D-Proline (CHEM003370)

Record Information
Version1.0
Creation Date2014-08-29 06:51:04 UTC
Update Date2026-05-14 17:46:46 UTC
Accession NumberCHEM003370
Identification
Common NameD-Proline
ClassSmall Molecule
Description
D-proline is an isomer of the naturally occurring amino acid, L-Proline. D-amino acids have been found in relatively high abundance in human plasma and saliva These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity. (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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 Mass115.131 g/mol
Monoisotopic Mass115.063 g/mol
CAS Registry Number344-25-2
IUPAC Name(2R)-pyrrolidine-2-carboxylic acid
Traditional NameD-proline
SMILESOC(=O)[C@H]1CCCN1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Lysosome
  • Membrane
  • Peroxisome
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Hyperprolinemia Type ISMP00361 Not Available
Hyperprolinemia Type IISMP00360 Not Available
Prolinemia Type IISMP00208 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point221°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility365 g/LALOGPS
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesD-amino acids have been found in relatively high abundance in human plasma and saliva These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB02853
HMDB IDHMDB0003411
FooDB IDFDB023166
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35916
BioCyc IDD-PROLINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkD-proline
Chemspider ID8640
ChEBI ID16313
PubChem Compound ID8988
Kegg Compound IDC00763
YMDB IDYMDB00903
ECMDB IDM2MDB004624
References
Synthesis Reference

MARTIN SAUTER, “PROCESS FOR PRODUCING N-PROTECTED D-PROLINE DERIVATIVES.” U.S. Patent US20020037559, issued March 28, 2002.

MSDSLink
General References
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