5-CHLORO-THIOPHENE-2-CARBOXYLIC ACID ((3S,4S)-4-FLUORO- 1-{[2-FLUORO-4-(2-OXO-2H-PYRIDIN-1-YL)-PHENYLCARBAMOYL]-METHYL}-PYRROLIDIN-3-YL)-AMIDE
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 5-CHLORO-THIOPHENE-2-CARBOXYLIC ACID ((3S,4S)-4-FLUORO- 1-{[2-FLUORO-4-(2-OXO-2H-PYRIDIN-1-YL)-PHENYLCARBAMOYL]-METHYL}-PYRROLIDIN-3-YL)-AMIDE
- DrugBank Accession Number
- DB08143
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5-CHLORO-THIOPHENE-2-CARBOXYLIC ACID ((3S,4S)-4-FLUORO- 1-{[2-FLUORO-4-(2-OXO-2H-PYRIDIN-1-YL)-PHENYLCARBAMOYL]-METHYL}-PYRROLIDIN-3-YL)-AMIDE (DB08143)
- Weight
- Average: 492.926
Monoisotopic: 492.083445301 - Chemical Formula
- C22H19ClF2N4O3S
- 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 UCoagulation factor X 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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid amides
- Alternative Parents
- Anilides / Thiophene carboxamides / 2-heteroaryl carboxamides / N-arylamides / Pyridinones / 2,5-disubstituted thiophenes / Fluorobenzenes / Dihydropyridines / Aryl chlorides / N-alkylpyrrolidines show 13 more
- Substituents
- 2,5-disubstituted thiophene / 2-heteroaryl carboxamide / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Amine / Anilide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl fluoride show 34 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- SXIYSYYSKHUTQQ-RDJZCZTQSA-N
- InChI
- InChI=1S/C22H19ClF2N4O3S/c23-19-7-6-18(33-19)22(32)27-17-11-28(10-15(17)25)12-20(30)26-16-5-4-13(9-14(16)24)29-8-2-1-3-21(29)31/h1-9,15,17H,10-12H2,(H,26,30)(H,27,32)/t15-,17-/m0/s1
- IUPAC Name
- 5-chloro-N-[(3S,4S)-4-fluoro-1-({[2-fluoro-4-(2-oxo-1,2-dihydropyridin-1-yl)phenyl]carbamoyl}methyl)pyrrolidin-3-yl]thiophene-2-carboxamide
- SMILES
- [H][C@]1(F)CN(CC(=O)NC2=CC=C(C=C2F)N2C=CC=CC2=O)C[C@]1([H])NC(=O)C1=CC=C(Cl)S1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 42628063
- PubChem Substance
- 99444614
- ChemSpider
- 24617096
- BindingDB
- 50295595
- ChEMBL
- CHEMBL550453
- ZINC
- ZINC000038995982
- PDBe Ligand
- LZG
- PDB Entries
- 2vwo
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 0.00139 mg/mL ALOGPS logP 3.37 ALOGPS logP 2.88 Chemaxon logS -5.6 ALOGPS pKa (Strongest Acidic) 11.57 Chemaxon pKa (Strongest Basic) 3.72 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 81.75 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 122.12 m3·mol-1 Chemaxon Polarizability 46.32 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9952 Blood Brain Barrier + 0.8908 Caco-2 permeable - 0.5478 P-glycoprotein substrate Substrate 0.7207 P-glycoprotein inhibitor I Non-inhibitor 0.5444 P-glycoprotein inhibitor II Non-inhibitor 0.9067 Renal organic cation transporter Non-inhibitor 0.7143 CYP450 2C9 substrate Non-substrate 0.7693 CYP450 2D6 substrate Non-substrate 0.8255 CYP450 3A4 substrate Substrate 0.6075 CYP450 1A2 substrate Non-inhibitor 0.6841 CYP450 2C9 inhibitor Inhibitor 0.6307 CYP450 2D6 inhibitor Non-inhibitor 0.6665 CYP450 2C19 inhibitor Inhibitor 0.6388 CYP450 3A4 inhibitor Inhibitor 0.5639 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8414 Ames test Non AMES toxic 0.7237 Carcinogenicity Non-carcinogens 0.8041 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4453 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9745 hERG inhibition (predictor II) Inhibitor 0.7959
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0000900000-7a081cf3ad231abc4a9d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-05fu-1720900000-6adbfe0602bfc3f6ce2f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0001900000-b8291e373cf6a686bb4a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03dl-0053900000-a3cd2a20555082f75e9c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0mi5-1485900000-85acab2722f5e2ffa9a6 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-3054900000-a9bbb407652d311e56ec 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]- 198.0743 predictedDeepCCS 1.0 (2019) [M+H]+ 200.46986 predictedDeepCCS 1.0 (2019) [M+Na]+ 207.75426 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting. Factor Xa activates pro-inflammatory signaling pathways in a protease-activated receptor (PAR)-dependent manner (PubMed:24041930, PubMed:30568593, PubMed:34831181). Up-regulates expression of protease-activated receptors (PARs) F2R, F2RL1 and F2RL2 in dermal microvascular endothelial cells (PubMed:35738824). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL6, in cardiac fibroblasts and umbilical vein endothelial cells in PAR-1 (F2R)-dependent manner (PubMed:30568593, PubMed:34831181). Triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2, IL6, TNF-alpha/TNF, IL-1beta/IL1B, IL8/CXCL8 and IL18, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Induces expression of adhesion molecules, such as ICAM1, VCAM1 and SELE, in endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824, PubMed:9780208). Increases expression of phosphorylated ERK1/2 in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Triggers activation of the transcription factor NF-kappa-B in dermal microvascular endothelial cells and atrial tissues (PubMed:24041930, PubMed:35738824). Up-regulates expression of plasminogen activator inhibitor 1 (SERPINE1) in atrial tissues (PubMed:24041930)
- Specific Function
- Calcium ion binding
- Gene Name
- F10
- Uniprot ID
- P00742
- Uniprot Name
- Coagulation factor X
- Molecular Weight
- 54731.255 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 21:28 / Updated at June 12, 2020 16:52