Showing Compound Pyrroline hydroxycarboxylic acid (FDB022582)

Record Information

Version

1.0

Creation date

2011-09-21 00:16:17 UTC

Update date

2024-11-29 22:26:16 UTC

Primary ID

FDB022582

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pyrroline hydroxycarboxylic acid

Description

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) [HMDB]

CAS Number

22573-88-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
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
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-1-Pyrroline-3-hydroxy-5-carboxylate	HMDB
L-Delta1-Pyrroline 3-hydroxy-5-carboxylate	HMDB
L-Delta1-pyrroline 3-hydroxy-5-carboxylate	hmdb
Pyrroline hydroxycarboxylate	Generator

Showing 1 to 10 of 12 entries

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

Chemical Formula

C5H7NO3

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

129.114

Monoisotopic Molecular Weight

129.042593095

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.

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 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Mitochondria

Biofluid and excreta:

Saliva

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Pyrroline hydroxycarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9100000000-81454e4422185c7858e4	Spectrum
Predicted GC-MS	Pyrroline hydroxycarboxylic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-5910000000-0d5241ee660e7a60b0f9	Spectrum
Predicted GC-MS	Pyrroline hydroxycarboxylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9600000000-8e7afe6ced148f01b715	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-91b528e579ac4acfac93	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02u0-9400000000-c804fee192934438c532	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-7da85099ac98a08f5741	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-ee7c942618fc6b2d94a9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02e9-9700000000-1d9848f227e64812ada6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-9000000000-0d2b20e1b4dbed83a144	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-06e1bd2d2793c5f0afaa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-9400000000-a84600f4fc13459b9448	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d2c2d7b1e05ce54b0932	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9300000000-c26ff3ebe1bb758e5252	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9000000000-97da4a76921516901d46	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc3-9000000000-8982b409276eceb00f1b	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

1030

ChEMBL ID

Not Available

KEGG Compound ID

C04281

Pubchem Compound ID

1059

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01369

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

43511

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

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Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Pyrroline hydroxycarboxylic acid (FDB022582)

Structure for FDB022582 (Pyrroline hydroxycarboxylic acid)