(6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one
Identification
- Generic Name
- (6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one
- DrugBank Accession Number
- DB07148
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (6S)-1-chloro-3-[(4-fluorobenzyl)oxy]-6-(pyrrolidin-1-ylcarbonyl)pyrrolo[1,2-a]pyrazin-4(6H)-one (DB07148)
- Weight
- Average: 389.808
Monoisotopic: 389.094247337 - Chemical Formula
- C19H17ClFN3O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UProlyl endopeptidase 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrrolidines
- Sub Class
- N-acylpyrrolidines
- Direct Parent
- N-acylpyrrolidines
- Alternative Parents
- Alkyl aryl ethers / Fluorobenzenes / Pyrazines / Aryl chlorides / Aryl fluorides / Tertiary carboxylic acid amides / Heteroaromatic compounds / Lactams / Azacyclic compounds / Hydrocarbon derivatives show 6 more
- Substituents
- Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- HPAFVLDARQIHPU-HNNXBMFYSA-N
- InChI
- InChI=1S/C19H17ClFN3O3/c20-16-14-7-8-15(18(25)23-9-1-2-10-23)24(14)19(26)17(22-16)27-11-12-3-5-13(21)6-4-12/h3-8,15H,1-2,9-11H2/t15-/m0/s1
- IUPAC Name
- (6S)-1-chloro-3-[(4-fluorophenyl)methoxy]-6-(pyrrolidine-1-carbonyl)-4H,6H-pyrrolo[1,2-a]pyrazin-4-one
- SMILES
- [H][C@]1(C=CC2=C(Cl)N=C(OCC3=CC=C(F)C=C3)C(=O)N12)C(=O)N1CCCC1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46937054
- PubChem Substance
- 99443619
- ChemSpider
- 25057581
- ZINC
- ZINC000039125249
- PDBe Ligand
- 552
- PDB Entries
- 3ddu
Clinical Trials
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 0.0289 mg/mL ALOGPS logP 2.66 ALOGPS logP 2.39 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 11.04 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 62.21 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 109.54 m3·mol-1 Chemaxon Polarizability 37.22 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9821 Caco-2 permeable - 0.5285 P-glycoprotein substrate Substrate 0.7299 P-glycoprotein inhibitor I Inhibitor 0.8001 P-glycoprotein inhibitor II Inhibitor 0.8723 Renal organic cation transporter Inhibitor 0.5198 CYP450 2C9 substrate Non-substrate 0.8208 CYP450 2D6 substrate Non-substrate 0.7276 CYP450 3A4 substrate Substrate 0.6264 CYP450 1A2 substrate Inhibitor 0.6004 CYP450 2C9 inhibitor Non-inhibitor 0.5483 CYP450 2D6 inhibitor Non-inhibitor 0.8515 CYP450 2C19 inhibitor Inhibitor 0.6315 CYP450 3A4 inhibitor Non-inhibitor 0.5698 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9241 Ames test Non AMES toxic 0.7313 Carcinogenicity Non-carcinogens 0.9337 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3563 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8578 hERG inhibition (predictor II) Inhibitor 0.8051
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine-type peptidase activity
- Specific Function
- Cleaves peptide bonds on the C-terminal side of prolyl residues within peptides that are up to approximately 30 amino acids long.
- Gene Name
- PREP
- Uniprot ID
- P48147
- Uniprot Name
- Prolyl endopeptidase
- Molecular Weight
- 80698.945 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52