ContaminantDB: 1-Pyrroline-5-carboxylic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-10-02 19:00:48 UTC

Update Date

2026-04-05 15:18:32 UTC

Accession Number

CHEM003921

Identification

Common Name

1-Pyrroline-5-carboxylic acid

Class

Small Molecule

Description

1-Pyrroline-5-carboxylic acid is an enamine or an amino acid that forms on spontaneous dehydration of L-glutamate γ-semialdehyde in aqueous solutions. The stereoisomer (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. In particular, it is synthesized with the oxidation of proline by pyrroline-5-carboxylate reductase 1 (EC 1.5.1.2, PYCR1) or by proline dehydrogenase (EC 1.5.99.8, PRODH) and it is hydrolyzed to L-glutamate by delta-1-pyrroline-5-carboxylate dehydrogenase (EC 1.5.1.12, ALDH4A1). It is also one of the few metabolites that can be a precursor to other metabolites of both the urea cycle and the tricarboxylic acid (TCA) cycle.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Animal Toxin
Metabolite
Natural Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
3,4-Dihydro-2H-pyrrole-2-carboxylate	ChEBI
Delta(1)-Pyrroline-5-carboxylic acid	ChEBI
3,4-Dihydro-2H-pyrrole-2-carboxylic acid	Generator
delta(1)-Pyrroline-5-carboxylate	Generator
Δ(1)-pyrroline-5-carboxylate	Generator
Δ(1)-pyrroline-5-carboxylic acid	Generator
1-Pyrroline-5-carboxylate	Generator
delta(1)Pyrroline-5-carboxylate	HMDB
delta-1-Pyrroline-5-carboxylate, 14C-labeled, (+-)-isomer	HMDB
Pyrroline-5-carboxylate	HMDB
delta-1-Pyrroline-5-carboxylate	HMDB
delta-1-Pyrroline-5-carboxylate, (+-)-isomer	HMDB
delta-1-Pyrroline-5-carboxylic acid	HMDB
(S)-1-Pyrroline-5-carboxylate	HMDB
D1-Pyrroline-5-carboxylate	HMDB
D1-Pyrroline-5-carboxylic acid	HMDB
DL-1-Pyrroline-5-carboxylate	HMDB
DL-1-Pyrroline-5-carboxylic acid	HMDB
L-1-Pyrroline-5-carboxylate	HMDB
L-delta 1-Pyrroline-5-carboxylate	HMDB
Pyrroline 5-carboxylate	HMDB

Chemical Formula

C₅H₇NO₂

Average Molecular Mass

113.115 g/mol

Monoisotopic Mass

113.048 g/mol

CAS Registry Number

2906-39-0

IUPAC Name

3,4-dihydro-2H-pyrrole-2-carboxylic acid

Traditional Name

1-pyrroline-5-carboxylic acid

SMILES

OC(=O)C1CCC=N1

InChI Identifier

InChI=1S/C5H7NO2/c7-5(8)4-2-1-3-6-4/h3-4H,1-2H2,(H,7,8)

InChI Key

DWAKNKKXGALPNW-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

1-pyrrolinecarboxylic acid (CHEBI:1372 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Intestine

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	13.1 g/L	ALOGPS
logP	-0.01	ALOGPS
logP	-2.3	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	1.82	ChemAxon
pKa (Strongest Basic)	6.07	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	27.4 m³·mol⁻¹	ChemAxon
Polarizability	10.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mo-9000000000-8ab2bc6c045679da1664	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-014i-9100000000-34b6b42e5a9e4ff8715f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-014i-9000000000-97191b38aeb79930b720	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-9700000000-f2bc2275638f96dc74ac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9100000000-72dff6639c24448bec9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9000000000-28eb1358005b28459deb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5900000000-0720aa91caee03b9364e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-9400000000-cfcc87863f675fb12691	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-a15b91c200295166bf9e	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of pyrroline-5-carboxylate are associated with at least 5 inborn errors of metabolism including: Hyperprolinemia Type I, Hyperprolinemia Type II, Iminoglycinuria, Prolinemia Type II and Pyruvate carboxylase deficiency.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001301

FooDB ID