A Similarity Search Using Molecular Topological Graphs

<table>The three top-ranked compounds by the MGD method for the template:   diphenhydramine. (a) The result with <svg height="12.4375" id="M150" style="vertical-align:-0.1638pt" version="1.1" viewbox="0 0 57.287498 12.4375" width="57.287498" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,12.162)"><path d="M529 97q-70 -109 -136 -109q-41 0 -56 94q-23 144 -37 284q-38 -88 -99 -202.5t-93 -156.5q-26 -8 -76 -19l-9 21q71 78 145.5 193t124.5 232q-5 84 -15 128q-12 55 -29.5 75.5t-42.5 20.5q-21 0 -45 -13l-8 24q16 17 46 30t55 13q43 0 70 -46.5t40 -169.5
q27 -249 51 -392q7 -46 23 -46q24 0 70 60z" id="x1D706"></path></g><g transform="matrix(.017,-0,0,-.017,14.154,12.162)"><path d="M535 323h-483v50h483v-50zM535 138h-483v50h483v-50z" id="x3D"></path></g><g transform="matrix(.017,-0,0,-.017,28.858,12.162)"><path d="M241 635q53 0 94 -28.5t63.5 -76t33.5 -102.5t11 -116q0 -58 -11 -112.5t-34 -103.5t-63.5 -78.5t-94.5 -29.5t-95 28t-64.5 75t-34.5 102.5t-11 118.5q0 58 11.5 112.5t34.5 103t64.5 78t95.5 29.5zM238 602q-32 0 -55.5 -25t-35.5 -68t-17.5 -91t-5.5 -105
q0 -76 10 -138.5t37 -107.5t69 -45q32 0 55.5 25t35.5 68.5t17.5 91.5t5.5 105t-5.5 105.5t-18 92t-36 68t-56.5 24.5z" id="x30"></path></g><g transform="matrix(.017,-0,0,-.017,37.018,12.162)"><path d="M113 -12q-24 0 -39.5 16t-15.5 42q0 24 16 40.5t40 16.5t40 -16.5t16 -40.5q0 -26 -16 -42t-41 -16z" id="x2E"></path></g><g transform="matrix(.017,-0,0,-.017,40.893,12.162)"><path d="M412 140l28 -9q0 -2 -35 -131h-373v23q112 112 161 170q59 70 92 127t33 115q0 63 -31 98t-86 35q-75 0 -137 -93l-22 20l57 81q55 59 135 59q69 0 118.5 -46.5t49.5 -122.5q0 -62 -29.5 -114t-102.5 -130l-141 -149h186q42 0 58.5 10.5t38.5 56.5z" id="x32"></path></g><g transform="matrix(.017,-0,0,-.017,49.053,12.162)"><path d="M153 550l-26 -186q79 31 111 31q90 0 141.5 -51t51.5 -119q0 -93 -89 -166q-85 -69 -173 -71q-32 0 -61.5 11.5t-41.5 23.5q-18 17 -17 34q2 16 22 33q14 9 26 -1q61 -50 124 -50q60 0 93 43.5t33 104.5q0 69 -41.5 110t-121.5 41q-53 0 -102 -20l38 305h286l6 -8
l-26 -65h-233z" id="x35"></path></g>
</svg>. (b) The result with <svg height="12.4375" id="M151" style="vertical-align:-0.1638pt" version="1.1" viewbox="0 0 37.087502 12.4375" width="37.087502" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,12.162)"><path d="M529 97q-70 -109 -136 -109q-41 0 -56 94q-23 144 -37 284q-38 -88 -99 -202.5t-93 -156.5q-26 -8 -76 -19l-9 21q71 78 145.5 193t124.5 232q-5 84 -15 128q-12 55 -29.5 75.5t-42.5 20.5q-21 0 -45 -13l-8 24q16 17 46 30t55 13q43 0 70 -46.5t40 -169.5
q27 -249 51 -392q7 -46 23 -46q24 0 70 60z" id="x1D706"></path></g><g transform="matrix(.017,-0,0,-.017,14.154,12.162)"><path d="M535 323h-483v50h483v-50zM535 138h-483v50h483v-50z" id="x3D"></path></g><g transform="matrix(.017,-0,0,-.017,28.858,12.162)"><path d="M241 635q53 0 94 -28.5t63.5 -76t33.5 -102.5t11 -116q0 -58 -11 -112.5t-34 -103.5t-63.5 -78.5t-94.5 -29.5t-95 28t-64.5 75t-34.5 102.5t-11 118.5q0 58 11.5 112.5t34.5 103t64.5 78t95.5 29.5zM238 602q-32 0 -55.5 -25t-35.5 -68t-17.5 -91t-5.5 -105
q0 -76 10 -138.5t37 -107.5t69 -45q32 0 55.5 25t35.5 68.5t17.5 91.5t5.5 105t-5.5 105.5t-18 92t-36 68t-56.5 24.5z" id="x30"></path></g>
</svg>. (c) The result with <svg height="12.4375" id="M152" style="vertical-align:-0.1638pt" version="1.1" viewbox="0 0 37.087502 12.4375" width="37.087502" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink">
<g transform="matrix(.017,-0,0,-.017,.062,12.162)"><path d="M529 97q-70 -109 -136 -109q-41 0 -56 94q-23 144 -37 284q-38 -88 -99 -202.5t-93 -156.5q-26 -8 -76 -19l-9 21q71 78 145.5 193t124.5 232q-5 84 -15 128q-12 55 -29.5 75.5t-42.5 20.5q-21 0 -45 -13l-8 24q16 17 46 30t55 13q43 0 70 -46.5t40 -169.5
q27 -249 51 -392q7 -46 23 -46q24 0 70 60z" id="x1D706"></path></g><g transform="matrix(.017,-0,0,-.017,14.154,12.162)"><path d="M535 323h-483v50h483v-50zM535 138h-483v50h483v-50z" id="x3D"></path></g><g transform="matrix(.017,-0,0,-.017,28.858,12.162)"><path d="M384 0h-275v27q67 5 81.5 18.5t14.5 68.5v385q0 38 -7.5 47.5t-40.5 10.5l-48 2v24q85 15 178 52v-521q0 -55 14.5 -68.5t82.5 -18.5v-27z" id="x31"></path></g>
</svg>.</table>

BioMed Research International

A Similarity Search Using Molecular Topological Graphs

Figure 5