ChemFOnt: Showing chemical card for Pyrroline hydroxycarboxylic acid (CFc000001057)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:36 UTC

Chemfont ID

CFc000001057

Molecule Identification

Common Name

Pyrroline hydroxycarboxylic acid

Definition

Pyrroline hydroxycarboxylic acid is a metabolite identified in the urine of patients with type II hyperprolinemia. (OMIM 239510 ). The urinary excretion of Pyrroline hydroxycarboxylic acid increased in hyperprolinemic patients but not in healthy controls during oral loading of hydroxyproline and hydroxyproline-ornithine. (PMID: 533224 ). Hyperprolinemia type II (HP II) is a rare inherited metabolic disease due to the deficiency of pyroline-5-carboxylate dehydrogenase. It is generally believed to be a benign condition although some patients have neurological problems such as refractory convulsions. (PMID: 15214748 ). The oxidation of pyrroline-carboxylate generates glutamate and pyrroline-hydroxycarboxylate, a reaction catalyzed by hydroxyproline oxidase (PMID: 500817 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pyrroline hydroxycarboxylate	Generator
3-Hydroxy-L-1-pyrroline-5-carboxylate	HMDB
L-1-Pyrroline 3-hydroxy-5-carboxylate	HMDB
L-1-Pyrroline-3-hydroxy-5-carboxylate	HMDB
L-Delta1-Pyrroline 3-hydroxy-5-carboxylate	HMDB
Pyrroline-hydroxy-carboxylate	HMDB
3,4-Dihydro-3-hydroxy-2H-pyrrole-5-carboxylic acid	HMDB
3-Hydroxy delta 1-pyrroline-5-carboxylic acid	HMDB
3-Hydroxy delta 1-pyrroline-5-carboxylic acid, anion	HMDB

Chemical Formula

C₅H₇NO₃

Average Molecular Weight

129.114

Monoisotopic Molecular Weight

129.042593095

IUPAC Name

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

Traditional Name

pyrroline-hydroxy-carboxylate

CAS Registry Number

22573-88-2

SMILES

OC1CC(N=C1)C(O)=O

InChI Identifier

InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h2-4,7H,1H2,(H,8,9)

InChI Key

WFOFKRKDDKGRIK-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
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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

1-pyrrolinecarboxylic acid (CHEBI:27391 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 20300169)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001369)

Source

Endogenous

Endogenous (HMDB: HMDB0001369)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Arginine and Proline Metabolism (PathBank: SMP0012004)
Arginine and Proline Metabolism (HMDB: HMDB0001369)

Disease pathway

Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency) (PathBank: SMP0120454)
Creatine Deficiency, Guanidinoacetate Methyltransferase Deficiency (PathBank: SMP0120569)
Hyperprolinemia Type I (PathBank: SMP0120719)
Hyperornithinemia with Gyrate Atrophy (HOGA) (PathBank: SMP0120789)
Hyperprolinemia Type II (PathBank: SMP0120501)
Prolinemia Type II (PathBank: SMP0120539)
Prolidase Deficiency (PD) (PathBank: SMP0120541)
L-Arginine:Glycine Amidinotransferase Deficiency (PathBank: SMP0120572)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0120790)
Ornithine Aminotransferase Deficiency (OAT Deficiency) (PathBank: SMP0120538)
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency) (PathBank: SMP0120710)
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome] (PathBank: SMP0000506)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	33.9 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.5	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	2.59	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.85 m³·mol⁻¹	ChemAxon
Polarizability	11.6 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon