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Identification
YMDB IDYMDB00243
Name1-Pyrroline-5-carboxylic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(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.
Structure
Thumb
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 + NADPHNADP + L-Proline
L-Proline + Ubiquinone Q1hydron + QH(2) + 1-Pyrroline-5-carboxylic acid
KEGG Reactions
water + NAD + 1-Pyrroline-5-carboxylic acidNADH + L-Glutamic acid + hydron
l-Glutamic-gamma-semialdehyde1-Pyrroline-5-carboxylic acid + water + hydron
L-Proline + NADNADH + 1-Pyrroline-5-carboxylic acid + hydron
1-Pyrroline-5-carboxylic acid + NADPH + hydronNADP + L-Proline
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.
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.