NPASS Compound

Natural Product: NPC75726

Natural Product ID	NPC75726
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cyclolinopeptide H
IUPAC Name	(3S,6S,9S,12S,15S,18S,21S,24S)-18,21-dibenzyl-12-[(2S)-butan-2-yl]-15-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3-(2-methylsulfanylethyl)-9-(2-methylsulfinylethyl)-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3785507
PubChem CID	10558089
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 151156 0 0 0 0 0 0 0 0999 V2000 8.1720 -5.9942 -2.9129 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7044 -6.7419 -2.2053 S 0 0 0 0 0 0 0 0 0 0 0 0 5.3028 -5.5639 -2.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6039 -4.4267 -1.2391 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4725 -3.4201 -1.1447 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9340 -2.3847 -0.2198 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7591 -1.1345 -0.5185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1557 -0.6725 -1.6542 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2803 -0.1109 0.4837 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6140 -0.8187 1.7303 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1936 -0.1013 2.8881 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 0.9741 3.5166 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5722 0.4974 2.5422 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6529 1.0900 0.3841 N 0 0 0 0 0 0 0 0 0 0 0 0 4.1273 2.1344 0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9505 2.9908 1.4604 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5467 2.7098 -0.9189 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4835 3.8915 -1.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9407 4.4881 -2.5579 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9124 5.8968 -3.1175 S 0 0 0 0 0 0 0 0 0 0 0 0 4.8072 7.0527 -2.1086 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6129 5.4828 -3.4527 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2465 3.1806 -0.8300 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1875 2.9668 -0.2403 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0233 1.9697 0.6866 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0024 3.8559 -0.5454 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1852 3.2000 -0.6982 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1927 2.7259 -0.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3188 2.8296 1.2434 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2448 2.0530 -0.9328 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2738 0.6008 -0.7259 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 -0.1813 -1.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9272 -1.6425 -1.5124 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2999 -2.2306 -0.3393 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.8290 -3.4159 -0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1928 -4.0224 0.8809 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8582 -3.9174 0.9386 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2973 -3.6529 1.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3201 -4.7060 0.7120 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6235 -4.1451 0.5192 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2082 -4.0151 -0.7573 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4801 -4.5139 -1.6333 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1660 -3.8180 1.7710 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8159 -5.0762 2.5817 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4916 -5.5203 1.9758 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7097 -2.3851 1.4783 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8497 -3.5909 2.1757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2780 -3.9542 2.2582 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5273 -5.2670 2.6651 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8087 -5.7672 2.8067 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8617 -4.9257 2.5321 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6311 -3.6124 2.1254 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3248 -3.1339 1.9910 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8986 -4.1869 -1.4580 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4125 -2.0233 -1.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1501 -1.5582 -2.6566 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1529 -2.2880 -3.8481 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8762 -1.8648 -4.9394 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6011 -0.6992 -4.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6228 0.0482 -3.6680 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9000 -0.3831 -2.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3759 0.4253 -2.7203 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5967 2.6297 -0.7965 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2251 2.6734 0.5093 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9197 1.6154 1.1142 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3000 1.9766 2.3501 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8803 3.2410 2.5821 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2082 3.6812 1.4327 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7142 4.9680 1.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8630 5.7889 2.4978 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5346 5.3249 3.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0463 4.0540 3.6845 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0102 5.0403 0.3792 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1330 5.9923 0.0997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0866 6.5445 -1.3081 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2862 5.8434 0.2857 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8430 -6.7956 -3.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7631 -5.4284 -2.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9695 -5.3231 -3.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3933 -6.1228 -1.9396 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2107 -5.1875 -3.2253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9690 -4.7696 -0.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4588 -3.8569 -1.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3867 -2.9491 -2.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3726 -1.2291 -2.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3512 0.0678 -0.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7520 -1.4811 2.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3852 -1.6177 1.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3931 -0.8823 3.6978 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5154 0.8947 4.6439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3178 0.7439 3.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7027 1.9885 3.2566 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1525 -0.3527 2.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4340 1.2930 1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0423 0.8349 3.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6164 2.7503 2.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6564 1.9451 -1.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4720 4.5806 -0.4448 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4878 3.4352 -1.4528 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9421 3.7333 -3.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9153 4.8664 -2.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9858 4.6875 -2.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7269 5.2873 -4.5355 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2215 6.4000 -3.2393 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8137 1.3146 0.8011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2824 4.3045 -1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5199 2.6402 1.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9626 2.1740 -2.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5056 -2.0593 -2.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4848 -5.1529 0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9866 -5.3476 -0.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8246 -2.9025 2.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2783 -3.7919 1.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 -5.8691 2.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7668 -4.8832 3.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7140 -5.3073 2.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4947 -6.6110 1.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0696 -1.6979 1.8431 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3363 -4.0441 3.0402 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7682 -2.4892 2.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7070 -5.9644 2.8901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0176 -6.7791 3.1164 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8743 -5.2805 2.6344 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4288 -2.9293 1.9023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1300 -2.1202 1.6887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0970 -3.9330 -2.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5070 -3.1367 -1.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9015 -1.5868 -0.5638 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5637 -3.1914 -3.8801 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8498 -2.4578 -5.8461 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1756 -0.3509 -5.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1997 0.9659 -3.5790 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8681 0.1469 -1.6351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0179 1.1971 -3.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3457 2.1349 -1.4957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5476 3.6803 -1.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0846 0.6823 0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8392 1.3699 3.0314 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2347 5.2615 0.4937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4732 6.7871 2.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6164 6.0341 4.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5565 3.7408 4.5812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0917 4.7292 1.4375 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0340 6.8281 0.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0609 5.4755 0.3177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1620 6.2710 -1.8201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1663 7.6575 -1.2471 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0099 6.2004 -1.8304 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1234 5.3571 0.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0875 6.8211 0.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5554 6.0283 -0.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 3 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 9 14 1 0 14 15 2 3 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 17 23 1 0 23 24 2 3 24 25 1 0 24 26 1 0 26 27 1 0 27 28 2 3 28 29 1 0 28 30 1 0 30 31 1 0 31 32 2 3 32 33 1 0 33 34 1 0 34 35 2 3 35 36 1 0 36 37 1 0 37 38 2 3 38 39 1 0 39 40 1 0 40 41 1 0 41 42 2 0 40 43 1 0 43 44 1 0 44 45 1 0 38 46 1 0 36 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 35 54 1 0 33 55 1 0 55 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 2 0 32 62 1 0 30 63 1 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 1 0 67 68 2 0 68 69 1 0 69 70 2 0 70 71 1 0 71 72 2 0 26 73 1 0 73 74 1 0 74 75 1 0 73 76 1 0 41 5 1 0 53 48 1 0 61 56 1 0 68 64 1 0 45 39 1 0 72 67 1 0 1 77 1 0 1 78 1 0 1 79 1 0 3 80 1 0 3 81 1 0 4 82 1 0 4 83 1 0 5 84 1 6 8 85 1 0 9 86 1 6 10 87 1 0 10 88 1 0 11 89 1 0 12 90 1 0 12 91 1 0 12 92 1 0 13 93 1 0 13 94 1 0 13 95 1 0 16 96 1 0 17 97 1 6 18 98 1 0 18 99 1 0 19100 1 0 19101 1 0 22102 1 0 22103 1 0 22104 1 0 25105 1 0 26106 1 6 29107 1 0 30108 1 6 33109 1 6 36110 1 6 39111 1 6 43112 1 0 43113 1 0 44114 1 0 44115 1 0 45116 1 0 45117 1 0 46118 1 0 47119 1 0 47120 1 0 49121 1 0 50122 1 0 51123 1 0 52124 1 0 53125 1 0 54126 1 0 55127 1 0 55128 1 0 57129 1 0 58130 1 0 59131 1 0 60132 1 0 61133 1 0 62134 1 0 63135 1 0 63136 1 0 65137 1 0 66138 1 0 69139 1 0 70140 1 0 71141 1 0 72142 1 0 73143 1 1 74144 1 0 74145 1 0 75146 1 0 75147 1 0 75148 1 0 76149 1 0 76150 1 0 76151 1 0 M END

Standard InCHIKey	RGLVOQUKDGQVGR-MYFHKKGJSA-N
Standard InCHI	InChI=1S/C56H75N9O9S2/c1-7-35(4)48-55(72)58-41(25-28-76(6)74)49(66)60-43(29-34(2)3)50(67)59-42(24-27-75-5)56(73)65-26-16-23-47(65)54(71)63-45(31-37-19-12-9-13-20-37)52(69)61-44(30-36-17-10-8-11-18-36)51(68)62-46(53(70)64-48)32-38-33-57-40-22-15-14-21-39(38)40/h8-15,17-22,33-35,41-48,57H,7,16,23-32H2,1-6H3,(H,58,72)(H,59,67)(H,60,66)(H,61,69)(H,62,68)(H,63,71)(H,64,70)/t35-,41-,42-,43-,44-,45-,46-,47-,48-,76?/m0/s1
SMILES	CSCC[C@@H]1N=C(O)[C@H](CC(C)C)N=C(O)[C@H](CCS(=O)C)N=C(O)[C@@H](N=C(O)[C@@H](N=C([C@@H](N=C([C@@H](N=C([C@H]2N(C1=O)CCC2)O)Cc1ccccc1)O)Cc1ccccc1)O)Cc1c[nH]c2c1cccc2)[C@H](CC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1081.51	Volume:	1093.438 ? Van der Waals volume.
Dense:	0.989	LogP:	1.413 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.433 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.865 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	51.0
TPSA:	287.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.014	Fsp³:	0.5
MCE-18:	140.262 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.726	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.028 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.616 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.749	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.302	MDCK Permeability:	-4.892
Pgp-inhibitor:	0.986	Pgp-substrate:	1.0
PAMPA:	0.247 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.887
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.481
Plasma Protein Binding (PPB):	82.693%	Volume Distribution (VD):	-0.527
Fu:	16.066% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.208	BCRP inhibitor:	0.082
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.918	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.79 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.769

Half-life (T1/2):

2.139

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.047	Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.981	Skin Sensitization:	1.0
Carcinogencity:	0.609	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.851
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	1.0
Hematotoxicity:	0.219	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.437 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.561 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.154 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.406 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	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	Organism Name	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	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21723	Cell line	Bone marrow cell	n.a.	IC50	=	830.0	nM	PMID[26923696]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC75726 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	25776
0.1-0.2	22218
0.2-0.3	1336
0.3-0.4	385
0.4-0.5	104
0.5-0.6	20
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC479076
0.9286	High Similarity	NPC479066
0.9175	High Similarity	NPC479065
0.8958	High Similarity	NPC110602
0.8958	High Similarity	NPC479071
0.87	High Similarity	NPC479073
0.8586	High Similarity	NPC479075
0.8367	Intermediate Similarity	NPC31385
0.6179	Remote Similarity	NPC325976
0.6179	Remote Similarity	NPC326363
0.614	Remote Similarity	NPC162860
0.6126	Remote Similarity	NPC223791
0.6106	Remote Similarity	NPC54420
0.6058	Remote Similarity	NPC479074
0.6019	Remote Similarity	NPC487314
0.6	Remote Similarity	NPC107077
0.6	Remote Similarity	NPC479574
0.598	Remote Similarity	NPC479072
0.5909	Remote Similarity	NPC293917
0.5748	Remote Similarity	NPC489555
0.5701	Remote Similarity	NPC479070
0.5688	Remote Similarity	NPC479069
0.5688	Remote Similarity	NPC489625
0.5683	Remote Similarity	NPC75634
0.5532	Remote Similarity	NPC484874
0.5417	Remote Similarity	NPC482001
0.5333	Remote Similarity	NPC155143
0.5317	Remote Similarity	NPC100321
0.5304	Remote Similarity	NPC483341
0.5268	Remote Similarity	NPC213629
0.5263	Remote Similarity	NPC49954
0.5238	Remote Similarity	NPC479068
0.5185	Remote Similarity	NPC34779
0.5154	Remote Similarity	NPC483985
0.51	Remote Similarity	NPC17059
0.5045	Remote Similarity	NPC322878
0.5033	Remote Similarity	NPC153400

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC75726 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3323
0.1-0.2	5480
0.2-0.3	304
0.3-0.4	27
0.4-0.5	11
0.5-0.6	4
0.6-0.7	1
0.7-0.8	0
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
0.6	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.5462	Remote Similarity	NPD8405	Pre-clinical
0.5122	Remote Similarity	NPD8272	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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