Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2021-09-14 15:00:09 UTC
HMDB IDHMDB0002234
Secondary Accession Numbers
  • HMDB02234
Metabolite Identification
Common Name1-Pyrroline-4-hydroxy-2-carboxylate
DescriptionMuch 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
Data?1582752237
Synonyms
ValueSource
1-Pyrroline-4-hydroxy-2-carboxylic acidGenerator
4-Hydroxy-1-pyrroline-2-carboxylateHMDB
4-Hydroxy-1-pyrroline-2-carboxylic acidHMDB
Chemical FormulaC5H7NO3
Average Molecular Weight129.114
Monoisotopic Molecular Weight129.042593095
IUPAC Name3-hydroxy-3,4-dihydro-2H-pyrrole-5-carboxylic acid
Traditional Name4-hydroxy-4,5-dihydro-3H-pyrrole-2-carboxylic acid
CAS Registry Number9054-77-7
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 KeyAOMLMYXPXUTBQH-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolines
Sub ClassNot Available
Direct ParentPyrrolines
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.3 g/LALOGPS
logP10(-0.87) g/LALOGPS
logP10(-0.39) g/LChemAxon
logS10(-0.85) g/LALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)0.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.05 m³·mol⁻¹ChemAxon
Polarizability11.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.60731661259
DarkChem[M-H]-122.72531661259
DeepCCS[M+H]+126.15530932474
DeepCCS[M-H]-123.35830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-4-hydroxy-2-carboxylateOC1CN=C(C1)C(O)=O2570.6Standard polar33892256
1-Pyrroline-4-hydroxy-2-carboxylateOC1CN=C(C1)C(O)=O1241.3Standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylateOC1CN=C(C1)C(O)=O1349.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Pyrroline-4-hydroxy-2-carboxylate,1TMS,isomer #1C[Si](C)(C)OC1CN=C(C(=O)O)C11445.4Semi standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TMS,isomer #2C[Si](C)(C)OC(=O)C1=NCC(O)C11420.9Semi standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylate,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=NCC(O[Si](C)(C)C)C11542.5Semi standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CN=C(C(=O)O)C11701.8Semi standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=NCC(O)C11656.0Semi standard non polar33892256
1-Pyrroline-4-hydroxy-2-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=NCC(O[Si](C)(C)C(C)(C)C)C11971.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-19a72e5b9fe9ac201f5c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-6920000000-dcc68a282266070ec2a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Positive-QTOFsplash10-03di-2900000000-58f204c991c38049140c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Positive-QTOFsplash10-01q9-9600000000-98ff648f381fb9cc7cf82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Positive-QTOFsplash10-0k9f-9000000000-a95381dc82b69dd8d6c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Negative-QTOFsplash10-004i-3900000000-b7556a7075f544b404e62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Negative-QTOFsplash10-040r-7900000000-9fd49cb04f666d2991a92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Negative-QTOFsplash10-014l-9000000000-5bb96788c36c7da5ada02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Negative-QTOFsplash10-004i-2900000000-8374277a23239adb1d332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Negative-QTOFsplash10-05p9-9200000000-92b64c62ee6df0e23b712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Negative-QTOFsplash10-0006-9000000000-0b9e569bdea8c12f6cef2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 10V, Positive-QTOFsplash10-01q9-2900000000-6e6b23467e5d79af65382021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 20V, Positive-QTOFsplash10-001l-9100000000-98423d0a57986487f3822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Pyrroline-4-hydroxy-2-carboxylate 40V, Positive-QTOFsplash10-0006-9000000000-fdc0e9b91597d49b9bf02021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022921
KNApSAcK IDNot Available
Chemspider ID389257
KEGG Compound IDC04282
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6564
PubChem Compound440282
PDB IDNot Available
ChEBI ID16352
Food Biomarker OntologyNot Available
VMH ID1P4H2CBXL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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

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 peroxidedetails