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

Identification

Name
5-[5,6-BIS(METHYLOXY)-1H-BENZIMIDAZOL-1-YL]-3-{[1-(2-CHLOROPHENYL)ETHYL]OXY}-2-THIOPHENECARBOXAMIDE
Accession Number
DB07471
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 457.93
Monoisotopic: 457.08630454
Chemical Formula
C22H20ClN3O4S
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][[email protected]](C)(OC1=C(SC(=C1)N1C=NC2=CC(OC)=C(OC)C=C12)C(N)=O)C1=CC=CC=C1Cl

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclin-A2Not AvailableHuman
UCyclin-dependent kinase 2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
11957417
PubChem Substance
99443942
ChemSpider
10131669
BindingDB
28206
ChEMBL
CHEMBL222419
HET
BLZ
PDB Entries
2i40

Clinical Trials

Clinical Trials
Not Available

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
logP3.1ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.13ChemAxon
pKa (Strongest Basic)6ChemAxon
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/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

Taxonomy

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
show 6 more
Substituents
Benzimidazole / 2-heteroaryl carboxamide / Anisole / Thiophene carboxamide / Thiophene carboxylic acid or derivatives / 2,3,5-trisubstituted thiophene / Alkyl aryl ether / Halobenzene / Chlorobenzene / N-substituted imidazole
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:22 / Updated on December 01, 2017 15:51