5-[5,6-BIS(METHYLOXY)-1H-BENZIMIDAZOL-1-YL]-3-{[1-(2-CHLOROPHENYL)ETHYL]OXY}-2-THIOPHENECARBOXAMIDE

Identification

Generic Name
5-[5,6-BIS(METHYLOXY)-1H-BENZIMIDAZOL-1-YL]-3-{[1-(2-CHLOROPHENYL)ETHYL]OXY}-2-THIOPHENECARBOXAMIDE
DrugBank Accession Number
DB07471
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 457.93
Monoisotopic: 457.08630454
Chemical Formula
C22H20ClN3O4S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCyclin-A2Not AvailableHumans
UCyclin-dependent kinase 2Not 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 benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Not Available
Direct Parent
Benzimidazoles
Alternative Parents
Thiophene carboxamides / 2,3,5-trisubstituted thiophenes / 2-heteroaryl carboxamides / Anisoles / Alkyl aryl ethers / Chlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Primary carboxylic acid amides
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Substituents
2,3,5-trisubstituted thiophene / 2-heteroaryl carboxamide / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UHCHLTQBLNUYRT-GFCCVEGCSA-N
InChI
InChI=1S/C22H20ClN3O4S/c1-12(13-6-4-5-7-14(13)23)30-19-10-20(31-21(19)22(24)27)26-11-25-15-8-17(28-2)18(29-3)9-16(15)26/h4-12H,1-3H3,(H2,24,27)/t12-/m1/s1
IUPAC Name
3-[(1R)-1-(2-chlorophenyl)ethoxy]-5-(5,6-dimethoxy-1H-1,3-benzodiazol-1-yl)thiophene-2-carboxamide
SMILES
[H][C@](C)(OC1=C(SC(=C1)N1C=NC2=CC(OC)=C(OC)C=C12)C(N)=O)C1=CC=CC=C1Cl

References

General References
Not Available
PubChem Compound
11957417
PubChem Substance
99443942
ChemSpider
10131669
BindingDB
28206
ChEMBL
CHEMBL222419
ZINC
ZINC000016052682
PDBe Ligand
BLZ
PDB Entries
2i40

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 Solubility0.0104 mg/mLALOGPS
logP4.02ALOGPS
logP4.34Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.94Chemaxon
pKa (Strongest Basic)5.56Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area88.6 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity128.32 m3·mol-1Chemaxon
Polarizability46.75 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9781
Blood Brain Barrier+0.8184
Caco-2 permeable+0.5626
P-glycoprotein substrateNon-substrate0.6608
P-glycoprotein inhibitor INon-inhibitor0.7677
P-glycoprotein inhibitor IINon-inhibitor0.5279
Renal organic cation transporterNon-inhibitor0.8909
CYP450 2C9 substrateNon-substrate0.799
CYP450 2D6 substrateNon-substrate0.8257
CYP450 3A4 substrateSubstrate0.6093
CYP450 1A2 substrateNon-inhibitor0.5766
CYP450 2C9 inhibitorInhibitor0.529
CYP450 2D6 inhibitorNon-inhibitor0.9509
CYP450 2C19 inhibitorInhibitor0.6522
CYP450 3A4 inhibitorInhibitor0.5676
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5849
Ames testNon AMES toxic0.6044
CarcinogenicityNon-carcinogens0.7609
BiodegradationNot ready biodegradable0.9974
Rat acute toxicity2.2926 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.997
hERG inhibition (predictor II)Inhibitor0.6081
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/MSsplash10-0a4i-0200900000-c4f9e1cb1a71064ae454
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-f8a327a988020448679e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0019100000-4e5eaacd792b9f17e625
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0093000000-5dc2cedc7bee40e5d2a4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0429100000-e59f5e90f17f662e4020
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-9277300000-a0265b8b8fedae963313
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]-194.09648
predicted
DeepCCS 1.0 (2019)
[M+H]+196.49205
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.4826
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Essential for the control of the cell cycle at the G1/S (start) and the G2/M (mitosis) transitions.
Gene Name
CCNA2
Uniprot ID
P20248
Uniprot Name
Cyclin-A2
Molecular Weight
48550.365 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis. Phosphorylates CTNNB1, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, N...
Gene Name
CDK2
Uniprot ID
P24941
Uniprot Name
Cyclin-dependent kinase 2
Molecular Weight
33929.215 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 21:22 / Updated at June 12, 2020 16:52