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Identification
NamePyroglutamic Acid
Accession NumberDB03088  (EXPT00247)
TypeSmall Molecule
GroupsExperimental
DescriptionA cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIISZB83O1W42
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)[[email protected]]1CCC(=O)N1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Alpha-amylase 2BProteinunknownNot AvailableHumanP19961 details
AngiogeninProteinunknownNot AvailableHumanP03950 details
Chondroitinase-BProteinunknownNot AvailablePedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)Q46079 details
Alpha-amylase 1ProteinunknownNot AvailableHumanP04745 details
Vascular endothelial growth factor AProteinunknownNot AvailableHumanP15692 details
Pancreatic alpha-amylaseProteinunknownNot AvailableHumanP04746 details
Ig lambda-1 chain C regionsProteinunknownNot AvailableHumanP0CG04 details
Ig lambda chain V-II region MGCProteinunknownNot AvailableHumanP01709 details
Trefoil factor 2ProteinunknownNot AvailableHumanQ03403 details
Cytochrome c2ProteinunknownNot AvailableRhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)P00091 details
Disintegrin and metalloproteinase domain-containing protein 28ProteinunknownNot AvailableHumanQ9UKQ2 details
Endo-1,4-beta-xylanaseProteinunknownNot AvailableBacillus agaradhaerensQ7SIE2 details
Copper-containing nitrite reductaseProteinunknownNot AvailableAlcaligenes xylosoxydans xylosoxydansO68601 details
Keratin-associated protein 5-2ProteinunknownNot AvailableHumanQ701N4 details
OrexinProteinunknownNot AvailableHumanO43612 details
C-C motif chemokine 8ProteinunknownNot AvailableHumanP80075 details
Cytochrome c'ProteinunknownNot AvailableAlcaligenes xylosoxydans xylosoxydansP00138 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
5-OxoprolinuriaDiseaseSMP00143
Glutathione Synthetase DeficiencyDiseaseSMP00337
5-oxoprolinase deficiencyDiseaseSMP00500
Glutathione MetabolismMetabolicSMP00015
Gamma-Glutamyltransferase DeficiencyDiseaseSMP00183
Gamma-glutamyl-transpeptidase deficiencyDiseaseSMP00501
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.844
Blood Brain Barrier+0.9612
Caco-2 permeable-0.7558
P-glycoprotein substrateNon-substrate0.6844
P-glycoprotein inhibitor INon-inhibitor0.9821
P-glycoprotein inhibitor IINon-inhibitor0.997
Renal organic cation transporterNon-inhibitor0.9233
CYP450 2C9 substrateNon-substrate0.8193
CYP450 2D6 substrateNon-substrate0.8251
CYP450 3A4 substrateNon-substrate0.6317
CYP450 1A2 substrateNon-inhibitor0.9641
CYP450 2C9 inhibitorNon-inhibitor0.9782
CYP450 2D6 inhibitorNon-inhibitor0.9678
CYP450 2C19 inhibitorNon-inhibitor0.9812
CYP450 3A4 inhibitorNon-inhibitor0.9931
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9973
Ames testNon AMES toxic0.9497
CarcinogenicityNon-carcinogens0.9744
BiodegradationReady biodegradable0.9363
Rat acute toxicity2.0801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9923
hERG inhibition (predictor II)Non-inhibitor0.9791
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility151.0 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-c811841958c6567b8e98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9400000000-3e005daef5239c2cecb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05o3-9000000000-a408e85310e25b6fa7b1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-c9543eaa9b5579e46ef5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-8900000000-265e5da8155fb3b596beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d7e64b39b411328bbb77View in MoNA
Taxonomy
DescriptionThis compound 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
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Oxoproline
  • 2-pyrrolidone
  • Pyrrolidone
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
AMY2B
Uniprot ID:
P19961
Molecular Weight:
57709.49 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Rrna binding
Specific Function:
Binds to actin on the surface of endothelial cells; once bound, angiogenin is endocytosed and translocated to the nucleus. Stimulates ribosomal RNA synthesis including that containing the initiation site sequences of 45S rRNA. Cleaves tRNA within anticodon loops to produce tRNA-derived stress-induced fragments (tiRNAs) which inhibit protein synthesis and triggers the assembly of stress granules...
Gene Name:
ANG
Uniprot ID:
P03950
Molecular Weight:
16549.95 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Pedobacter heparinus (strain ATCC 13125 / DSM 2366 / NCIB 9290)
Pharmacological action
unknown
General Function:
Chondroitin b lyase activity
Specific Function:
Cleaves the glycosaminoglycan, dermatan sulfate.
Gene Name:
cslB
Uniprot ID:
Q46079
Molecular Weight:
56336.075 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
AMY1A
Uniprot ID:
P04745
Molecular Weight:
57767.49 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Vascular endothelial growth factor receptor binding
Specific Function:
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of blood vessels. Binds to the FLT1/VEGFR1 and KDR/VEGFR2 receptors, heparan sulfate and heparin. NRP1/Neuropilin-1 binds isoforms VEGF-165 and VEGF-145. Isoform VEGF165B binds to KDR but does not activ...
Gene Name:
VEGFA
Uniprot ID:
P15692
Molecular Weight:
27042.205 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Chloride ion binding
Specific Function:
Not Available
Gene Name:
AMY2A
Uniprot ID:
P04746
Molecular Weight:
57706.51 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Immunoglobulin receptor binding
Specific Function:
Not Available
Gene Name:
IGLC1
Uniprot ID:
P0CG04
Molecular Weight:
11347.585 Da
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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Antigen binding
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
P01709
Molecular Weight:
11557.51 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Inhibits gastrointestinal motility and gastric acid secretion. Could function as a structural component of gastric mucus, possibly by stabilizing glycoproteins in the mucus gel through interactions with carbohydrate side chains (By similarity).
Gene Name:
TFF2
Uniprot ID:
Q03403
Molecular Weight:
14284.12 Da
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:10592235 ]
Kind
Protein
Organism
Rhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Cytochrome c2 is found mainly in purple, non-sulfur, photosynthetic bacteria where it functions as the electron donor to the oxidized bacteriochlorophyll in the photophosphorylation pathway. However, it may also have a role in the respiratory chain and is found in some non-photosynthetic bacteria.
Gene Name:
cycA
Uniprot ID:
P00091
Molecular Weight:
14632.81 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. May be involved in sperm maturation.
Gene Name:
ADAM28
Uniprot ID:
Q9UKQ2
Molecular Weight:
87147.04 Da
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:10592235 ]
Kind
Protein
Organism
Bacillus agaradhaerens
Pharmacological action
unknown
General Function:
Endo-1,4-beta-xylanase activity
Specific Function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q7SIE2
Molecular Weight:
23307.82 Da
Kind
Protein
Organism
Alcaligenes xylosoxydans xylosoxydans
Pharmacological action
unknown
General Function:
Nitrite reductase (no-forming) activity
Specific Function:
Not Available
Gene Name:
nir
Uniprot ID:
O68601
Molecular Weight:
38939.295 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
In the hair cortex, hair keratin intermediate filaments are embedded in an interfilamentous matrix, consisting of hair keratin-associated protein (KRTAP), which are essential for the formation of a rigid and resistant hair shaft through their extensive disulfide bond cross-linking with abundant cysteine residues of hair keratins. The matrix proteins include the high-sulfur and high-glycine-tyro...
Gene Name:
KRTAP5-2
Uniprot ID:
Q701N4
Molecular Weight:
16270.68 Da
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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Neuropeptides that play a significant role in the regulation of food intake and sleep-wakefulness, possibly by coordinating the complex behavioral and physiologic responses of these complementary homeostatic functions. A broader role in the homeostatic regulation of energy metabolism, autonomic function, hormonal balance and the regulation of body fluids, is also suggested. Orexin-A binds to bo...
Gene Name:
HCRT
Uniprot ID:
O43612
Molecular Weight:
13362.51 Da
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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein kinase activity
Specific Function:
Chemotactic factor that attracts monocytes, lymphocytes, basophils and eosinophils. May play a role in neoplasia and inflammatory host responses. This protein can bind heparin. The processed form MCP-2(6-76) does not show monocyte chemotactic activity, but inhibits the chemotactic effect most predominantly of CCL7, and also of CCL2 and CCL5 and CCL8.
Gene Name:
CCL8
Uniprot ID:
P80075
Molecular Weight:
11246.24 Da
Kind
Protein
Organism
Alcaligenes xylosoxydans xylosoxydans
Pharmacological action
unknown
General Function:
Iron ion binding
Specific Function:
Cytochrome c' is the most widely occurring bacterial c-type cytochrome. Cytochromes c' are high-spin proteins and the heme has no sixth ligand. Their exact function is not known.
Gene Name:
Not Available
Uniprot ID:
P00138
Molecular Weight:
13628.35 Da

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Chloride ion binding
Specific Function:
Not Available
Gene Name:
AMY2A
Uniprot ID:
P04746
Molecular Weight:
57706.51 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23