NPASS Compound

Natural Product: NPC158445

Natural Product ID	NPC158445
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Renieroside A3
IUPAC Name	(Z,2R)-2-hydroxy-N-[(2S,3R,4E,8E,10E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8,10-trien-2-yl]pentacos-16-enamide
Synonyms	renieroside A3
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL253326
PubChem CID	23643324
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003258] Glycosphingolipids [CHEMONTID:0001419] Neutral glycosphingolipids [CHEMONTID:0001428] Simple glycosylceramides [CHEMONTID:0004305] Glycosyl-N-acylsphingosines

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 148148 0 0 0 0 0 0 0 0999 V2000 18.9356 2.7053 1.2219 C 0 0 0 0 0 0 0 0 0 0 0 0 17.9786 3.8531 1.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6198 3.5228 1.6864 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0149 2.3166 1.0124 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6599 2.0020 1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0387 0.7947 0.9535 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6746 0.4816 1.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1071 -0.7508 0.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9870 -0.5124 -0.6271 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8539 -0.5622 -1.2712 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5638 -0.8622 -0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5931 0.2909 -0.8089 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2258 0.0043 -0.2091 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5907 -1.2003 -0.8994 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4027 -0.9718 -2.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4397 0.0577 -2.7958 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0072 -0.1703 -2.7003 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2715 -0.4449 -1.4514 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3645 0.6036 -0.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5604 0.5103 0.8112 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6723 -0.5813 1.7608 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3303 -1.9695 1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9496 -2.1405 0.8494 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1601 -1.7925 1.7751 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4638 -1.9981 1.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0818 -1.0113 0.6931 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1799 -0.4485 0.0770 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9107 0.5372 0.9193 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7336 1.5463 0.3141 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7541 1.9187 -0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5804 2.9485 -1.5756 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4343 2.3130 -2.6416 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3847 1.3141 -2.0236 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6625 1.5279 -2.1947 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7338 0.7037 -1.6900 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0087 0.9766 -1.9030 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1330 0.1542 -1.3981 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9607 1.1010 -0.5085 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1149 1.6180 0.6111 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8789 2.5479 1.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3851 3.7461 0.7508 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1514 4.6732 1.6935 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.6583 5.8830 0.9300 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4821 -0.0065 2.0505 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2010 -1.4455 -0.4599 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7426 -2.2763 0.4697 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6342 -3.1465 -0.1526 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9199 -2.9413 0.3460 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7435 -3.8343 -0.3232 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2026 -3.4617 -0.3069 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8944 -4.4701 -1.0238 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5596 -5.1761 0.3485 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1482 -5.6093 0.1832 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1358 -4.5484 -0.0242 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4612 -4.8665 -1.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8006 -6.2930 1.3765 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4447 -6.0588 -0.2725 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8751 -3.2837 0.7346 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0601 -0.5290 2.3084 O 0 0 0 0 0 0 0 0 0 0 0 0 18.8774 2.2794 2.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7101 1.9413 0.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 19.9866 3.0562 1.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8584 4.0766 -0.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 18.4075 4.7408 1.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7897 3.2701 2.7583 H 0 0 0 0 0 0 0 0 0 0 0 0 15.9680 4.4029 1.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 16.6608 1.4272 1.1516 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8420 2.5498 -0.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9775 2.8672 1.6063 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7978 1.7373 2.7022 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7311 -0.0749 1.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9066 1.0666 -0.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0338 1.3690 1.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7048 0.2851 2.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2622 -1.1697 1.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9395 -1.5128 0.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8805 -0.2737 -1.2492 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8069 -0.3710 -2.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5634 -1.2274 0.3695 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1159 -1.7017 -1.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0146 1.1448 -0.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5346 0.6497 -1.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3595 -0.2403 0.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6320 0.8874 -0.3939 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6406 -1.3700 -0.3903 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2058 -2.1238 -0.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3717 -0.7533 -2.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0957 -1.9568 -2.8123 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7228 1.0471 -2.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6852 0.3703 -3.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5030 0.7742 -3.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7447 -0.9872 -3.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1563 -0.5095 -1.7402 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4912 -1.4747 -1.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4507 0.7145 -0.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1783 1.5895 -0.9592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4811 0.6848 0.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8014 1.4937 1.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2083 -0.3209 2.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7808 -0.6313 2.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4126 -2.5826 2.3507 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0683 -2.4271 0.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8285 -1.6508 -0.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8352 -3.2411 0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1297 -2.4989 2.6401 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8046 0.0241 -0.8911 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0244 1.1566 1.3913 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4376 2.0755 0.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0604 1.3840 -1.5891 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2469 3.4874 -0.8707 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9394 3.7062 -2.0960 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7678 1.6836 -3.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9589 3.0060 -3.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0675 0.4636 -1.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9621 2.4082 -2.7727 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4967 -0.1733 -1.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2184 1.8794 -2.4959 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7077 -0.6712 -0.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7798 -0.1927 -2.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2280 1.9548 -1.1787 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8583 0.6138 -0.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2437 2.1776 0.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6659 0.7939 1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1921 2.9170 2.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7020 1.9870 1.9961 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5042 4.3373 0.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9950 3.5117 -0.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4641 5.0177 2.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0046 4.1540 2.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.0459 6.6481 1.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4728 5.6143 0.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7626 6.2965 0.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3052 -0.5067 1.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7757 -2.0036 -1.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0424 -0.8528 -0.9163 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6473 -2.8789 -1.2369 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3897 -3.8716 -1.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4101 -2.5357 -0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6234 -3.4760 0.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7789 -4.3133 -2.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8776 -5.0601 1.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1319 -6.3953 -0.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3120 -4.5718 0.7516 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7282 -5.5124 -1.0831 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8364 -6.4734 1.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4162 -6.9484 0.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3593 -3.5142 -0.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8131 0.0381 1.9982 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 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 3 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 28 44 1 0 27 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 25 58 1 0 24 59 1 0 54 47 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 0 2 64 1 0 3 65 1 0 3 66 1 0 4 67 1 0 4 68 1 0 5 69 1 0 5 70 1 0 6 71 1 0 6 72 1 0 7 73 1 0 7 74 1 0 8 75 1 0 8 76 1 0 9 77 1 0 10 78 1 0 11 79 1 0 11 80 1 0 12 81 1 0 12 82 1 0 13 83 1 0 13 84 1 0 14 85 1 0 14 86 1 0 15 87 1 0 15 88 1 0 16 89 1 0 16 90 1 0 17 91 1 0 17 92 1 0 18 93 1 0 18 94 1 0 19 95 1 0 19 96 1 0 20 97 1 0 20 98 1 0 21 99 1 0 21100 1 0 22101 1 0 22102 1 0 23103 1 0 23104 1 0 24105 1 1 27106 1 6 28107 1 1 29108 1 0 30109 1 0 31110 1 0 31111 1 0 32112 1 0 32113 1 0 33114 1 0 34115 1 0 35116 1 0 36117 1 0 37118 1 0 37119 1 0 38120 1 0 38121 1 0 39122 1 0 39123 1 0 40124 1 0 40125 1 0 41126 1 0 41127 1 0 42128 1 0 42129 1 0 43130 1 0 43131 1 0 43132 1 0 44133 1 0 45134 1 0 45135 1 0 47136 1 6 49137 1 6 50138 1 0 50139 1 0 51140 1 0 52141 1 1 53142 1 6 54143 1 1 55144 1 0 56145 1 0 57146 1 0 58147 1 0 59148 1 0 M END

Standard InCHIKey	BMKPZYPJRFUPQE-AFGMKLDUSA-N
Standard InCHI	InChI=1S/C49H89NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-43(53)48(57)50-41(40-58-49-47(56)46(55)45(54)44(39-51)59-49)42(52)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h16-18,25,27,29,35,37,41-47,49,51-56H,3-15,19-24,26,28,30-34,36,38-40H2,1-2H3,(H,50,57)/b18-17-,25-16+,29-27+,37-35+/t41-,42+,43+,44+,45+,46-,47+,49+/m0/s1
SMILES	CCCCCCCC/C=CCCCCCCCCCCCCC[C@H](C(=N[C@H]([C@@H](/C=C/CC/C=C/C=C/CCCCCCC)O)CO[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	835.65	Volume:	924.43 ? Van der Waals volume.
Dense:	0.904	LogP:	9.527 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.692 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.168 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	39.0	Rigid Bonds:	11.0
TPSA:	172.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	1.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.01	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.298	Fsp³:	0.816
MCE-18:	25.348 ? 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:	0.673	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.062 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.202	Promiscuous compounds:	0.031

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.331	MDCK Permeability:	-4.65
Pgp-inhibitor:	0.0	Pgp-substrate:	0.003
PAMPA:	0.0 ? 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):	0.198
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.003
Plasma Protein Binding (PPB):	97.741%	Volume Distribution (VD):	-0.415
Fu:	0.614% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.57
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.679	CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.995	CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.007 ? 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):

2.163

Half-life (T1/2):

3.319

ADMET: Toxicity

hERG Blockers:	0.231	hERG Blockers (10um):	0.346
Human Hepatotoxicity (H-HT):	0.996	Drug-induced Liver Injury (DILI):	0.032
AMES Toxicity:	0.098	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.04	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.186	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.964
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.718
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.731
BCF:	0.495 ? 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:	5.593 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.206 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.959 ? 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
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575970]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17848089]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Pacific	n.a.	PMID[19133758]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Culasian Point, Leyte, Philippines (S 1119.00', E 12435.60')	1991-MAR	PMID[22873824]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[24128145]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
ED50	5

Activity Type	# Activity
Cell line	5

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
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[17764148]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[23398362]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[23398362]
NPT574	Cell line	XF498	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[19487444]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[12672248]

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 NPC158445 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	22757
0.1-0.2	22692
0.2-0.3	4086
0.3-0.4	238
0.4-0.5	34
0.5-0.6	6
0.6-0.7	1
0.7-0.8	1
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC157353
1.0	High Similarity	NPC282088
0.9833	High Similarity	NPC156782
0.9833	High Similarity	NPC54961
0.95	High Similarity	NPC263545
0.95	High Similarity	NPC473950
0.95	High Similarity	NPC111567
0.95	High Similarity	NPC186840
0.95	High Similarity	NPC144916
0.95	High Similarity	NPC486421
0.95	High Similarity	NPC309898
0.95	High Similarity	NPC273493
0.95	High Similarity	NPC475125
0.95	High Similarity	NPC486419
0.95	High Similarity	NPC15851
0.95	High Similarity	NPC115448
0.95	High Similarity	NPC20819
0.95	High Similarity	NPC486418
0.95	High Similarity	NPC473604
0.95	High Similarity	NPC486420
0.95	High Similarity	NPC479188
0.95	High Similarity	NPC81468
0.8281	Intermediate Similarity	NPC282705
0.8281	Intermediate Similarity	NPC182632
0.8261	Intermediate Similarity	NPC8098
0.8261	Intermediate Similarity	NPC183449
0.8261	Intermediate Similarity	NPC197294
0.7941	Intermediate Similarity	NPC3568
0.7941	Intermediate Similarity	NPC17290
0.7941	Intermediate Similarity	NPC192066
0.7941	Intermediate Similarity	NPC256570
0.7727	Intermediate Similarity	NPC242503
0.7692	Intermediate Similarity	NPC61894
0.7692	Intermediate Similarity	NPC297079
0.7424	Intermediate Similarity	NPC43074
0.7424	Intermediate Similarity	NPC139782
0.7424	Intermediate Similarity	NPC74672
0.7424	Intermediate Similarity	NPC209047
0.7222	Intermediate Similarity	NPC23454
0.7222	Intermediate Similarity	NPC70323
0.7222	Intermediate Similarity	NPC262312
0.7222	Intermediate Similarity	NPC35269
0.7123	Intermediate Similarity	NPC45313
0.6623	Remote Similarity	NPC201128
0.5658	Remote Similarity	NPC473581
0.5526	Remote Similarity	NPC602861
0.5325	Remote Similarity	NPC475603
0.5325	Remote Similarity	NPC600808
0.5312	Remote Similarity	NPC288086
0.5135	Remote Similarity	NPC488689

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158445 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6420
0.1-0.2	2586
0.2-0.3	138
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7424	Intermediate Similarity	NPD8522	Clinical (unspecified phase)

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