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Showing Compound 1-Pyrroline-5-carboxylic acid (FDB022542)

Record Information
Version1.0
Creation date2011-09-21 00:15:37 UTC
Update date2024-11-29 22:26:43 UTC
Primary IDFDB022542
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1-Pyrroline-5-carboxylic acid
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. A 1-pyrrolinecarboxylic acid that is 1-pyrroline in which one of the hydrogens at position 5 is replaced by a carboxy group. 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 humans, 1-pyrroline-5-carboxylic acid participates in a number of enzymatic reactions. In particular, 1-pyrroline-5-carboxylic acid can be converted into L-glutamic acid through the action of the enzyme Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial. In addition, 1-pyrroline-5-carboxylic acid can be converted into L-proline through the action of the enzyme proline dehydrogenase 1, mitochondrial. In humans, 1-pyrroline-5-carboxylic acid is involved in the metabolic disorder called hyperprolinemia type II. 1-Pyrroline-5-carboxylic acid is a potentially toxic compound.
CAS Number2906-39-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
3,4-Dihydro-2H-pyrrole-2-carboxylateChEBI
Delta(1)-Pyrroline-5-carboxylic acidChEBI
3,4-Dihydro-2H-pyrrole-2-carboxylic acidGenerator
delta(1)-Pyrroline-5-carboxylateGenerator
Δ(1)-pyrroline-5-carboxylateGenerator
Δ(1)-pyrroline-5-carboxylic acidGenerator
1-Pyrroline-5-carboxylateGenerator
delta(1)Pyrroline-5-carboxylateHMDB
delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomerHMDB
Pyrroline-5-carboxylateHMDB
delta-1-Pyrroline-5-carboxylateHMDB
delta-1-Pyrroline-5-carboxylate, (+-)-isomerHMDB
delta-1-Pyrroline-5-carboxylic acidHMDB
(S)-1-Pyrroline-5-carboxylateHMDB
D1-Pyrroline-5-carboxylateHMDB
D1-Pyrroline-5-carboxylic acidHMDB
DL-1-Pyrroline-5-carboxylateHMDB
DL-1-Pyrroline-5-carboxylic acidHMDB
L-1-Pyrroline-5-carboxylateHMDB
L-delta 1-Pyrroline-5-carboxylateHMDB
Pyrroline 5-carboxylateHMDB
(S)-1-pyrroline-5-carboxylatehmdb
1-pyrroline-5-carboxylatehmdb
1-Pyrroline-5-carboxylic acidhmdb
3,4-dihydro-2h-pyrrole-2-carboxylatehmdb
3,4-dihydro-2h-pyrrole-2-carboxylic acidhmdb
delta-1-pyrroline-5-carboxylatehmdb
delta-1-pyrroline-5-carboxylic acidhmdb
delta(1)pyrroline-5-carboxylatehmdb
L-1-pyrroline-5-carboxylatehmdb
L-Delta 1-pyrroline-5-carboxylatehmdb
pyrroline 5-carboxylatehmdb
pyrroline-5-carboxylatehmdb
δ(1)-pyrroline-5-carboxylateGenerator
δ(1)-pyrroline-5-carboxylic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H7NO2
IUPAC name3,4-dihydro-2H-pyrrole-2-carboxylic acid
InChI IdentifierInChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
InChI KeyDWAKNKKXGALPNW-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1CCC=N1
Average Molecular Weight113.1146
Monoisotopic Molecular Weight113.047678473
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Indirect biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS1-Pyrroline-5-carboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00mo-9000000000-8ab2bc6c045679da1664Spectrum
Predicted GC-MS1-Pyrroline-5-carboxylic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-9100000000-34b6b42e5a9e4ff8715fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 20V, positivesplash10-014i-9000000000-97191b38aeb79930b7202020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-9700000000-f2bc2275638f96dc74ac2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9100000000-72dff6639c24448bec9c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-28eb1358005b28459deb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-5900000000-0720aa91caee03b9364e2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-cfcc87863f675fb126912015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-a15b91c200295166bf9e2015-09-15View Spectrum
NMRNot Available
ChemSpider ID1159
ChEMBL IDCHEMBL1161508
KEGG Compound IDC04322
Pubchem Compound ID1196
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01301
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID42766
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID1-pyrroline-5-carboxylate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Glutamate MetabolismSMP00072 map00250
Metabolsim and Physiological Effects of Argininic acid SMP0125504 Not Available
Metabolism and Physiological Effects of N-alpha-Acetyl-L-arginine SMP0125530 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference