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Identification
NamePyroglutamic Acid
Accession NumberDB03088  (EXPT00247)
TypeSmall Molecule
GroupsExperimental
Description

A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number98-79-3
WeightAverage: 129.114
Monoisotopic: 129.042593095
Chemical FormulaC5H7NO3
InChI KeyODHCTXKNWHHXJC-GSVOUGTGSA-N
InChI
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m1/s1
IUPAC Name
(2R)-5-oxopyrrolidine-2-carboxylic acid
SMILES
OC(=O)[C@H]1CCC(=O)N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acids and Derivatives
Alternative parentsOxoprolines; Pyrrolidine Carboxylic Acids; Secondary Carboxylic Acid Amides; Lactams; Polyamines; Enolates; Carboxylic Acids
Substituentspyrrolidine carboxylic acid; oxoproline; pyrrolidine carboxylic acid or derivative; pyrrolidone; pyrrolidine; carboxamide group; lactam; secondary carboxylic acid amide; carboxylic acid; polyamine; enolate; organonitrogen compound
Classification descriptionThis compound belongs to the 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.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
5-OxoprolinuriaDiseaseSMP00143
Gamma-Glutamyltransferase DeficiencyDiseaseSMP00183
5-oxoprolinase deficiencyDiseaseSMP00500
Glutathione MetabolismMetabolicSMP00015
Glutathione Synthetase DeficiencyDiseaseSMP00337
Gamma-glutamyl-transpeptidase deficiencyDiseaseSMP00501
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.844
Blood Brain Barrier + 0.9612
Caco-2 permeable - 0.7558
P-glycoprotein substrate Non-substrate 0.6844
P-glycoprotein inhibitor I Non-inhibitor 0.9821
P-glycoprotein inhibitor II Non-inhibitor 0.997
Renal organic cation transporter Non-inhibitor 0.9233
CYP450 2C9 substrate Non-substrate 0.8193
CYP450 2D6 substrate Non-substrate 0.8251
CYP450 3A4 substrate Non-substrate 0.6317
CYP450 1A2 substrate Non-inhibitor 0.9641
CYP450 2C9 substrate Non-inhibitor 0.9782
CYP450 2D6 substrate Non-inhibitor 0.9678
CYP450 2C19 substrate Non-inhibitor 0.9812
CYP450 3A4 substrate Non-inhibitor 0.9931
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9973
Ames test Non AMES toxic 0.9497
Carcinogenicity Non-carcinogens 0.9744
Biodegradation Ready biodegradable 0.9363
Rat acute toxicity 2.0801 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9923
hERG inhibition (predictor II) Non-inhibitor 0.9791
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point184.7 °CPhysProp
water solubility4.76E+005 mg/L (at 13 °C)BEILSTEIN
Predicted Properties
PropertyValueSource
Water Solubility151.0ALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.09 m3·mol-1ChemAxon
Polarizability11.42 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

John G. Black, Ian R. Scott, “Pyroglutamic acid esters, their synthesis and use in topical products.” U.S. Patent US4774255, issued December, 1974.

US4774255
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC01879
PubChem Compound439685
PubChem Substance46506886
ChEBI18183
ChEMBL
HET5HP
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Vascular endothelial growth factor A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Vascular endothelial growth factor A P15692 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Pancreatic alpha-amylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Pancreatic alpha-amylase P04746 Details

3. Ig lambda-1 chain C regions

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ig lambda-1 chain C regions P0CG04 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

4. Ig lambda chain V-II region MGC

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ig lambda chain V-II region MGC P01709 Details

5. Trefoil factor 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Trefoil factor 2 Q03403 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

6. Cytochrome c2

Kind: protein

Organism: Rhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome c2 P00091 Details

7. Disintegrin and metalloproteinase domain-containing protein 28

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Disintegrin and metalloproteinase domain-containing protein 28 Q9UKQ2 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

8. Endo-1,4-beta-xylanase

Kind: protein

Organism: Bacillus agaradhaerens

Pharmacological action: unknown

Components

Name UniProt ID Details
Endo-1,4-beta-xylanase Q7SIE2 Details

9. Dissimilatory copper-containing nitrite reductase

Kind: protein

Organism: Alcaligenes xylosoxydans xylosoxydans

Pharmacological action: unknown

Components

Name UniProt ID Details
Dissimilatory copper-containing nitrite reductase O68601 Details

10. Keratin-associated protein 5-2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Keratin-associated protein 5-2 Q701N4 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

11. Orexin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Orexin O43612 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

12. C-C motif chemokine 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
C-C motif chemokine 8 P80075 Details

13. Cytochrome c'

Kind: protein

Organism: Alcaligenes xylosoxydans xylosoxydans

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome c' P00138 Details

14. Alpha-amylase 2B

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-amylase 2B P19961 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

15. Angiogenin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Angiogenin P03950 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

16. Chondroitinase-B

Kind: protein

Organism: Pedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)

Pharmacological action: unknown

Components

Name UniProt ID Details
Chondroitinase-B Q46079 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

17. Alpha-amylase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Alpha-amylase 1 P04745 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Enzymes

1. Pancreatic alpha-amylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Pancreatic alpha-amylase P04746 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:20