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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2020-04-22 23:34:11 UTC
HMDB IDHMDB0002039
Secondary Accession Numbers
  • HMDB02039
Metabolite Identification
Common Name2-Pyrrolidinone
Description2-Pyrrolidinone is a lactam cyclization product of gamma-aminobutyric acid (GABA). (PMID 10332870 ). Vigabatrin (VGB, an antiepileptic drug) increases human brain gamma-aminobutyric acid (GABA) and the related metabolites, including 2-pyrrolidinone. Patients taking VGB are expected to have an increase of these metabolites. (PMID 10403220 , 10840398 ). 2-Pyrrolidone is an organic compound consisting of a five-membered lactam. It is a colorless liquid which is used in industrial settings as a high-boiling non-corrosive polar solvent for a wide variety of applications. It is miscible with a wide variety of other solvents including water, ethanol, diethyl ether, chloroform, benzene, ethyl acetate and carbon disulfide. -- Wikipedia .
Structure
Data?1582752225
Synonyms
ValueSource
1-Azacyclopentan-2-oneChEBI
2-KetopyrrolidineChEBI
2-OxopyrrolidineChEBI
2-PyrrolidoneChEBI
4-Aminobutyric acid lactamChEBI
alpha-PyrrolidinoneChEBI
alpha-PyrrolidoneChEBI
ButyrolactamChEBI
gamma-Aminobutyric acid lactamChEBI
gamma-Aminobutyric lactamChEBI
gamma-ButyrolactamChEBI
PyrrolidinoneChEBI
PyrrolidoneChEBI
4-Aminobutyrate lactamGenerator
a-PyrrolidinoneGenerator
Α-pyrrolidinoneGenerator
a-PyrrolidoneGenerator
Α-pyrrolidoneGenerator
g-Aminobutyrate lactamGenerator
g-Aminobutyric acid lactamGenerator
gamma-Aminobutyrate lactamGenerator
Γ-aminobutyrate lactamGenerator
Γ-aminobutyric acid lactamGenerator
g-Aminobutyric lactamGenerator
Γ-aminobutyric lactamGenerator
g-ButyrolactamGenerator
Γ-butyrolactamGenerator
2-Pyrrolidone, hydrotribromideHMDB
2-Pyrrolidone, rubidium saltHMDB
2-Pyrrolidone, (18)O-labeledHMDB
2-Pyrrolidone, 5-(14)C-labeledHMDB
2-Pyrrolidone, potassium saltHMDB
2-Pyrrolidone, sodium saltHMDB
2-Pyrrolidone, aluminum saltHMDB
2-Pyrrolidone, cerium saltHMDB
2-Pyrrolidone, hydrobromideHMDB
2-Pyrrolidone, hydrochlorideHMDB
2-Pyrrolidone, lithium saltHMDB
1-Methyl-2-pyrrolidinoneHMDB
2-Pyrol4-aminobutyric acid lactamHMDB
2-Pyrrolidone for synthesisHMDB
2-Pyrrolidone-butyrolactamHMDB
Aminobutyric acid lactamHMDB
Aminobutyric lactamHMDB
AminobutyrolactamHMDB
N-Methyl-2-pyrrolidinoneHMDB
Pyrrolidin-2-oneHMDB
PyrrolidonHMDB
Pyrrolidone-2HMDB
TetrahydropyrroloneHMDB
2-PyrrolidinoneChEBI
Chemical FormulaC4H7NO
Average Molecular Weight85.1045
Monoisotopic Molecular Weight85.052763851
IUPAC Namepyrrolidin-2-one
Traditional Namepyrrolidone
CAS Registry Number616-45-5
SMILES
O=C1CCCN1
InChI Identifier
InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
InChI KeyHNJBEVLQSNELDL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolidine-2-ones. These are pyrrolidines which bear a C=O group at position 2 of the pyrrolidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPyrrolidones
Direct ParentPyrrolidine-2-ones
Alternative Parents
Substituents
  • 2-pyrrolidone
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point23 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogP-0.85SASAKI,H ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility537 g/LALOGPS
logP-0.9ALOGPS
logP-0.58ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)14.75ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.26 m³·mol⁻¹ChemAxon
Polarizability8.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052o-9000000000-d44f6a4946e1e56b0ffdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001c-9000000000-7fd58ea01b9edb8fc097Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052o-9000000000-d44f6a4946e1e56b0ffdSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001c-9000000000-7fd58ea01b9edb8fc097Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004u-9000000000-8bce2b1b7929b037ee02Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-ac4fb667bd839cbe2147Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000f-9000000000-7afd271c8dc78f370c0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-6edec43d002984d510ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-001c-9000000000-7fd58ea01b9edb8fc097Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-ea2049081fa6f29e9374Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9000000000-cf8e02717d036ce75838Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-60b2774f4df85cf35f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-a6c63aa4660c4b4a55a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-e1cf6ff92627fd5af9d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d318928d5db43685e331Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Brain
  • Epidermis
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0975 +/- 0.0300 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.23 (0.0-26.0) uMAdult (>18 years old)Both
Bladder infections
details
Associated Disorders and Diseases
Disease References
Bladder infections
  1. Tricker AR, Pfundstein B, Kalble T, Preussmann R: Secondary amine precursors to nitrosamines in human saliva, gastric juice, blood, urine and faeces. Carcinogenesis. 1992 Apr;13(4):563-8. [PubMed:1576707 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000741
KNApSAcK IDNot Available
Chemspider ID11530
KEGG Compound IDC11118
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Pyrrolidone
METLIN ID6452
PubChem Compound12025
PDB IDNot Available
ChEBI ID36592
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sun X, Qiao H, Jiang H, Zhi X, Liu F, Wang J, Liu M, Dong D, Kanwar JR, Xu R, Krissansen GW: Intramuscular delivery of antiangiogenic genes suppresses secondary metastases after removal of primary tumors. Cancer Gene Ther. 2005 Jan;12(1):35-45. [PubMed:15486558 ]
  2. Hyder F, Petroff OA, Mattson RH, Rothman DL: Localized 1H NMR measurements of 2-pyrrolidinone in human brain in vivo. Magn Reson Med. 1999 May;41(5):889-96. [PubMed:10332870 ]
  3. Rambabu K, Pattabiraman TN: Studies on gamma-glutamyl transpeptidase of human urine. Clin Chim Acta. 1976 Dec 1;73(2):251-5. [PubMed:11907 ]
  4. Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]
  5. Matsudo T, Ogawa K, Kokufuta E: Complex formation of protein with different water-soluble synthetic polymers. Biomacromolecules. 2003 Nov-Dec;4(6):1794-9. [PubMed:14606910 ]
  6. Fedi AM, Leoncini P, Farella V, Lotti T: [Study of filaggrin in psoriasis]. G Ital Dermatol Venereol. 1989 Apr;124(4):141-5. [PubMed:2680915 ]
  7. Gobbels M, Spitznas M: Effects of artificial tears on corneal epithelial permeability in dry eyes. Graefes Arch Clin Exp Ophthalmol. 1991;229(4):345-9. [PubMed:1916322 ]
  8. Gobbels M, Spitznas M: Corneal epithelial permeability of dry eyes before and after treatment with artificial tears. Ophthalmology. 1992 Jun;99(6):873-8. [PubMed:1630776 ]
  9. Onorato JM, Henion JD, Lefebvre PM, Kiplinger JP: Selected reaction monitoring LC-MS determination of idoxifene and its pyrrolidinone metabolite in human plasma using robotic high-throughput, sequential sample injection. Anal Chem. 2001 Jan 1;73(1):119-25. [PubMed:11195494 ]
  10. Zimmermann W, Donhardt A, Braun W: [2-Br-2-ethyl-4-hydroxybutyramide and 2-Br-2-ethyl-4-butyrolactam as carbromal metabolites (author's transl)]. Arch Toxicol. 1978 Apr 27;40(2):119-24. [PubMed:26319 ]
  11. Voigt R, Korner I, Roth P: [Interactions between macromolecular adjuvants and drugs. Part 16: Effects of human serum albumin and Mg2+ on oxytetracycline-polyvinylpyrrolidone interactions (author's transl)]. Pharmazie. 1979 Jan;34(1):45-8. [PubMed:432255 ]
  12. Petroff OA, Hyder F, Collins T, Mattson RH, Rothman DL: Acute effects of vigabatrin on brain GABA and homocarnosine in patients with complex partial seizures. Epilepsia. 1999 Jul;40(7):958-64. [PubMed:10403220 ]
  13. Petroff OA, Hyder F, Rothman DL, Mattson RH: Effects of gabapentin on brain GABA, homocarnosine, and pyrrolidinone in epilepsy patients. Epilepsia. 2000 Jun;41(6):675-80. [PubMed:10840398 ]