Pyrroline hydroxycarboxylic acid (ECMDB01369) (M2MDB000359)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (700)
Record Information
Version2.0
Creation Date2012-05-31 13:51:04 -0600
Update Date2015-06-03 15:53:58 -0600
Secondary Accession Numbers
  • ECMDB01369
Identification
Name:Pyrroline hydroxycarboxylic acid
DescriptionPyrroline 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 129.114
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Pyrroline
  • Secondary alcohol
  • 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
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Imine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility33.9 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.85 m³·mol⁻¹ChemAxon
Polarizability11.6 ųChemAxon
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
SMPDB Pathways:Not Available
KEGG Pathways:
  • Arginine and proline metabolism ec00330
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9100000000-81454e4422185c7858e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-5910000000-0d5241ee660e7a60b0f9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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, Positivesplash10-03di-3900000000-91b528e579ac4acfac93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u0-9400000000-c804fee192934438c532View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-7da85099ac98a08f5741View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-ee7c942618fc6b2d94a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02e9-9700000000-1d9848f227e64812ada6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-9000000000-0d2b20e1b4dbed83a144View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-06e1bd2d2793c5f0afaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-9400000000-a84600f4fc13459b9448View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d2c2d7b1e05ce54b0932View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9300000000-c26ff3ebe1bb758e5252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-9000000000-97da4a76921516901d46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc3-9000000000-8982b409276eceb00f1bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

Protein Details
1. Bifunctional protein putA
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.
Protein Details
2. Pyrroline-5-carboxylate reductase
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.