Back to Compounds

Showing Compound Pyrrolidonecarboxylic acid (FDB022254)

Record Information
Version1.0
Creation date2011-09-21 00:10:56 UTC
Update date2018-05-28 18:32:05 UTC
Primary IDFDB022254
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number4042-36-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
2-Pyrrolidone-5-carboxylateGenerator
2-Pyrrolidone-5-carboxylic acidChEBI
5-Oxo-D-prolinehmdb
5-oxo-DL-ProlineChEBI
D-2-Pyrrolidone-5-carboxylichmdb
D-5-Pyrrolidone-2-carboxylatehmdb
D-5-Pyrrolidone-2-carboxylic acidhmdb
D-Pyroglutamatehmdb
D-Pyroglutamic acidhmdb
GlpChEBI
Predicted Properties
PropertyValueSource
Water Solubility324 g/LALOGPS
logP-0.12ALOGPS
logP-0.12ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.61 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.68 m³·mol⁻¹ChemAxon
Polarizability11.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H7NO3
IUPAC name2-oxopyrrolidine-1-carboxylic acid
InChI IdentifierInChI=1S/C5H7NO3/c7-4-2-1-3-6(4)5(8)9/h1-3H2,(H,8,9)
InChI KeyDQAKJEWZWDQURW-UHFFFAOYSA-N
Isomeric SMILESOC(=O)N1CCCC1=O
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
Classification
Description Belongs to the class of organic compounds known as oxoprolines. Oxoprolines are compounds containing an oxoproline moiety, which consists of a pyrrolidine ring bearing a carboxylic acid group at the ring position 2, and a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentOxoprolines
Alternative Parents
Substituents
  • Oxoproline
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • 2-pyrrolidone
  • Dicarboximide
  • Carbonic acid derivative
  • Lactam
  • Carbamic acid derivative
  • Carbamic acid
  • Azacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPyrrolidonecarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002f-9200000000-444c3cf2df865e2c01acSpectrum
Predicted GC-MSPyrrolidonecarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrrolidonecarboxylic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPyrrolidonecarboxylic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MSNot Available
NMRNot Available
ChemSpider ID485
ChEMBL IDCHEMBL284718
KEGG Compound IDC02237
Pubchem Compound ID499
Pubchem Substance IDNot Available
ChEBI ID16924
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00805
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Gamma-glutamylcyclotransferaseGGCTO75223
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference