NAV

(5R)-4-HYDROXY-3,5-DIMETHYL-5-[(1E,3E)-2-METHYLPENTA-1,3-DIENYL]THIOPHEN-2(5H)-ONE

Identification

Generic Name
(5R)-4-HYDROXY-3,5-DIMETHYL-5-[(1E,3E)-2-METHYLPENTA-1,3-DIENYL]THIOPHEN-2(5H)-ONE
DrugBank Accession Number
DB08627
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 224.319
Monoisotopic: 224.087100446
Chemical Formula
C12H16O2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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
FVTQYHVYLPKMOX-SJFBBLFCSA-N
InChI
InChI=1S/C12H16O2S/c1-5-6-8(2)7-12(4)10(13)9(3)11(14)15-12/h5-7,13H,1-4H3/b6-5+,8-7+/t12-/m1/s1
IUPAC Name
(5R)-4-hydroxy-3,5-dimethyl-5-[(1E,3E)-2-methylpenta-1,3-dien-1-yl]-2,5-dihydrothiophen-2-one
SMILES
C\C=C\C(\C)=C\[C@@]1(C)SC(=O)C(C)=C1O

References

General References
Not Available
PubChem Compound
5494446
PubChem Substance
99445098
ChemSpider
20130562
ZINC
ZINC000053160904
PDBe Ligand
TL5
PDB Entries
2aq7

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 Solubility0.151 mg/mLALOGPS
logP2.68ALOGPS
logP2.93Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.67Chemaxon
pKa (Strongest Basic)-6.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity67.69 m3·mol-1Chemaxon
Polarizability24.79 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9164
Caco-2 permeable+0.5946
P-glycoprotein substrateNon-substrate0.6399
P-glycoprotein inhibitor INon-inhibitor0.6338
P-glycoprotein inhibitor IINon-inhibitor0.9257
Renal organic cation transporterNon-inhibitor0.8866
CYP450 2C9 substrateNon-substrate0.7327
CYP450 2D6 substrateNon-substrate0.8555
CYP450 3A4 substrateNon-substrate0.5397
CYP450 1A2 substrateNon-inhibitor0.8902
CYP450 2C9 inhibitorNon-inhibitor0.8898
CYP450 2D6 inhibitorNon-inhibitor0.9252
CYP450 2C19 inhibitorNon-inhibitor0.8856
CYP450 3A4 inhibitorNon-inhibitor0.9389
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5136
Ames testNon AMES toxic0.8521
CarcinogenicityNon-carcinogens0.7556
BiodegradationNot ready biodegradable0.8746
Rat acute toxicity2.5353 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9807
hERG inhibition (predictor II)Non-inhibitor0.9525
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-MSsplash10-0a4i-3920000000-0b6de453b57b6cd9afd6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-129ae87852d067ba9dcc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0290000000-7561f6189f1f4e4e1449
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052o-8900000000-f5366df4f33aad3f4111
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-3960000000-3829217266fd169e0904
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9200000000-22161503e8f88618ae73
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-7900000000-bc761543449756bb3a36
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]-166.2101
predicted
DeepCCS 1.0 (2019)
[M+H]+168.5681
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.98463
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-oxoacyl-[acyl-carrier-protein] synthase 1
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