MiMeDB: Showing metabocard for Pyrroline hydroxycarboxylic acid (MMDBc0029634)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:35:29 UTC

Update Date

2022-08-31 14:15:19 UTC

Metabolite ID

MMDBc0029634

Metabolite Identification

Common Name

Pyrroline hydroxycarboxylic acid

Description

Pyrroline hydroxycarboxylic acid is an intermediate in arginine and proline metabolism. It is converted to trans-4-hydroxy-L-proline via pyrroline-5-carboxylate reductase, and to L-erythro-4-Hydroxyglutamate via delta-1-pyrroline-5-carboxylate dehydrogenase. (KEGG)

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

Molecular Formula

C₅H₇NO₃

Average Mass

129.114

Monoisotopic Mass

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

Not Available

Physical Properties

State

Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9100000000-81454e4422185c7858e4	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-5910000000-0d5241ee660e7a60b0f9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-001i-9600000000-8e7afe6ced148f01b715	2012-07-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-91b528e579ac4acfac93	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02u0-9400000000-c804fee192934438c532	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-7da85099ac98a08f5741	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-ee7c942618fc6b2d94a9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02e9-9700000000-1d9848f227e64812ada6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-9000000000-0d2b20e1b4dbed83a144	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-06e1bd2d2793c5f0afaa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-9400000000-a84600f4fc13459b9448	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-d2c2d7b1e05ce54b0932	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9300000000-c26ff3ebe1bb758e5252	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-9000000000-97da4a76921516901d46	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pc3-9000000000-8982b409276eceb00f1b	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191827	Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial	Unknown	P30038	Homo sapiens
MMDBp0191973	Pyrroline-5-carboxylate reductase 1, mitochondrial	Unknown	P32322	Homo sapiens
MMDBp0191975	Pyrroline-5-carboxylate reductase 2	Unknown	Q96C36	Homo sapiens
MMDBp0193751	Pyrroline-5-carboxylate reductase 3	Unknown	Q53H96	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0001928	Pyrroline hydroxycarboxylic acid	L-Glutamyl-tRNA(Glu)	Aldehyde dehydrogenase 4 family, member a1	L-1-Pyrroline-3-Hydroxy-5-Carboxylate Dehydrogenase	VMH	30371894
MMDBr0001929	Pyrroline hydroxycarboxylic acid	L-4-hydroxyglutamic semialdehyde	Not Available	L-1-Pyrroline-3-Hydroxy-5-Carboxylate Spontaneous Conversion to L-4-Hydroxyglutamate Semialdehyde, Mitochondrial	VMH	30371894
MMDBr0002623	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NAD+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002624	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NAD+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002625	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NADP+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002626	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Pyrroline-5-carboxylate reductase 1	Trans-4-Hydroxy-L-Proline:NADP+ 5-Oxidoreductase	VMH	12514185 3768405 6250440 675382
MMDBr0002664	Pyrroline hydroxycarboxylic acid	L-Glutamyl-tRNA(Glu)	Aldehyde dehydrogenase 4 family, member a1	L-1-Pyrroline-3-Hydroxy-5-Carboxylate:NADP+ Oxidoreductase	VMH	30371894
MMDBr0007212	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	Proline dehydrogenase (trans-4-Hydroxy-L-proline)	VMH	30371894
MMDBr0008356	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	L-hydroxyproline oxidase (NAD), reversible	VMH	30371894
MMDBr0008357	Pyrroline hydroxycarboxylic acid	4-Hydroxyproline	Not Available	L-hydroxyproline oxidase (NADP), reversible	VMH	30371894
MMDBr0010308	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	HMR_4782	VMH	30371894
MMDBr0010309	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	HMR_4783	VMH	30371894
MMDBr0010746	Pyrroline hydroxycarboxylic acid	Pyrroline hydroxycarboxylic acid	Not Available	HMR_9677	VMH	30371894
MMDBr0010989	4-Hydroxyproline	Pyrroline hydroxycarboxylic acid	Not Available	Proline dehydrogenase (trans-4-Hydroxy-L-proline), irreversible	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	145	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	57	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Firmicutes	91	Human feces; Human ; Human subgingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	22	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	2		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	20300169

External Links

HMDB ID

HMDB0001369

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022582

KNApSAcK ID

Not Available

Chemspider ID

1030

KEGG Compound ID

C04281

BioCyc ID

Not Available

BiGG ID

43511

Wikipedia Link

Not Available

METLIN ID

6196

PubChem Compound

1059

PDB ID

Not Available

ChEBI ID

27391

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Valle D, Goodman SI, Harris SC, Phang JM: Genetic evidence for a common enzyme catalyzing the second step in the degradation of proline and hydroxyproline. J Clin Invest. 1979 Nov;64(5):1365-70. doi: 10.1172/JCI109593. [PubMed:500817 ]
Simila S: Hydroxyproline metabolism in type II hyperprolinaemia. Ann Clin Biochem. 1979 Jul;16(4):177-81. doi: 10.1177/000456327901600143. [PubMed:533224 ]
Onenli-Mungan N, Yuksel B, Elkay M, Topaloglu AK, Baykal T, Ozer G: Type II hyperprolinemia: a case report. Turk J Pediatr. 2004 Apr-Jun;46(2):167-9. [PubMed:15214748 ]

Showing metabocard for Pyrroline hydroxycarboxylic acid (MMDBc0029634)

MOL for #<Metabolite:0x00007f5a8802d598>

3D MOL for #<Metabolite:0x00007f5a8802d598>

3D SDF for #<Metabolite:0x00007f5a8802d598>

3D-SDF for #<Metabolite:0x00007f5a8802d598>

PDB for #<Metabolite:0x00007f5a8802d598>

3D PDB for #<Metabolite:0x00007f5a8802d598>

SMILES for #<Metabolite:0x00007f5a8802d598>

INCHI for #<Metabolite:0x00007f5a8802d598>

Structure for #<Metabolite:0x00007f5a8802d598>

3D Structure for #<Metabolite:0x00007f5a8802d598>