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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:24 UTC
Update Date2022-03-07 02:52:09 UTC
HMDB IDHMDB0029434
Secondary Accession Numbers
  • HMDB29434
Metabolite Identification
Common Name(±)-4-Methylene-2-pyrrolidinecarboxylic acid
Description(±)-4-Methylene-2-pyrrolidinecarboxylic acid, also known as 4-methylene-L-proline or 4-methylidenepyrrolidine-2-carboxylate, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (±)-4-Methylene-2-pyrrolidinecarboxylic acid has been detected, but not quantified in, fruits. This could make (±)-4-methylene-2-pyrrolidinecarboxylic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (±)-4-Methylene-2-pyrrolidinecarboxylic acid.
Structure
Data?1582753418
Synonyms
ValueSource
(±)-4-methylene-2-pyrrolidinecarboxylateGenerator
4-Methyleneproline, (DL)-isomerHMDB
4-Methylene-L-prolineHMDB
4-Methylidenepyrrolidine-2-carboxylateHMDB
4-MethyleneprolineHMDB
Chemical FormulaC6H9NO2
Average Molecular Weight127.1412
Monoisotopic Molecular Weight127.063328537
IUPAC Name4-methylidenepyrrolidine-2-carboxylic acid
Traditional Name4-methylidenepyrrolidine-2-carboxylic acid
CAS Registry Number2370-38-9
SMILES
OC(=O)C1CC(=C)CN1
InChI Identifier
InChI=1S/C6H9NO2/c1-4-2-5(6(8)9)7-3-4/h5,7H,1-3H2,(H,8,9)
InChI KeyPEYQZZMUNYLHII-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point224 - 245 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility177 g/LALOGPS
logP-2.2ALOGPS
logP-2.5ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)10.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.24 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.03731661259
DarkChem[M-H]-120.86231661259
DeepCCS[M+H]+124.14130932474
DeepCCS[M-H]-120.62930932474
DeepCCS[M-2H]-157.92130932474
DeepCCS[M+Na]+132.9330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-4-Methylene-2-pyrrolidinecarboxylic acidOC(=O)C1CC(=C)CN12031.3Standard polar33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acidOC(=O)C1CC(=C)CN11101.4Standard non polar33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acidOC(=O)C1CC(=C)CN11312.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TMS,isomer #1C=C1CNC(C(=O)O[Si](C)(C)C)C11241.3Semi standard non polar33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TMS,isomer #2C=C1CC(C(=O)O)N([Si](C)(C)C)C11311.8Semi standard non polar33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TMS,isomer #1C=C1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C11337.2Semi standard non polar33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TMS,isomer #1C=C1CC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C11342.4Standard non polar33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TBDMS,isomer #1C=C1CNC(C(=O)O[Si](C)(C)C(C)(C)C)C11450.6Semi standard non polar33892256
(??)-4-Methylene-2-pyrrolidinecarboxylic acid,1TBDMS,isomer #2C=C1CC(C(=O)O)N([Si](C)(C)C(C)(C)C)C11545.4Semi standard non polar33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TBDMS,isomer #1C=C1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C11771.8Semi standard non polar33892256
(±)-4-Methylene-2-pyrrolidinecarboxylic acid,2TBDMS,isomer #1C=C1CC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C11765.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-358a6914480ac6e64ab72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9100000000-7cd7f99b38507da019152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 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 - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Positive-QTOFsplash10-004i-3900000000-9274706ee64020acc1432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Positive-QTOFsplash10-001i-9300000000-03ef1e475ad33bba3ee02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Positive-QTOFsplash10-0pvl-9000000000-c818f95849c168eb02e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Negative-QTOFsplash10-004i-2900000000-7c89ea5165a6365aee8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Negative-QTOFsplash10-003r-9700000000-ab38f832cb8b8e41a4e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Negative-QTOFsplash10-0fsr-9000000000-4abd3484276ce24f4d0e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Positive-QTOFsplash10-001i-9000000000-2431731543c23668dd162021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Positive-QTOFsplash10-001i-9000000000-6fedfb706f5c40e6ed182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Positive-QTOFsplash10-001c-9000000000-7661f522e86e11d63fe12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 10V, Negative-QTOFsplash10-004i-0900000000-92dabc7e1e831e6f38472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 20V, Negative-QTOFsplash10-003r-9800000000-711e14a5b1a54935c1872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-4-Methylene-2-pyrrolidinecarboxylic acid 40V, Negative-QTOFsplash10-0006-9000000000-1f1ec61dcf07e73774b42021-09-24Wishart 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
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 IDFDB000538
KNApSAcK IDC00050723
Chemspider ID485385
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound558375
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .