(S)-1-pyrroline-5-carboxylate (PAMDB110710)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110710
Identification
Name: (S)-1-pyrroline-5-carboxylate
Description:A 1-pyrroline-5-carboxylate resulting from the removal of the proton from the carboxy group of (S)-1-pyrroline-5-carboxylic acid.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • pyrroline 5-carboxylate
  • L-Δ1-pyrroline-5-carboxylate
  • 1-pyrroline-5-carboxylate
  • L-1-pyrroline-5-carboxylate
  • δ-1-pyrroline-5-carboxylic acid
  • δ-1-pyrroline-5-carboxylate
Chemical Formula: C5H6NO2
Average Molecular Weight: 112.11
Monoisotopic Molecular Weight: 113.0476784741
InChI Key: DWAKNKKXGALPNW-BYPYZUCNSA-M
InChI: InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)/p-1/t4-/m0/s1
CAS number: 2906-39-0
IUPAC Name:(2S)-3,4-dihydro-2H-pyrrole-2-carboxylate
Traditional IUPAC Name: 1-pyrroline-5-carboxylic acid
SMILES:C1(=NC(CC1)C(=O)[O-])
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Alpha 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 Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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: Not Available
Reactions:
(S)-1-pyrroline-5-carboxylate + NAD+ + Water → Hydrogen ion + L-glutamate + NADH
Ubiquinones + L-Proline → Ubiquinols + (S)-1-pyrroline-5-carboxylate + Hydrogen ion
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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:
  • Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. [533224 ]
  • 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. [11510941 ]
  • 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. [3392037 ]
  • Wakabayashi Y: Tissue-selective expression of enzymes of arginine synthesis. Curr Opin Clin Nutr Metab Care. 1998 Jul;1(4):335-9. [10565370 ]
  • 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. [15214748 ]
  • Fleming GA, Hagedorn CH, Granger AS, Phang JM: Pyrroline-5-carboxylate in human plasma. Metabolism. 1984 Aug;33(8):739-42. [6748947 ]
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
CAS2906-39-0
ChEBI17388
ChemSpider10140174
HMDBHMDB01301
IAF126042766
KEGGC03912
MetaboLightsMTBLC17388
PubChem11966181