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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:53:39 UTC
Update Date2020-09-15 20:43:15 UTC
HMDB IDHMDB0006875
Secondary Accession Numbers
  • HMDB06875
Metabolite Identification
Common Name1-Pyrroline-2-carboxylic acid
Description1-Pyrroline-2-carboxylic acid, also known as delta1-pyrroline 2-carboxylate, 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. 1-Pyrroline-2-carboxylic acid is a moderately basic compound (based on its pKa). 1-Pyrroline-2-carboxylic acid exists in all living organisms, ranging from bacteria to humans. 1-pyrroline-2-carboxylic acid can be biosynthesized from D-proline through its interaction with the enzyme D-amino-acid oxidase. The product resulting from formal oxidation of DL-proline by loss of hydrogen from the nitrogen and from the carbon alpha to the carboxylic acid, with the formation of a C=N bond. In humans, 1-pyrroline-2-carboxylic acid is involved in the metabolic disorder called hyperprolinemia type II.
Structure
Data?1600202595
Synonyms
ValueSource
1-Pyrroline-2-carboxylateChEBI
delta1-Pyrroline 2-carboxylateChEBI
1-Pyrroline 2-carboxylateKegg
delta1-Pyrroline 2-carboxylic acidGenerator
Δ1-pyrroline 2-carboxylateGenerator
Δ1-pyrroline 2-carboxylic acidGenerator
1-Pyrroline 2-carboxylic acidGenerator
3,4-Dihydro-2H-pyrrole-5-carboxylateHMDB
3,4-Dihydro-2H-pyrrole-5-carboxylic acidHMDB
D1-Pyrroline 2-carboxylateHMDB
D1-Pyrroline 2-carboxylic acidHMDB
delta-1-Pyrroline-2-carboxylateHMDB
1,2-DidehydroprolineHMDB
1-Pyrroline-2-carboxylic acidHMDB
delta1-Pyrroline-2-carboxylic acidHMDB
Δ1-Pyrroline-2-carboxylic acidHMDB
Chemical FormulaC5H7NO2
Average Molecular Weight113.1146
Monoisotopic Molecular Weight113.047678473
IUPAC Name3,4-dihydro-2H-pyrrol-1-ium-5-carboxylate
Traditional Name4,5-dihydro-3H-pyrrol-1-ium-2-carboxylate
CAS Registry Number2139-03-9
SMILES
OC(=O)C1=NCCC1
InChI Identifier
InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h1-3H2,(H,7,8)
InChI KeyRHTAIKJZSXNELN-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
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.26 g/LALOGPS
logP10(0.25) g/LALOGPS
logP10(0.53) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.89 m³·mol⁻¹ChemAxon
Polarizability10.81 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]+122.84231661259
DarkChem[M-H]-115.15531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-2-carboxylic acidOC(=O)C1=NCCC11925.2Standard polar33892256
1-Pyrroline-2-carboxylic acidOC(=O)C1=NCCC11069.2Standard non polar33892256
1-Pyrroline-2-carboxylic acidOC(=O)C1=NCCC11126.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-2-carboxylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=NCCC11285.0Semi standard non polar33892256
1-Pyrroline-2-carboxylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=NCCC11489.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 1-Pyrroline-2-carboxylic acid GC-MS (1 TMS)splash10-00di-2900000000-66ac333a416ee8f7a4782014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 1-Pyrroline-2-carboxylic acid GC-MS (Non-derivatized)splash10-00di-2900000000-66ac333a416ee8f7a4782017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Pyrroline-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-9000000000-a7ad471aae5db0467dfa2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Pyrroline-2-carboxylic 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 - 1-Pyrroline-2-carboxylic acid 10V, Positive-QTOFsplash10-03dj-9700000000-06b3e3d5411a8f7057582017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 20V, Positive-QTOFsplash10-014i-9100000000-8fa6f17fa32d2dc2a3762017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 40V, Positive-QTOFsplash10-0006-9000000000-c48f7e9292b52e3d7a542017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 10V, Negative-QTOFsplash10-03di-5900000000-b4814a13bcbaa249948d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 20V, Negative-QTOFsplash10-02t9-9400000000-d7552022e5be14c1afea2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 40V, Negative-QTOFsplash10-014l-9000000000-c850159936b776efff872017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 10V, Positive-QTOFsplash10-014i-9300000000-e23eb312ac037d0645142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 20V, Positive-QTOFsplash10-014i-9000000000-4b6f8dab3c747051784c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 40V, Positive-QTOFsplash10-014i-9000000000-43454e9f111a08bb09942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 10V, Negative-QTOFsplash10-03di-3900000000-8779645df27f611a22732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 20V, Negative-QTOFsplash10-014i-9200000000-e49e646efe87cb2ac8f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-2-carboxylic acid 40V, Negative-QTOFsplash10-00kf-9000000000-b0c27aa3a5a4bfd16ebf2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB02838
Phenol Explorer Compound IDNot Available
FooDB IDFDB024129
KNApSAcK IDNot Available
Chemspider ID389057
KEGG Compound IDC03564
BioCyc IDDELTA1-PYRROLINE_2-CARBOXYLATE
BiGG ID42087
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440046
PDB ID2PC
ChEBI ID36761
Food Biomarker OntologyNot Available
VMH ID1P2CBXL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in D-amino-acid oxidase activity
Specific function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular weight:
39473.75
Reactions
D-Proline + Oxygen → 1-Pyrroline-2-carboxylic acid + Hydrogen peroxidedetails