Identification
- Generic Name
- Picolinic acid
- DrugBank Accession Number
- DB05483
- Background
PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator and is produced in approximately 25-50 mg quantities by the body on a daily basis through the breakdown of tryptophan. PCL-016 plays a key role in zinc transport. As a therapeutic agent, the molecule works by binding to zinc finger proteins (ZFPs) in a way that changes their structures and disrupts zinc binding, inhibiting function. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions. Picolinic acid has been shown to be an anti-viral in vitro and in vivo, and sometimes works in conjunction with other cytokines such as interferon gamma to affect immune responses. Acne vulgaris, herpes and other viral infections therefore pose potential therapeutic targets of PCL-016.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Picolinic acid (DB05483)
- Weight
- Average: 123.111
Monoisotopic: 123.032028405 - Chemical Formula
- C6H5NO2
- Synonyms
- 2-Carboxypyridine
- Acide picolique
- External IDs
- PCL-016
Pharmacology
- Indication
Investigated for use/treatment in acne, herpes labialis infections (cold sores), and venereal disease.
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PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator through its role in zinc transport. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions. Picolinic acid has been shown to be an anti-viral in vitro and in vivo.
- Mechanism of action
As a therapeutic agent, the molecule works by binding to zinc finger proteins (ZFPs) in a way that changes their structures and disrupts zinc binding, inhibiting function.
Target Actions Organism UE3 ubiquitin-protein ligase UBR4 Not Available Humans UZinc finger Y-chromosomal protein Not Available Humans - 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- QZV2W997JQ
- CAS number
- 98-98-6
- InChI Key
- SIOXPEMLGUPBBT-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
- IUPAC Name
- pyridine-2-carboxylic acid
- SMILES
- OC(=O)C1=CC=CC=N1
References
- General References
- Heffernan MP, Nelson MM, Anadkat MJ: A pilot study of the safety and efficacy of picolinic acid gel in the treatment of acne vulgaris. Br J Dermatol. 2007 Mar;156(3):548-52. [Article]
- External Links
- Human Metabolome Database
- HMDB0002243
- KEGG Compound
- C10164
- PubChem Substance
- 347910165
- ChemSpider
- 993
- BindingDB
- 50000407
- 33684
- ChEBI
- 28747
- ChEMBL
- CHEMBL72628
- ZINC
- ZINC000000039905
- PDBe Ligand
- 6PC
- Wikipedia
- Picolinic_acid
- PDB Entries
- 2oln / 2olo / 3hzl / 4hsj / 4m1e / 4yic / 4yzz / 5gja / 5wol / 6o4d … show 2 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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 61.1 mg/mL ALOGPS logP 0.22 ALOGPS logP -0.65 Chemaxon logS -0.3 ALOGPS pKa (Strongest Acidic) 1 Chemaxon pKa (Strongest Basic) 5.52 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 50.19 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 30.79 m3·mol-1 Chemaxon Polarizability 11.38 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 MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05fr-0900000000-cb0fdc064f0b1b3d7a74 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-4900000000-44eb4f06b91662e0adfc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pb9-9600000000-741e6bf795b5f7105165 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9100000000-b4134c9148d2520effd2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-9000000000-6942ce7a3ca3cb4221f1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9000000000-6ab2b571cca81cc8e43a 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]- 120.8361436 predictedDarkChem Lite v0.1.0 [M-H]- 120.8130436 predictedDarkChem Lite v0.1.0 [M-H]- 117.15506 predictedDeepCCS 1.0 (2019) [M+H]+ 121.4840436 predictedDarkChem Lite v0.1.0 [M+H]+ 121.2476436 predictedDarkChem Lite v0.1.0 [M+H]+ 120.48029 predictedDeepCCS 1.0 (2019) [M+Na]+ 121.0253436 predictedDarkChem Lite v0.1.0 [M+Na]+ 121.2529436 predictedDarkChem Lite v0.1.0 [M+Na]+ 129.04404 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- E3 ubiquitin-protein ligase which is a component of the N-end rule pathway. Recognizes and binds to proteins bearing specific N-terminal residues that are destabilizing according to the N-end rule,...
- Gene Name
- UBR4
- Uniprot ID
- Q5T4S7
- Uniprot Name
- E3 ubiquitin-protein ligase UBR4
- Molecular Weight
- 573835.26 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription factor activity, sequence-specific dna binding
- Specific Function
- Probable transcriptional activator. Binds to the consensus sequence 5'-AGGCCY-3'.
- Gene Name
- ZFY
- Uniprot ID
- P08048
- Uniprot Name
- Zinc finger Y-chromosomal protein
- Molecular Weight
- 90504.29 Da
Drug created at November 18, 2007 18:25 / Updated at August 26, 2022 21:50