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Supporting Information Supporting Information © Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Supporting Information Prediction of Tyrosinase Inhibition Spectra for Chemicals Using Novel Atom-Based Bilinear Indices. Yovani Marrero Ponce, Mahmud Tareq Hassan Khan, Gerardo M. Casañola Martín, Arjumand Ather, Mukhlis N. Sultankhodzhaev, Francisco Torrens and Richard Rotondo. Table of Contents Table 1. Structures of Compounds Selected From the Literature for Developing the QSAR Models……………………………………………………................. 2 Table 2. Results of the Classification of Active Compounds in the Training Set by the Use of LDA-QSAR Models Developed Using non-Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme…........... 17 Table 3. Results of the Classification of Active Compounds in the Training Set by the Use of LDA-QSAR Models Developed Using Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………………. 23 Table 4. Results of the Classification of Inactive Compounds in the Training Set by the Use of LDA-QSAR Models Developed Using non-Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………... 31 Table 5. Results of the Classification of Inactive Compounds in the Training Set by the Use of LDA-QSAR Models Developed Using Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………... 41 Table 6. Results of the Classification of Active Compounds in the Test Set by the Use of LDA-QSAR Models Developed Using non-Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………………. 51 Table 7. Results of the Classification of Active Compounds in the Test Set by the Use of LDA-QSAR Models Developed Using Stochastic Total and Local Quadratic Indices Calculated with Different Weighting Scheme………………. 54 Table 8. Results of the Classification of Inactive Compounds in the Test Set by the Use of LDA-QSAR Models Developed Using non-Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………... 57 Table 9. Results of the Classification of Inactive Compounds in the Test Set by the Use of LDA-QSAR Models Developed Using Stochastic Total and Local Bilinear Indices Calculated with Different Weighting Scheme………………. 61 Table 10. Structures of the Compounds Used in Virtual Screening……………….. 65 Table 11. Results of the Classification of Compounds in the Virtual Screening Set. 69 Table 1. Structures of Compounds Selected From the Literature for Developing the QSAR Models. OH O O O HO O O OH HO HO OH O HO OH OH 1 Kojic acid N OH HO NH2 4 Hydroquinone 2 Arbutin 3 L-mimosine OH HO OH OH OH OH O HO OH HO O 5 Tropolone OH O O OH 6 Ascorbic acid HO OH 7 Oxyresveratrol OH O 8 Quercetin + - HO O NH4 O O N O O O N 9 Benzoic acid 10 Benzaldehyde 11 Cupferron O O HO OH HO OH OH 12 Aloesin O HO OH O O OH 14 Anisaldehyde 15 Cinnamic acid OH 13 Trans- OH resveratrol 16 Gnetol OH HO HO OH OH OH HO HO OH OH 18 3,3´,4-trihydroxy-trans-stilbene 19 3,3´,4,4´-tetrahydroxy-trans-stilbene OH 17 Dihydrognetol HO HO O H2N HO OH H N NH HO 2 2 20 3-amino-L-tyrosine 21 2-aminophenol OH O 22 Isoliquiritigenin 2 Table 1. Cont. OH OH HO H OH O O OH O O 23 4-hydroxychalcone 24 Butein 25 4´-hydroxychalcone HO OH HO N N O OH O OH O 28 trans-4-azobenzene carboxylic acid 26 2´,4´-dihydroxychalcone 27 2´,4-dihydroxychalcone O O N N N O HO HO N OH N HO O N 30 trans-4,4´-azobenzene dicarboxylic acid 29 cis-4-azobenzene carboxylic O HO acid 31 cis-4,4´-azobenzene dicarboxylic acid SH HO OH N HO H C C 2 HO OH HO HC H NH O NH H C HO CH OH HO O NH H C OH 32 Castanospermine C 2 O OH HC O NH O 33 Deosynojirimycin O O 34 Ko-YGC CH OH H C 3 OH O HO 3 CH C C CH H C O NH 2 OH H HO H C C C 2 HC CH O NH H C OH O C 2 O NH H HC C O NH O HC O O NH H C OH C 2 O CH O O NH O 35 Ko-YGV O O 36 Ko-YGE CH CH HO 3 OH H C 3 HO CH 3 CH C OH HC HO H2C O NH H C C HC HC O NH H O NH H C OH C C 2 O HC OH CH O NH H C O O C 2 O NH O HC O O NH O O 37 Ko-YGT O 38 Ko-YGL 3 Table 1. Cont. NH OH HO H2C OH C HO H C CH C 2 O NH H CH C O NH H HC C O NH H C OH C 2 O HC OH HC O NH H C O O C 2 O NH O HC O NH O O O 40 Ko-YGF O 39 Ko-YGW NH O 2 H C N OH HO H C C 2 CH N O OH NH H HO H C C C 2 HC HC O NH H C OH O NH C 2 O H HC C O O HC NH O O NH H C OH C 2 O CH O O O NH O 42 Ko-YGN O 41 Ko-YGH OH HO H OH C O HC C O OH NH H HO H C C C 2 HC HC O NH H C OH O NH C 2 O H CH C O O HC NH O O NH H C OH C 2 O CH O O O NH O 44 Ko-YGG O 43 Ko-YGD OH OH HO H CH3 C H C HC H C 2 OH O NH 3 CH HO H C C CH HC O NH H C OH O NH H C C 2 O C 2 HC HC O NH O O NH H C OH O C 2 O HC O O O NH O 45 Ko-YIG O 46 Ko-YYG 4 Table 1. Cont. HO H OH CH3 C OH HC HO H S O NH OH C H2C H2C HC C O NH H C HC C 2 O NH OH H2C O CH C O NH H C OH HC C 2 O O NH O HC O O O NH O O 47 Ko-YSG O 48 Ko-YMG NH2 NH2 O OH HN HO H C C C CH H2C NH O NH H C H C OH C 2 HO H 2 HC C H C O OH CH 2 NH H C O NH C 2 O H2C HC C O NH O CH O O NH H C OH C 2 O CH O O NH O O 49 Ko-YQG O 50 Ko-YRG H NH OH N HO H O 2 OH C C HO H CH C O NH H C HC N C 2 O NH H C HC C 2 O NH H C OH CH C 2 O O NH H C OH HC C 2 O O NH O HC O O NH O O O 52 Ko-YNG O 51 Ko-YHG OH OH HO H OH C O HC C O NH H C C 2 HC O NH OH HO CH H2C O H2C 3 C C H C HC HC H C 2 O NH O O NH 3 CH O C HC O O NH H C OH C 2 O 53 Ko-YDG HC O O NH O O 54 Ko-FIY 5 Table 1. Cont. OH OH NH HN 2 C OH NH HO H C H2C HO H C C 2 C 2 HC H2C HC O NH H C O NH H C C 2 C 2 HC HC O NH H C OH O NH H C OH C 2 O C 2 O HC HC O O O O NH O NH O O O 55 Ko-FRY 56 Ko-FYY OH OH OH OH NH O O O O H2C H C H C O H2C H C H C O 2 2 H H 2 2 H HO C CHNH C CHNH C C N HO C C N C CHNH C C N H H H O O O O O O O O 57 Ko-FWY 58 Ko-FFY OH NH2 NH2 OH H2C OH HN C NH2 NH OH H C NH H C 2 O O 2 H C H C H2C 2 2 O O H C H C H C H C H C 2 H 2 H 2 O 2 2 HO C C N C C N C C NH H2C H2C H2C O H H H H H O O O O HO C C NH C C N C C N H H H O O O O 59 Ko-KWY 60 Ko-KRY OH NH2 NH2 OH H C H C OH NH2 2 2 OH H C H C H2C 2 2 O O CH H C H2C H2C 3 2 O O H C H C H C H2C H2C 2 2 H 2 O H2C H3C CH H C O HO C CHNH C C N C C NH H 2 H H H O O O O HO C C NH C C N C C N H H H 61 Ko-KKY O O O O 62 Ko-KIY 6 Table 1.
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