2-[(CYCLOPROPYLCARBONYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXAMIDE

Identification

Generic Name
2-[(CYCLOPROPYLCARBONYL)AMINO]-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXAMIDE
DrugBank Accession Number
DB07398
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 264.343
Monoisotopic: 264.093248456
Chemical Formula
C13H16N2O2S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase PknGNot AvailableMycobacterium tuberculosis
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 thiophene carboxamides. These are compounds containing a thiophene ring which bears a carboxamide.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thiophenes
Sub Class
Thiophene carboxylic acids and derivatives
Direct Parent
Thiophene carboxamides
Alternative Parents
N-arylamides / Cyclopropanecarboxylic acids and derivatives / Vinylogous amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Primary carboxylic acid amides / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aromatic heteropolycyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Cyclopropanecarboxylic acid or derivatives / Heteroaromatic compound / Hydrocarbon derivative / N-arylamide / Organic nitrogen compound / Organic oxide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VATFNEMGBRWLHI-UHFFFAOYSA-N
InChI
InChI=1S/C13H16N2O2S/c14-11(16)10-8-3-1-2-4-9(8)18-13(10)15-12(17)7-5-6-7/h7H,1-6H2,(H2,14,16)(H,15,17)
IUPAC Name
2-cyclopropaneamido-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
SMILES
NC(=O)C1=C(NC(=O)C2CC2)SC2=C1CCCC2

References

General References
Not Available
PubChem Compound
673481
PubChem Substance
99443869
ChemSpider
586370
BindingDB
50185119
ChEMBL
CHEMBL379367
ZINC
ZINC000000035547
PDBe Ligand
AXX
PDB Entries
2pzi

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 Solubility0.0547 mg/mLALOGPS
logP1.79ALOGPS
logP3.02Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)10.8Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area72.19 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity71.08 m3·mol-1Chemaxon
Polarizability28.2 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7928
Blood Brain Barrier+0.9373
Caco-2 permeable-0.6077
P-glycoprotein substrateNon-substrate0.7415
P-glycoprotein inhibitor INon-inhibitor0.8032
P-glycoprotein inhibitor IINon-inhibitor0.7152
Renal organic cation transporterNon-inhibitor0.8923
CYP450 2C9 substrateNon-substrate0.7588
CYP450 2D6 substrateNon-substrate0.8517
CYP450 3A4 substrateNon-substrate0.6829
CYP450 1A2 substrateInhibitor0.8918
CYP450 2C9 inhibitorNon-inhibitor0.8376
CYP450 2D6 inhibitorNon-inhibitor0.9075
CYP450 2C19 inhibitorNon-inhibitor0.7096
CYP450 3A4 inhibitorNon-inhibitor0.6405
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6524
Ames testAMES toxic0.5243
CarcinogenicityNon-carcinogens0.9024
BiodegradationNot ready biodegradable0.7836
Rat acute toxicity2.3619 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9931
hERG inhibition (predictor II)Non-inhibitor0.6749
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00kg-9860000000-9c6dd800880c1b2d105c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0190000000-cd3f32195d4cce411810
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ow-0940000000-aaf9d30ca94470531493
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-0910000000-a530e507a372bbb57be2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-2290000000-4a5289b011610aa4d4bf
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-6920000000-0c4c1262de8e504bd9ed
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-07yr-1940000000-0ec4648a2cb445c8f2ca
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]-155.81332
predicted
DeepCCS 1.0 (2019)
[M+H]+158.2089
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.2213
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Phosphorylates GarA. May play a role in metabolic regulation via control of the phosphorylation status of GarA. Plays a crucial role in the survival of mycobacteria within host macrophages, by blocking the intracellular degradation of mycobacteria in lysosomes. Required for intrinsic antibiotic resistance.
Specific Function
Atp binding
Gene Name
pknG
Uniprot ID
P9WI73
Uniprot Name
Serine/threonine-protein kinase PknG
Molecular Weight
81576.575 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 21:21 / Updated at June 12, 2020 16:52