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Identification
YMDB IDYMDB00718
Name1-pyrroline-3-hydroxy-5-carboxylic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPyrroline hydroxycarboxylic acid, also known as L-1-pyrroline 3-hydroxy-5-carboxylate or 3-hydroxy-L-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. Pyrroline hydroxycarboxylic acid is a moderately basic compound (based on its pKa). Pyrroline hydroxycarboxylic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (3R,5S)-1-Pyrroline-3-hydroxy-5-carboxylate
  • 1-(p-Nitrophenoxy)-2,3-epoxypropane
  • 1,2-Epoxy-3-(p-nitrophenoxy)propane
  • 2, 3-Epoxy-1-(p-nitrophenoxy)propane
  • 3-hydroxy-l-1-pyrroline-5-carboxylate
  • Glycidyl 4-nitrophenyl ether
  • Glycidylnitrophenyl ether
  • L-1-pyrroline 3-hydroxy-5-carboxylate
  • L-1-Pyrroline-3-hydroxy-5-carboxylate
  • L-Delta1-pyrroline 3-hydroxy-5-carboxylate
  • Oxirane, {[(4-nitrophenoxy)methyl]-}
  • p-Nitrophenol glycidyl ether
  • p-Nitrophenyl glycidyl ether
  • Propane, 1, 2-epoxy-3-(p-nitrophenoxy)-
  • pyrroline-hydroxy-carboxylate
  • Pyrroline hydroxycarboxylate
  • 3,4-Dihydro-3-hydroxy-2H-pyrrole-5-carboxylic acid
  • 3-Hydroxy delta 1-pyrroline-5-carboxylic acid
  • 3-Hydroxy delta 1-pyrroline-5-carboxylic acid, anion
CAS numberNot Available
WeightAverage: 129.114
Monoisotopic: 129.042593095
InChI KeyWFOFKRKDDKGRIK-UHFFFAOYSA-N
InChIInChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)
IUPAC Name4-hydroxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid
Traditional IUPAC Namepyrroline-hydroxy-carboxylate
Chemical FormulaC5H7NO3
SMILESOC1CC(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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
NADPH + hydron + 1-pyrroline-3-hydroxy-5-carboxylic acidNADP + trans-4-hydroxy-L-proline
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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:Not Available
External Links:
ResourceLink
CHEBI ID27391
HMDB IDHMDB0001369
Pubchem Compound ID1059
Kegg IDC04281
ChemSpider ID1030
FOODB IDFDB022582
Wikipedia IDNot Available
BioCyc IDNot Available

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 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.