NPASS Compound

Structure

NPC475649 OpenBabel07101718242D 141154 0 0 1 0 0 0 0 0999 V2000 -14.7753 -2.5410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6634 -2.9080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -2.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2336 1.1521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1933 3.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1619 3.7445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -2.7759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8394 -2.7759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4056 -2.0396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5164 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0904 -3.2258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7895 1.3356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1047 0.6507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7251 1.0849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5345 -3.4093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8496 -4.0942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3553 -0.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9758 0.1493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5416 -1.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8567 -2.1559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -1.9371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1940 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4700 -3.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 -1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 2.4214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -5.8113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7431 -7.7484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0655 -4.8428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3679 -5.8310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1745 -6.5830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6705 -0.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7103 -4.8428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4786 -10.0601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1668 -9.1999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9140 -3.8435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5164 -3.3899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4842 0.2165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2909 -0.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 1.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7431 -8.7170 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0655 -5.8113 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6830 -6.5159 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8594 -5.8982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5164 -6.2956 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9856 -1.6546 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8715 -4.3585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5164 -1.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6776 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5164 2.4214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6776 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1940 -1.4528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1074 -3.0915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1940 -3.3899 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9043 -9.2013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5164 -7.2642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2363 -2.5901 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1940 -4.3585 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3552 -7.7484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0655 -8.7170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1940 -7.2642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3879 -5.8113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4968 -5.3296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2267 -6.2956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7475 -6.2652 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6087 -4.9626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0328 -4.8428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5514 -3.2750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6732 -4.7119 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6159 -3.0243 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7038 -8.6383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2292 -4.5284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 -2.9057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3879 -4.8428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0655 -7.7484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1817 -4.6448 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1940 -6.2956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9883 -5.3968 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3652 -2.0888 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3133 -7.8856 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9927 0.2837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6776 2.9057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -1.9371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1549 -2.9752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5164 -0.4843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8388 -0.4843 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 -2.2313 -9.4506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6776 0.9686 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3552 -2.9057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 -6.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5743 -9.7130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5164 -4.3585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7994 -0.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5819 -9.2013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9043 -6.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9337 -7.4514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7950 -6.1488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3552 2.9057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -0.4843 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0429 -3.3422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9043 -10.1698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6776 -7.7484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1718 -2.8408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -4.8428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -8.7170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2267 -9.2013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 -7.7484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5491 -6.2956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5612 -5.0789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7365 -8.5876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4798 -5.4640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8784 0.7850 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4700 -2.2903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3828 -10.4072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4198 -0.0342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2267 -4.3585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9043 -7.2642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1172 -4.8954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2390 -6.3323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5491 -4.3585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2175 -8.2327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -5.8113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0500 -1.4039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8715 -3.3899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 -1.9371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4225 -3.7764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2936 -4.2777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2267 -7.2642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0626 -6.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 -5.8113 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0528 -5.1461 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9310 -3.7092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4941 -1.5874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 42 1 0 0 0 0 3 43 1 0 0 0 0 4 44 1 0 0 0 0 5 89 1 0 0 0 0 6 89 1 0 0 0 0 7 90 1 0 0 0 0 8 90 1 0 0 0 0 11 93 1 0 0 0 0 13 91 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 42 2 0 0 0 0 19 45 2 0 0 0 0 20 45 1 0 0 0 0 21 24 2 0 0 0 0 21 45 1 0 0 0 0 22 23 1 0 0 0 0 22 46 2 0 0 0 0 23 56 1 0 0 0 0 24 60 1 0 0 0 0 25 29 1 0 0 0 0 25 55 1 0 0 0 0 26 28 1 0 0 0 0 26 59 1 0 0 0 0 27 91 1 0 0 0 0 28 92 1 0 0 0 0 29 93 1 0 0 0 0 30 47 1 0 0 0 0 30 89 1 0 0 0 0 31 58 1 0 0 0 0 31 94 1 0 0 0 0 32 57 1 0 0 0 0 32 96 1 0 0 0 0 33 98 1 0 0 0 0 34 48 1 0 0 0 0 34125 1 0 0 0 0 35 49 1 0 0 0 0 35124 1 0 0 0 0 36 50 1 0 0 0 0 36126 1 0 0 0 0 37 51 1 0 0 0 0 37127 1 0 0 0 0 38123 1 0 0 0 0 39128 1 0 0 0 0 40 95 1 0 0 0 0 40 99 1 0 0 0 0 41 95 1 0 0 0 0 41129 1 0 0 0 0 42 79 1 0 0 0 0 43 97 2 3 0 0 0 43100 1 0 0 0 0 44101 2 0 0 0 0 44123 1 0 0 0 0 46 47 1 0 0 0 0 46 94 1 0 0 0 0 47 96 1 1 0 0 0 48 62 1 0 0 0 0 48102 1 6 0 0 0 49 71 1 0 0 0 0 49103 1 6 0 0 0 50 72 1 0 0 0 0 50104 1 6 0 0 0 51 73 1 0 0 0 0 51105 1 1 0 0 0 52 33 1 1 0 0 0 52 63 1 0 0 0 0 52130 1 0 0 0 0 53 38 1 1 0 0 0 53 64 1 0 0 0 0 53131 1 0 0 0 0 54 39 1 6 0 0 0 54 74 1 0 0 0 0 54132 1 0 0 0 0 55 90 1 0 0 0 0 55 92 1 6 0 0 0 56 92 1 6 0 0 0 56 93 1 0 0 0 0 57 89 1 0 0 0 0 57106 1 6 0 0 0 58 96 1 1 0 0 0 58107 1 0 0 0 0 59 90 1 0 0 0 0 59133 1 6 0 0 0 60108 2 0 0 0 0 60134 1 0 0 0 0 61 65 1 0 0 0 0 61 80 1 0 0 0 0 61 97 1 1 0 0 0 62 67 1 0 0 0 0 62109 1 6 0 0 0 63 66 1 0 0 0 0 63110 1 6 0 0 0 64 75 1 0 0 0 0 64111 1 6 0 0 0 65 74 1 0 0 0 0 65112 1 6 0 0 0 66 68 1 0 0 0 0 66113 1 1 0 0 0 67 82 1 0 0 0 0 67114 1 1 0 0 0 68 84 1 0 0 0 0 68115 1 6 0 0 0 69 71 1 0 0 0 0 69 81 1 0 0 0 0 69116 1 1 0 0 0 70 72 1 0 0 0 0 70 83 1 0 0 0 0 70117 1 6 0 0 0 71136 1 6 0 0 0 72137 1 1 0 0 0 73 76 1 0 0 0 0 73135 1 6 0 0 0 74138 1 1 0 0 0 75 77 1 0 0 0 0 75139 1 1 0 0 0 76 85 1 0 0 0 0 76134 1 1 0 0 0 77 86 1 0 0 0 0 77140 1 6 0 0 0 78 87 1 0 0 0 0 78 95 1 6 0 0 0 78118 1 0 0 0 0 79119 2 0 0 0 0 79135 1 0 0 0 0 80132 1 0 0 0 0 80133 1 6 0 0 0 81124 1 0 0 0 0 81128 1 6 0 0 0 82125 1 0 0 0 0 82136 1 6 0 0 0 83126 1 0 0 0 0 83140 1 1 0 0 0 84130 1 0 0 0 0 84138 1 1 0 0 0 85127 1 0 0 0 0 85139 1 6 0 0 0 86131 1 0 0 0 0 86141 1 1 0 0 0 87129 1 0 0 0 0 87137 1 1 0 0 0 88120 2 0 0 0 0 88141 1 0 0 0 0 91 9 1 6 0 0 0 91121 1 0 0 0 0 92 10 1 6 0 0 0 93 94 1 1 0 0 0 94 12 1 1 0 0 0 95122 1 6 0 0 0 96 88 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	2013.9
Volume:	1915.31
LogP:	1.416
LogD:	0.722
LogS:	-2.463
# Rotatable Bonds:	36
TPSA:	677.35
# H-Bond Aceptor:	45
# H-Bond Donor:	21
# Rings:	14
# Heavy Atoms:	45

MedChem Properties

QED Drug-Likeness Score:	0.011
Synthetic Accessibility Score:	8.6
Fsp3:	0.802
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.114
MDCK Permeability:	0.0009710540762171149
Pgp-inhibitor:	0.05
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	42.879947662353516%
Volume Distribution (VD):	-0.546
Pgp-substrate:	19.171567916870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.0
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.004

ADMET: Excretion

Clearance (CL):	-1.789
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.103
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.04
Carcinogencity:	0.003
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC475649

Natural Product ID:	NPC475649
*Common Name:**	3Beta-O-{Alpha-L-Arabinopyranosyl-(1->3)-Alpha-L-Arabinopyranosyl-(1->6)-[Beta-D-Glucopyranosyl-(1->4)]-2-(Acetamido)-2-Deoxy-Beta-D-Glucopyranosyl}Echinocystic Acid 28-O-{Beta-D-Apiofuranosyl-(1->3)-Beta-D-Xylopyranosyl-(1->2)-[(2-Ocinnamoyl)-Beta-D-Xylopyranosyl-(1->4)]-(6-O-Acetyl)-Beta-D-Glucopyranosylester
IUPAC Name:	[(2S,3R,4S,5R,6R)-6-(acetyloxymethyl)-3-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5R)-5-hydroxy-4-[(2E,6S)-6-hydroxy-2,6-dimethylocta-2,7-dienoyl]oxy-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxyoxan-2-yl] (3S,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-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:
Standard InCHIKey:	QGRBYADWKWKVRA-OYYMBGRASA-N
Standard InCHI:	InChI=1S/C96H143NO44/c1-13-91(9,121)27-17-18-42(2)79(119)135-73-51(105)37-127-85(76(73)134-60(108)24-21-45-19-15-14-16-20-45)139-75-64(111)53(38-123-44(4)101)131-86(77(75)140-83-70(117)72(50(104)36-126-83)137-87-78(118)95(122,40-99)41-129-87)141-88(120)96-32-57(106)89(5,6)30-47(96)46-22-23-56-92(10)28-26-59(90(7,8)55(92)25-29-93(56,11)94(46,12)31-58(96)107)133-80-61(97-43(3)100)65(112)74(138-84-68(115)66(113)63(110)52(33-98)130-84)54(132-80)39-128-81-69(116)71(49(103)35-124-81)136-82-67(114)62(109)48(102)34-125-82/h13-16,18-22,24,47-59,61-78,80-87,98-99,102-107,109-118,121-122H,1,17,23,25-41H2,2-12H3,(H,97,100)/b24-21+,42-18+/t47-,48-,49-,50+,51+,52+,53+,54+,55-,56+,57-,58+,59-,61+,62-,63+,64+,65+,66-,67+,68+,69+,70+,71-,72-,73-,74+,75-,76+,77+,78-,80-,81-,82-,83-,84-,85-,86-,87-,91+,92-,93+,94+,95+,96+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO[C@@H]3OC[C@@H]([C@@H]([C@H]3O)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O)O)O)O)O[C@H]([C@@H]([C@H]2O)N=C(O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)[C@H](C2)O)C(=O)O[C@@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@]([C@H]2O)(O)CO)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2OC(=O)/C=C/c2ccccc2)OC(=O)/C(=C/CC[C@@](C=C)(O)C)/C)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510401
PubChem CID:	44566576
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
NPO11507	Entada africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989528]
NPO11507	Entada africana	Species	Fabaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	2800.0	nM	PMID[506727]
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	3000.0	nM	PMID[506727]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	=	2700.0	nM	PMID[506727]

☑ 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 NPC475649 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	234
0.1-0.2	937
0.2-0.3	2289
0.3-0.4	5470
0.4-0.5	16591
0.5-0.6	13243
0.6-0.7	3463
0.7-0.8	422
0.8-0.85	33
0.85-0.9	8
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC475345
0.9693	High Similarity	NPC476113
0.963	High Similarity	NPC120667
0.963	High Similarity	NPC278272
0.8642	High Similarity	NPC100612
0.8642	High Similarity	NPC174336
0.8642	High Similarity	NPC475599
0.8642	High Similarity	NPC187497
0.8642	High Similarity	NPC113620
0.858	High Similarity	NPC265699
0.858	High Similarity	NPC475527
0.8395	Intermediate Similarity	NPC264270
0.8395	Intermediate Similarity	NPC40085
0.8333	Intermediate Similarity	NPC111466
0.8284	Intermediate Similarity	NPC477467
0.8225	Intermediate Similarity	NPC477470
0.8225	Intermediate Similarity	NPC477474
0.8225	Intermediate Similarity	NPC477472
0.8086	Intermediate Similarity	NPC475892
0.8047	Intermediate Similarity	NPC69425
0.8025	Intermediate Similarity	NPC475394
0.8025	Intermediate Similarity	NPC475584
0.8025	Intermediate Similarity	NPC475152
0.7988	Intermediate Similarity	NPC473755
0.7988	Intermediate Similarity	NPC475513
0.7937	Intermediate Similarity	NPC472375
0.7929	Intermediate Similarity	NPC329657
0.7901	Intermediate Similarity	NPC210729
0.7901	Intermediate Similarity	NPC82931
0.7901	Intermediate Similarity	NPC172365
0.7865	Intermediate Similarity	NPC477471
0.7865	Intermediate Similarity	NPC477469
0.7865	Intermediate Similarity	NPC477466
0.7865	Intermediate Similarity	NPC477473
0.7842	Intermediate Similarity	NPC472392
0.7812	Intermediate Similarity	NPC289383
0.7801	Intermediate Similarity	NPC472391
0.779	Intermediate Similarity	NPC13989
0.7784	Intermediate Similarity	NPC150893
0.7784	Intermediate Similarity	NPC329960
0.7784	Intermediate Similarity	NPC295408
0.7778	Intermediate Similarity	NPC200788
0.7778	Intermediate Similarity	NPC243680
0.7772	Intermediate Similarity	NPC116862
0.7725	Intermediate Similarity	NPC61717
0.7725	Intermediate Similarity	NPC244380
0.7684	Intermediate Similarity	NPC473641
0.7684	Intermediate Similarity	NPC473797
0.7684	Intermediate Similarity	NPC475505
0.7684	Intermediate Similarity	NPC475437
0.7684	Intermediate Similarity	NPC475300
0.7684	Intermediate Similarity	NPC475464
0.7654	Intermediate Similarity	NPC145899
0.7627	Intermediate Similarity	NPC475536
0.7627	Intermediate Similarity	NPC165234
0.7605	Intermediate Similarity	NPC214821
0.7605	Intermediate Similarity	NPC298067
0.7593	Intermediate Similarity	NPC280941
0.7593	Intermediate Similarity	NPC75318
0.7593	Intermediate Similarity	NPC235772
0.7574	Intermediate Similarity	NPC237240
0.7574	Intermediate Similarity	NPC31171
0.7558	Intermediate Similarity	NPC476092
0.7558	Intermediate Similarity	NPC475218
0.7558	Intermediate Similarity	NPC475447
0.7558	Intermediate Similarity	NPC70236
0.7557	Intermediate Similarity	NPC476784
0.7556	Intermediate Similarity	NPC475175
0.7556	Intermediate Similarity	NPC475198
0.7556	Intermediate Similarity	NPC475531
0.7531	Intermediate Similarity	NPC76999
0.7529	Intermediate Similarity	NPC36463
0.7529	Intermediate Similarity	NPC298005
0.7514	Intermediate Similarity	NPC102465
0.7514	Intermediate Similarity	NPC469420
0.7513	Intermediate Similarity	NPC471754
0.7513	Intermediate Similarity	NPC317882
0.75	Intermediate Similarity	NPC474564
0.75	Intermediate Similarity	NPC473557
0.75	Intermediate Similarity	NPC475567
0.75	Intermediate Similarity	NPC473468
0.7469	Intermediate Similarity	NPC119794
0.7469	Intermediate Similarity	NPC73829
0.7461	Intermediate Similarity	NPC473558
0.7461	Intermediate Similarity	NPC473490
0.746	Intermediate Similarity	NPC471623
0.7457	Intermediate Similarity	NPC472761
0.7448	Intermediate Similarity	NPC215892
0.7448	Intermediate Similarity	NPC242662
0.7448	Intermediate Similarity	NPC191193
0.7448	Intermediate Similarity	NPC321072
0.7442	Intermediate Similarity	NPC201692
0.744	Intermediate Similarity	NPC141669
0.744	Intermediate Similarity	NPC111586
0.744	Intermediate Similarity	NPC298469
0.744	Intermediate Similarity	NPC108852
0.744	Intermediate Similarity	NPC261709
0.744	Intermediate Similarity	NPC193579
0.7421	Intermediate Similarity	NPC475336
0.7421	Intermediate Similarity	NPC324251
0.7421	Intermediate Similarity	NPC471629
0.7421	Intermediate Similarity	NPC275170
0.7421	Intermediate Similarity	NPC306001
0.7421	Intermediate Similarity	NPC453583
0.7421	Intermediate Similarity	NPC473400
0.7421	Intermediate Similarity	NPC206211
0.7421	Intermediate Similarity	NPC473300
0.7416	Intermediate Similarity	NPC477623
0.7409	Intermediate Similarity	NPC181964
0.7409	Intermediate Similarity	NPC208553
0.7409	Intermediate Similarity	NPC471606
0.7407	Intermediate Similarity	NPC473679
0.7407	Intermediate Similarity	NPC319719
0.7407	Intermediate Similarity	NPC183816
0.7407	Intermediate Similarity	NPC233223
0.7407	Intermediate Similarity	NPC322904
0.7407	Intermediate Similarity	NPC196874
0.7407	Intermediate Similarity	NPC327699
0.7407	Intermediate Similarity	NPC475472
0.7407	Intermediate Similarity	NPC475444
0.7407	Intermediate Similarity	NPC475177
0.7407	Intermediate Similarity	NPC324933
0.7401	Intermediate Similarity	NPC469417
0.7382	Intermediate Similarity	NPC67246
0.7382	Intermediate Similarity	NPC33372
0.7377	Intermediate Similarity	NPC477488
0.7371	Intermediate Similarity	NPC477905
0.7371	Intermediate Similarity	NPC472548
0.7366	Intermediate Similarity	NPC124828
0.7362	Intermediate Similarity	NPC471024
0.736	Intermediate Similarity	NPC477736
0.736	Intermediate Similarity	NPC469399
0.7356	Intermediate Similarity	NPC469448
0.7351	Intermediate Similarity	NPC469421
0.7346	Intermediate Similarity	NPC10121
0.7346	Intermediate Similarity	NPC300655
0.7346	Intermediate Similarity	NPC311178
0.7346	Intermediate Similarity	NPC231888
0.7346	Intermediate Similarity	NPC63404
0.7346	Intermediate Similarity	NPC92283
0.7346	Intermediate Similarity	NPC222951
0.7346	Intermediate Similarity	NPC290276
0.7346	Intermediate Similarity	NPC10883
0.7346	Intermediate Similarity	NPC35338
0.7346	Intermediate Similarity	NPC43589
0.7346	Intermediate Similarity	NPC198918
0.7346	Intermediate Similarity	NPC204214
0.7346	Intermediate Similarity	NPC124878
0.733	Intermediate Similarity	NPC472658
0.733	Intermediate Similarity	NPC472657
0.7326	Intermediate Similarity	NPC173934
0.7323	Intermediate Similarity	NPC314941
0.7321	Intermediate Similarity	NPC162910
0.7312	Intermediate Similarity	NPC469774
0.7312	Intermediate Similarity	NPC469778
0.7312	Intermediate Similarity	NPC469776
0.7312	Intermediate Similarity	NPC135334
0.7312	Intermediate Similarity	NPC100925
0.7312	Intermediate Similarity	NPC469777
0.7312	Intermediate Similarity	NPC295941
0.7312	Intermediate Similarity	NPC32723
0.7312	Intermediate Similarity	NPC469775
0.7312	Intermediate Similarity	NPC469773
0.7312	Intermediate Similarity	NPC469772
0.7305	Intermediate Similarity	NPC302276
0.7303	Intermediate Similarity	NPC477735
0.7301	Intermediate Similarity	NPC471025
0.7301	Intermediate Similarity	NPC230331
0.73	Intermediate Similarity	NPC315889
0.7299	Intermediate Similarity	NPC470274
0.7288	Intermediate Similarity	NPC5115
0.7288	Intermediate Similarity	NPC469398
0.7288	Intermediate Similarity	NPC472549
0.7284	Intermediate Similarity	NPC77651
0.7284	Intermediate Similarity	NPC28069
0.7257	Intermediate Similarity	NPC475417
0.7257	Intermediate Similarity	NPC475561
0.7239	Intermediate Similarity	NPC190849
0.7239	Intermediate Similarity	NPC147032
0.7239	Intermediate Similarity	NPC171007
0.7232	Intermediate Similarity	NPC469477
0.7232	Intermediate Similarity	NPC133430
0.7229	Intermediate Similarity	NPC209851
0.7225	Intermediate Similarity	NPC301946
0.7225	Intermediate Similarity	NPC277053
0.7222	Intermediate Similarity	NPC112492
0.7222	Intermediate Similarity	NPC162925
0.7222	Intermediate Similarity	NPC472268
0.7222	Intermediate Similarity	NPC87153
0.7222	Intermediate Similarity	NPC472269
0.7222	Intermediate Similarity	NPC45606
0.7222	Intermediate Similarity	NPC472270
0.7222	Intermediate Similarity	NPC23020
0.7222	Intermediate Similarity	NPC220838
0.7216	Intermediate Similarity	NPC470153
0.7213	Intermediate Similarity	NPC477491
0.7209	Intermediate Similarity	NPC262216
0.7206	Intermediate Similarity	NPC315253
0.7204	Intermediate Similarity	NPC471870
0.7202	Intermediate Similarity	NPC180770

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 NPC475649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	490
0.2-0.3	1167
0.3-0.4	2872
0.4-0.5	3236
0.5-0.6	1022
0.6-0.7	188
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7778	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD8407	Phase 2
0.7574	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8368	Discontinued
0.7553	Intermediate Similarity	NPD8360	Approved
0.7553	Intermediate Similarity	NPD8361	Approved
0.746	Intermediate Similarity	NPD8435	Approved
0.7409	Intermediate Similarity	NPD8485	Approved
0.7354	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD8320	Phase 1
0.7323	Intermediate Similarity	NPD8319	Approved
0.7241	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7874	Approved
0.7024	Intermediate Similarity	NPD7783	Phase 2
0.7024	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7801	Approved
0.702	Intermediate Similarity	NPD7700	Phase 2
0.702	Intermediate Similarity	NPD7699	Phase 2
0.7019	Intermediate Similarity	NPD8404	Phase 2
0.701	Intermediate Similarity	NPD8151	Discontinued
0.6982	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7799	Discontinued
0.6881	Remote Similarity	NPD6823	Phase 2
0.6878	Remote Similarity	NPD7701	Phase 2
0.6869	Remote Similarity	NPD6534	Approved
0.6869	Remote Similarity	NPD6535	Approved
0.6847	Remote Similarity	NPD7697	Approved
0.6847	Remote Similarity	NPD7698	Approved
0.6847	Remote Similarity	NPD7696	Phase 3
0.6814	Remote Similarity	NPD7870	Phase 2
0.6814	Remote Similarity	NPD7871	Phase 2
0.6753	Remote Similarity	NPD8312	Approved
0.6753	Remote Similarity	NPD8313	Approved
0.6746	Remote Similarity	NPD8462	Phase 1
0.67	Remote Similarity	NPD6780	Approved
0.67	Remote Similarity	NPD6781	Approved
0.67	Remote Similarity	NPD6782	Approved
0.67	Remote Similarity	NPD6776	Approved
0.67	Remote Similarity	NPD6778	Approved
0.67	Remote Similarity	NPD6779	Approved
0.67	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD8417	Discontinued
0.6651	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6213	Phase 3
0.665	Remote Similarity	NPD6212	Phase 3
0.665	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2575	Approved
0.6604	Remote Similarity	NPD7930	Approved
0.6575	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD8059	Phase 3
0.6566	Remote Similarity	NPD8150	Discontinued
0.6545	Remote Similarity	NPD8515	Approved
0.6545	Remote Similarity	NPD8517	Approved
0.6545	Remote Similarity	NPD8516	Approved
0.6538	Remote Similarity	NPD7999	Approved
0.6522	Remote Similarity	NPD7497	Discontinued
0.6522	Remote Similarity	NPD7435	Discontinued
0.6514	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD2613	Approved
0.645	Remote Similarity	NPD8074	Phase 3
0.6446	Remote Similarity	NPD8513	Phase 3
0.6443	Remote Similarity	NPD7228	Approved
0.6437	Remote Similarity	NPD3090	Approved
0.6437	Remote Similarity	NPD3614	Approved
0.6437	Remote Similarity	NPD3616	Approved
0.6437	Remote Similarity	NPD3088	Approved
0.6437	Remote Similarity	NPD3087	Approved
0.6437	Remote Similarity	NPD2573	Approved
0.6437	Remote Similarity	NPD2566	Approved
0.6437	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD2570	Approved
0.6437	Remote Similarity	NPD3615	Approved
0.6437	Remote Similarity	NPD3089	Approved
0.6437	Remote Similarity	NPD2574	Discontinued
0.6437	Remote Similarity	NPD4745	Approved
0.6437	Remote Similarity	NPD4746	Phase 3
0.6437	Remote Similarity	NPD2571	Approved
0.6436	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8323	Discontinued
0.6383	Remote Similarity	NPD8455	Phase 2
0.6369	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD4685	Phase 3
0.6364	Remote Similarity	NPD4684	Phase 3
0.6364	Remote Similarity	NPD4686	Approved
0.6364	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8468	Phase 2
0.6355	Remote Similarity	NPD7827	Phase 1
0.6354	Remote Similarity	NPD8166	Discontinued
0.635	Remote Similarity	NPD5036	Approved
0.6344	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7715	Approved
0.6343	Remote Similarity	NPD7714	Approved
0.6337	Remote Similarity	NPD8392	Approved
0.6337	Remote Similarity	NPD8391	Approved
0.6337	Remote Similarity	NPD8390	Approved
0.6329	Remote Similarity	NPD7565	Approved
0.6322	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7315	Approved
0.6318	Remote Similarity	NPD8434	Phase 2
0.6318	Remote Similarity	NPD5038	Approved
0.6318	Remote Similarity	NPD5037	Approved
0.6313	Remote Similarity	NPD7240	Approved
0.6292	Remote Similarity	NPD6852	Discontinued
0.629	Remote Similarity	NPD7239	Suspended
0.6284	Remote Similarity	NPD7236	Approved
0.6278	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD5035	Approved
0.625	Remote Similarity	NPD8285	Discontinued
0.625	Remote Similarity	NPD5981	Approved
0.6231	Remote Similarity	NPD5030	Phase 2
0.6215	Remote Similarity	NPD5119	Approved
0.6215	Remote Similarity	NPD5121	Approved
0.6215	Remote Similarity	NPD5120	Approved
0.6205	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD4420	Approved
0.62	Remote Similarity	NPD4954	Approved
0.62	Remote Similarity	NPD4955	Approved
0.62	Remote Similarity	NPD5028	Approved
0.62	Remote Similarity	NPD36	Approved
0.62	Remote Similarity	NPD5034	Approved
0.62	Remote Similarity	NPD5026	Approved
0.6199	Remote Similarity	NPD8451	Approved
0.6195	Remote Similarity	NPD7296	Approved
0.6188	Remote Similarity	NPD7266	Discontinued
0.6186	Remote Similarity	NPD8127	Discontinued
0.6176	Remote Similarity	NPD6836	Approved
0.6176	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD3400	Discontinued
0.6175	Remote Similarity	NPD7625	Phase 1
0.6173	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5005	Approved
0.6161	Remote Similarity	NPD5006	Approved
0.6158	Remote Similarity	NPD7961	Discontinued
0.6158	Remote Similarity	NPD37	Approved
0.6146	Remote Similarity	NPD4965	Approved
0.6146	Remote Similarity	NPD4967	Phase 2
0.6146	Remote Similarity	NPD4966	Approved
0.614	Remote Similarity	NPD8340	Approved
0.614	Remote Similarity	NPD3131	Approved
0.614	Remote Similarity	NPD3132	Approved
0.614	Remote Similarity	NPD4218	Approved
0.614	Remote Similarity	NPD4217	Approved
0.614	Remote Similarity	NPD4216	Approved
0.614	Remote Similarity	NPD8299	Approved
0.614	Remote Similarity	NPD8342	Approved
0.614	Remote Similarity	NPD2612	Approved
0.614	Remote Similarity	NPD8341	Approved
0.614	Remote Similarity	NPD2610	Approved
0.614	Remote Similarity	NPD4215	Approved
0.614	Remote Similarity	NPD2609	Approved
0.614	Remote Similarity	NPD2611	Approved
0.614	Remote Similarity	NPD2608	Approved
0.6139	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4738	Phase 2
0.6126	Remote Similarity	NPD7972	Discontinued
0.6121	Remote Similarity	NPD8133	Approved
0.6119	Remote Similarity	NPD5032	Approved
0.6114	Remote Similarity	NPD2494	Approved
0.6114	Remote Similarity	NPD2493	Approved
0.6114	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2567	Approved
0.6111	Remote Similarity	NPD2569	Approved
0.6103	Remote Similarity	NPD4582	Approved
0.6103	Remote Similarity	NPD4583	Approved
0.6102	Remote Similarity	NPD4621	Approved
0.6102	Remote Similarity	NPD4619	Approved
0.6095	Remote Similarity	NPD8294	Approved
0.6095	Remote Similarity	NPD8377	Approved
0.6092	Remote Similarity	NPD7319	Approved
0.6087	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD7458	Discontinued
0.6082	Remote Similarity	NPD7830	Approved
0.6082	Remote Similarity	NPD7829	Approved
0.6082	Remote Similarity	NPD6234	Discontinued
0.608	Remote Similarity	NPD4620	Approved
0.608	Remote Similarity	NPD4617	Approved
0.608	Remote Similarity	NPD5201	Approved
0.608	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5203	Approved
0.6077	Remote Similarity	NPD2975	Approved
0.6077	Remote Similarity	NPD2973	Approved
0.6077	Remote Similarity	NPD2974	Approved
0.6077	Remote Similarity	NPD7282	Approved
0.607	Remote Similarity	NPD5029	Approved
0.607	Remote Similarity	NPD5027	Approved
0.607	Remote Similarity	NPD5031	Approved
0.6066	Remote Similarity	NPD4580	Approved
0.6059	Remote Similarity	NPD8378	Approved
0.6059	Remote Similarity	NPD8380	Approved
0.6059	Remote Similarity	NPD8335	Approved
0.6059	Remote Similarity	NPD7503	Approved
0.6059	Remote Similarity	NPD8379	Approved
0.6059	Remote Similarity	NPD8296	Approved

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