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Identification
YMDB IDYMDB00107
NamePyroglutamic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPyroglutamic acid, also known as pyroglutamate or pidolate, 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. Pyroglutamic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyroglutamic acid exists in all living species, ranging from bacteria to humans. Pyroglutamic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (-)-2-Pyrrolidone-5-carboxylate
  • (-)-2-Pyrrolidone-5-carboxylic acid
  • (-)-Pyroglutamate
  • (-)-Pyroglutamic acid
  • (5S)-2-Oxopyrrolidine-5-carboxylate
  • (5S)-2-Oxopyrrolidine-5-carboxylic acid
  • (S)-(-)-2-Pyrrolidone-5-carboxylate
  • (S)-(-)-2-Pyrrolidone-5-carboxylic acid
  • (S)-(-)-g-Butyrolactam-g-carboxylate
  • (S)-(-)-g-Butyrolactam-g-carboxylic acid
  • (S)-(-)-gamma-Butyrolactam-gamma-carboxylate
  • (S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid
  • (S)-2-Pyrrolidone-5-carboxylate
  • (S)-2-Pyrrolidone-5-carboxylic acid
  • (S)-5-Oxo-2-pyrrolidinecarboxylate
  • (S)-5-Oxo-2-pyrrolidinecarboxylic acid
  • (S)-Pyroglutamate
  • (S)-Pyroglutamic acid
  • 2-L-Pyrrolidone-5-carboxylate
  • 2-L-Pyrrolidone-5-carboxylic acid
  • 2-Oxopyrrolidine-5(S)-carboxylate
  • 2-Oxopyrrolidine-5(S)-carboxylic acid
  • 2-Pyrrolidinone-5-carboxylate
  • 2-Pyrrolidinone-5-carboxylic acid
  • 5-Carboxy-2-pyrrolidinone
  • 5-L-oxoproline
  • 5-Oxo-L-proline
  • 5-Oxoproline
  • 5-Pyrrolidinone-2-carboxylate
  • 5-Pyrrolidinone-2-carboxylic acid
  • Glutimate
  • Glutimic acid
  • Glutiminate
  • Glutiminic acid
  • L-2-Pyrrolidone-5-carboxylate
  • L-2-Pyrrolidone-5-carboxylic acid
  • L-5-Carboxy-2-pyrrolidinone
  • L-5-Oxo-2-pyrrolidinecarboxylate
  • L-5-Oxo-2-pyrrolidinecarboxylic acid
  • L-5-Oxoproline
  • L-Glutamic acid g-lactam
  • L-Glutimate
  • L-Glutimic acid
  • L-Glutiminate
  • L-Glutiminic acid
  • L-Pyroglutamate
  • L-Pyroglutamic acid
  • L-Pyrrolidinonecarboxylate
  • L-Pyrrolidinonecarboxylic acid
  • L-Pyrrolidonecarboxylate
  • L-Pyrrolidonecarboxylic acid
  • Oxoproline
  • Oxopyrrolidinecarboxylate
  • Oxopyrrolidinecarboxylic acid
  • Pidolate
  • Pidolic acid
  • Pidolidone
  • Pyroglutamate
  • Pyroglutamic acid
  • Pyrrolidinonecarboxylate
  • Pyrrolidinonecarboxylic acid
  • Pyrrolidone-5-carboxylate
  • Pyrrolidone-5-carboxylic acid
  • Pyrrolidonecarboxylic acid
  • 5-Pyrrolidone-2-carboxylic acid
  • L-5-Pyrrolidone-2-carboxylic acid
  • 5-Pyrrolidone-2-carboxylate
  • L-5-Pyrrolidone-2-carboxylate
  • Ajidew a 100
  • 5-Ketoproline
  • Pidolate, magnesium
  • 5-Oxopyrrolidine-2-carboxylic acid
  • Magnesium pidolate
  • 2-Pyrrolidone-5-carboxylic acid
  • 5-Oxoprolinate
  • PCA
CAS number98-79-3
WeightAverage: 129.114
Monoisotopic: 129.042593095
InChI KeyODHCTXKNWHHXJC-VKHMYHEASA-N
InChIInChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
IUPAC Name(2S)-5-oxopyrrolidine-2-carboxylic acid
Traditional IUPAC Namepyroglutamic acid
Chemical FormulaC5H7NO3
SMILES[H]OC(=O)[C@@]1([H])N([H])C(=O)C([H])([H])C1([H])[H]
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point184.7 °C
Experimental Properties
PropertyValueReference
Water Solubility476 mg/mL at 13 oC [BEILSTEIN]PhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic Properties
Flavour/OdourSource
EtherealFDB014506
MildFDB014506
SweetFDB014506
SMPDB Pathways
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glutathione metabolismec00480 Map00480
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Pumpor, Ksenia; Boettcher, Christoph; Fehn, Susanna; Burger, Klaus. Hexafluoroacetone as protecting and activating reagent: an efficient strategy for activation of pyroglutamic acid and homologs.Heterocycles (2003), 61 259-269.
External Links:
ResourceLink
CHEBI ID18183
HMDB IDHMDB00267
Pubchem Compound ID7405
Kegg IDC01879
ChemSpider ID7127
FOODB IDFDB014506
WikipediaPyroglutamic_acid
BioCyc IDCPD-589

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P28273
Molecular weight:
140426.0
Reactions
ATP + 5-oxo-L-proline + 2 H(2)O → ADP + phosphate + L-glutamate.