Showing metabocard for Pyrrolidonecarboxylic acid (BMDB0000805)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:36:50 UTC
Update Date2020-05-05 03:16:32 UTC
BMDB IDBMDB0000805
Secondary Accession Numbers
  • BMDB00805
Metabolite Identification
Common NamePyrrolidonecarboxylic acid
DescriptionPyrrolidonecarboxylic acid, also known as pyroglutamate or pyroglutamic acid, 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. Pyrrolidonecarboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
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-Pyrrolidone-2-carboxylateGenerator
PyrrolidonecarboxylateGenerator
(+)-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
5-KetoprolineMeSH, HMDB
5-OxoprolineMeSH, HMDB
Pidolate, magnesiumMeSH, HMDB
Pidolic acidMeSH, HMDB
5-Oxopyrrolidine-2-carboxylic acidMeSH, HMDB
Magnesium pidolateMeSH, HMDB
Pyrrolidonecarboxylic acidMeSH
Chemical FormulaC5H7NO3
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
IUPAC Name5-oxopyrrolidine-2-carboxylic acid
Traditional Namepyroglutamate
CAS Registry Number149-87-1
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 KeyODHCTXKNWHHXJC-UHFFFAOYSA-N
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability11.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
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) (Non-derivatized)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
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-0910000000-7965a220921380301b85View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-b41e3a258706b48b80adView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9300000000-b5c23f97f5bd408c2910View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4i-1910000000-7a4c0287311301949021View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9100000000-f14d615c29a3dda06991View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-0207d9b33e7505df2b17View 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
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-11bdcfc4a30eb010684fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-eb1ffde5dba339f1ae8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-4900000000-08bc0ae8cf0b3809b84eView 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 Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 22.53 MHz, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000805
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyroglutamic_acid
METLIN IDNot Available
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 ReferencesNot Available