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Record Information
Version4.0
Creation Date2008-08-13 17:53:39 UTC
Update Date2017-09-27 08:24:49 UTC
HMDB IDHMDB0006875
Secondary Accession Numbers
  • HMDB06875
Metabolite Identification
Common Name1-Pyrroline-2-carboxylic acid
Description1-Pyrroline-2-carboxylic acid is a terminal product of D-proline metabolism. Specifically D-proline is converted to 1-Pyrroline-2-carboxylic acid via D-amino acid oxidase. This spontaneously breaks down to 2-oxo-5-amino-valerate.
Structure
Thumb
Synonyms
ValueSource
1-Pyrroline-2-carboxylateChEBI
delta1-Pyrroline 2-carboxylateChEBI
delta1-Pyrroline 2-carboxylic acidGenerator
δ1-pyrroline 2-carboxylateGenerator
δ1-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-carboxylateMeSH
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
[O-]C(=O)C1=[NH+]CCC1
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
DescriptionThis compound belongs to the class of chemical entities known as pyrrolines. These are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrrolines
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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.26 g/LALOGPS
logP0.38ALOGPS
logP0.53ChemAxon
logS-0.85ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)1.72ChemAxon
Physiological Charge-1ChemAxon
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-2900000000-66ac333a416ee8f7a478View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2900000000-66ac333a416ee8f7a478View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-06b3e3d5411a8f705758View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-8fa6f17fa32d2dc2a376View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c48f7e9292b52e3d7a54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-b4814a13bcbaa249948dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-d7552022e5be14c1afeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-c850159936b776efff87View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Arginine and Proline MetabolismPw000010Pw000010 greyscalePw000010 simpleMap00330
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Pw000084Pw000084 greyscalePw000084 simpleNot Available
Creatine deficiency, guanidinoacetate methyltransferase deficiencyPw000480Pw000480 greyscalePw000480 simpleNot Available
D-Arginine and D-Ornithine MetabolismPw000019Pw000019 greyscalePw000019 simpleMap00472
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Pw000088Pw000088 greyscalePw000088 simpleNot Available
Displaying entries 1 - 5 of 13 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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