D-Proline

Identification

Generic Name
D-Proline
DrugBank Accession Number
DB02853
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 115.1305
Monoisotopic: 115.063328537
Chemical Formula
C5H9NO2
Synonyms
  • (2R)-pyrrolidine-2-carboxylic acid
  • (R)-2-Carboxypyrrolidine
  • (R)-pyrrolidine-2-carboxylic acid
  • D-Prolin
  • DPR

Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Aliphatic heteromonocyclic compound / Alpha-amino acid / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Hydrocarbon derivative / 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)
Affected organisms
Not Available

Chemical Identifiers

UNII
L01Q4LGZ5L
CAS number
344-25-2
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)[C@H]1CCCN1

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0003411
KEGG Compound
C00763
PubChem Compound
8988
PubChem Substance
46504839
ChemSpider
8640
BindingDB
50357224
ChEBI
16313
ChEMBL
CHEMBL80257
ZINC
ZINC000000895071
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
DPR
PDB Entries
1bfw / 1h0g / 1ic9 / 1icl / 1ico / 1jy4 / 1jy6 / 1jy9 / 1mcb / 1mcc
show 202 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-00fu-9000000000-d203e3dfb0701403a75b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9300000000-75b72c1f8607dfc161f3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-59c50c4e27dc80d423d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-7900000000-a625a79755cb0b6754e4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-ad31be62228c9b3c4870
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-8a0a8c96db2fe335f7fa
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fkc-9000000000-a82f96e3da976ba30aa8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-118.0640864
predicted
DarkChem Lite v0.1.0
[M-H]-122.8770888
predicted
DarkChem Standard v0.1.0
[M-H]-118.1047864
predicted
DarkChem Lite v0.1.0
[M-H]-114.921524
predicted
DeepCCS 1.0 (2019)
[M+H]+119.0086864
predicted
DarkChem Lite v0.1.0
[M+H]+124.6309817
predicted
DarkChem Standard v0.1.0
[M+H]+119.0490864
predicted
DarkChem Lite v0.1.0
[M+H]+118.569565
predicted
DeepCCS 1.0 (2019)
[M+Na]+118.4262864
predicted
DarkChem Lite v0.1.0
[M+Na]+118.3546864
predicted
DarkChem Lite v0.1.0
[M+Na]+118.3572864
predicted
DarkChem Lite v0.1.0
[M+Na]+127.3013
predicted
DeepCCS 1.0 (2019)

Transporters

Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52