NPASS Compound

Natural Product: NPC265841

Natural Product ID	NPC265841
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside I
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	gordonoside I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782843
PubChem CID	54581244
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

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 171179 0 0 0 0 0 0 0 0999 V2000 -3.5908 -4.0492 -3.9589 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2712 -2.8573 -3.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5128 -2.3594 -2.6337 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2418 -1.1553 -1.9724 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1874 -1.0509 -0.9167 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0136 0.1706 -0.3175 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5282 0.1572 0.9859 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2964 1.0322 1.1248 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5360 1.9544 2.1683 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8515 1.4416 3.3693 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0002 0.4131 3.3440 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6019 0.6418 1.9158 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7933 -0.0014 1.8529 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8656 0.8515 2.0941 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4335 0.4149 3.3090 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4972 -0.9840 3.2674 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2845 -1.4983 2.0944 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7216 -0.4736 1.1207 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9231 0.7859 1.0747 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8166 1.8822 1.1762 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7639 2.5910 0.0088 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3304 3.9220 0.1948 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8561 4.3426 -1.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9856 4.4489 -2.0574 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8596 3.2199 -2.0848 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.1049 2.6643 -0.6987 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6829 1.3981 -0.8011 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0580 3.5351 -2.7199 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4154 4.6083 -3.3256 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7622 -1.0802 -0.1507 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4588 -2.4240 1.4051 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9442 0.6534 4.2940 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8216 0.8834 4.2246 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6228 0.8350 3.9298 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1443 0.3416 5.4951 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0993 0.4706 1.4163 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0718 0.7558 0.4782 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2354 1.9256 0.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2276 1.8103 0.7185 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8043 0.4765 1.1652 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1257 -0.5237 0.2959 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3419 -0.4383 0.1055 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9449 -1.6536 0.8324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6560 -0.7414 -1.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6683 -1.8645 0.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1036 -1.9123 0.1377 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9765 -0.8225 0.7941 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2597 0.4760 0.7896 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0664 1.5092 1.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3372 1.5913 0.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9020 0.6058 0.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2859 -0.7294 0.0745 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0974 -1.3261 -1.3040 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3525 -1.6337 0.7069 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7095 -1.4766 0.1157 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2010 -0.1097 -0.1446 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1879 0.9055 -0.6044 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0665 1.1596 -2.0609 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2381 0.8417 -2.9075 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8230 0.5742 -4.3409 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1474 2.0775 -2.9477 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1016 -0.2979 -2.4773 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4202 -0.1017 -1.0120 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4546 -0.8938 -0.5280 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6970 -0.3788 -0.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8218 0.8865 -0.2609 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7965 -1.1351 0.3641 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7055 -2.4386 0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4704 -3.1913 0.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0632 -0.4655 0.7322 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7097 0.3991 1.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2024 1.6761 1.1562 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9627 -2.4032 -0.9255 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2227 -1.3945 2.1880 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5664 0.3632 2.6346 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5511 -1.2317 -1.5095 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4822 -0.9356 -3.0210 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5939 -2.0068 -3.6576 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0021 -1.4736 -4.7676 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9231 0.3234 -3.1761 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0318 -2.5261 -1.3076 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1474 -4.6019 -3.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8402 -2.1049 -3.9568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5288 -3.0953 -2.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8827 -3.0830 -1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9468 -1.8535 -0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3304 -0.9070 1.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2782 1.6419 0.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3137 2.3173 3.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6541 -0.6155 3.3715 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7445 1.7587 1.9471 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5371 1.8990 2.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9668 -1.3643 4.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4703 -1.4213 3.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1452 -2.1328 2.4539 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8028 -0.2320 1.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4629 0.8704 0.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0611 2.1575 -0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3605 5.3208 -0.9900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0851 3.6047 -1.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5384 5.3819 -1.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3022 2.4460 -2.6806 H 0 0 0 0 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0 0 0 0 0 10.1773 1.8222 -3.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0815 2.6366 -1.9938 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0981 -0.1470 -3.0006 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7837 -1.2910 -2.7667 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8082 0.9697 -0.9778 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5827 -2.9777 0.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3077 -3.0841 -0.9636 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6592 -4.2746 0.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5901 -2.9165 0.7399 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5672 -0.8799 1.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7362 -0.4325 -0.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8427 0.6109 1.0014 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8918 0.2695 1.9848 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4957 -0.3366 1.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6265 2.3434 1.6079 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7329 -3.2928 -0.5969 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6981 -2.4077 2.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2699 -1.6830 2.6983 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7857 -0.7466 2.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 0.5040 3.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9390 1.1891 3.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1537 -0.5964 2.9813 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3030 -0.5485 -1.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4800 -0.9836 -3.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2084 -2.8974 -3.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6036 -2.2341 -5.2856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0319 0.3198 -3.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8177 -2.7091 -1.8939 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 1 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 1 0 26 27 1 0 25 28 1 0 24 29 1 0 18 30 1 0 17 31 1 0 11 32 1 0 10 33 1 0 33 34 2 0 33 35 1 0 8 36 1 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 42 44 1 0 41 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 2 0 51 52 1 0 52 53 1 6 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 59 61 1 0 59 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 2 0 65 67 1 0 67 68 2 0 68 69 1 0 67 70 1 0 56 71 1 1 71 72 1 0 55 73 1 0 47 74 1 1 40 75 1 1 5 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 76 81 1 0 78 3 1 0 12 7 1 0 19 14 1 0 26 21 1 0 42 37 1 0 52 47 1 0 63 56 1 0 48 40 1 0 57 51 1 0 1 82 1 0 2 83 1 0 2 84 1 0 3 85 1 1 5 86 1 1 7 87 1 1 8 88 1 6 10 89 1 1 11 90 1 6 12 91 1 6 14 92 1 1 16 93 1 0 16 94 1 0 17 95 1 1 18 96 1 1 19 97 1 6 21 98 1 6 23 99 1 0 23100 1 0 24101 1 1 25102 1 6 26103 1 1 27104 1 0 28105 1 0 29106 1 0 30107 1 0 31108 1 0 32109 1 0 35110 1 0 37111 1 6 38112 1 0 38113 1 0 39114 1 0 39115 1 0 41116 1 6 43117 1 0 43118 1 0 43119 1 0 44120 1 0 44121 1 0 44122 1 0 45123 1 0 45124 1 0 46125 1 0 46126 1 0 48127 1 6 49128 1 0 49129 1 0 50130 1 0 53131 1 0 53132 1 0 53133 1 0 54134 1 0 54135 1 0 55136 1 1 57137 1 1 58138 1 0 58139 1 0 60140 1 0 60141 1 0 60142 1 0 61143 1 0 61144 1 0 61145 1 0 62146 1 0 62147 1 0 63148 1 6 68149 1 0 69150 1 0 69151 1 0 69152 1 0 70153 1 0 70154 1 0 70155 1 0 71156 1 0 71157 1 0 72158 1 0 73159 1 0 74160 1 0 74161 1 0 74162 1 0 75163 1 0 75164 1 0 75165 1 0 76166 1 1 77167 1 6 78168 1 6 79169 1 0 80170 1 0 81171 1 0 M END

Standard InCHIKey	BHKKNGSHLSYLPN-KOYGLFPPSA-N
Standard InCHI	InChI=1S/C57H90O24/c1-10-24(2)47(72)76-34-19-52(3,4)17-26-25-11-12-31-54(7)15-14-33(53(5,6)30(54)13-16-55(31,8)56(25,9)18-32(62)57(26,34)23-59)77-51-45(81-49-40(68)38(66)37(65)29(20-58)75-49)42(41(69)43(79-51)46(70)71)78-50-44(36(64)28(61)22-74-50)80-48-39(67)35(63)27(60)21-73-48/h10-11,26-45,48-51,58-69H,12-23H2,1-9H3,(H,70,71)/b24-10-/t26-,27+,28-,29+,30-,31+,32+,33-,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,48-,49-,50-,51+,54-,55+,56+,57-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O)O)O)C(=O)O)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[C@@H]2OC(=O)/C(=CC)/C)CO)O)C)C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1158.58	Volume:	1117.839 ? Van der Waals volume.
Dense:	1.036	LogP:	1.377 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.31 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	53.0
TPSA:	380.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	9.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.047	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.131	Fsp³:	0.895
MCE-18:	200.074 ? 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:	0.77	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.232	Promiscuous compounds:	0.203

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.167	MDCK Permeability:	-5.161
Pgp-inhibitor:	0.0	Pgp-substrate:	0.985
PAMPA:	1.0 ? 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):	0.995
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.844
Plasma Protein Binding (PPB):	63.743%	Volume Distribution (VD):	-0.459
Fu:	23.113% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.652	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.071 ? 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):

-0.256

Half-life (T1/2):

2.958

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.554	Drug-induced Liver Injury (DILI):	0.889
AMES Toxicity:	0.939	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	1.0
Carcinogencity:	0.04	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.801	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.313	RPMI-8226 Immunitoxicity:	0.211
A549 Cytotoxicity:	0.562	Hek293 Cytotoxicity:	0.191
BCF:	0.286 ? 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:	3.458 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.465 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.146 ? 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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]
NPO31118	Gordonia chrysandra	Species	Theaceae	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
Inhibition	1
IC50	1

Activity Type	# Activity
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	96.6	%	PMID[21473609]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	140.0	nM	PMID[21473609]

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 NPC265841 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	21973
0.1-0.2	23616
0.2-0.3	3101
0.3-0.4	556
0.4-0.5	377
0.5-0.6	133
0.6-0.7	36
0.7-0.8	0
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9107	High Similarity	NPC476779
0.8684	High Similarity	NPC271610
0.8584	High Similarity	NPC71391
0.8291	Intermediate Similarity	NPC484059
0.8291	Intermediate Similarity	NPC484060
0.812	Intermediate Similarity	NPC488308
0.812	Intermediate Similarity	NPC476780
0.8087	Intermediate Similarity	NPC602995
0.8051	Intermediate Similarity	NPC312650
0.7931	Intermediate Similarity	NPC283417
0.7931	Intermediate Similarity	NPC200049
0.7917	Intermediate Similarity	NPC476777
0.7815	Intermediate Similarity	NPC476774
0.7724	Intermediate Similarity	NPC488309
0.7647	Intermediate Similarity	NPC192765
0.7583	Intermediate Similarity	NPC178264
0.75	Intermediate Similarity	NPC25998
0.75	Intermediate Similarity	NPC476775
0.7339	Intermediate Similarity	NPC110700
0.7273	Intermediate Similarity	NPC277212
0.7273	Intermediate Similarity	NPC30279
0.7244	Intermediate Similarity	NPC476778
0.7188	Intermediate Similarity	NPC476776
0.7167	Intermediate Similarity	NPC284449
0.7165	Intermediate Similarity	NPC484063
0.7165	Intermediate Similarity	NPC484064
0.7154	Intermediate Similarity	NPC484061
0.7154	Intermediate Similarity	NPC484062
0.7143	Intermediate Similarity	NPC609119
0.7073	Intermediate Similarity	NPC329828
0.6983	Remote Similarity	NPC302887
0.6855	Remote Similarity	NPC47995
0.6855	Remote Similarity	NPC473918
0.6807	Remote Similarity	NPC160452
0.68	Remote Similarity	NPC4749
0.675	Remote Similarity	NPC187290
0.6744	Remote Similarity	NPC302543
0.6724	Remote Similarity	NPC44716
0.6614	Remote Similarity	NPC470518
0.6591	Remote Similarity	NPC279915
0.6496	Remote Similarity	NPC605226
0.6484	Remote Similarity	NPC21691
0.6475	Remote Similarity	NPC329976
0.6457	Remote Similarity	NPC46823
0.6452	Remote Similarity	NPC610204
0.6417	Remote Similarity	NPC64715
0.6393	Remote Similarity	NPC477193
0.629	Remote Similarity	NPC605294
0.627	Remote Similarity	NPC478155
0.627	Remote Similarity	NPC478154
0.626	Remote Similarity	NPC225791
0.625	Remote Similarity	NPC475591
0.625	Remote Similarity	NPC236870
0.6218	Remote Similarity	NPC117714
0.621	Remote Similarity	NPC104137
0.621	Remote Similarity	NPC26626
0.6179	Remote Similarity	NPC301449
0.6179	Remote Similarity	NPC601290
0.616	Remote Similarity	NPC11242
0.6154	Remote Similarity	NPC82380
0.6154	Remote Similarity	NPC244296
0.6129	Remote Similarity	NPC187618
0.6111	Remote Similarity	NPC470475
0.6083	Remote Similarity	NPC30289
0.6048	Remote Similarity	NPC23275
0.6033	Remote Similarity	NPC164389
0.5984	Remote Similarity	NPC107536
0.5984	Remote Similarity	NPC280029
0.5984	Remote Similarity	NPC9470
0.597	Remote Similarity	NPC484833
0.5952	Remote Similarity	NPC609281
0.592	Remote Similarity	NPC477191
0.5917	Remote Similarity	NPC263756
0.5917	Remote Similarity	NPC80843
0.5917	Remote Similarity	NPC22956
0.5906	Remote Similarity	NPC480939
0.5882	Remote Similarity	NPC127056
0.5827	Remote Similarity	NPC469947
0.5827	Remote Similarity	NPC207738
0.5827	Remote Similarity	NPC480948
0.5821	Remote Similarity	NPC286457
0.5814	Remote Similarity	NPC313110
0.5814	Remote Similarity	NPC610461
0.5812	Remote Similarity	NPC1046
0.5802	Remote Similarity	NPC470476
0.5794	Remote Similarity	NPC477076
0.5789	Remote Similarity	NPC85154
0.5786	Remote Similarity	NPC489209
0.5785	Remote Similarity	NPC213674
0.5781	Remote Similarity	NPC477195
0.5772	Remote Similarity	NPC251768
0.5766	Remote Similarity	NPC11577
0.5766	Remote Similarity	NPC141600
0.5758	Remote Similarity	NPC475140
0.5736	Remote Similarity	NPC472267
0.5736	Remote Similarity	NPC475119
0.5736	Remote Similarity	NPC115656
0.5736	Remote Similarity	NPC288205
0.5736	Remote Similarity	NPC51465
0.5736	Remote Similarity	NPC477196
0.5702	Remote Similarity	NPC603026
0.5672	Remote Similarity	NPC181066
0.5669	Remote Similarity	NPC218954
0.5669	Remote Similarity	NPC477075
0.5655	Remote Similarity	NPC489208
0.5649	Remote Similarity	NPC123522
0.5645	Remote Similarity	NPC488526
0.5645	Remote Similarity	NPC232237
0.5639	Remote Similarity	NPC269484
0.5639	Remote Similarity	NPC97918
0.5635	Remote Similarity	NPC79718
0.5625	Remote Similarity	NPC477077
0.561	Remote Similarity	NPC112352
0.56	Remote Similarity	NPC63159
0.5597	Remote Similarity	NPC252289
0.5597	Remote Similarity	NPC305793
0.5581	Remote Similarity	NPC481078
0.5581	Remote Similarity	NPC477194
0.5573	Remote Similarity	NPC252657
0.5573	Remote Similarity	NPC88311
0.5564	Remote Similarity	NPC603137
0.5528	Remote Similarity	NPC469946
0.5496	Remote Similarity	NPC185466
0.5484	Remote Similarity	NPC192791
0.5474	Remote Similarity	NPC473452
0.5462	Remote Similarity	NPC475486
0.5461	Remote Similarity	NPC220160
0.5455	Remote Similarity	NPC473824
0.5455	Remote Similarity	NPC485563
0.5447	Remote Similarity	NPC472949
0.5447	Remote Similarity	NPC488561
0.5435	Remote Similarity	NPC470876
0.5426	Remote Similarity	NPC324875
0.5426	Remote Similarity	NPC292677
0.5426	Remote Similarity	NPC291903
0.5426	Remote Similarity	NPC477079
0.5426	Remote Similarity	NPC606145
0.542	Remote Similarity	NPC815
0.542	Remote Similarity	NPC606553
0.541	Remote Similarity	NPC59804
0.5407	Remote Similarity	NPC264566
0.5391	Remote Similarity	NPC488515
0.5385	Remote Similarity	NPC480474
0.5379	Remote Similarity	NPC478152
0.5379	Remote Similarity	NPC478151
0.5354	Remote Similarity	NPC105800
0.5354	Remote Similarity	NPC118440
0.5349	Remote Similarity	NPC470914
0.5333	Remote Similarity	NPC123199
0.5312	Remote Similarity	NPC297263
0.5303	Remote Similarity	NPC210729
0.5303	Remote Similarity	NPC470915
0.5303	Remote Similarity	NPC82931
0.529	Remote Similarity	NPC57484
0.5285	Remote Similarity	NPC56713
0.5276	Remote Similarity	NPC104400
0.5276	Remote Similarity	NPC10320
0.5276	Remote Similarity	NPC2370
0.5276	Remote Similarity	NPC480475
0.5274	Remote Similarity	NPC485562
0.5274	Remote Similarity	NPC33012
0.527	Remote Similarity	NPC475368
0.5267	Remote Similarity	NPC480473
0.5231	Remote Similarity	NPC114692
0.5227	Remote Similarity	NPC31838
0.5224	Remote Similarity	NPC475287
0.5224	Remote Similarity	NPC607904
0.5221	Remote Similarity	NPC166422
0.5221	Remote Similarity	NPC219180
0.5221	Remote Similarity	NPC251263
0.5221	Remote Similarity	NPC135904
0.5221	Remote Similarity	NPC478150
0.5217	Remote Similarity	NPC329923
0.5217	Remote Similarity	NPC475281
0.5217	Remote Similarity	NPC478597
0.5214	Remote Similarity	NPC258617
0.5205	Remote Similarity	NPC8524
0.5194	Remote Similarity	NPC481082
0.5194	Remote Similarity	NPC470913
0.5194	Remote Similarity	NPC164419
0.5194	Remote Similarity	NPC131469
0.5191	Remote Similarity	NPC481079
0.5185	Remote Similarity	NPC151543
0.5185	Remote Similarity	NPC79643
0.5182	Remote Similarity	NPC470517
0.5182	Remote Similarity	NPC470218
0.5161	Remote Similarity	NPC300655
0.5156	Remote Similarity	NPC159309
0.5156	Remote Similarity	NPC86222
0.5154	Remote Similarity	NPC95437
0.5154	Remote Similarity	NPC471435
0.5154	Remote Similarity	NPC471434
0.5154	Remote Similarity	NPC603832
0.5152	Remote Similarity	NPC477078
0.5152	Remote Similarity	NPC477192
0.5147	Remote Similarity	NPC471384
0.5143	Remote Similarity	NPC478596
0.5143	Remote Similarity	NPC13998
0.5115	Remote Similarity	NPC236657

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC265841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6696
0.1-0.2	2403
0.2-0.3	46
0.3-0.4	4
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
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
		NPD

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