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THIENO[3,2-B]PYRIDINE-2-SULFONIC ACID [1-(1-AMINO-ISOQUINOLIN-7-YLMETHYL)-2-OXO-PYRROLDIN-3-YL]-AMIDE

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Identification

Generic Name
THIENO[3,2-B]PYRIDINE-2-SULFONIC ACID [1-(1-AMINO-ISOQUINOLIN-7-YLMETHYL)-2-OXO-PYRROLDIN-3-YL]-AMIDE
DrugBank Accession Number
DB07261
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 453.537
Monoisotopic: 453.092930879
Chemical Formula
C21H19N5O3S2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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 isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Not Available
Direct Parent
Isoquinolines and derivatives
Alternative Parents
Alpha amino acids and derivatives / Thienopyridines / 2,3,5-trisubstituted thiophenes / Aminopyridines and derivatives / Pyrrolidine-2-ones / Organosulfonamides / N-alkylpyrrolidines / Imidolactams / Benzenoids / Tertiary carboxylic acid amides
show 9 more
Substituents
2,3,5-trisubstituted thiophene / 2-pyrrolidone / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aminopyridine / Aminosulfonyl compound / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolidin-2-ones, isoquinolines, thienopyridine (CHEBI:40318)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NVKDOURNRJCKJE-INIZCTEOSA-N
InChI
InChI=1S/C21H19N5O3S2/c22-20-15-10-13(3-4-14(15)5-8-24-20)12-26-9-6-16(21(26)27)25-31(28,29)19-11-17-18(30-19)2-1-7-23-17/h1-5,7-8,10-11,16,25H,6,9,12H2,(H2,22,24)/t16-/m0/s1
IUPAC Name
N-[(3S)-1-[(1-aminoisoquinolin-7-yl)methyl]-2-oxopyrrolidin-3-yl]thieno[3,2-b]pyridine-2-sulfonamide
SMILES
[H][C@@]1(CCN(CC2=CC3=C(C=CN=C3N)C=C2)C1=O)NS(=O)(=O)C1=CC2=C(S1)C=CC=N2

References

General References
Not Available
PubChem Compound
445480
PubChem Substance
99443732
ChemSpider
393111
BindingDB
14058
ChEMBL
CHEMBL316053
ZINC
ZINC000018275342
PDBe Ligand
815
PDB Entries
1f0r

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
PropertyValueSource
Water Solubility0.0293 mg/mLALOGPS
logP1.43ALOGPS
logP1.37Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.65Chemaxon
pKa (Strongest Basic)7.08Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area118.28 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity117.35 m3·mol-1Chemaxon
Polarizability46.94 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.7677
Caco-2 permeable-0.7066
P-glycoprotein substrateSubstrate0.7124
P-glycoprotein inhibitor INon-inhibitor0.5054
P-glycoprotein inhibitor IINon-inhibitor0.606
Renal organic cation transporterNon-inhibitor0.6827
CYP450 2C9 substrateNon-substrate0.7111
CYP450 2D6 substrateNon-substrate0.703
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6891
CYP450 2C9 inhibitorNon-inhibitor0.6606
CYP450 2D6 inhibitorNon-inhibitor0.7846
CYP450 2C19 inhibitorInhibitor0.6326
CYP450 3A4 inhibitorInhibitor0.645
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7447
Ames testNon AMES toxic0.6578
CarcinogenicityNon-carcinogens0.837
BiodegradationNot ready biodegradable0.9851
Rat acute toxicity2.3934 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.861
hERG inhibition (predictor II)Inhibitor0.6388
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/MSsplash10-0udi-0003900000-4cfee0ed332f341d4db2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-0291800000-8c2d4dbdc42d3bf962f4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-2170900000-5e00e988b94c44330160
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0010900000-d027845675d0bce160f8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pdi-0850900000-492f0406cd634bb6ce2f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-008c-2930100000-490f41aadc559513e3b9
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]-195.7971
predicted
DeepCCS 1.0 (2019)
[M+H]+198.1551
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.20012
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Coagulation factor X
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
  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 21:19 / Updated at June 12, 2020 16:52