NAV

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

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
3D
Similar Structures
Weight
Average: 492.926
Monoisotopic: 492.083445301
Chemical Formula
C22H19ClF2N4O3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCoagulation factor XNot AvailableHumans
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 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
PubChem Compound
42628063
PubChem Substance
99444614
ChemSpider
24617096
BindingDB
50295595
ChEMBL
CHEMBL550453
ZINC
ZINC000038995982
PDBe Ligand
LZG
PDB Entries
2vwo

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 Solubility0.00139 mg/mLALOGPS
logP3.37ALOGPS
logP2.88Chemaxon
logS-5.6ALOGPS
pKa (Strongest Acidic)11.57Chemaxon
pKa (Strongest Basic)3.72Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area81.75 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity122.12 m3·mol-1Chemaxon
Polarizability46.32 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.8908
Caco-2 permeable-0.5478
P-glycoprotein substrateSubstrate0.7207
P-glycoprotein inhibitor INon-inhibitor0.5444
P-glycoprotein inhibitor IINon-inhibitor0.9067
Renal organic cation transporterNon-inhibitor0.7143
CYP450 2C9 substrateNon-substrate0.7693
CYP450 2D6 substrateNon-substrate0.8255
CYP450 3A4 substrateSubstrate0.6075
CYP450 1A2 substrateNon-inhibitor0.6841
CYP450 2C9 inhibitorInhibitor0.6307
CYP450 2D6 inhibitorNon-inhibitor0.6665
CYP450 2C19 inhibitorInhibitor0.6388
CYP450 3A4 inhibitorInhibitor0.5639
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8414
Ames testNon AMES toxic0.7237
CarcinogenicityNon-carcinogens0.8041
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4453 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9745
hERG inhibition (predictor II)Inhibitor0.7959
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000900000-7a081cf3ad231abc4a9d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fu-1720900000-6adbfe0602bfc3f6ce2f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0001900000-b8291e373cf6a686bb4a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-0053900000-a3cd2a20555082f75e9c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0mi5-1485900000-85acab2722f5e2ffa9a6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-3054900000-a9bbb407652d311e56ec
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]-198.0743
predicted
DeepCCS 1.0 (2019)
[M+H]+200.46986
predicted
DeepCCS 1.0 (2019)
[M+Na]+207.75426
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Coagulation factor X
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific 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.
Gene Name
F10
Uniprot ID
P00742
Uniprot Name
Coagulation factor X
Molecular Weight
54731.255 Da
References
  1. 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