Identification
NameD-Proline
Accession NumberDB02853  (EXPT01259)
TypeSmall Molecule
GroupsExperimental
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 [1]. These amino acids may be of bacterial origin, but there is also evidence that they are endogenously produced through amino acid racemase activity [2].

Structure
Thumb
Synonyms
(2R)-pyrrolidine-2-carboxylic acid
(R)-2-Carboxypyrrolidine
(R)-pyrrolidine-2-carboxylic acid
D-Prolin
DPR
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS number344-25-2
WeightAverage: 115.1305
Monoisotopic: 115.063328537
Chemical FormulaC5H9NO2
InChI KeyONIBWKKTOPOVIA-SCSAIBSYSA-N
InChI
InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
IUPAC Name
(2R)-pyrrolidine-2-carboxylic acid
SMILES
OC(=O)[C@H]1CCCN1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

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

US20020037559
General References
  1. Nagata Y, Higashi M, Ishii Y, Sano H, Tanigawa M, Nagata K, Noguchi K, Urade M: The presence of high concentrations of free D-amino acids in human saliva. Life Sci. 2006 Mar 6;78(15):1677-81. Epub 2006 Feb 9. [PubMed:16480744 ]
  2. Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8. [PubMed:1426150 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility365.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.06 m3·mol-1ChemAxon
Polarizability11.39 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as proline and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentProline and derivatives
Alternative ParentsD-alpha-amino acids / Pyrrolidine carboxylic acids / Amino acids / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsProline 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
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsD-alpha-amino acid, proline (CHEBI:16313 ) / Other amino acids (C00763 )

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Uniprot Name:
Proton-coupled amino acid transporter 1
Molecular Weight:
53075.045 Da
References
  1. Metzner L, Kalbitz J, Brandsch M: Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1. J Pharmacol Exp Ther. 2004 Apr;309(1):28-35. Epub 2004 Jan 12. [PubMed:14718599 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:46