4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One
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Identification
- Generic Name
- 4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One
- DrugBank Accession Number
- DB04302
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 210.293
Monoisotopic: 210.071450382 - Chemical Formula
- C11H14O2S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U3-oxoacyl-[acyl-carrier-protein] synthase 1 Not Available Mycobacterium tuberculosis U3-oxoacyl-[acyl-carrier-protein] synthase 1 Not Available Escherichia coli (strain K12) - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 dihydrothiophenes. These are compounds containing a dihydrothiophene moiety, which is a thiophene derivative with only one double bond.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Dihydrothiophenes
- Sub Class
- Not Available
- Direct Parent
- Dihydrothiophenes
- Alternative Parents
- Vinylogous acids / Carbothioic S-lactones / Thioesters / Enols / Carboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 2,5-dihydrothiophene / Aliphatic heteromonocyclic compound / Carbonyl group / Carbothioic s-lactone / Carboxylic acid derivative / Enol / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 82079-32-1
- InChI Key
- SYQNUQSGEWNWKV-XUIVZRPNSA-N
- InChI
- InChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,12H,1H2,2-4H3/b7-6+/t11-/m1/s1
- IUPAC Name
- (5R)-4-hydroxy-3,5-dimethyl-5-[(1E)-2-methylbuta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one
- SMILES
- C\C(C=C)=C/[C@@]1(C)SC(=O)C(C)=C1O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C11165
- PubChem Compound
- 445629
- PubChem Substance
- 46505720
- ChemSpider
- 16744232
- BindingDB
- 50180132
- ChEMBL
- CHEMBL399043
- ZINC
- ZINC000004099011
- PDBe Ligand
- TLM
- PDB Entries
- 1fj4 / 2vb8 / 2wge / 2wgg / 4c6x
Clinical Trials
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
Property Value Source Water Solubility 0.499 mg/mL ALOGPS logP 2.14 ALOGPS logP 2.55 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 6.62 Chemaxon pKa (Strongest Basic) -6.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 62.01 m3·mol-1 Chemaxon Polarizability 22.6 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9929 Blood Brain Barrier + 0.914 Caco-2 permeable + 0.5869 P-glycoprotein substrate Non-substrate 0.6333 P-glycoprotein inhibitor I Non-inhibitor 0.5433 P-glycoprotein inhibitor II Non-inhibitor 0.93 Renal organic cation transporter Non-inhibitor 0.8796 CYP450 2C9 substrate Non-substrate 0.7676 CYP450 2D6 substrate Non-substrate 0.8523 CYP450 3A4 substrate Non-substrate 0.5376 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9268 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8907 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5616 Ames test Non AMES toxic 0.8558 Carcinogenicity Non-carcinogens 0.7471 Biodegradation Not ready biodegradable 0.9132 Rat acute toxicity 2.5895 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9807 hERG inhibition (predictor II) Non-inhibitor 0.9555
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0kbf-5900000000-52244e42311e19cc08ee Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-1900000000-768328ac667a739f94de Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-9f844151d89c7fadeb79 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-9300000000-caaabfc2ef47e6e5e5e1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-3960000000-62c67a7fb8da10a9187b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-9400000000-cdb20ad82bd90a0623d8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f7c-9000000000-a2f3bbf70ad6471b5069 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 154.7163857 predictedDarkChem Lite v0.1.0 [M-H]- 162.02386 predictedDeepCCS 1.0 (2019) [M+H]+ 154.9710857 predictedDarkChem Lite v0.1.0 [M+H]+ 164.38187 predictedDeepCCS 1.0 (2019) [M+Na]+ 154.6031857 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.475 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP.
- Specific Function
- 3-oxoacyl-[acyl-carrier-protein] synthase activity
- Gene Name
- kasA
- Uniprot ID
- P9WQD9
- Uniprot Name
- 3-oxoacyl-[acyl-carrier-protein] synthase 1
- Molecular Weight
- 43315.725 Da
References
- 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
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- 3-oxoacyl-[acyl-carrier-protein] synthase activity
- Specific Function
- Catalyzes the condensation reaction of fatty acid synthesis by the addition to an acyl acceptor of two carbons from malonyl-ACP. Specific for elongation from C-10 to unsaturated C-16 and C-18 fatty...
- Gene Name
- fabB
- Uniprot ID
- P0A953
- Uniprot Name
- 3-oxoacyl-[acyl-carrier-protein] synthase 1
- Molecular Weight
- 42612.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52