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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-05-16 17:41:01 UTC
HMDB IDHMDB00805
Secondary Accession NumbersNone
Metabolite Identification
Common NamePyrrolidonecarboxylic acid
Description2-Pyrrolidone-5-carboxylic acid (PCA) is a cyclic derivative of glutamic acid, physiologically present in mammalian tissues. It has been shown that PCA releases GABA from the cerebral cortex and displays anti-anxiety effects in a simple approach-avoidance conflict situation in the rat. In clinical pharmacology experiments, PCA significantly shortens the plasma half-life of ethanol during acute intoxication.
Structure
Thumb
Synonyms
ValueSource
2-Pyrrolidone-5-carboxylic acidChEBI
5-oxo-DL-ProlineChEBI
5-Pyrrolidone-2-carboxylic acidChEBI
GlpChEBI
PyroglutamateChEBI
Pyroglutamic acidChEBI
2-Pyrrolidone-5-carboxylateGenerator
5-Oxopyrrolidine-2-carboxylateGenerator
5-Pyrrolidone-2-carboxylateGenerator
(+)-2-Pyrrolidone-5-carboxylateHMDB
(+)-2-Pyrrolidone-5-carboxylic acidHMDB
(+)-PyroglutamateHMDB
(+)-Pyroglutamic acidHMDB
(2R)-2-Carboxy-5-pyrrolidinoneHMDB
(R)-(+)-2-Pyrrolidone-5-carboxylateHMDB
(R)-(+)-2-Pyrrolidone-5-carboxylic acidHMDB
(R)-2-Pyrrolidone-5-carboxylateHMDB
(R)-2-Pyrrolidone-5-carboxylic acidHMDB
(R)-5-Oxopyrrolidine-2-carboxylateHMDB
(R)-5-Oxopyrrolidine-2-carboxylic acidHMDB
5-oxo-D-ProlineHMDB
D-2-Pyrrolidone-5-carboxylicHMDB
D-5-Pyrrolidone-2-carboxylateHMDB
D-5-Pyrrolidone-2-carboxylic acidHMDB
D-PyroglutamateHMDB
D-Pyroglutamic acidHMDB
Chemical FormulaC5H7NO3
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
IUPAC Name5-oxopyrrolidine-2-carboxylic acid
Traditional Namepyroglutamate
CAS Registry Number4042-36-8
SMILES
OC(=O)C1CCC(=O)N1
InChI Identifier
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)
InChI KeyInChIKey=ODHCTXKNWHHXJC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline carboxylic acid
  • Cyclic carboximidic acid
  • Pyrroline
  • Lactim
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of rn00471 D-Glutamine and D-glutamate metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 162 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility736 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility151.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m3·mol-1ChemAxon
Polarizability11.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a4i-0900000000-b41e3a258706b48b80adView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-001i-9300000000-b5c23f97f5bd408c2910View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0a4i-1910000000-7a4c0287311301949021View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9600000000-8e7afe6ced148f01b715View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9000000000-21b65f5a05735d8f6916View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a5c-9000000000-87d3859fb9096e75c2a9View in MoNA
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
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-6c87253da642bb4800dfView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue Location
  • Most Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified5.65 +/- 4.71 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified8.70 +/- 7.55 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified15.0 +/- 32.5 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified18.2 +/- 20.9 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.82 +/- 5.16 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified3.84 +/- 2.81 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.618 +/- 0.758 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.481 +/- 0.853 uMAdult (>18 years old)BothDental caries
    • Sugimoto et al. (...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022254
KNApSAcK IDNot Available
Chemspider ID485
KEGG Compound IDC02237
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00805
Metagene LinkHMDB00805
METLIN ID5769
PubChem Compound499
PDB IDNot Available
ChEBI ID16010
References
Synthesis ReferenceMeister, Alton; Bukenberger, Martha W. Enzymic conversion of D-glutamic acid to D-pyrrolidonecarboxylic acid by mammalian tissues. Nature (London, United Kingdom) (1962), 194 557-9.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Palekar AG, Tate SS, Sullivan JF, Meister A: Accumulation of 50oxo-L-proline and 5-oxo-D-proline in the blood plasma in end stage renal disease. Biochem Med. 1975 Nov;14(3):339-45. [1225334 ]
  2. Monsigny M, Rondanino C, Duverger E, Fajac I, Roche AC: Glyco-dependent nuclear import of glycoproteins, glycoplexes and glycosylated plasmids. Biochim Biophys Acta. 2004 Jul 6;1673(1-2):94-103. [15238252 ]

Enzymes

General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:
GGCT
Uniprot ID:
O75223
Molecular weight:
19091.635
Reactions
(Gamma-L-glutamyl)-L-amino acid → Pyrrolidonecarboxylic acid + L-amino aciddetails
General function:
Not Available
Specific function:
Contributes to degradation of proteins cross-linked by transglutaminases. Degrades the cross-link between a lysine and a glutamic acid residue from two proteins that have been cross-linked by transglutaminases. Catalyzes the formation of 5-oxoproline from L-gamma-glutamyl-L-epsilon-lysine. Inactive with L-gamma-glutamyl-alpha-amino acid substrates such as L-gamma-glutamyl-L-alpha-cysteine and L-gamma-glutamyl-L-alpha-alanine.
Gene Name:
GGACT
Uniprot ID:
Q9BVM4
Molecular weight:
17328.44
Reactions
(Gamma-L-glutamyl)-L-amino acid → Pyrrolidonecarboxylic acid + L-amino aciddetails