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Record Information
Version1.0
Creation Date2016-09-30 22:43:49 UTC
Update Date2020-05-21 16:28:29 UTC
BMDB IDBMDB0001301
Secondary Accession Numbers
  • BMDB01301
Metabolite Identification
Common 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. 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. 1-Pyrroline-5-carboxylic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC5H7NO2
Average Molecular Weight113.1146
Monoisotopic Molecular Weight113.047678473
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number2906-39-0
SMILESNot Available
InChI Identifier
InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)
InChI KeyDWAKNKKXGALPNW-UHFFFAOYSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001301
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022542
KNApSAcK IDC00007606
Chemspider ID1159
KEGG Compound IDC04322
BioCyc IDl-delta(1)-pyrroline_5-carboxylate
BiGG ID42766
Wikipedia Link1-Pyrroline-5-carboxylic acid
METLIN ID6145
PubChem Compound1196
PDB IDNot Available
ChEBI ID1372
References
Synthesis ReferenceVogel, 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
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes (By similarity).
Gene Name:
ALDH4A1
Uniprot ID:
A7YWE4
Molecular weight:
61495.0
Reactions
1-Pyrroline-5-carboxylic acid + NAD + 2 Water → L-Glutamic acid + NADHdetails
General function:
Amino acid transport and metabolism
Specific function:
Dehydrogenase that converts trans-4-L-hydroxyproline to delta-1-pyrroline-3-hydroxy-5-carboxylate (Hyp) using ubiquinone-10 as the terminal electron acceptor. Can also use proline as a substrate but with a very much lower efficiency. Does not react with other diastereomers of Hyp: trans-4-D-hydroxyproline and cis-4-L-hydroxyproline. Ubiquininone analogs such as menadione, duroquinone and ubiquinone-1 react more efficiently than oxygen as the terminal electron acceptor during catalysis.
Gene Name:
PRODH2
Uniprot ID:
A6QQ74
Molecular weight:
51262.0
General function:
Amino acid transport and metabolism
Specific function:
Enzyme that catalyzes the last step in proline biosynthesis. Proline is synthesized from either glutamate or ornithine; both are converted to pyrroline-5-carboxylate (P5C), and then to proline via pyrroline-5-carboxylate reductases (PYCRs). PYCRL is exclusively linked to the conversion of ornithine to proline.
Gene Name:
PYCR3
Uniprot ID:
Q58D08
Molecular weight:
32035.0
General function:
Amino acid transport and metabolism
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. In some cell types, such as erythrocytes, its primary function may be the generation of NADP(+). Can utilize both NAD and NADP. Has higher affinity for NADP, but higher catalytic efficiency with NADH (By similarity). Involved in cellular response to oxidative stress (By similarity).
Gene Name:
PYCR2
Uniprot ID:
Q17QJ7
Molecular weight:
33630.0
Reactions
L-Proline + NAD → 1-Pyrroline-5-carboxylic acid + NADHdetails
General function:
Amino acid transport and metabolism
Specific function:
Housekeeping enzyme that catalyzes the last step in proline biosynthesis. Can utilize both NAD and NADP, but has higher affinity for NAD. Involved in the cellular response to oxidative stress.
Gene Name:
PYCR1
Uniprot ID:
Q58DT4
Molecular weight:
33454.0
General function:
Not Available
Specific function:
Converts proline to delta-1-pyrroline-5-carboxylate.
Gene Name:
PRODH
Uniprot ID:
Q148G5
Molecular weight:
67080.0
Reactions
1-Pyrroline-5-carboxylic acid → L-Prolinedetails