Explore a selection of our essential drug information below, or:
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
Structure for D-Proline (DB02853)
- 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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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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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
- 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]
- 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]
- External Links
- 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 204 more
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 365.0 mg/mL ALOGPS logP -2.7 ALOGPS logP -2.6 Chemaxon logS 0.5 ALOGPS pKa (Strongest Acidic) 1.94 Chemaxon pKa (Strongest Basic) 11.33 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.33 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 28.06 m3·mol-1 Chemaxon Polarizability 11.39 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00fu-9000000000-d203e3dfb0701403a75b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9300000000-75b72c1f8607dfc161f3 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0900000000-59c50c4e27dc80d423d4 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-7900000000-a625a79755cb0b6754e4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9000000000-ad31be62228c9b3c4870 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-8a0a8c96db2fe335f7fa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fkc-9000000000-a82f96e3da976ba30aa8 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 118.0640864 predictedDarkChem Lite v0.1.0 [M-H]- 122.8770888 predictedDarkChem Standard v0.1.0 [M-H]- 118.1047864 predictedDarkChem Lite v0.1.0 [M-H]- 114.921524 predictedDeepCCS 1.0 (2019) [M+H]+ 119.0086864 predictedDarkChem Lite v0.1.0 [M+H]+ 124.6309817 predictedDarkChem Standard v0.1.0 [M+H]+ 119.0490864 predictedDarkChem Lite v0.1.0 [M+H]+ 118.569565 predictedDeepCCS 1.0 (2019) [M+Na]+ 118.4262864 predictedDarkChem Lite v0.1.0 [M+Na]+ 118.3546864 predictedDarkChem Lite v0.1.0 [M+Na]+ 118.3572864 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.3013 predictedDeepCCS 1.0 (2019)
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Electrogenic proton/amino acid symporter with selectivity for small apolar L-amino acids, their D-enantiomers and selected amino acid derivatives such as 4-aminobutanoate/GABA (PubMed:12527723, PubMed:12809675, PubMed:19549785). May be involved in the efflux from the lysosomal compartment of neutral amino acids resulting from proteolysis (By similarity). May play a role in specifying sites for exocytosis in neurons (By similarity)
- Specific Function
- Alanine transmembrane transporter activity
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- 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