NPASS Compound

Structure

NPC135334 OpenBabel07101719132D 149164 0 0 1 0 0 0 0 0999 V2000 19.7979 -7.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7724 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7470 -5.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0793 4.3396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0854 4.3396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0793 -2.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0854 -2.3517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7216 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8608 -1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8608 -0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8862 -9.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4685 -8.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -8.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6078 -8.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8608 1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0509 -8.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8608 -1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4431 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4431 2.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4431 1.9879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5823 0.4970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3293 -9.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 2.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3548 -8.4485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3293 3.9758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6332 -7.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4431 -3.9758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0763 -11.4303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7470 1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -4.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.7979 -8.4485 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.7724 0.9939 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7470 -4.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3293 -8.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8608 1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7216 1.9879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4685 -10.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3039 -4.4727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6078 -9.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4940 -8.9455 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3293 2.9818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7724 -6.9576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 17.2155 -11.9273 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8862 0.9939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0509 -3.9758 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7216 -0.9939 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8608 0.4970 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4431 -0.9939 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0509 -9.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.6586 -8.9455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.6332 1.4909 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6078 -3.9758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1647 -3.9758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 17.2155 -12.9212 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8862 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0509 -2.9818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.4940 -9.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 20.6586 -9.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.6332 2.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.3548 -13.4182 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0254 -0.4970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1901 1.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0509 -6.9576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1901 -2.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 19.7979 -10.4364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.7724 2.9818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.4940 -12.9212 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1647 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3293 0.9939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0509 -5.9636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7470 -2.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1901 2.4848 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9117 -7.4545 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6078 -2.9818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.6332 -10.4364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1647 -2.9818 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7724 -9.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 18.9371 -9.9394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4685 1.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3293 -2.9818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.9117 2.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.9117 -5.4667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 15.4940 -11.9273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1647 0.9939 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8862 -2.9818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3039 -2.4848 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.7724 -8.9455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4431 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5823 3.4788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 -1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7216 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8608 0.4970 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5823 1.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 16.3548 -7.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1901 4.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4940 -6.9576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4685 -11.4303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3039 -5.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 21.5194 -8.4485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4940 0.9939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4685 -4.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0254 -4.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0763 -13.4182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7470 -0.4970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9117 -2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3548 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 21.5194 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4940 2.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3548 -14.4121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0254 -1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0509 0.9939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -7.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 19.7979 -11.4303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7724 3.9758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6332 -13.4182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3039 -0.4970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3293 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1901 -5.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7470 -1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4431 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7470 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4431 -2.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.0763 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6078 0.9939 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3293 -3.9758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 18.9371 -8.9455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9117 1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8862 -3.9758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6332 -8.4485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4685 2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7724 -5.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9117 -4.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3548 -11.4303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0254 1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3039 -1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9117 -10.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0509 2.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.9117 -8.4485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4685 -2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6332 -11.4303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0254 -2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3039 1.4909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 93 1 0 0 0 0 5 93 1 0 0 0 0 6 94 1 0 0 0 0 7 94 1 0 0 0 0 9 96 1 0 0 0 0 11128 1 0 0 0 0 12 15 2 0 0 0 0 12 38 1 0 0 0 0 13 17 2 0 0 0 0 13 38 1 0 0 0 0 14 16 1 0 0 0 0 14 39 2 0 0 0 0 15 43 1 0 0 0 0 16 51 1 0 0 0 0 17 53 1 0 0 0 0 18 21 1 0 0 0 0 18 50 1 0 0 0 0 19 20 1 0 0 0 0 19 52 1 0 0 0 0 20 95 1 0 0 0 0 21 97 1 0 0 0 0 22 24 1 0 0 0 0 22 93 1 0 0 0 0 23 25 1 0 0 0 0 23 96 1 0 0 0 0 24 98 1 0 0 0 0 25 98 1 0 0 0 0 26 38 2 0 0 0 0 26 41 1 0 0 0 0 27 40 1 0 0 0 0 27 93 1 0 0 0 0 28 99 1 0 0 0 0 29100 1 0 0 0 0 30101 1 0 0 0 0 31 42 1 0 0 0 0 31129 1 0 0 0 0 32130 1 0 0 0 0 33131 1 0 0 0 0 34 49 1 0 0 0 0 34132 1 0 0 0 0 35 1 1 1 0 0 0 35 54 1 0 0 0 0 35133 1 0 0 0 0 36 2 1 1 0 0 0 36 55 1 0 0 0 0 36134 1 0 0 0 0 37 3 1 6 0 0 0 37 56 1 0 0 0 0 37135 1 0 0 0 0 39 40 1 0 0 0 0 39 96 1 0 0 0 0 40 98 1 1 0 0 0 41 43 2 0 0 0 0 41102 1 0 0 0 0 42 57 1 0 0 0 0 42103 1 1 0 0 0 43128 1 0 0 0 0 44 28 1 6 0 0 0 44 61 1 0 0 0 0 44136 1 0 0 0 0 45 29 1 1 0 0 0 45 76 1 0 0 0 0 45137 1 0 0 0 0 46 30 1 6 0 0 0 46 77 1 0 0 0 0 46138 1 0 0 0 0 47 32 1 6 0 0 0 47 58 1 0 0 0 0 47140 1 0 0 0 0 48 33 1 1 0 0 0 48 59 1 0 0 0 0 48141 1 0 0 0 0 49 60 1 0 0 0 0 49139 1 6 0 0 0 50 94 1 0 0 0 0 50 95 1 6 0 0 0 51 95 1 6 0 0 0 51 97 1 0 0 0 0 52 94 1 0 0 0 0 52142 1 6 0 0 0 53104 2 0 0 0 0 53143 1 0 0 0 0 54 62 1 0 0 0 0 54105 1 6 0 0 0 55 63 1 0 0 0 0 55106 1 6 0 0 0 56 78 1 0 0 0 0 56107 1 1 0 0 0 57 80 1 0 0 0 0 57108 1 1 0 0 0 58 64 1 0 0 0 0 58109 1 1 0 0 0 59 65 1 0 0 0 0 59110 1 6 0 0 0 60 68 1 0 0 0 0 60111 1 6 0 0 0 61 79 1 0 0 0 0 61112 1 1 0 0 0 62 69 1 0 0 0 0 62113 1 1 0 0 0 63 70 1 0 0 0 0 63114 1 1 0 0 0 64 71 1 0 0 0 0 64115 1 6 0 0 0 65 72 1 0 0 0 0 65116 1 1 0 0 0 66 73 1 0 0 0 0 66 76 1 0 0 0 0 66117 1 1 0 0 0 67 74 1 0 0 0 0 67 77 1 0 0 0 0 67118 1 6 0 0 0 68 84 1 0 0 0 0 68119 1 6 0 0 0 69 82 1 0 0 0 0 69120 1 1 0 0 0 70 85 1 0 0 0 0 70121 1 1 0 0 0 71 87 1 0 0 0 0 71122 1 1 0 0 0 72 88 1 0 0 0 0 72123 1 6 0 0 0 73 83 1 0 0 0 0 73124 1 6 0 0 0 74 86 1 0 0 0 0 74125 1 1 0 0 0 75 78 1 0 0 0 0 75 89 1 0 0 0 0 75126 1 6 0 0 0 76144 1 6 0 0 0 77145 1 1 0 0 0 78146 1 6 0 0 0 79 81 1 0 0 0 0 79147 1 6 0 0 0 80 90 1 0 0 0 0 80148 1 6 0 0 0 81 91 1 0 0 0 0 81143 1 1 0 0 0 82130 1 6 0 0 0 82133 1 0 0 0 0 83131 1 1 0 0 0 83137 1 0 0 0 0 84132 1 0 0 0 0 84146 1 1 0 0 0 85134 1 0 0 0 0 85144 1 6 0 0 0 86138 1 0 0 0 0 86139 1 6 0 0 0 87140 1 0 0 0 0 87147 1 6 0 0 0 88141 1 0 0 0 0 88149 1 1 0 0 0 89135 1 0 0 0 0 89148 1 1 0 0 0 90129 1 0 0 0 0 90142 1 1 0 0 0 91136 1 0 0 0 0 91145 1 6 0 0 0 92127 2 0 0 0 0 92149 1 0 0 0 0 95 8 1 6 0 0 0 96 97 1 6 0 0 0 97 10 1 6 0 0 0 98 92 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	2144.93
Volume:	1996.506
LogP:	0.709
LogD:	0.499
LogS:	-2.076
# Rotatable Bonds:	31
TPSA:	783.41
# H-Bond Aceptor:	51
# H-Bond Donor:	27
# Rings:	16
# Heavy Atoms:	51

MedChem Properties

QED Drug-Likeness Score:	0.015
Synthetic Accessibility Score:	8.682
Fsp3:	0.878
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.603
MDCK Permeability:	0.002833159174770117
Pgp-inhibitor:	0.0
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.306
Plasma Protein Binding (PPB):	52.24867248535156%
Volume Distribution (VD):	-1.161
Pgp-substrate:	20.68317222595215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.011
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-2.807
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.208
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.613
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.019

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC135334

Natural Product ID:	NPC135334
*Common Name:**	Clematernoside E
IUPAC Name:	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-4-[(2S,3R,4S,5R)-5-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-5-hydroxy-3-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:	Clematernoside E
Standard InCHIKey:	LYZNTGCVMWIGPU-YWLSKINTSA-N
Standard InCHI:	InChI=1S/C98H152O51/c1-35-54(105)62(113)69(120)82(133-35)130-32-47-58(109)64(115)71(122)87(140-47)147-79-61(112)44(28-99)136-91(81(79)143-53(104)17-13-38-12-15-43(128-11)41(102)26-38)145-77-46(30-101)138-86(74(125)67(77)118)139-49-34-132-84(68(119)60(49)111)146-78-56(107)37(3)135-89(75(78)126)148-80-57(108)42(103)31-129-90(80)142-52-19-20-95(8)50(94(52,6)7)18-21-97(10)51(95)16-14-39-40-27-93(4,5)22-24-98(40,25-23-96(39,97)9)92(127)149-88-72(123)65(116)59(110)48(141-88)33-131-83-73(124)66(117)76(45(29-100)137-83)144-85-70(121)63(114)55(106)36(2)134-85/h12-15,17,26,35-37,40,42,44-52,54-91,99-103,105-126H,16,18-25,27-34H2,1-11H3/b17-13+/t35-,36-,37-,40-,42-,44+,45+,46+,47+,48+,49+,50-,51+,52-,54-,55-,56-,57-,58+,59+,60+,61+,62+,63+,64-,65-,66+,67+,68+,69+,70+,71+,72+,73+,74+,75+,76+,77+,78+,79-,80+,81+,82+,83+,84-,85-,86-,87-,88-,89-,90-,91-,95-,96+,97+,98-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@@H]2O)O)O[C@H]2[C@@H](O)[C@H](O[C@H]3[C@@H](OC[C@@H]([C@@H]3O)O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]3([C@@H]4CC=C4[C@@]3(C)CC[C@@]3([C@H]4CC(C)(C)CC3)C(=O)O[C@@H]3O[C@H](CO[C@@H]4O[C@H](CO)[C@H]([C@@H]([C@H]4O)O)O[C@@H]4O[C@@H](C)[C@@H]([C@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O)O)O)C)C)O[C@H]([C@@H]2O)C)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)OC)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1171446
PubChem CID:	49799266
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[15387651]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	roots and rhizomes	Shaoguan, Guangdong Province, China	2007-Dec	PMID[20540535]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6583	Clematis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	8300.0	nM	PMID[534771]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	8500.0	nM	PMID[534771]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC135334 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	1489
0.2-0.3	3165
0.3-0.4	6240
0.4-0.5	8967
0.5-0.6	8370
0.6-0.7	9932
0.7-0.8	3760
0.8-0.85	267
0.85-0.9	71
0.9-0.95	15
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469776
1.0	High Similarity	NPC469775
1.0	High Similarity	NPC469773
1.0	High Similarity	NPC469778
1.0	High Similarity	NPC469772
1.0	High Similarity	NPC469777
1.0	High Similarity	NPC32723
1.0	High Similarity	NPC469774
1.0	High Similarity	NPC100925
1.0	High Similarity	NPC295941
0.9	High Similarity	NPC473773
0.9	High Similarity	NPC475579
0.8957	High Similarity	NPC471878
0.8938	High Similarity	NPC118033
0.8929	High Similarity	NPC471870
0.8916	High Similarity	NPC25889
0.8882	High Similarity	NPC124828
0.887	High Similarity	NPC475299
0.883	High Similarity	NPC473630
0.882	High Similarity	NPC475311
0.882	High Similarity	NPC473579
0.882	High Similarity	NPC473680
0.882	High Similarity	NPC475454
0.8772	High Similarity	NPC471871
0.8758	High Similarity	NPC470927
0.8758	High Similarity	NPC257970
0.8757	High Similarity	NPC286809
0.8743	High Similarity	NPC246024
0.8743	High Similarity	NPC471873
0.8713	High Similarity	NPC13989
0.8712	High Similarity	NPC471874
0.8701	High Similarity	NPC476067
0.8701	High Similarity	NPC475121
0.8696	High Similarity	NPC473427
0.8696	High Similarity	NPC471062
0.8696	High Similarity	NPC306890
0.8696	High Similarity	NPC259347
0.8696	High Similarity	NPC476398
0.8696	High Similarity	NPC470933
0.8696	High Similarity	NPC94871
0.8696	High Similarity	NPC476386
0.869	High Similarity	NPC100420
0.8683	High Similarity	NPC471869
0.8671	High Similarity	NPC469397
0.8655	High Similarity	NPC472803
0.8655	High Similarity	NPC179240
0.8644	High Similarity	NPC189704
0.8606	High Similarity	NPC131532
0.8598	High Similarity	NPC205392
0.8598	High Similarity	NPC105942
0.8596	High Similarity	NPC266545
0.8596	High Similarity	NPC202428
0.8588	High Similarity	NPC96194
0.8588	High Similarity	NPC299855
0.8588	High Similarity	NPC200726
0.858	High Similarity	NPC473205
0.858	High Similarity	NPC473776
0.8571	High Similarity	NPC232992
0.8562	High Similarity	NPC307205
0.8555	High Similarity	NPC475197
0.8555	High Similarity	NPC473467
0.8538	High Similarity	NPC185498
0.8538	High Similarity	NPC177362
0.8537	High Similarity	NPC478268
0.8528	High Similarity	NPC470619
0.8528	High Similarity	NPC145527
0.8528	High Similarity	NPC470618
0.8528	High Similarity	NPC208785
0.8523	High Similarity	NPC188217
0.8506	High Similarity	NPC469354
0.848	Intermediate Similarity	NPC306475
0.8466	Intermediate Similarity	NPC478242
0.8462	Intermediate Similarity	NPC7191
0.8462	Intermediate Similarity	NPC149873
0.8457	Intermediate Similarity	NPC475054
0.8453	Intermediate Similarity	NPC473711
0.8452	Intermediate Similarity	NPC478269
0.8448	Intermediate Similarity	NPC316539
0.8447	Intermediate Similarity	NPC53520
0.8447	Intermediate Similarity	NPC34927
0.8447	Intermediate Similarity	NPC252292
0.8447	Intermediate Similarity	NPC34587
0.8447	Intermediate Similarity	NPC100998
0.8447	Intermediate Similarity	NPC476382
0.8438	Intermediate Similarity	NPC469447
0.8438	Intermediate Similarity	NPC477873
0.8424	Intermediate Similarity	NPC106818
0.8415	Intermediate Similarity	NPC470934
0.8415	Intermediate Similarity	NPC12006
0.8415	Intermediate Similarity	NPC188393
0.8407	Intermediate Similarity	NPC476358
0.84	Intermediate Similarity	NPC469438
0.8398	Intermediate Similarity	NPC112708
0.8395	Intermediate Similarity	NPC320734
0.8385	Intermediate Similarity	NPC264270
0.8385	Intermediate Similarity	NPC64195
0.8385	Intermediate Similarity	NPC40085
0.8373	Intermediate Similarity	NPC106669
0.8373	Intermediate Similarity	NPC299706
0.8373	Intermediate Similarity	NPC115466
0.8373	Intermediate Similarity	NPC475227
0.8373	Intermediate Similarity	NPC200645
0.8373	Intermediate Similarity	NPC61604
0.8373	Intermediate Similarity	NPC87403
0.8373	Intermediate Similarity	NPC245615
0.8364	Intermediate Similarity	NPC7145
0.8364	Intermediate Similarity	NPC143480
0.8364	Intermediate Similarity	NPC85192
0.8364	Intermediate Similarity	NPC125823
0.8363	Intermediate Similarity	NPC116759
0.8363	Intermediate Similarity	NPC227297
0.8363	Intermediate Similarity	NPC14294
0.8353	Intermediate Similarity	NPC266365
0.8353	Intermediate Similarity	NPC478267
0.8352	Intermediate Similarity	NPC475613
0.8352	Intermediate Similarity	NPC472723
0.8343	Intermediate Similarity	NPC179914
0.8343	Intermediate Similarity	NPC230670
0.8343	Intermediate Similarity	NPC71385
0.8333	Intermediate Similarity	NPC272619
0.8333	Intermediate Similarity	NPC228357
0.8333	Intermediate Similarity	NPC43434
0.8333	Intermediate Similarity	NPC52598
0.8333	Intermediate Similarity	NPC286245
0.8333	Intermediate Similarity	NPC472129
0.8333	Intermediate Similarity	NPC11411
0.8323	Intermediate Similarity	NPC476397
0.8323	Intermediate Similarity	NPC96795
0.8323	Intermediate Similarity	NPC278961
0.8323	Intermediate Similarity	NPC205864
0.8323	Intermediate Similarity	NPC476381
0.8323	Intermediate Similarity	NPC247032
0.8323	Intermediate Similarity	NPC476375
0.8323	Intermediate Similarity	NPC476384
0.8323	Intermediate Similarity	NPC476380
0.8323	Intermediate Similarity	NPC264632
0.8323	Intermediate Similarity	NPC204644
0.8323	Intermediate Similarity	NPC476378
0.8323	Intermediate Similarity	NPC175214
0.8323	Intermediate Similarity	NPC298257
0.8323	Intermediate Similarity	NPC111466
0.8323	Intermediate Similarity	NPC119537
0.8323	Intermediate Similarity	NPC112
0.8323	Intermediate Similarity	NPC269141
0.8323	Intermediate Similarity	NPC76406
0.8323	Intermediate Similarity	NPC113680
0.8313	Intermediate Similarity	NPC304110
0.8313	Intermediate Similarity	NPC27518
0.8304	Intermediate Similarity	NPC140346
0.8304	Intermediate Similarity	NPC12326
0.8303	Intermediate Similarity	NPC476871
0.8295	Intermediate Similarity	NPC475244
0.8293	Intermediate Similarity	NPC3460
0.8293	Intermediate Similarity	NPC300262
0.8293	Intermediate Similarity	NPC192763
0.8293	Intermediate Similarity	NPC28651
0.8293	Intermediate Similarity	NPC201148
0.8293	Intermediate Similarity	NPC210611
0.8293	Intermediate Similarity	NPC261122
0.8293	Intermediate Similarity	NPC23677
0.8293	Intermediate Similarity	NPC199311
0.8293	Intermediate Similarity	NPC116229
0.8293	Intermediate Similarity	NPC80732
0.8293	Intermediate Similarity	NPC215095
0.8286	Intermediate Similarity	NPC148185
0.8286	Intermediate Similarity	NPC477617
0.8282	Intermediate Similarity	NPC476865
0.8276	Intermediate Similarity	NPC658
0.8276	Intermediate Similarity	NPC472133
0.8276	Intermediate Similarity	NPC197708
0.8276	Intermediate Similarity	NPC21956
0.8274	Intermediate Similarity	NPC38699
0.8272	Intermediate Similarity	NPC471065
0.8272	Intermediate Similarity	NPC253015
0.8272	Intermediate Similarity	NPC25491
0.8268	Intermediate Similarity	NPC476203
0.8266	Intermediate Similarity	NPC59516
0.8261	Intermediate Similarity	NPC222433
0.8261	Intermediate Similarity	NPC140502
0.8261	Intermediate Similarity	NPC265648
0.8258	Intermediate Similarity	NPC161609
0.8258	Intermediate Similarity	NPC275690
0.8256	Intermediate Similarity	NPC121290
0.825	Intermediate Similarity	NPC155192
0.825	Intermediate Similarity	NPC271494
0.825	Intermediate Similarity	NPC473591
0.8249	Intermediate Similarity	NPC66820
0.8249	Intermediate Similarity	NPC67629
0.8249	Intermediate Similarity	NPC79736
0.8249	Intermediate Similarity	NPC92403
0.8249	Intermediate Similarity	NPC76112
0.8249	Intermediate Similarity	NPC170018
0.8246	Intermediate Similarity	NPC100465
0.8246	Intermediate Similarity	NPC152424
0.8242	Intermediate Similarity	NPC44452
0.8235	Intermediate Similarity	NPC469384
0.8232	Intermediate Similarity	NPC470330
0.8225	Intermediate Similarity	NPC163635
0.8222	Intermediate Similarity	NPC318119
0.8221	Intermediate Similarity	NPC476869

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC135334 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	927
0.2-0.3	1853
0.3-0.4	2684
0.4-0.5	1938
0.5-0.6	988
0.6-0.7	352
0.7-0.8	55
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD7228	Approved
0.8261	Intermediate Similarity	NPD8166	Discontinued
0.8249	Intermediate Similarity	NPD8313	Approved
0.8249	Intermediate Similarity	NPD8312	Approved
0.8156	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD8127	Discontinued
0.8136	Intermediate Similarity	NPD7240	Approved
0.8129	Intermediate Similarity	NPD6234	Discontinued
0.8122	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD8455	Phase 2
0.8075	Intermediate Similarity	NPD7266	Discontinued
0.8047	Intermediate Similarity	NPD37	Approved
0.8023	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD4967	Phase 2
0.8012	Intermediate Similarity	NPD4965	Approved
0.8012	Intermediate Similarity	NPD4966	Approved
0.7933	Intermediate Similarity	NPD7685	Pre-registration
0.7921	Intermediate Similarity	NPD7472	Approved
0.7865	Intermediate Similarity	NPD7054	Approved
0.779	Intermediate Similarity	NPD7808	Phase 3
0.7765	Intermediate Similarity	NPD7458	Discontinued
0.7742	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7251	Discontinued
0.7708	Intermediate Similarity	NPD7680	Approved
0.7684	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6797	Phase 2
0.768	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6674	Discontinued
0.7602	Intermediate Similarity	NPD1653	Approved
0.76	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5844	Phase 1
0.7528	Intermediate Similarity	NPD7199	Phase 2
0.7514	Intermediate Similarity	NPD3818	Discontinued
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7028	Phase 2
0.7396	Intermediate Similarity	NPD4628	Phase 3
0.7396	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7473	Discontinued
0.736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6190	Approved
0.7351	Intermediate Similarity	NPD6559	Discontinued
0.7349	Intermediate Similarity	NPD7097	Phase 1
0.7348	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7003	Approved
0.7293	Intermediate Similarity	NPD6232	Discontinued
0.7288	Intermediate Similarity	NPD1465	Phase 2
0.7283	Intermediate Similarity	NPD6273	Approved
0.7264	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7435	Discontinued
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1934	Approved
0.7225	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8319	Approved
0.7222	Intermediate Similarity	NPD8320	Phase 1
0.7193	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4110	Phase 3
0.7191	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7697	Approved
0.7172	Intermediate Similarity	NPD7696	Phase 3
0.7172	Intermediate Similarity	NPD7698	Approved
0.7169	Intermediate Similarity	NPD3620	Phase 2
0.7169	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7136	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7129	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD6823	Phase 2
0.7119	Intermediate Similarity	NPD4380	Phase 2
0.7114	Intermediate Similarity	NPD7701	Phase 2
0.7107	Intermediate Similarity	NPD6776	Approved
0.7107	Intermediate Similarity	NPD6782	Approved
0.7107	Intermediate Similarity	NPD6780	Approved
0.7107	Intermediate Similarity	NPD6777	Approved
0.7107	Intermediate Similarity	NPD6781	Approved
0.7107	Intermediate Similarity	NPD6779	Approved
0.7107	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7819	Suspended
0.7091	Intermediate Similarity	NPD3027	Phase 3
0.7072	Intermediate Similarity	NPD7075	Discontinued
0.7062	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6959	Discontinued
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7768	Phase 2
0.7011	Intermediate Similarity	NPD3787	Discontinued
0.701	Intermediate Similarity	NPD7801	Approved
0.7005	Intermediate Similarity	NPD7699	Phase 2
0.7005	Intermediate Similarity	NPD7700	Phase 2
0.6995	Remote Similarity	NPD5494	Approved
0.6964	Remote Similarity	NPD1613	Approved
0.6964	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD3817	Phase 2
0.6961	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7799	Discontinued
0.6935	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6906	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2801	Approved
0.6905	Remote Similarity	NPD8032	Phase 2
0.6905	Remote Similarity	NPD6663	Approved
0.6897	Remote Similarity	NPD3750	Approved
0.6886	Remote Similarity	NPD7095	Approved
0.6872	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5736	Approved
0.6864	Remote Similarity	NPD4060	Phase 1
0.6864	Remote Similarity	NPD4140	Approved
0.686	Remote Similarity	NPD6099	Approved
0.686	Remote Similarity	NPD6100	Approved
0.686	Remote Similarity	NPD2935	Discontinued
0.686	Remote Similarity	NPD2438	Suspended
0.6853	Remote Similarity	NPD6534	Approved
0.6853	Remote Similarity	NPD6535	Approved
0.6845	Remote Similarity	NPD6798	Discontinued
0.6839	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7497	Discontinued
0.6831	Remote Similarity	NPD3882	Suspended
0.6824	Remote Similarity	NPD230	Phase 1
0.6823	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5762	Approved
0.6821	Remote Similarity	NPD5763	Approved
0.681	Remote Similarity	NPD3705	Approved
0.6805	Remote Similarity	NPD6233	Phase 2
0.6796	Remote Similarity	NPD7411	Suspended
0.6778	Remote Similarity	NPD3226	Approved
0.6776	Remote Similarity	NPD5402	Approved
0.6758	Remote Similarity	NPD6801	Discontinued
0.6746	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6599	Discontinued
0.6736	Remote Similarity	NPD7313	Approved
0.6736	Remote Similarity	NPD7310	Approved
0.6736	Remote Similarity	NPD7311	Approved
0.6736	Remote Similarity	NPD7312	Approved
0.6728	Remote Similarity	NPD1357	Approved
0.6726	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5735	Approved
0.6725	Remote Similarity	NPD1933	Approved
0.6719	Remote Similarity	NPD8368	Discontinued
0.6719	Remote Similarity	NPD7038	Approved
0.6719	Remote Similarity	NPD7039	Approved
0.6717	Remote Similarity	NPD6212	Phase 3
0.6717	Remote Similarity	NPD6213	Phase 3
0.6717	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD1091	Approved
0.6703	Remote Similarity	NPD6677	Suspended
0.6701	Remote Similarity	NPD2488	Approved
0.6701	Remote Similarity	NPD2490	Approved
0.6701	Remote Similarity	NPD7309	Approved
0.6687	Remote Similarity	NPD8651	Approved
0.6687	Remote Similarity	NPD1283	Approved
0.6686	Remote Similarity	NPD6653	Approved
0.6686	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD1511	Approved
0.6684	Remote Similarity	NPD7906	Approved
0.6684	Remote Similarity	NPD7549	Discontinued
0.6683	Remote Similarity	NPD7999	Approved
0.6667	Remote Similarity	NPD27	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2489	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD7930	Approved
0.665	Remote Similarity	NPD2493	Approved
0.665	Remote Similarity	NPD2494	Approved
0.6648	Remote Similarity	NPD2534	Approved
0.6648	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2532	Approved
0.6648	Remote Similarity	NPD2533	Approved
0.6647	Remote Similarity	NPD2797	Approved
0.6647	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3764	Approved
0.6634	Remote Similarity	NPD4583	Approved
0.6634	Remote Similarity	NPD4582	Approved
0.6629	Remote Similarity	NPD2346	Discontinued
0.6629	Remote Similarity	NPD7236	Approved
0.6629	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6005	Phase 3
0.6629	Remote Similarity	NPD6004	Phase 3
0.6629	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6002	Phase 3
0.6628	Remote Similarity	NPD5124	Phase 1
0.6628	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD447	Suspended
0.6627	Remote Similarity	NPD4908	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data