Dataset Information

Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples.

ABSTRACT: We investigated how many cases of the same chemical sold as different products (at possibly different prices) occurred in a prototypical large aggregated database and simultaneously tested the tautomerism definitions in the chemoinformatics toolkit CACTVS. We applied the standard CACTVS tautomeric transforms plus a set of recently developed ring-chain transforms to the Aldrich Market Select (AMS) database of 6 million screening samples and building blocks. In 30 000 cases, two or more AMS products were found to be just different tautomeric forms of the same compound. We purchased and analyzed 166 such tautomer pairs and triplets by ¹H and ¹³C NMR to determine whether the CACTVS transforms accurately predicted what is the same "stuff in the bottle". Essentially all prototropic transforms with examples in the AMS were confirmed. Some of the ring-chain transforms were found to be too "aggressive", i.e. to equate structures with one another that were different compounds.

SUBMITTER: Guasch L

PROVIDER: S-EPMC5129033 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples.

Guasch Laura L Yapamudiyansel Waruna W Peach Megan L ML Kelley James A JA Barchi Joseph J JJ Nicklaus Marc C MC

Journal of chemical information and modeling 20161016 11

We investigated how many cases of the same chemical sold as different products (at possibly different prices) occurred in a prototypical large aggregated database and simultaneously tested the tautomerism definitions in the chemoinformatics toolkit CACTVS. We applied the standard CACTVS tautomeric transforms plus a set of recently developed ring-chain transforms to the Aldrich Market Select (AMS) database of 6 million screening samples and building blocks. In 30 000 cases, two or more AMS produc ...[more]

PMID: 27669079

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Project description:Essential oils (EOs) have gained economic importance due to their biological activities, and increasing amounts are demanded everywhere. However, substantial differences between the same essential oil samples from different suppliers are reported-concerning their chemical composition and bioactivities-due to numerous companies involved in EOs production and the continuous development of online sales. The present study investigates the antibacterial and antibiofilm activities of two to four samples of five commercially available essential oils (Oregano, Eucalyptus, Rosemary, Clove, and Peppermint oils) produced by autochthonous companies. The manufacturers provided all EOs' chemical compositions determined through GC-MS. The EOs' bioactivities were investigated in vitro against Gram-positive (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa). The antibacterial and antibiofilm effects (ABE% and, respectively, ABfE%) were evaluated spectrophotometrically at 562 and 570 nm using microplate cultivation techniques. The essential oils' calculated parameters were compared with those of three standard broad-spectrum antibiotics: Amoxicillin/Clavulanic acid, Gentamycin, and Streptomycin. The results showed that at the first dilution (D1 = 25 mg/mL), all EOs exhibited antibacterial and antibiofilm activity against all Gram-positive and Gram-negative bacteria tested, and MIC value > 25 mg/mL. Generally, both effects progressively decreased from D1 to D3. Only EOs with a considerable content of highly active metabolites revealed insignificant differences. E. coli showed the lowest susceptibility to all commercially available essential oils-15 EO samples had undetected antibacterial and antibiofilm effects at D2 and D3. Peppermint and Clove oils recorded the most significant differences regarding chemical composition and antibacterial/antibiofilm activities. All registered differences could be due to different places for harvesting the raw plant material, various technological processes through which these essential oils were obtained, the preservation conditions, and complex interactions between constituents.

Dataset Information

Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples.

Publications

Experimental and Chemoinformatics Study of Tautomerism in a Database of Commercially Available Screening Samples.

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