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2-(methylsulfanyl)-5-(thiophen-2-ylmethyl)-1H-imidazol-4-ol

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Identification

Generic Name
2-(methylsulfanyl)-5-(thiophen-2-ylmethyl)-1H-imidazol-4-ol
DrugBank Accession Number
DB08779
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 226.318
Monoisotopic: 226.023454332
Chemical Formula
C9H10N2OS2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase Chk1Not 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 2,4,5-trisubstituted imidazoles. These are imidazoles in which the imidazole ring is substituted at positions 2, 4, and 5.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Imidazoles
Direct Parent
2,4,5-trisubstituted imidazoles
Alternative Parents
Alkylarylthioethers / Thiophenes / Heteroaromatic compounds / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
2,4,5-trisubstituted-imidazole / Alkylarylthioether / Aromatic heteromonocyclic compound / Aryl thioether / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QWYGHJVEZLVLSU-UHFFFAOYSA-N
InChI
InChI=1S/C9H10N2OS2/c1-13-9-10-7(8(12)11-9)5-6-3-2-4-14-6/h2-4,12H,5H2,1H3,(H,10,11)
IUPAC Name
2-(methylsulfanyl)-5-[(thiophen-2-yl)methyl]-1H-imidazol-4-ol
SMILES
CSC1=NC(O)=C(CC2=CC=CS2)N1

References

General References
Not Available
PubChem Compound
46937179
PubChem Substance
99445250
ChemSpider
25058675
ZINC
ZINC000100037029
PDBe Ligand
ZYT
PDB Entries
2wmt

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 Solubility0.384 mg/mLALOGPS
logP2.51ALOGPS
logP3.23Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.33Chemaxon
pKa (Strongest Basic)2.06Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area48.91 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity60.31 m3·mol-1Chemaxon
Polarizability23.09 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier+0.5598
Caco-2 permeable-0.5717
P-glycoprotein substrateNon-substrate0.5157
P-glycoprotein inhibitor INon-inhibitor0.9589
P-glycoprotein inhibitor IINon-inhibitor0.9934
Renal organic cation transporterNon-inhibitor0.9085
CYP450 2C9 substrateNon-substrate0.7123
CYP450 2D6 substrateNon-substrate0.7906
CYP450 3A4 substrateNon-substrate0.6804
CYP450 1A2 substrateNon-inhibitor0.5644
CYP450 2C9 inhibitorNon-inhibitor0.6556
CYP450 2D6 inhibitorNon-inhibitor0.8663
CYP450 2C19 inhibitorNon-inhibitor0.5768
CYP450 3A4 inhibitorNon-inhibitor0.7475
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5373
Ames testNon AMES toxic0.7114
CarcinogenicityNon-carcinogens0.9364
BiodegradationNot ready biodegradable0.8953
Rat acute toxicity2.2313 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9768
hERG inhibition (predictor II)Non-inhibitor0.8587
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-MSsplash10-002b-6940000000-065599f86f3e983e2e76
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0090000000-2f5596a34d07a6bfe36f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-4950000000-e65ab31e5787c157d109
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1970000000-b8a83b500ecc68bb1694
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-9510000000-a1b789cb73d561dd87f4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-1000-9300000000-27491060f16df747b79a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bta-9600000000-e6af2b7d6f926bd690b9
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]-143.08621
predicted
DeepCCS 1.0 (2019)
[M+H]+145.50488
predicted
DeepCCS 1.0 (2019)
[M+Na]+154.07285
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine/threonine-protein kinase Chk1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856, PubMed:32357935). May also negatively regulate cell cycle progression during unperturbed cell cycles (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). This regulation is achieved by a number of mechanisms that together help to preserve the integrity of the genome (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). Recognizes the substrate consensus sequence [R-X-X-S/T] (PubMed:11535615, PubMed:12399544, PubMed:12446774, PubMed:14559997, PubMed:14988723, PubMed:15311285, PubMed:15650047, PubMed:15665856). Binds to and phosphorylates CDC25A, CDC25B and CDC25C (PubMed:12676583, PubMed:12676925, PubMed:12759351, PubMed:14559997, PubMed:14681206, PubMed:19734889, PubMed:9278511). Phosphorylation of CDC25A at 'Ser-178' and 'Thr-507' and phosphorylation of CDC25C at 'Ser-216' creates binding sites for 14-3-3 proteins which inhibit CDC25A and CDC25C (PubMed:9278511). Phosphorylation of CDC25A at 'Ser-76', 'Ser-124', 'Ser-178', 'Ser-279' and 'Ser-293' promotes proteolysis of CDC25A (PubMed:12676583, PubMed:12676925, PubMed:12759351, PubMed:14681206, PubMed:19734889, PubMed:9278511). Phosphorylation of CDC25A at 'Ser-76' primes the protein for subsequent phosphorylation at 'Ser-79', 'Ser-82' and 'Ser-88' by NEK11, which is required for polyubiquitination and degradation of CDCD25A (PubMed:19734889, PubMed:20090422, PubMed:9278511). Inhibition of CDC25 leads to increased inhibitory tyrosine phosphorylation of CDK-cyclin complexes and blocks cell cycle progression (PubMed:9278511). Also phosphorylates NEK6 (PubMed:18728393). Binds to and phosphorylates RAD51 at 'Thr-309', which promotes the release of RAD51 from BRCA2 and enhances the association of RAD51 with chromatin, thereby promoting DNA repair by homologous recombination (PubMed:15665856). Phosphorylates multiple sites within the C-terminus of TP53, which promotes activation of TP53 by acetylation and promotes cell cycle arrest and suppression of cellular proliferation (PubMed:10673501, PubMed:15659650, PubMed:16511572). Also promotes repair of DNA cross-links through phosphorylation of FANCE (PubMed:17296736). Binds to and phosphorylates TLK1 at 'Ser-743', which prevents the TLK1-dependent phosphorylation of the chromatin assembly factor ASF1A (PubMed:12660173, PubMed:12955071). This may enhance chromatin assembly both in the presence or absence of DNA damage (PubMed:12660173, PubMed:12955071). May also play a role in replication fork maintenance through regulation of PCNA (PubMed:18451105). May regulate the transcription of genes that regulate cell-cycle progression through the phosphorylation of histones (By similarity). Phosphorylates histone H3.1 (to form H3T11ph), which leads to epigenetic inhibition of a subset of genes (By similarity). May also phosphorylate RB1 to promote its interaction with the E2F family of transcription factors and subsequent cell cycle arrest (PubMed:17380128). Phosphorylates SPRTN, promoting SPRTN recruitment to chromatin (PubMed:31316063). Reduces replication stress and activates the G2/M checkpoint, by phosphorylating and inactivating PABIR1/FAM122A and promoting the serine/threonine-protein phosphatase 2A-mediated dephosphorylation and stabilization of WEE1 levels and activity (PubMed:33108758)
Specific Function
ATP binding
Gene Name
CHEK1
Uniprot ID
O14757
Uniprot Name
Serine/threonine-protein kinase Chk1
Molecular Weight
54433.115 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 21:34 / Updated at June 12, 2020 16:52