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Record Information
Version1.0
Creation Date2016-09-30 23:04:23 UTC
Update Date2020-05-21 16:28:29 UTC
BMDB IDBMDB0003411
Secondary Accession Numbers
  • BMDB03411
Metabolite Identification
Common NameD-Proline
DescriptionD-Proline, also known as D-prolin or DPR, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. D-Proline is a very strong basic compound (based on its pKa). D-Proline exists in all living species, ranging from bacteria to humans. D-proline can be converted into 1-pyrroline-2-carboxylic acid through the action of the enzyme D-amino-acid oxidase. In cattle, D-proline is involved in the metabolic pathway called the arginine and proline metabolism pathway. D-Proline is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
(2R)-Pyrrolidine-2-carboxylic acidChEBI
(R)-2-CarboxypyrrolidineChEBI
(R)-Pyrrolidine-2-carboxylic acidChEBI
D-ProlinChEBI
DPRChEBI
(2R)-Pyrrolidine-2-carboxylateGenerator
(R)-Pyrrolidine-2-carboxylateGenerator
R)-2-CarboxypyrrolidineHMDB
R-ProlineHMDB
ProlineHMDB
Chemical FormulaC5H9NO2
Average Molecular Weight115.1305
Monoisotopic Molecular Weight115.063328537
IUPAC Name(2R)-pyrrolidine-2-carboxylic acid
Traditional NameD-proline
CAS Registry Number344-25-2
SMILES
OC(=O)[C@H]1CCCN1
InChI Identifier
InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
InChI KeyONIBWKKTOPOVIA-SCSAIBSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Lysosome
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-2.6ChemAxon
logS0.5ALOGPS
pKa (Strongest Acidic)1.94ChemAxon
pKa (Strongest Basic)11.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.06 m³·mol⁻¹ChemAxon
Polarizability11.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-d203e3dfb0701403a75bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9000000000-56471980a375d26046caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000000-eba8ceb2a71d2726acd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9200000000-c52871a4097a833a301aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-50a811fa0506a025048aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-ba371efbf747c7eed1a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-9600000000-f8a0815fbf4d1b2713afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-133753f87329f1da7d39View in MoNA
Biological Properties
Cellular Locations
  • Lysosome
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003411
DrugBank IDDB02853
Phenol Explorer Compound IDNot Available
FooDB IDFDB023166
KNApSAcK IDNot Available
Chemspider ID8640
KEGG Compound IDC00763
BioCyc IDD-PROLINE
BiGG ID35916
Wikipedia LinkD-proline
METLIN IDNot Available
PubChem Compound8988
PDB IDNot Available
ChEBI ID16313
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
DDO
Uniprot ID:
P31228
Molecular weight:
37660.0
Reactions
D-Proline + Water + Oxygen → 1-Pyrroline-2-carboxylic acid + Ammonia + Hydrogen peroxidedetails
General function:
Involved in proline racemase activity
Specific function:
Catalyzes the dehydration of trans-3-hydroxy-L-proline to Delta(1)-pyrroline-2-carboxylate (Pyr2C).
Gene Name:
L3HYPDH
Uniprot ID:
Q3SX04
Molecular weight:
37957.0