Identification

Name
D-Proline
Accession Number
DB02853  (EXPT01259)
Type
Small Molecule
Groups
Experimental
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
Categories
Not Available
UNII
Not Available
CAS number
344-25-2
Weight
Average: 115.1305
Monoisotopic: 115.063328537
Chemical Formula
C5H9NO2
InChI Key
ONIBWKKTOPOVIA-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)[[email protected]]1CCCN1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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
Human Metabolome Database
HMDB03411
KEGG Compound
C00763
ChemSpider
8640
BindingDB
50357224
ChEBI
16313
ChEMBL
CHEMBL80257
IUPHAR
3314
Guide to Pharmacology
GtP Drug Page
HET
DPR
PDB Entries
1bfw / 1h0g / 1ic9 / 1icl / 1ico / 1jy4 / 1jy6 / 1jy9 / 1mcb / 1mcc
show 112 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
D-alpha-amino acids / Pyrrolidine carboxylic acids / Amino acids / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
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
show 13 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
D-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 recog...
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 October 02, 2017 05:15