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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:43 UTC

Update Date

2023-02-21 17:16:17 UTC

HMDB ID

HMDB0002234

Secondary Accession Numbers

HMDB02234

Metabolite Identification

Common Name

1-Pyrroline-4-hydroxy-2-carboxylate

Description

Much or all of the pyrrole-2-carboxylate (PCA) in human urine may be formed in urine from a labile precursor, presumably delta(1)-pyrroline-4-hydroxy-2-carboxylate. Normal human values for endogenous urinary PCA in 16 individuals averaged 0.51 mumol/day, with a range of 0.20-1.3 mumol and a SD of 0.31 mumol. The probable source of human PCA is free hydroxy-L-proline, as inferred from the high value for PCA in the urine of a subject with hereditary hydroxyprolinemia, and from the threeto eightfold elevation in PCA excretion by two normal subjects after a large oral load of hydroxyl-L-proline. (PMID: 4430715 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Pyrroline-4-hydroxy-2-carboxylic acid	Generator
4-Hydroxy-1-pyrroline-2-carboxylate	HMDB
4-Hydroxy-1-pyrroline-2-carboxylic acid	HMDB

Chemical Formula

C₅H₇NO₃

Average Molecular Weight

129.114

Monoisotopic Molecular Weight

129.042593095

IUPAC Name

3-hydroxy-3,4-dihydro-2H-pyrrole-5-carboxylic acid

Traditional Name

4-hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid

CAS Registry Number

9054-77-7

SMILES

OC1CN=C(C1)C(O)=O

InChI Identifier

InChI=1S/C5H7NO3/c7-3-1-4(5(8)9)6-2-3/h3,7H,1-2H2,(H,8,9)

InChI Key

AOMLMYXPXUTBQH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolines

Sub Class

Not Available

Direct Parent

Pyrrolines

Alternative Parents

Substituents

Pyrroline
Ketimine
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Imine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

1-pyrrolinecarboxylic acid (CHEBI:16352 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0002234)

Source

Endogenous

Endogenous (HMDB: HMDB0002234)

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: HMDB0002234)

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

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	18.3 g/L	ALOGPS
logP	-0.87	ALOGPS
logP	-0.39	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	0.53	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	29.05 m³·mol⁻¹	ChemAxon
Polarizability	11.76 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	126.607	31661259
DarkChem	[M-H]-	122.725	31661259
DeepCCS	[M+H]+	126.155	30932474
DeepCCS	[M-H]-	123.358	30932474
DeepCCS	[M-2H]-	159.893	30932474
DeepCCS	[M+Na]+	134.714	30932474
AllCCS	[M+H]+	127.8	32859911
AllCCS	[M+H-H2O]+	123.1	32859911
AllCCS	[M+NH4]+	132.2	32859911
AllCCS	[M+Na]+	133.4	32859911
AllCCS	[M-H]-	122.4	32859911
AllCCS	[M+Na-2H]-	124.5	32859911
AllCCS	[M+HCOO]-	126.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Pyrroline-4-hydroxy-2-carboxylate	OC1CN=C(C1)C(O)=O	2570.6	Standard polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate	OC1CN=C(C1)C(O)=O	1241.3	Standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate	OC1CN=C(C1)C(O)=O	1349.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Pyrroline-4-hydroxy-2-carboxylate,1TMS,isomer #1	C[Si](C)(C)OC1CN=C(C(=O)O)C1	1445.4	Semi standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TMS,isomer #2	C[Si](C)(C)OC(=O)C1=NCC(O)C1	1420.9	Semi standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=NCC(O[Si](C)(C)C)C1	1542.5	Semi standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CN=C(C(=O)O)C1	1701.8	Semi standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=NCC(O)C1	1656.0	Semi standard non polar	33892256
1-Pyrroline-4-hydroxy-2-carboxylate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=NCC(O[Si](C)(C)C(C)(C)C)C1	1971.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-19a72e5b9fe9ac201f5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-6920000000-dcc68a282266070ec2a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Positive-QTOF	splash10-03di-2900000000-58f204c991c38049140c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Positive-QTOF	splash10-01q9-9600000000-98ff648f381fb9cc7cf8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Positive-QTOF	splash10-0k9f-9000000000-a95381dc82b69dd8d6c7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Negative-QTOF	splash10-004i-3900000000-b7556a7075f544b404e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Negative-QTOF	splash10-040r-7900000000-9fd49cb04f666d2991a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Negative-QTOF	splash10-014l-9000000000-5bb96788c36c7da5ada0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Negative-QTOF	splash10-004i-2900000000-8374277a23239adb1d33	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Negative-QTOF	splash10-05p9-9200000000-92b64c62ee6df0e23b71	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Negative-QTOF	splash10-0006-9000000000-0b9e569bdea8c12f6cef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Positive-QTOF	splash10-01q9-2900000000-6e6b23467e5d79af6538	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Positive-QTOF	splash10-001l-9100000000-98423d0a57986487f382	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Positive-QTOF	splash10-0006-9000000000-fdc0e9b91597d49b9bf0	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Arginine and proline metabolism	Not Available
Prolidase Deficiency (PD)		Not Available
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)		Not Available
Hyperprolinemia Type II		Not Available
Hyperprolinemia Type I		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022921

KNApSAcK ID

Not Available

Chemspider ID

389257

KEGG Compound ID

C04282

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6564

PubChem Compound

440282

PDB ID

Not Available

ChEBI ID

16352

Food Biomarker Ontology

Not Available

VMH ID

1P4H2CBXL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Heacock AM, Adams E: Formation and excretion of pyrrole-2-carboxylate in man. J Clin Invest. 1974 Oct;54(4):810-8. [PubMed:4430715 ]

Enzymes

Enzyme Details

1. D-amino-acid oxidase

General function:: Involved in D-amino-acid oxidase activity
Specific function:: Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:: DAO
Uniprot ID:: P14920
Molecular weight:: 39473.75

Reactions

cis-4-Hydroxy-D-proline + Oxygen → 1-Pyrroline-4-hydroxy-2-carboxylate + Hydrogen peroxide	details

Showing metabocard for 1-Pyrroline-4-hydroxy-2-carboxylate (HMDB0002234)

MOL for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

3D MOL for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

3D SDF for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

3D-SDF for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

PDB for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

3D PDB for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

SMILES for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

INCHI for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

Structure for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

3D Structure for HMDB0002234 (1-Pyrroline-4-hydroxy-2-carboxylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions