MiMeDB: Showing metabocard for L-D-1-Pyrroline-5-carboxylic acid (MMDBc0029611)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:34:30 UTC

Update Date

2024-10-09 19:49:54 UTC

Metabolite ID

MMDBc0029611

Metabolite Identification

Common Name

L-D-1-Pyrroline-5-carboxylic acid

Description

(S)-1-Pyrroline-5-carboxylate Pyrroline 5-carboxylate is an enamine or an imino 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.

Structure

MOL SDF PDB SMILES InChI

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

Molecular Formula

C₅H₇NO₂

Average Mass

113.1146

Monoisotopic Mass

113.047678473

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

2906-39-0

SMILES

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001256	L-Glutamic-gamma-semialdehyde	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH; KEGG	30371894
MMDBr0001884	L-D-1-Pyrroline-5-carboxylic acid	L-Glutamic acid	aldehyde dehydrogenase 4 family, member A1	VMH; KEGG	30371894
MMDBr0001885	L-D-1-Pyrroline-5-carboxylic acid	L-Proline	pyrroline-5-carboxylate reductase 1	VMH; KEGG	30371894
MMDBr0001886	L-D-1-Pyrroline-5-carboxylic acid	L-Proline	pyrroline-5-carboxylate reductase 1	VMH; KEGG	30371894
MMDBr0001997	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	proline dehydrogenase (oxidase) 1	VMH	10192398
MMDBr0001999	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	proline dehydrogenase (oxidase) 1	VMH; KEGG	30371894
MMDBr0002965	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	proline dehydrogenase (oxidase) 1	VMH	18506409
MMDBr0005505	L-D-1-Pyrroline-5-carboxylic acid	L-Proline	Not Available	VMH; KEGG	30371894
MMDBr0007206	L-D-1-Pyrroline-5-carboxylic acid	L-Glutamic acid	Not Available	VMH	30371894
MMDBr0007416	L-Glutamic-gamma-semialdehyde	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH; KEGG	30371894
MMDBr0007517	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH	30371894
MMDBr0007544	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH; KEGG	30371894
MMDBr0011003	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	VMH	30371894
MMDBr0012681	4-Hydroxyproline	L-D-1-Pyrroline-5-carboxylic acid	Not Available	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	174	Human ; Human feces; Human sputum; Human unknown; Pig ; Human pleural fluid plaque; Human feces; pleural fluid plaque; bal; Human stool; Human dental plaque; Human nasal swab	Unknown; Metabolic reconstruction
Bacteria	Bacteroidetes	116	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva; Human appendix biopsy; Human stool; Human gastric fluid; Human urine	Metabolic reconstruction
Bacteria	Actinobacteria	119	Human feces; Human pleural fluid plaque; Human dental plaque; Human sputum; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human nasopharyngeal swab; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Firmicutes	369	Human feces; Human ; Human subgingival plaque; Cattle ; Human pleural fluid plaque; Pig ; Human stool; Human saliva	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Not Available	Neurotoxicity	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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

External Links

HMDB ID

HMDB0001301

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

l-delta(1)-pyrroline_5-carboxylate

BiGG ID

42766

Wikipedia Link

1-Pyrroline-5-carboxylic acid

METLIN ID

6145

PubChem Compound

1196

PDB ID

Not Available

ChEBI ID

1372

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gogos JA, Santha M, Takacs Z, Beck KD, Luine V, Lucas LR, Nadler JV, Karayiorgou M: The gene encoding proline dehydrogenase modulates sensorimotor gating in mice. Nat Genet. 1999 Apr;21(4):434-9. doi: 10.1038/7777. [PubMed:10192398 ]
Hu CA, Bart Williams D, Zhaorigetu S, Khalil S, Wan G, Valle D: Functional genomics and SNP analysis of human genes encoding proline metabolic enzymes. Amino Acids. 2008 Nov;35(4):655-64. doi: 10.1007/s00726-008-0107-9. Epub 2008 May 28. [PubMed:18506409 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for L-D-1-Pyrroline-5-carboxylic acid (MMDBc0029611)

MOL for #<Metabolite:0x00007fdb483a10a8>

3D MOL for #<Metabolite:0x00007fdb483a10a8>

3D SDF for #<Metabolite:0x00007fdb483a10a8>

3D-SDF for #<Metabolite:0x00007fdb483a10a8>

PDB for #<Metabolite:0x00007fdb483a10a8>

3D PDB for #<Metabolite:0x00007fdb483a10a8>

SMILES for #<Metabolite:0x00007fdb483a10a8>

INCHI for #<Metabolite:0x00007fdb483a10a8>

Structure for #<Metabolite:0x00007fdb483a10a8>

3D Structure for #<Metabolite:0x00007fdb483a10a8>