S-(2-Acetamidoethyl) hexadecanethioate
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Identification
- Generic Name
- S-(2-Acetamidoethyl) hexadecanethioate
- DrugBank Accession Number
- DB02990
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 357.594
Monoisotopic: 357.270150187 - Chemical Formula
- C20H39NO2S
- Synonyms
- C16-fatty-acyl-substrate-mimic
- S-palmitoyl-N-acetylcysteamine
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEnoyl-[acyl-carrier-protein] reductase [NADH] Not Available Mycobacterium 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
- 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 fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty acyl thioesters
- Direct Parent
- Fatty acyl thioesters
- Alternative Parents
- Acetamides / Thioesters / Secondary carboxylic acid amides / Carbothioic S-esters / Sulfenyl compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Acetamide / Aliphatic acyclic compound / Carbonyl group / Carbothioic s-ester / Carboxamide group / Carboxylic acid derivative / Fatty acyl thioester / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- GDVZALUOXPTSHD-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H39NO2S/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(23)24-18-17-21-19(2)22/h3-18H2,1-2H3,(H,21,22)
- IUPAC Name
- N-[2-(hexadecanoylsulfanyl)ethyl]acetamide
- SMILES
- CCCCCCCCCCCCCCCC(=O)SCCNC(C)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 3378216
- PubChem Substance
- 46508640
- ChemSpider
- 2623508
- ZINC
- ZINC000014880555
- PDBe Ligand
- THT
- PDB Entries
- 1bvr
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 0.000217 mg/mL ALOGPS logP 7.27 ALOGPS logP 5.92 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 15.78 Chemaxon pKa (Strongest Basic) -1.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.17 Å2 Chemaxon Rotatable Bond Count 18 Chemaxon Refractivity 105.75 m3·mol-1 Chemaxon Polarizability 46.41 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9972 Blood Brain Barrier + 0.9957 Caco-2 permeable + 0.6172 P-glycoprotein substrate Non-substrate 0.6473 P-glycoprotein inhibitor I Non-inhibitor 0.6522 P-glycoprotein inhibitor II Non-inhibitor 0.9291 Renal organic cation transporter Non-inhibitor 0.8614 CYP450 2C9 substrate Non-substrate 0.8245 CYP450 2D6 substrate Non-substrate 0.7164 CYP450 3A4 substrate Non-substrate 0.6387 CYP450 1A2 substrate Non-inhibitor 0.5177 CYP450 2C9 inhibitor Non-inhibitor 0.7847 CYP450 2D6 inhibitor Non-inhibitor 0.9046 CYP450 2C19 inhibitor Non-inhibitor 0.7544 CYP450 3A4 inhibitor Non-inhibitor 0.9288 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8667 Ames test Non AMES toxic 0.8712 Carcinogenicity Non-carcinogens 0.6326 Biodegradation Ready biodegradable 0.7363 Rat acute toxicity 2.1627 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9595 hERG inhibition (predictor II) Non-inhibitor 0.7908
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000l-8590000000-f532498b9564caeb6877 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-6229000000-2918525454058e942bca Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-ed9ce4ae49ef782d8bd6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0uki-5954000000-76845c7cc0961d8629b6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05bf-9231000000-fb92ed4c1a65067f6838 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-9210000000-ae4660190ffbb5a49673 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4m-9200000000-e646fcdca17be0a4aca9 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]- 185.15364 predictedDeepCCS 1.0 (2019) [M+H]+ 188.12016 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.34879 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Enoyl-ACP reductase of the type II fatty acid syntase (FAS-II) system, which is involved in the biosynthesis of mycolic acids, a major component of mycobacterial cell walls (PubMed:25227413). Catalyzes the NADH-dependent reduction of the double bond of 2-trans-enoyl-[acyl-carrier protein], an essential step in the fatty acid elongation cycle of the FAS-II pathway (PubMed:7599116). Shows preference for long-chain fatty acyl thioester substrates (>C16), and can also use 2-trans-enoyl-CoAs as alternative substrates (PubMed:7599116). The mycobacterial FAS-II system utilizes the products of the FAS-I system as primers to extend fatty acyl chain lengths up to C56, forming the meromycolate chain that serves as the precursor for final mycolic acids (PubMed:25227413).
- Specific Function
- Enoyl-[acyl-carrier-protein] reductase (nadh) activity
- Gene Name
- inhA
- Uniprot ID
- P9WGR1
- Uniprot Name
- Enoyl-[acyl-carrier-protein] reductase [NADH]
- Molecular Weight
- 28527.55 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52