QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.

QSPR modeling of octanol/water partition coefficient for vitamins by optimal descriptors calculated with SMILES.

European journal of medicinal chemistry (2007-07-17)

A A Toropov, A P Toropova, I Raska

ABSTRACT

Simplified molecular input line entry system (SMILES) has been utilized in constructing quantitative structure-property relationships (QSPR) for octanol/water partition coefficient of vitamins and organic compounds of different classes by optimal descriptors. Statistical characteristics of the best model (vitamins) are the following: n=17, R(2)=0.9841, s=0.634, F=931 (training set); n=7, R(2)=0.9928, s=0.773, F=690 (test set). Using this approach for modeling octanol/water partition coefficient for a set of organic compounds gives a model that is statistically characterized by n=69, R(2)=0.9872, s=0.156, F=5184 (training set) and n=70, R(2)=0.9841, s=0.179, F=4195 (test set).

MATERIALS

Product Number

Brand

Product Description

371696

Sigma-Aldrich

Tetrachloroethylene, anhydrous, ≥99%

P2000

Sigma-Aldrich

Pentachloroethane, 95%

296988

Sigma-Aldrich

Octane, anhydrous, ≥99%

184500

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Naphthalene, suitable for scintillation, ≥99%

M29606

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9-Methylanthracene, 98%

W510505

Sigma-Aldrich

Undecane, ≥99%

34873

Sigma-Aldrich

Heptane, suitable for HPLC, ≥99%

33117

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Cyclohexane, puriss. p.a., ACS reagent, ≥99.5% (GC)

51730

Supelco

Heptane, analytical standard

571245

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Pyrene, sublimed grade, 99%

D170801

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2,3-Dimethylnaphthalene, 97%

612065

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d (99.8 atom % D), TMS 0.01 %, NMR tube size 10 mm × 8 in.

717967

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d (99.8 atom % D), TMS 0.1 %

48490

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Benzo[b]fluoranthene, analytical standard

710725

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740306

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47863

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338303

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40053

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Naphthalene solution, certified reference material, 5000 μg/mL in methanol

708054

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d ("100%", 99.96 atom % D)

R7632

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Retinol, synthetic, ≥95% (HPLC), (Powder or Powder with Lumps)

714917

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d (99.8 atom % D), TMS 0.01 %, NMR tube size 5 mm × 8 in. , ultra-thin wall

710717

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Trichlorofluoromethane solution, suitable for NMR (reference standard), 10% in acetone-d₆ (99.9 atom % D), TMS 6 %, 1,2-dichloro-1,1-difluoroethane 1 %

487104

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d (99.8 atom % D), TMS 0.01 %, NMR tube size 5 mm × 8 in.

487120

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Ethylbenzene solution, suitable for NMR (reference standard), 0.1% in chloroform-d (99.8 atom % D), TMS 0.01 %, NMR tube size 8 mm × 8 in.

270512

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Heptane, HPLC grade, ≥99%

59060

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2-Methylbutane, analytical standard

443786

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51411

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