4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One

Identification

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Name
4-Hydroxy-3,5-Dimethyl-5-(2-Methyl-Buta-1,3-Dienyl)-5h-Thiophen-2-One
Accession Number
DB04302  (EXPT03065)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
82079-32-1
Weight
Average: 210.293
Monoisotopic: 210.071450382
Chemical Formula
C11H14O2S
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 1Not AvailableEscherichia coli (strain K12)
U3-oxoacyl-[acyl-carrier-protein] synthase 1Not 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
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
KEGG Compound
C11165
PubChem Compound
445629
PubChem Substance
46505720
ChemSpider
16744232
BindingDB
50180132
ChEMBL
CHEMBL399043
HET
TLM
PDB Entries
1fj4 / 2vb8 / 2wge / 2wgg / 4c6x

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 Solubility0.499 mg/mLALOGPS
logP2.14ALOGPS
logP2.55ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.82ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.01 m3·mol-1ChemAxon
Polarizability22.6 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9929
Blood Brain Barrier+0.914
Caco-2 permeable+0.5869
P-glycoprotein substrateNon-substrate0.6333
P-glycoprotein inhibitor INon-inhibitor0.5433
P-glycoprotein inhibitor IINon-inhibitor0.93
Renal organic cation transporterNon-inhibitor0.8796
CYP450 2C9 substrateNon-substrate0.7676
CYP450 2D6 substrateNon-substrate0.8523
CYP450 3A4 substrateNon-substrate0.5376
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9268
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8907
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5616
Ames testNon AMES toxic0.8558
CarcinogenicityNon-carcinogens0.7471
BiodegradationNot ready biodegradable0.9132
Rat acute toxicity2.5895 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9807
hERG inhibition (predictor II)Non-inhibitor0.9555
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-MSNot Available
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 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
Vinylogous acid / Carbothioic s-lactone / 2,5-dihydrothiophene / Thiocarboxylic acid ester / Thiocarboxylic acid or derivatives / Enol / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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
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
  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 June 13, 2005 07:24 / Updated on June 04, 2019 06:04