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Human Metabolome Database Version 3.5

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Showing metabocard for Pyroglutamic acid (HMDB00267)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:12 -0700
HMDB ID HMDB00267
Secondary Accession Numbers None
Metabolite Identification
Common Name Pyroglutamic acid
Description Pyroglutamic acid is 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. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissue in bound form, especially skin. Also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (-)-2-Pyrrolidone-5-carboxylate
  2. (-)-2-Pyrrolidone-5-carboxylic acid
  3. (-)-Pyroglutamate
  4. (-)-Pyroglutamic acid
  5. (5S)-2-Oxopyrrolidine-5-carboxylate
  6. (5S)-2-Oxopyrrolidine-5-carboxylic acid
  7. (S)-(-)-2-Pyrrolidone-5-carboxylate
  8. (S)-(-)-2-Pyrrolidone-5-carboxylic acid
  9. (S)-(-)-g-Butyrolactam-g-carboxylate
  10. (S)-(-)-g-Butyrolactam-g-carboxylic acid
  11. (S)-(-)-gamma-Butyrolactam-gamma-carboxylate
  12. (S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid
  13. (S)-2-Pyrrolidone-5-carboxylate
  14. (S)-2-Pyrrolidone-5-carboxylic acid
  15. (S)-5-Oxo-2-pyrrolidinecarboxylate
  16. (S)-5-Oxo-2-pyrrolidinecarboxylic acid
  17. (S)-Pyroglutamate
  18. (S)-Pyroglutamic acid
  19. 2-L-Pyrrolidone-5-carboxylate
  20. 2-L-Pyrrolidone-5-carboxylic acid
  21. 2-Oxopyrrolidine-5(S)-carboxylate
  22. 2-Oxopyrrolidine-5(S)-carboxylic acid
  23. 2-Pyrrolidinone-5-carboxylate
  24. 2-Pyrrolidinone-5-carboxylic acid
  25. 5-Carboxy-2-pyrrolidinone
  26. 5-L-Oxoproline
  27. 5-Oxo-L-proline
  28. 5-Oxoproline
  29. 5-Pyrrolidinone-2-carboxylate
  30. 5-Pyrrolidinone-2-carboxylic acid
  31. Ajidew A 100
  32. Glutimate
  33. Glutimic acid
  34. Glutiminate
  35. Glutiminic acid
  36. L-2-Pyrrolidone-5-carboxylate
  37. L-2-Pyrrolidone-5-carboxylic acid
  38. L-5-Carboxy-2-pyrrolidinone
  39. L-5-Oxo-2-pyrrolidinecarboxylate
  40. L-5-Oxo-2-pyrrolidinecarboxylic acid
  41. L-5-Oxoproline
  42. L-Glutamic acid g-lactam
  43. L-Glutimate
  44. L-Glutimic acid
  45. L-Glutiminate
  46. L-Glutiminic acid
  47. L-Pyroglutamate
  48. L-Pyroglutamic acid
  49. L-Pyrrolidinonecarboxylate
  50. L-Pyrrolidinonecarboxylic acid
  51. L-Pyrrolidonecarboxylate
  52. L-Pyrrolidonecarboxylic acid
  53. Oxoproline
  54. Oxopyrrolidinecarboxylate
  55. Oxopyrrolidinecarboxylic acid
  56. Pidolate
  57. Pidolic acid
  58. Pidolidone
  59. Pyroglutamate
  60. Pyroglutamic acid
  61. Pyrrolidinonecarboxylate
  62. Pyrrolidinonecarboxylic acid
  63. Pyrrolidone-5-carboxylate
  64. Pyrrolidone-5-carboxylic acid
  65. Pyrrolidonecarboxylic acid
Chemical Formula C5H7NO3
Average Molecular Weight 129.114
Monoisotopic Molecular Weight 129.042593095
IUPAC Name (2S)-5-oxopyrrolidine-2-carboxylic acid
Traditional IUPAC Name pyroglutamic acid
CAS Registry Number 98-79-3
SMILES OC(=O)[C@@H]1CCC(=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)/t3-/m0/s1
InChI Key ODHCTXKNWHHXJC-VKHMYHEASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteromonocyclic Compounds
Class Pyrrolidines
Sub Class Pyrrolidine Carboxylic Acids and Derivatives
Other Descriptors
  • 5-oxoproline(ChEBI)
  • Aliphatic Heteromonocyclic Compounds
  • Other amino acids(KEGG)
  • Oxoprolines
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Lactam
  • Pyrrolidone
  • Secondary Carboxylic Acid Amide
Direct Parent Pyrrolidine Carboxylic Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glutathione metabolism
  • Essential amino acid
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 476.0 mg/mL at 13 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 151 g/L ALOGPS
LogP -1.01 ALOGPS
LogP -0.89 ChemAxon
LogS 0.07 ALOGPS
pKa (strongest acidic) 3.61 ChemAxon
pKa (strongest basic) -1.8 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.4 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 28.09 ChemAxon
Polarizability 11.56 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Prostate
  • Skin
Pathways
Name SMPDB Link KEGG Link
Glutathione Metabolism SMP00015 map00480 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
19.5 +/- 3.7 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
47 +/- 30 uM Not Specified Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
41.0 +/- 31.0 uM Adult (>18 years old) Not Specified Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Urine compound detected by GC-MS
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
20.7 (10.2-32.6) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
14.0 +/- 7.2 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
7.3 (0.1-29.3) umol/mmol creatinine Newborn (0-30 days old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
24.1 (3.4-54.2) umol/mmol creatinine Infant (0-1 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
5.3 (2.9-10.4) umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
3.1 (1.9-11.3) umol/mmol creatinine Adolescent (13-18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
18.6(4.5-24.9) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
87.00 (13.00-161.00) uM Adult (>18 years old) Both Glutathione synthetase deficiency Not Available
Blood Detected and Quantified
Article_icon
3.5 (3.00-4.00) uM Adult (>18 years old) Both Glutathione synthetase deficiency Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
2326.0 uM Adult (>18 years old) Both Pyroglutamic aciduria Not Available
Urine Detected and Quantified
Article_icon
28.8 (3.4-54.2) umol/mmol creatinine Adult (>18 years old) Both 5-Oxoprolinase deficiency Not Available
Urine Detected and Quantified
Article_icon
3500.0 (1000.0-6000.0) umol/mmol creatinine Adult (>18 years old) Both 5-Oxoprolinase Deficiency Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Both Autosomal dominant polycystic kidney disease Not Available
Urine Detected and Quantified
Article_icon
17000.00 (4000.00-30000.00) umol/mmol creatinine Adult (>18 years old) Both Glutathione synthetase deficiency Not Available
Urine Detected and Quantified
Article_icon
1.9 umol/mmol creatinine Adult (>18 years old) Both Pyroglutamic aciduria Not Available
Associated Disorders and Diseases
Disease References
Glutathione synthetase deficiency
  • Jellum E, Stokke O, Eldjarn L: Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Clin Chem. 1972 Aug;18(8):800-9. Pubmed: 4557757 Link_out
  • Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. Pubmed: 8013094 Link_out
  • http://www.metagene.de/program/d.prg?mp=GLUTATHIONE%20SYNTHETASE%20DEFICIENCY
5-oxoprolinase deficiency
    • http://www.metagene.de/program/d.prg?mp=5-OXOPROLINASE%20DEFICIENCY
    Associated OMIM IDs
    • 266130 Link_out (Glutathione synthetase deficiency)
    • 260005 Link_out (5-oxoprolinase deficiency)
    DrugBank ID DB03088 Link_out
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB014506
    KNApSAcK ID C00007403 Link_out
    Chemspider ID 7127 Link_out
    KEGG Compound ID C01879 Link_out
    BioCyc ID CPD-589 Link_out
    BiGG ID 1800372 Link_out
    Wikipedia Link Pyroglutamic acid Link_out
    NuGOwiki Link HMDB00267 Link_out
    Metagene Link HMDB00267 Link_out
    METLIN ID 3251 Link_out
    PubChem Compound 7405 Link_out
    PDB ID PCA Link_out
    ChEBI ID 18183 Link_out
    References
    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.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Manning NJ, Davies NP, Olpin SE, Carpenter KH, Smith MF, Pollitt RJ, Duncan SL, Larsson A, Carlsson B: Prenatal diagnosis of glutathione synthase deficiency. Prenat Diagn. 1994 Jun;14(6):475-8. Pubmed: 7937585 Link_out
    2. Caspers PJ, Lucassen GW, Carter EA, Bruining HA, Puppels GJ: In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles. J Invest Dermatol. 2001 Mar;116(3):434-42. Pubmed: 11231318 Link_out
    3. Hussain Z, Lannigan R, Stoakes L: A new approach for presumptive identification of clinically important streptococci. Zentralbl Bakteriol Mikrobiol Hyg [A]. 1984 Oct;258(1):74-9. Pubmed: 6441390 Link_out
    4. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979 Link_out
    5. Creer MH, Lau BW, Jones JD, Chan KM: Pyroglutamic acidemia in an adult patient. Clin Chem. 1989 Apr;35(4):684-6. Pubmed: 2702756 Link_out
    6. Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. Pubmed: 2093471 Link_out
    7. Uhlhaas S, Lange H: Striatal deficiency of L-pyroglutamic acid in Huntington's disease is accompanied by increased plasma levels. Brain Res. 1988 Aug 2;457(1):196-9. Pubmed: 2971422 Link_out
    8. Jellum E, Stokke O, Eldjarn L: Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Clin Chem. 1972 Aug;18(8):800-9. Pubmed: 4557757 Link_out
    9. Croal BL, Glen AC, Kelly CJ, Logan RW: Transient 5-oxoprolinuria (pyroglutamic aciduria) with systemic acidosis in an adult receiving antibiotic therapy. Clin Chem. 1998 Feb;44(2):336-40. Pubmed: 9474033 Link_out
    10. Winslow JW, Shih A, Bourell JH, Weiss G, Reed B, Stults JT, Goldsmith LT: Human seminal relaxin is a product of the same gene as human luteal relaxin. Endocrinology. 1992 May;130(5):2660-8. Pubmed: 1572287 Link_out
    11. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012 Link_out
    12. Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. Pubmed: 8013094 Link_out
    13. Erasmus E, Mienie LJ, de Vries WN, de Wet WJ, Carlsson B, Larsson A: Prenatal analysis in two suspected cases of glutathione synthetase deficiency. J Inherit Metab Dis. 1993;16(5):837-43. Pubmed: 8295398 Link_out
    14. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
    Enzymes
    Name: Glutaminyl-peptide cyclotransferase
    Reactions:
    • L-glutaminyl-peptide = 5-oxoprolyl-peptide + NH3 [RN:R04058]
    Gene Name: QPCT
    Uniprot ID: Q16769 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 5-oxoprolinase
    Reactions:
    • ATP + 5-oxo-L-proline + 2 H2O = ADP + phosphate + L-glutamate [RN:R00251]
    Gene Name: OPLAH
    Uniprot ID: O14841 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Angiogenin
    Reactions:
      Gene Name: ANG
      Uniprot ID: P03950 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ig lambda chain V-II region MGC
      Reactions:
        Gene Name: Not Available
        Uniprot ID: P01709 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Alpha-amylase 1
        Reactions:
        • Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units ALL_REAC (other) R02108 R06209(G)
        Gene Name: AMY1A
        Uniprot ID: P04745 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Pancreatic alpha-amylase
        Reactions:
        • Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units ALL_REAC (other) R02108 R06209(G)
        Gene Name: AMY2A
        Uniprot ID: P04746 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Vascular endothelial growth factor A
        Reactions:
          Gene Name: VEGFA
          Uniprot ID: P15692 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Alpha-amylase 2B
          Reactions:
          • Endohydrolysis of (1->4)-alpha-D-glucosidic linkages in polysaccharides containing three or more (1->4)-alpha-linked D-glucose units ALL_REAC (other) R02108 R06209(G)
          Gene Name: AMY2B
          Uniprot ID: P19961 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Orexin
          Reactions:
            Gene Name: HCRT
            Uniprot ID: O43612 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Gamma-glutamylcyclotransferase
            Reactions:
            • (gamma-L-glutamyl)-L-amino acid = 5-oxoproline + L-amino acid [RN:R03749]
            Gene Name: GGCT
            Uniprot ID: O75223 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Ig lambda-1 chain C regions
            Reactions:
              Gene Name: IGLC1
              Uniprot ID: P0CG04 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA