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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:14 UTC
Update Date2023-02-21 17:20:19 UTC
HMDB IDHMDB0031308
Secondary Accession Numbers
  • HMDB31308
Metabolite Identification
Common Name5-Acetyl-3,4-dihydro-2H-pyrrole
Description5-Acetyl-3,4-dihydro-2H-pyrrole, also known as 2AP or APR, belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. 5-Acetyl-3,4-dihydro-2H-pyrrole is a sweet, ham, and nut tasting compound. 5-Acetyl-3,4-dihydro-2H-pyrrole has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), taco, and tortilla chip. This could make 5-acetyl-3,4-dihydro-2H-pyrrole a potential biomarker for the consumption of these foods. 5-Acetyl-3,4-dihydro-2H-pyrrole is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-Acetyl-3,4-dihydro-2H-pyrrole.
Structure
Data?1677000019
Synonyms
ValueSource
2-Acetyl-4,5-dihydro-3H-pyrroleChEBI
2APChEBI
APRChEBI
1-(3,4-dihydro-2H-Pyrrol-5-yl)ethanoneHMDB
1-(3,4-dihydro-2H-Pyrrol-5-yl)ethanone, 9ciHMDB
1-Pyrroline, 2-acetylHMDB
2-Acetyl-1-pyrollineHMDB
2-Acetyl-1-pyrrolineHMDB, MeSH
2-AcetylpyrrolineMeSH, HMDB
Chemical FormulaC6H9NO
Average Molecular Weight111.1418
Monoisotopic Molecular Weight111.068413915
IUPAC Name1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one
Traditional Name2-acetyl-1-pyrroline
CAS Registry Number85213-22-5
SMILES
CC(=O)C1=NCCC1
InChI Identifier
InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
InChI KeyDQBQWWSFRPLIAX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolines
Sub ClassNot Available
Direct ParentPyrrolines
Alternative Parents
Substituents
  • Pyrroline
  • Ketimine
  • Ketone
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Imine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point19.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point182.00 to 183.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4103 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.019 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.09 g/LALOGPS
logP0.19ALOGPS
logP0.86ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)18.44ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability12.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+123.50231661259
DarkChem[M-H]-116.65231661259
DeepCCS[M+H]+128.57330932474
DeepCCS[M-H]-126.21430932474
DeepCCS[M-2H]-161.99530932474
DeepCCS[M+Na]+136.92230932474
AllCCS[M+H]+121.632859911
AllCCS[M+H-H2O]+116.732859911
AllCCS[M+NH4]+126.232859911
AllCCS[M+Na]+127.532859911
AllCCS[M-H]-122.532859911
AllCCS[M+Na-2H]-125.132859911
AllCCS[M+HCOO]-127.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Acetyl-3,4-dihydro-2H-pyrroleCC(=O)C1=NCCC11366.4Standard polar33892256
5-Acetyl-3,4-dihydro-2H-pyrroleCC(=O)C1=NCCC1876.7Standard non polar33892256
5-Acetyl-3,4-dihydro-2H-pyrroleCC(=O)C1=NCCC1945.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Acetyl-3,4-dihydro-2H-pyrrole,1TMS,isomer #1C=C(O[Si](C)(C)C)C1=NCCC11235.9Semi standard non polar33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TMS,isomer #1C=C(O[Si](C)(C)C)C1=NCCC11214.2Standard non polar33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=NCCC11435.7Semi standard non polar33892256
5-Acetyl-3,4-dihydro-2H-pyrrole,1TBDMS,isomer #1C=C(O[Si](C)(C)C(C)(C)C)C1=NCCC11414.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-9000000000-b2ec2a5a737593af18762016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Positive-QTOFsplash10-03di-5900000000-ba7d8b3068bce1b47b392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Positive-QTOFsplash10-01ox-9300000000-d40b8a0858de158c3dd12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Positive-QTOFsplash10-00kf-9000000000-93e30e06cf0f3fac2e9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Negative-QTOFsplash10-03di-1900000000-c99599e8eef94b8c00682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Negative-QTOFsplash10-03di-3900000000-24d2c60642b5511950272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Negative-QTOFsplash10-014l-9000000000-a6046c2688bcfbb4c3132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Negative-QTOFsplash10-03di-1900000000-24735682b0a5560e64ae2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Negative-QTOFsplash10-02t9-9500000000-2e635455b88717ca2f972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Negative-QTOFsplash10-014l-9000000000-a0c8a0fe2acbc430c4382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 10V, Positive-QTOFsplash10-03di-3900000000-7cddab0b1712fe3943e62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 20V, Positive-QTOFsplash10-014l-9100000000-a2ea5be954e40e1ce67b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Acetyl-3,4-dihydro-2H-pyrrole 40V, Positive-QTOFsplash10-0006-9000000000-efc17d3cfd9d54e8a0c42021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003364
KNApSAcK IDNot Available
Chemspider ID456071
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Acetyl-1-pyrroline
METLIN IDNot Available
PubChem Compound522834
PDB IDNot Available
ChEBI ID67125
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1583501
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .