5-Chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-4-hydroxy-pyrrolidin-3-yl)-amide

Identification

Generic Name
5-Chloro-thiophene-2-carboxylic acid ((3S,4S)-1-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-4-hydroxy-pyrrolidin-3-yl)-amide
DrugBank Accession Number
DB07875
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 490.935
Monoisotopic: 490.08778175
Chemical Formula
C22H20ClFN4O4S
Synonyms
Not Available

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 / N-arylamides / Thiophene carboxamides / 2-heteroaryl carboxamides / Dihydropyridines / Fluorobenzenes / 2,5-disubstituted thiophenes / Pyridinones / N-alkylpyrrolidines / Aryl chlorides
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Substituents
1,2-aminoalcohol / 2,5-disubstituted thiophene / 2-heteroaryl carboxamide / Alcohol / Alpha-amino acid amide / Amine / Anilide / Aromatic heteromonocyclic compound / Aryl chloride / Aryl fluoride
show 35 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
ARAVOODWJJJNBY-IRXDYDNUSA-N
InChI
InChI=1S/C22H20ClFN4O4S/c23-19-7-6-18(33-19)22(32)26-16-10-27(11-17(16)29)12-20(30)25-15-5-4-13(9-14(15)24)28-8-2-1-3-21(28)31/h1-9,16-17,29H,10-12H2,(H,25,30)(H,26,32)/t16-,17-/m0/s1
IUPAC Name
5-chloro-N-[(3S,4S)-1-({[2-fluoro-4-(2-oxo-1,2-dihydropyridin-1-yl)phenyl]carbamoyl}methyl)-4-hydroxypyrrolidin-3-yl]thiophene-2-carboxamide
SMILES
[H][C@]1(O)CN(CC(=O)NC2=C(F)C=C(C=C2)N2C=CC=CC2=O)C[C@]1([H])NC(=O)C1=CC=C(Cl)S1

References

General References
Not Available
PubChem Compound
11979006
PubChem Substance
99444346
ChemSpider
10152348
BindingDB
50295587
ChEMBL
CHEMBL561318
ZINC
ZINC000038995983
PDBe Ligand
H25
PDB Entries
2vwn

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 Solubility0.00312 mg/mLALOGPS
logP2.44ALOGPS
logP1.99Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)11.57Chemaxon
pKa (Strongest Basic)4.78Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area101.98 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity123.81 m3·mol-1Chemaxon
Polarizability47.86 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9514
Blood Brain Barrier-0.7644
Caco-2 permeable-0.6356
P-glycoprotein substrateSubstrate0.7434
P-glycoprotein inhibitor INon-inhibitor0.7958
P-glycoprotein inhibitor IINon-inhibitor0.8734
Renal organic cation transporterNon-inhibitor0.8255
CYP450 2C9 substrateNon-substrate0.7441
CYP450 2D6 substrateNon-substrate0.8091
CYP450 3A4 substrateSubstrate0.5701
CYP450 1A2 substrateNon-inhibitor0.8285
CYP450 2C9 inhibitorInhibitor0.535
CYP450 2D6 inhibitorNon-inhibitor0.7471
CYP450 2C19 inhibitorNon-inhibitor0.6647
CYP450 3A4 inhibitorNon-inhibitor0.805
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.547
Ames testNon AMES toxic0.7155
CarcinogenicityNon-carcinogens0.7672
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4537 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9702
hERG inhibition (predictor II)Inhibitor0.7157
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details
1. 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 21:26 / Updated at June 12, 2020 16:52