Record Information
Version2.0
Creation Date2012-05-31 13:49:25 -0600
Update Date2015-06-03 15:53:54 -0600
Secondary Accession Numbers
  • ECMDB01301
Identification
Name:L-D-1-Pyrroline-5-carboxylic acid
Description:(S)-1-Pyrroline-5-carboxylate Pyrroline 5-carboxylate is an enamine or an imino acid that forms on spontaneous dehydration of L-glutamate γ-semialdehyde in aqueous solutions. The stereoisomer (S)-1-Pyrroline-5-carboxylate is an intermediate in glutamate metabolism, in arginine degradation and in proline biosynthesis and degradation and it can be converted to or be formed from the three amino acids L-glutamate, L-ornithine and L-proline. In particular, it is synthesized with the oxidation of proline by pyrroline-5-carboxylate reductase 1 (EC 1.5.1.2, PYCR1) or by proline dehydrogenase (EC 1.5.99.8, PRODH) and it is hydrolyzed to L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (EC 1.5.1.12, ALDH4A1). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle.
Structure
Thumb
Synonyms:
  • δ-1-pyrroline-5-carboxylate
  • δ-1-pyrroline-5-carboxylic acid
  • (S)-1-pyrroline-5-carboxylate
  • (S)-1-pyrroline-5-carboxylic acid
  • 1-Pyrroline-5-carboxylate
  • 1-Pyrroline-5-carboxylic acid
  • 3,4-Dihydro-2h-pyrrole-2-carboxylate
  • 3,4-Dihydro-2h-pyrrole-2-carboxylic acid
  • D1-Pyrroline-5-carboxylate
  • D1-Pyrroline-5-carboxylic acid
  • Delta(1)Pyrroline-5-carboxylate
  • Delta(1)Pyrroline-5-carboxylic acid
  • Delta-1-Pyrroline-5-carboxylate
  • Delta-1-Pyrroline-5-carboxylic acid
  • DL-1-Pyrroline-5-carboxylate
  • DL-1-Pyrroline-5-carboxylic acid
  • L-Δ1-pyrroline-5-carboxylate
  • L-Δ1-pyrroline-5-carboxylic acid
  • L-Δ1-pyrroline-5-carboxylate
  • L-1-Pyrroline-5-carboxylate
  • L-1-Pyrroline-5-carboxylic acid
  • L-D-1-Pyrroline-5-carboxylate
  • L-delta 1-Pyrroline-5-carboxylate
  • L-delta 1-Pyrroline-5-carboxylic acid
  • L-Delta1-pyrroline-5-carboxylate
  • L-Delta1-pyrroline-5-carboxylic acid
  • L-δ 1-Pyrroline-5-carboxylate
  • L-δ 1-Pyrroline-5-carboxylic acid
  • L-δ1-Pyrroline-5-carboxylate
  • L-δ1-Pyrroline-5-carboxylic acid
  • Pyrroline 5-carboxylate
  • Pyrroline 5-carboxylic acid
  • Pyrroline-5-carboxylate
  • Pyrroline-5-carboxylic acid
  • δ(1)Pyrroline-5-carboxylate
  • δ(1)Pyrroline-5-carboxylic acid
  • δ-1-Pyrroline-5-carboxylate
  • δ-1-Pyrroline-5-carboxylic acid
Chemical Formula:C5H7NO2
Weight:Average: 113.1146
Monoisotopic: 113.047678473
InChI Key:DWAKNKKXGALPNW-UHFFFAOYSA-N
InChI:InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
CAS number:2906-39-0
IUPAC Name:3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional IUPAC Name:1-pyrroline-5-carboxylic acid
SMILES:OC(=O)C1CCC=N1
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Imine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-0.503PhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.1 mg/mLALOGPS
logP-0.01ALOGPS
logP-2.3ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)6.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.4 m3·mol-1ChemAxon
Polarizability10.7 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
proline metabolismPW000794 Pw000794Pw000794 greyscalePw000794 simple
KEGG Pathways:
  • Alanine, aspartate and glutamate metabolism ec00250
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-00mo-9000000000-8ab2bc6c045679da1664View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-9100000000-34b6b42e5a9e4ff8715fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-f2bc2275638f96dc74acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-72dff6639c24448bec9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-28eb1358005b28459debView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-0720aa91caee03b9364eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-cfcc87863f675fb12691View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-a15b91c200295166bf9eView in MoNA
References
References:
  • Fleming GA, Hagedorn CH, Granger AS, Phang JM: Pyrroline-5-carboxylate in human plasma. Metabolism. 1984 Aug;33(8):739-42. Pubmed: 6748947
  • Humbertclaude V, Rivier F, Roubertie A, Echenne B, Bellet H, Vallat C, Morin D: Is hyperprolinemia type I actually a benign trait? Report of a case with severe neurologic involvement and vigabatrin intolerance. J Child Neurol. 2001 Aug;16(8):622-3. Pubmed: 11510941
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Mixson AJ, Phang JM: The uptake of pyrroline 5-carboxylate. Group translocation mediating the transfer of reducing-oxidizing potential. J Biol Chem. 1988 Aug 5;263(22):10720-4. Pubmed: 3392037
  • Onenli-Mungan N, Yuksel B, Elkay M, Topaloglu AK, Baykal T, Ozer G: Type II hyperprolinemia: a case report. Turk J Pediatr. 2004 Apr-Jun;46(2):167-9. Pubmed: 15214748
  • Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. Pubmed: 533224
  • Wakabayashi Y: Tissue-selective expression of enzymes of arginine synthesis. Curr Opin Clin Nutr Metab Care. 1998 Jul;1(4):335-9. Pubmed: 10565370
Synthesis Reference:Vogel, Henry J.; Davis, Bernard D. Glutamic g-semialdehyde and D1-pyrroline-5-carboxylic acid, intermediates in the biosynthesis of proline. Journal of the American Chemical Society (1952), 74 109-12.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID1372
HMDB IDHMDB01301
Pubchem Compound ID1196
Kegg IDC04322
ChemSpider ID1159
Wikipedia1-pyrroline-5-carboxylate
BioCyc IDL-DELTA1-PYRROLINE_5-CARBOXYLATE
EcoCyc IDL-DELTA1-PYRROLINE_5-CARBOXYLATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes proline to glutamate for use as a carbon and nitrogen source and also function as a transcriptional repressor of the put operon
Gene Name:
putA
Uniprot ID:
P09546
Molecular weight:
143814
Reactions
L-proline + acceptor = (S)-1-pyrroline-5-carboxylate + reduced acceptor.
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H.
General function:
Involved in oxidation-reduction process
Specific function:
L-proline + NAD(P)(+) = 1-pyrroline-5- carboxylate + NAD(P)H
Gene Name:
proC
Uniprot ID:
P0A9L8
Molecular weight:
28145
Reactions
L-proline + NAD(P)(+) = 1-pyrroline-5-carboxylate + NAD(P)H.