Pyrroline hydroxycarboxylic acid (PAMDB000359)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000359
Identification
Name: Pyrroline hydroxycarboxylic acid
Description:Pyrroline hydroxycarboxylic acid is an intermediate in arginine and proline metabolism. It is converted to trans-4-hydroxy-L-proline via pyrroline-5-carboxylate reductase, and to L-erythro-4-Hydroxyglutamate via delta-1-pyrroline-5-carboxylate dehydrogenase. (KEGG)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (3R,5S)-1-pyrroline-3-hydroxy-5-carboxylate
  • (3R,5S)-1-Pyrroline-3-hydroxy-5-carboxylic acid
  • 3-Hydroxy-L-1-pyrroline-5-carboxylate
  • 3-Hydroxy-L-1-pyrroline-5-carboxylic acid
  • L-Δ1-pyrroline 3-hydroxy-5-carboxylate
  • L-Δ1-pyrroline 3-hydroxy-5-carboxylic acid
  • L-Δ1-pyrroline 3-hydroxy-5-carboxylate
  • L-1-Pyrroline 3-hydroxy-5-carboxylate
  • L-1-Pyrroline 3-hydroxy-5-carboxylic acid
  • L-1-Pyrroline-3-hydroxy-5-carboxylate
  • L-1-Pyrroline-3-hydroxy-5-carboxylic acid
  • L-1pyrroline-3-hydroxy-5-carboxylate
  • L-1Pyrroline-3-hydroxy-5-carboxylic acid
  • L-Delta1-pyrroline 3-hydroxy-5-carboxylate
  • L-Delta1-pyrroline 3-hydroxy-5-carboxylic acid
  • L-δ1-Pyrroline 3-hydroxy-5-carboxylate
  • L-δ1-Pyrroline 3-hydroxy-5-carboxylic acid
  • Pyrroline hydroxycarboxylate
  • Pyrroline-hydroxy-carboxylate
  • Pyrroline-hydroxy-carboxylic acid
Chemical Formula: C5H7NO3
Average Molecular Weight: 129.114
Monoisotopic Molecular Weight: 129.042593095
InChI Key: WFOFKRKDDKGRIK-UHFFFAOYSA-N
InChI:InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)
CAS number: 22573-88-2
IUPAC Name:4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional IUPAC Name: pyrroline-hydroxy-carboxylate
SMILES:OC1CC(N=C1)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline
  • Secondary alcohol
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility33.9 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.5ChemAxon
logS-0.58ALOGPS
pKa (Strongest Acidic)3.72ChemAxon
pKa (Strongest Basic)2.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.85 m3·mol-1ChemAxon
Polarizability11.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Hydroxyproline + NAD <> Pyrroline hydroxycarboxylic acid + NADH + Hydrogen ion
Hydroxyproline + NADP <> Pyrroline hydroxycarboxylic acid + NADPH + Hydrogen ion
Pyrroline hydroxycarboxylic acid + NAD + 2 Water <> L-erythro-4-Hydroxyglutamate + NADH + Hydrogen ion
Pyrroline hydroxycarboxylic acid + NADP + 2 Water <> L-erythro-4-Hydroxyglutamate + NADPH + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9600000000-8e7afe6ced148f01b715View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • 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
  • 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
  • Valle D, Goodman SI, Harris SC, Phang JM: Genetic evidence for a common enzyme catalyzing the second step in the degradation of proline and hydroxyproline. J Clin Invest. 1979 Nov;64(5):1365-70. Pubmed: 500817
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID27391
HMDB IDHMDB01369
Pubchem Compound ID1059
Kegg IDC04281
ChemSpider ID1030
Wikipedia IDNot Available
BioCyc IDPYRROLINE-HYDROXY-CARBOXYLATE
EcoCyc IDPYRROLINE-HYDROXY-CARBOXYLATE