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Record Information
Version3.6
Creation Date2008-08-13 17:53:39 UTC
Update Date2016-02-11 01:08:03 UTC
HMDB IDHMDB06875
Secondary Accession NumbersNone
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
delta1-Pyrroline 2-carboxylateKegg
1-Pyrroline 2-carboxylateKegg
delta1-Pyrroline 2-carboxylic acidGenerator
δ1-pyrroline 2-carboxylateGenerator
δ1-pyrroline 2-carboxylic acidGenerator
1-Pyrroline-2-carboxylateGenerator
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
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 KeyInChIKey=RHTAIKJZSXNELN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolines
Sub ClassNot Available
Direct ParentPyrrolines
Alternative Parents
Substituents
  • Pyrroline
  • Ketimine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.89 m3·mol-1ChemAxon
Polarizability10.81 Å3ChemAxon
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
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)SMP00362Not Available
Creatine deficiency, guanidinoacetate methyltransferase deficiencySMP00504Not Available
D-Arginine and D-Ornithine MetabolismSMP00036map00472
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)SMP00188Not Available
Hyperornithinemia with gyrate atrophy (HOGA)SMP00505Not Available
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]SMP00506Not Available
Hyperprolinemia Type ISMP00361Not Available
Hyperprolinemia Type IISMP00360Not Available
L-arginine:glycine amidinotransferase deficiencySMP00507Not Available
Ornithine Aminotransferase Deficiency (OAT Deficiency)SMP00363Not Available
Prolidase Deficiency (PD)SMP00207Not Available
Prolinemia Type IISMP00208Not Available
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
NuGOwiki LinkHMDB06875
Metagene LinkHMDB06875
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