(S)-2-CHLORO-N-(1-(2-(2-HYDROXYETHYLAMINO)-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL)-6H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE

Identification

Generic Name
(S)-2-CHLORO-N-(1-(2-(2-HYDROXYETHYLAMINO)-2-OXOETHYL)-2-OXO-1,2,3,4-TETRAHYDROQUINOLIN-3-YL)-6H-THIENO[2,3-B]PYRROLE-5-CARBOXAMIDE
DrugBank Accession Number
DB07792
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 446.907
Monoisotopic: 446.081553513
Chemical Formula
C20H19ClN4O4S
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlycogen phosphorylase, muscle formNot 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
Adverseeffects
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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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
N-acyl-alpha amino acids and derivatives / Hydroquinolones / Hydroquinolines / Thienopyrroles / 2,3,5-trisubstituted thiophenes / Pyrrole carboxamides / 2-heteroaryl carboxamides / N-acylethanolamines / Substituted pyrroles / Aryl chlorides
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Substituents
2,3,5-trisubstituted thiophene / 2-heteroaryl carboxamide / Alcohol / Alkanolamine / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VUKPNWLGSLOHIF-AWEZNQCLSA-N
InChI
InChI=1S/C20H19ClN4O4S/c21-16-9-12-8-13(24-19(12)30-16)18(28)23-14-7-11-3-1-2-4-15(11)25(20(14)29)10-17(27)22-5-6-26/h1-4,8-9,14,24,26H,5-7,10H2,(H,22,27)(H,23,28)/t14-/m0/s1
IUPAC Name
2-chloro-N-[(3S)-1-{[(2-hydroxyethyl)carbamoyl]methyl}-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide
SMILES
[H][C@@]1(CC2=C(C=CC=C2)N(CC(=O)NCCO)C1=O)NC(=O)C1=CC2=C(N1)SC(Cl)=C2

References

General References
Not Available
PubChem Compound
11987874
PubChem Substance
99444263
ChemSpider
10160347
ZINC
ZINC000028818268
PDBe Ligand
FRX
PDB Entries
2iei

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 Solubility0.00712 mg/mLALOGPS
logP1.81ALOGPS
logP1.2ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area114.53 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.62 m3·mol-1ChemAxon
Polarizability45.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8133
Blood Brain Barrier-0.6114
Caco-2 permeable-0.6843
P-glycoprotein substrateSubstrate0.731
P-glycoprotein inhibitor INon-inhibitor0.7516
P-glycoprotein inhibitor IINon-inhibitor0.8817
Renal organic cation transporterNon-inhibitor0.7663
CYP450 2C9 substrateNon-substrate0.7843
CYP450 2D6 substrateNon-substrate0.8595
CYP450 3A4 substrateNon-substrate0.5106
CYP450 1A2 substrateNon-inhibitor0.6302
CYP450 2C9 inhibitorInhibitor0.5795
CYP450 2D6 inhibitorNon-inhibitor0.7453
CYP450 2C19 inhibitorInhibitor0.5251
CYP450 3A4 inhibitorNon-inhibitor0.5658
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6565
Ames testNon AMES toxic0.743
CarcinogenicityNon-carcinogens0.8465
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2973 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9352
hERG inhibition (predictor II)Inhibitor0.6662
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

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Phosphorylase is an important allosteric enzyme in carbohydrate metabolism. Enzymes from different sources differ in their regulatory mechanisms and in their natural substrates. However, all known ...
Gene Name
PYGM
Uniprot ID
P11217
Uniprot Name
Glycogen phosphorylase, muscle form
Molecular Weight
97091.265 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