(5R)-5-[(1E)-BUTA-1,3-DIENYL]-4-HYDROXY-3,5-DIMETHYLTHIOPHEN-2(5H)-ONE

Identification

Generic Name
(5R)-5-[(1E)-BUTA-1,3-DIENYL]-4-HYDROXY-3,5-DIMETHYLTHIOPHEN-2(5H)-ONE
DrugBank Accession Number
DB08628
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 196.266
Monoisotopic: 196.055800318
Chemical Formula
C10H12O2S
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-oxoacyl-[acyl-carrier-protein] synthase 1Not AvailableEscherichia 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
Adverseeffects
Improve decision support & research outcomes
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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 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
Not Available
InChI Key
TXGVAQMIEXZDPM-BRAIEQGRSA-N
InChI
InChI=1S/C10H12O2S/c1-4-5-6-10(3)8(11)7(2)9(12)13-10/h4-6,11H,1H2,2-3H3/b6-5+/t10-/m1/s1
IUPAC Name
(5R)-5-[(1E)-buta-1,3-dien-1-yl]-4-hydroxy-3,5-dimethyl-2,5-dihydrothiophen-2-one
SMILES
CC1=C(O)[C@](C)(SC1=O)\C=C\C=C

References

General References
Not Available
PubChem Compound
5494447
PubChem Substance
99445099
ChemSpider
20130563
PDBe Ligand
TL6
PDB Entries
2aqb

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 Solubility0.582 mg/mLALOGPS
logP1.93ALOGPS
logP2.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)6.76ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity57.73 m3·mol-1ChemAxon
Polarizability20.57 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.9201
Caco-2 permeable+0.5912
P-glycoprotein substrateNon-substrate0.6268
P-glycoprotein inhibitor INon-inhibitor0.6222
P-glycoprotein inhibitor IINon-inhibitor0.9657
Renal organic cation transporterNon-inhibitor0.8674
CYP450 2C9 substrateNon-substrate0.7789
CYP450 2D6 substrateNon-substrate0.8694
CYP450 3A4 substrateNon-substrate0.5712
CYP450 1A2 substrateNon-inhibitor0.8928
CYP450 2C9 inhibitorNon-inhibitor0.901
CYP450 2D6 inhibitorNon-inhibitor0.916
CYP450 2C19 inhibitorNon-inhibitor0.8648
CYP450 3A4 inhibitorNon-inhibitor0.8993
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5729
Ames testNon AMES toxic0.8564
CarcinogenicityNon-carcinogens0.7684
BiodegradationNot ready biodegradable0.8566
Rat acute toxicity2.5197 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9822
hERG inhibition (predictor II)Non-inhibitor0.9567
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

Targets

Drugtargets2
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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. 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 21:33 / Updated at June 12, 2020 16:52