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1-Pyrroline-5-carboxylic acid (YMDB00243)

Identification
YMDB IDYMDB00243
Name1-Pyrroline-5-carboxylic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-Pyrroline-5-carboxylic acid, also known as delta(1)-pyrroline-5-carboxylate, 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. 1-Pyrroline-5-carboxylic acid is a very strong basic compound (based on its pKa). 1-Pyrroline-5-carboxylic acid exists in all living species, ranging from bacteria to humans. Within yeast, 1-pyrroline-5-carboxylic acid participates in a number of enzymatic reactions. In particular, 1-pyrroline-5-carboxylic acid can be converted into L-proline; which is mediated by the enzyme pyrroline-5-carboxylate reductase. In addition, ubiquinol-1 and 1-pyrroline-5-carboxylic acid can be biosynthesized from L-proline and ubiquinone-1 through the action of the enzyme proline dehydrogenase. In yeast, 1-pyrroline-5-carboxylic acid is involved in the metabolic pathway called the proline metabolism pathway. 1-Pyrroline-5-carboxylic acid is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • (S)-1-pyrroline-5-carboxylate
  • 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
  • DL-1-Pyrroline-5-carboxylate
  • DL-1-Pyrroline-5-carboxylic acid
  • L-1-pyrroline-5-carboxylate
  • L-Delta 1-pyrroline-5-carboxylate
  • pyrroline 5-carboxylate
  • pyrroline-5-carboxylate
  • Delta(1)-Pyrroline-5-carboxylic acid
  • delta(1)-Pyrroline-5-carboxylate
  • Δ(1)-pyrroline-5-carboxylate
  • Δ(1)-pyrroline-5-carboxylic acid
  • delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomer
  • delta-1-Pyrroline-5-carboxylate, (+-)-isomer
CAS number2906-39-0
WeightAverage: 113.1146
Monoisotopic: 113.047678473
InChI KeyDWAKNKKXGALPNW-UHFFFAOYSA-N
InChIInChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
IUPAC Name3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional IUPAC Name1-pyrroline-5-carboxylic acid
Chemical FormulaC5H7NO2
SMILES[H]OC(=O)C1([H])N=C([H])C([H])([H])C1([H])[H]
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
  • 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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.1 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.4 m³·mol⁻¹ChemAxon
Polarizability10.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondrion
Organoleptic PropertiesNot Available
SMPDB Pathways
Proline MetabolismPW002365 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Arginine and proline metabolismec00330 Map00330
SMPDB Reactions
1-Pyrroline-5-carboxylic acid + hydron + NADPH → NADP + L-Proline
L-Proline + Ubiquinone Q1 → hydron + QH(2) + 1-Pyrroline-5-carboxylic acid
KEGG Reactions
water + NAD + 1-Pyrroline-5-carboxylic acid → NADH + L-Glutamic acid + hydron
l-Glutamic-gamma-semialdehyde ↔ 1-Pyrroline-5-carboxylic acid + water + hydron
L-Proline + NAD → NADH + 1-Pyrroline-5-carboxylic acid + hydron
1-Pyrroline-5-carboxylic acid + NADPH + hydron → NADP + L-Proline
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mo-9000000000-8ab2bc6c045679da1664JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-9100000000-34b6b42e5a9e4ff8715fJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-014i-9000000000-97191b38aeb79930b720JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-f2bc2275638f96dc74acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-72dff6639c24448bec9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-28eb1358005b28459debJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-0720aa91caee03b9364eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-cfcc87863f675fb12691JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-a15b91c200295166bf9eJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
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.
External Links:
ResourceLink
CHEBI ID1372
HMDB IDHMDB01301
Pubchem Compound ID1196
Kegg IDC04322
ChemSpider ID1159
FOODB IDFDB022542
Wikipedia1-Pyrroline-5-carboxylic_acid
BioCyc IDL-DELTA1-PYRROLINE_5-CARBOXYLATE

Enzymes

Protein Details
1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H
Gene Name:
PUT2
Uniprot ID:
P07275
Molecular weight:
64434.60156
Reactions
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O → L-glutamate + NAD(P)H.
Protein Details
2. Proline dehydrogenase, mitochondrial
General function:
Involved in proline dehydrogenase activity
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate
Gene Name:
PUT1
Uniprot ID:
P09368
Molecular weight:
53270.89844
Reactions
L-proline + acceptor → (S)-1-pyrroline-5-carboxylate + reduced acceptor.
Protein Details
3. Pyrroline-5-carboxylate reductase
General function:
Involved in oxidoreductase activity
Specific function:
L-proline + NAD(P)(+) = 1-pyrroline-5- carboxylate + NAD(P)H
Gene Name:
PRO3
Uniprot ID:
P32263
Molecular weight:
30131.59961
Reactions
L-proline + NAD(P)(+) → 1-pyrroline-5-carboxylate + NAD(P)H.