Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2017-10-05 14:54:15 UTC
Primary IDFDB014506
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-5-Oxo-2-pyrrolidinecarboxylic acid
DescriptionFound in vegetables, fruits and molasses. A cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. Pyroglutamate in the urine is a biomarker for the consumption of cheese
CAS Number98-79-3
Structure
Thumb
Synonyms
SynonymSource
(-)-2-Pyrrolidone-5-carboxylic acidChEBI
(S)-(-)-2-Pyrrolidone-5-carboxylic acidChEBI
(S)-Pyroglutamic acidChEBI
5-Pyrrolidone-2-carboxylic acidChEBI
L-5-Pyrrolidone-2-carboxylic acidChEBI
L-Pyroglutamic acidChEBI
Pidolic acidChEBI
PyroglutamateChEBI
5-oxo-L-ProlineKegg
(-)-2-Pyrrolidone-5-carboxylateGenerator
(S)-(-)-2-Pyrrolidone-5-carboxylateGenerator
(S)-PyroglutamateGenerator
5-Pyrrolidone-2-carboxylateGenerator
L-5-Pyrrolidone-2-carboxylateGenerator
L-PyroglutamateGenerator
PidolateGenerator
(-)-PyroglutamateHMDB
(-)-Pyroglutamic acidHMDB
(5S)-2-Oxopyrrolidine-5-carboxylateHMDB
(5S)-2-Oxopyrrolidine-5-carboxylic acidHMDB
(S)-(-)-g-Butyrolactam-g-carboxylateHMDB
(S)-(-)-g-Butyrolactam-g-carboxylic acidHMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylateHMDB
(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acidHMDB
(S)-2-Pyrrolidone-5-carboxylateHMDB
(S)-2-Pyrrolidone-5-carboxylic acidHMDB
(S)-5-oxo-2-PyrrolidinecarboxylateHMDB
(S)-5-oxo-2-Pyrrolidinecarboxylic acidHMDB
2-L-Pyrrolidone-5-carboxylateHMDB
2-L-Pyrrolidone-5-carboxylic acidHMDB
2-Oxopyrrolidine-5(S)-carboxylateHMDB
2-Oxopyrrolidine-5(S)-carboxylic acidHMDB
2-Pyrrolidinone-5-carboxylateHMDB
2-Pyrrolidinone-5-carboxylic acidHMDB
5-Carboxy-2-pyrrolidinoneHMDB
5-L-OxoprolineHMDB
5-OxoprolineHMDB
5-Pyrrolidinone-2-carboxylateHMDB
5-Pyrrolidinone-2-carboxylic acidHMDB
Ajidew a 100HMDB
GlutimateHMDB
Glutimic acidHMDB
GlutiminateHMDB
Glutiminic acidHMDB
L-2-Pyrrolidone-5-carboxylateHMDB
L-2-Pyrrolidone-5-carboxylic acidHMDB
L-5-Carboxy-2-pyrrolidinoneHMDB
L-5-oxo-2-PyrrolidinecarboxylateHMDB
L-5-oxo-2-Pyrrolidinecarboxylic acidHMDB
L-5-OxoprolineHMDB
L-Glutamic acid g-lactamHMDB
L-GlutimateHMDB
L-Glutimic acidHMDB
L-GlutiminateHMDB
L-Glutiminic acidHMDB
L-PyrrolidinonecarboxylateHMDB
L-Pyrrolidinonecarboxylic acidHMDB
L-PyrrolidonecarboxylateHMDB
L-Pyrrolidonecarboxylic acidHMDB
OxoprolineHMDB
OxopyrrolidinecarboxylateHMDB
Oxopyrrolidinecarboxylic acidHMDB
PidolidoneHMDB
PyrrolidinonecarboxylateHMDB
Pyrrolidinonecarboxylic acidHMDB
Pyrrolidone-5-carboxylateHMDB
Pyrrolidone-5-carboxylic acidHMDB
Pyrrolidonecarboxylic acidHMDB
5-KetoprolineHMDB
Pidolate, magnesiumHMDB
5-Oxopyrrolidine-2-carboxylic acidHMDB
Magnesium pidolateHMDB
2-Pyrrolidone-5-carboxylic acidHMDB
5-OxoprolinateHMDB
PCAHMDB
(2S)-5-oxopyrrolidine-2-carboxylic acidbiospider
(s)-(-)-g-butyrolactam-g-carboxylatebiospider
(s)-(-)-g-butyrolactam-g-carboxylic acidbiospider
(s)-(-)-gamma-butyrolactam-gamma-carboxylatebiospider
(s)-(-)-gamma-butyrolactam-gamma-carboxylic acidbiospider
(S)-5-Oxo-2-pyrrolidinecarboxylatebiospider
(S)-5-Oxo-2-pyrrolidinecarboxylic acidbiospider
(s)-pyroglutamatebiospider
(s)-pyroglutamic acidbiospider
5-L-oxoprolinebiospider
5-Oxo-2-pyrrolidinecarboxylic acid; L-formdb_source
5-Oxo-L-prolinebiospider
L-5-Oxo-2-pyrrolidinecarboxylatebiospider
L-5-Oxo-2-pyrrolidinecarboxylic acidbiospider
l-5-Pyrrolidone-2-carboxylic acidbiospider
L-glutamic acid g-lactambiospider
L-glutamic acid gamma-lactambiospider
L-glutimatebiospider
L-glutimic acidbiospider
L-glutiminatebiospider
L-glutiminic acidbiospider
L-pyroglutamatebiospider
L-pyroglutamic acidbiospider
L-pyrrolidinonecarboxylatebiospider
L-pyrrolidinonecarboxylic acidbiospider
L-pyrrolidonecarboxylatebiospider
L-pyrrolidonecarboxylic acidbiospider
Pyroglutamic acidChEBI
Predicted Properties
PropertyValueSource
Water Solubility151 g/LALOGPS
logP-1ALOGPS
logP-0.89ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m³·mol⁻¹ChemAxon
Polarizability11.56 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H7NO3
IUPAC name(2S)-5-oxopyrrolidine-2-carboxylic acid
InChI IdentifierInChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
InChI KeyODHCTXKNWHHXJC-VKHMYHEASA-N
Isomeric SMILESOC(=O)[C@@H]1CCC(=O)N1
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
Classification
Description 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
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline
  • Cyclic carboximidic acid
  • Lactim
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 46.51%; H 5.46%; N 10.85%; O 37.17%DFC
Melting PointMp 156-157°DFC
Boiling PointNot Available
Experimental Water Solubility476 mg/mL at 13 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -11.45 (c, 4.44 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0ab9-8900000000-f79dc90370ba38f587c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-8900000000-f79dc90370ba38f587c9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-90fb43273551aeb9b2c4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9000000000-130a8f31f82e83c4be07View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9200000000-d69b52257404ab658d5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9500000000-ebc64308ec5d5bdb303eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9000000000-7377cb17491942e9589cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053u-9000000000-fcab1396867356ebd6aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-5b0c6536e1b3217b8544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-c30ac0bd264c8007ef92View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-5900000000-ea3a164653e4235716aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0f89-9000000000-f6620738e68f990d0594View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0udi-9000000000-7937bee2e9a6d6b29cbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-f20401903b234914b936View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-9446bb65e0edd72cfd59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0059-7900000000-74eccdeb9f0d5fd17614View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0f8a-9000000000-8786a9cd5e488192f34dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0f6t-9000000000-ebcc1ac4acd525218e80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-01q9-2900000000-754ae9b699ec1b22cd76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-9300000000-eabb8c4dc0d1111e0431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00lr-9100000000-1dd17702aee7e5bce618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-067i-9000000000-c9669794d3a8746be498View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-9e103abb0a6ed890051eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03e9-3900000000-da8cf252285c1d616586View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-01q9-9400000000-96a7fe5a81188c49d1baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-356215339a43217dea66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-02vl-9000000000-ed47ec6e675eb338da19View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-f647da344adbdf7bfb1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9200000000-0bddc68d58c6fb981d1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-0900000000-c70c79fa828bbf137ebcView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-6c87253da642bb4800dfView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID7127
ChEMBL IDCHEMBL397976
KEGG Compound IDC01879
Pubchem Compound ID7405
Pubchem Substance IDNot Available
ChEBI ID18183
Phenol-Explorer IDNot Available
DrugBank IDDB03088
HMDB IDHMDB00267
CRC / DFC (Dictionary of Food Compounds) IDHQL64-D:JRM15-X
EAFUS IDNot Available
Dr. Duke IDPYROGLUTAMIC-ACID
BIGG ID1800372
KNApSAcK IDC00007403
HET IDPCA
Flavornet IDNot Available
GoodScent IDrw1142131
SuperScent IDNot Available
Wikipedia IDPyroglutamic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti lipolyticDUKE
insulinicDUKE
Enzymes
NameGene NameUniProt ID
Gamma-glutamylcyclotransferaseGGCTO75223
5-oxoprolinaseOPLAHO14841
AngiogeninANGP03950
Vascular endothelial growth factor AVEGFAP15692
OrexinHCRTO43612
Ig lambda-1 chain C regionsIGLC1P0CG04
Pathways
NameSMPDB LinkKEGG Link
Glutathione MetabolismSMP00015 map00480
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
ethereal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).