6567b8e98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9400000000-3e005daef5239c2cecb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-9000000000-a408e85310e25b6fa7b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-c9543eaa9b5579e46ef5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-8900000000-265e5da8155fb3b596beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d7e64b39b411328bbb77View in MoNA
References
References:
  • Hayzer, D. J., Leisinger, T. (1981). "Proline biosynthesis in Escherichia coli. Stoichiometry and end-product identification of the reaction catalysed by glutamate semialdehyde dehydrogenase." Biochem J 197:269-274. Pubmed: 7034716
  • 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. Pubmed: 17379776
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16924
HMDB IDHMDB00805
Pubchem Compound ID439685
Kegg IDC02237
ChemSpider ID388752
Wikipedia IDPyroglutamic acid
BioCyc IDCPD-656
EcoCyc IDCPD-656

Enzymes

Protein Details
1. Gamma-glutamyl phosphate reductase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH dependent reduction of L-gamma- glutamyl 5-phosphate into L-glutamate 5-semialdehyde and phosphate. The product spontaneously undergoes cyclization to form 1-pyrroline-5-carboxylate
Gene Name:
proA
Uniprot ID:
P07004
Molecular weight:
44630
Reactions
L-glutamate 5-semialdehyde + phosphate + NADP(+) = L-glutamyl 5-phosphate + NADPH.