NPASS Compound

Natural Product: NPC164389

Natural Product ID	NPC164389
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asterlingulatoside B
IUPAC Name	[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL525427
PubChem CID	10772092
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 140147 0 0 0 0 0 0 0 0999 V2000 8.2646 2.5918 1.6263 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6190 2.8661 0.1958 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1242 2.9886 -0.0166 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5398 1.8391 -0.9039 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9346 0.5527 -0.3673 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4497 0.6590 -0.5060 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0490 1.9802 -0.6972 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0503 -0.0631 -1.6412 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1801 -1.0974 -1.2962 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8044 -2.3800 -1.7483 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8067 -3.4553 -2.0741 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6241 -2.9142 -2.8445 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7187 -1.5563 -3.0750 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8455 -0.8115 -1.9268 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7784 -1.0223 -1.0141 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9502 0.0007 -0.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1857 1.1319 -1.1379 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8128 -0.1565 0.3110 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3558 -0.4842 1.6464 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9206 -1.8662 1.6672 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8935 -2.8512 1.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0926 -3.2284 2.5233 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6727 -4.1518 0.9547 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0116 -2.5432 0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8414 -1.1281 -0.2685 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4024 -0.6896 -0.2131 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3781 -1.2264 -1.1517 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8276 -0.9611 -1.3195 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3154 -0.2348 -0.0882 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7461 0.0457 -0.2287 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1656 0.0905 -1.6758 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5420 -1.1444 0.3494 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0012 -0.9779 0.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5893 0.3612 0.4496 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6861 1.5256 0.4310 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0072 2.3488 1.7005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9460 2.4615 -0.7241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2209 1.1914 0.6038 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3244 2.3639 0.5451 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9911 1.9214 1.1548 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3808 0.8959 0.2217 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9306 1.6669 -0.9977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1315 0.2640 0.8125 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5282 -0.5919 2.0138 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9322 1.2522 1.1775 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1247 1.2143 0.2956 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0615 2.1422 0.7802 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5949 0.5525 -0.5274 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8684 0.5523 -0.0436 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5308 1.8592 -0.4060 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9935 1.7021 -0.7636 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.6035 0.6671 0.1524 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7738 -0.5754 0.2360 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5381 -1.8439 -0.0067 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0428 -1.9678 -1.2817 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6711 -0.4477 -0.6107 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7604 1.2670 1.4100 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1772 1.4126 -2.1101 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3146 2.8635 0.5267 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4077 -4.1336 -0.9282 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6645 -2.9009 -0.7633 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3251 0.3954 0.9684 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9079 1.7430 -1.0642 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4465 4.1594 -0.7005 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6845 1.6524 1.7675 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1401 2.5162 2.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6024 3.3936 2.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1941 3.8745 -0.0528 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6678 2.9914 0.9382 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0993 2.0502 -1.9164 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3510 -0.2868 -0.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9616 0.1988 0.3605 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0133 -1.1064 -0.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4528 -2.2457 -2.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3366 -4.2067 -2.7104 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6770 -3.0926 -2.2928 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5326 -3.4243 -3.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8281 0.2723 -2.2258 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1630 0.2546 1.8781 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6115 -0.4292 2.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7916 -1.9263 0.9962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2331 -2.1578 2.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5349 -2.3924 2.9379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4857 -4.1413 2.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8359 -3.5406 3.3161 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0434 -5.0277 1.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6612 -4.1519 1.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7706 -4.1725 -0.1634 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9805 -2.9367 0.3996 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2851 -3.2182 -0.7351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0609 -1.1090 -1.3887 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0362 -1.9360 -1.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9921 -0.3680 -2.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3232 -1.9509 -1.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1853 -0.9912 0.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2336 0.1988 -1.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6457 0.8112 -2.2934 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9213 -0.9347 -2.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2207 -2.0864 -0.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3308 -1.1351 1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4914 -1.7670 0.8066 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2373 -1.3384 -0.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1847 0.2680 1.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7545 3.4087 1.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0586 2.3024 1.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4338 1.9517 2.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0516 2.7496 -1.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4138 3.4381 -0.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6687 2.0623 -1.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1444 0.8199 1.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2235 2.8903 -0.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7229 3.1259 1.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3864 2.8203 1.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2262 1.5607 2.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2117 1.1432 -1.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3712 2.5633 -0.5907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7665 2.1129 -1.5721 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4623 -1.6663 1.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4716 -0.2746 2.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2533 -0.3826 2.8015 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2582 1.0523 2.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5742 2.3010 1.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9752 1.4620 -0.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7811 2.5034 1.6453 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9402 0.4261 1.0546 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0462 2.2387 -1.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4737 2.6790 -0.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6353 0.4705 -0.2124 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3540 -0.6625 1.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8086 -2.6844 0.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3626 -1.8712 0.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4872 -2.8691 -1.3075 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9059 1.6351 1.7116 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3092 1.0660 -2.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9506 3.6932 0.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1845 -4.6352 -0.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2150 -2.9262 0.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5989 -0.5591 1.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1563 1.4978 -1.9993 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1585 4.0242 -1.3710 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 6 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 2 0 18 16 1 6 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 35 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 6 41 43 1 0 43 44 1 1 43 45 1 0 45 46 1 0 46 47 1 0 34 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 51 58 1 0 50 59 1 0 11 60 1 0 10 61 1 0 5 62 1 0 4 63 1 0 3 64 1 0 7 2 1 0 14 9 1 0 25 18 1 0 43 26 1 0 56 49 1 0 46 18 1 0 41 29 1 0 38 30 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 6 3 69 1 1 4 70 1 6 5 71 1 6 6 72 1 1 9 73 1 1 10 74 1 6 11 75 1 6 12 76 1 0 12 77 1 0 14 78 1 6 19 79 1 0 19 80 1 0 20 81 1 0 20 82 1 0 22 83 1 0 22 84 1 0 22 85 1 0 23 86 1 0 23 87 1 0 23 88 1 0 24 89 1 0 24 90 1 0 25 91 1 6 27 92 1 0 28 93 1 0 28 94 1 0 29 95 1 1 31 96 1 0 31 97 1 0 31 98 1 0 32 99 1 0 32100 1 0 33101 1 0 33102 1 0 34103 1 1 36104 1 0 36105 1 0 36106 1 0 37107 1 0 37108 1 0 37109 1 0 38110 1 1 39111 1 0 39112 1 0 40113 1 0 40114 1 0 42115 1 0 42116 1 0 42117 1 0 44118 1 0 44119 1 0 44120 1 0 45121 1 0 45122 1 0 46123 1 6 47124 1 0 49125 1 1 50126 1 6 51127 1 1 52128 1 6 53129 1 1 54130 1 0 54131 1 0 55132 1 0 57133 1 0 58134 1 0 59135 1 0 60136 1 0 61137 1 0 62138 1 0 63139 1 0 64140 1 0 M END

Standard InCHIKey	LKZZRBXFKDZGIP-GCWSANJMSA-N
Standard InCHI	InChI=1S/C47H76O17/c1-21-30(51)33(54)35(56)38(60-21)63-37-31(52)24(49)20-59-40(37)64-41(58)47-16-15-42(2,3)17-23(47)22-9-10-27-44(6)13-12-29(62-39-36(57)34(55)32(53)25(19-48)61-39)43(4,5)26(44)11-14-45(27,7)46(22,8)18-28(47)50/h9,21,23-40,48-57H,10-20H2,1-8H3/t21-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+,33+,34-,35+,36+,37+,38-,39-,40-,44-,45+,46+,47+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9249983]
NPO26359	Aster lingulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26359	Aster lingulatus	Species	Asteraceae	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	70400.0	nM	Open TG-GATES in vivo data: Hematology

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 NPC164389 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	21261
0.1-0.2	23618
0.2-0.3	3461
0.3-0.4	789
0.4-0.5	399
0.5-0.6	115
0.6-0.7	66
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8485	Intermediate Similarity	NPC104137
0.8485	Intermediate Similarity	NPC26626
0.8302	Intermediate Similarity	NPC286457
0.8152	Intermediate Similarity	NPC1046
0.8037	Intermediate Similarity	NPC21691
0.7981	Intermediate Similarity	NPC123522
0.7778	Intermediate Similarity	NPC85154
0.7636	Intermediate Similarity	NPC473452
0.7576	Intermediate Similarity	NPC112352
0.7455	Intermediate Similarity	NPC4749
0.7431	Intermediate Similarity	NPC283417
0.7431	Intermediate Similarity	NPC200049
0.7426	Intermediate Similarity	NPC488526
0.7411	Intermediate Similarity	NPC470876
0.7391	Intermediate Similarity	NPC220160
0.7212	Intermediate Similarity	NPC64715
0.7075	Intermediate Similarity	NPC481079
0.7037	Intermediate Similarity	NPC815
0.697	Remote Similarity	NPC475208
0.6923	Remote Similarity	NPC302543
0.6917	Remote Similarity	NPC489209
0.687	Remote Similarity	NPC13998
0.6833	Remote Similarity	NPC102505
0.6833	Remote Similarity	NPC488514
0.6803	Remote Similarity	NPC33012
0.6783	Remote Similarity	NPC57484
0.6727	Remote Similarity	NPC11242
0.6721	Remote Similarity	NPC8524
0.6698	Remote Similarity	NPC63159
0.6667	Remote Similarity	NPC475514
0.6639	Remote Similarity	NPC309223
0.6636	Remote Similarity	NPC207738
0.6636	Remote Similarity	NPC481078
0.6604	Remote Similarity	NPC232237
0.66	Remote Similarity	NPC238935
0.6587	Remote Similarity	NPC489208
0.6579	Remote Similarity	NPC135904
0.6509	Remote Similarity	NPC160415
0.6509	Remote Similarity	NPC117714
0.6496	Remote Similarity	NPC237191
0.6476	Remote Similarity	NPC76497
0.6476	Remote Similarity	NPC469946
0.6449	Remote Similarity	NPC305267
0.6449	Remote Similarity	NPC46665
0.6404	Remote Similarity	NPC79643
0.6389	Remote Similarity	NPC105800
0.6355	Remote Similarity	NPC30289
0.6316	Remote Similarity	NPC60557
0.6316	Remote Similarity	NPC475287
0.6316	Remote Similarity	NPC67857
0.6293	Remote Similarity	NPC123199
0.6286	Remote Similarity	NPC480420
0.6239	Remote Similarity	NPC480423
0.623	Remote Similarity	NPC144644
0.623	Remote Similarity	NPC37860
0.623	Remote Similarity	NPC170407
0.6182	Remote Similarity	NPC475504
0.6182	Remote Similarity	NPC297263
0.6168	Remote Similarity	NPC263756
0.6168	Remote Similarity	NPC80843
0.6154	Remote Similarity	NPC48499
0.6148	Remote Similarity	NPC305981
0.6147	Remote Similarity	NPC480475
0.6129	Remote Similarity	NPC482010
0.6129	Remote Similarity	NPC142151
0.6129	Remote Similarity	NPC267694
0.6117	Remote Similarity	NPC214484
0.6106	Remote Similarity	NPC470477
0.6106	Remote Similarity	NPC69811
0.6098	Remote Similarity	NPC261506
0.6098	Remote Similarity	NPC4328
0.6094	Remote Similarity	NPC480421
0.6075	Remote Similarity	NPC39211
0.6053	Remote Similarity	NPC31838
0.6038	Remote Similarity	NPC475516
0.6036	Remote Similarity	NPC222580
0.6036	Remote Similarity	NPC123796
0.6033	Remote Similarity	NPC265841
0.6032	Remote Similarity	NPC68767
0.6032	Remote Similarity	NPC293031
0.6019	Remote Similarity	NPC213674
0.6018	Remote Similarity	NPC301449
0.6018	Remote Similarity	NPC601290
0.6017	Remote Similarity	NPC475209
0.5984	Remote Similarity	NPC110385
0.5984	Remote Similarity	NPC41061
0.5984	Remote Similarity	NPC153673
0.5984	Remote Similarity	NPC227551
0.5984	Remote Similarity	NPC51099
0.5982	Remote Similarity	NPC302887
0.5981	Remote Similarity	NPC127056
0.5971	Remote Similarity	NPC23020
0.5965	Remote Similarity	NPC295823
0.5965	Remote Similarity	NPC174720
0.5965	Remote Similarity	NPC160452
0.5965	Remote Similarity	NPC475467
0.5935	Remote Similarity	NPC484059
0.5935	Remote Similarity	NPC484060
0.5913	Remote Similarity	NPC475486
0.5897	Remote Similarity	NPC610204
0.5888	Remote Similarity	NPC56713
0.5887	Remote Similarity	NPC236638
0.5887	Remote Similarity	NPC294453
0.5856	Remote Similarity	NPC44716
0.5856	Remote Similarity	NPC251768
0.5856	Remote Similarity	NPC173859
0.5856	Remote Similarity	NPC148603
0.5856	Remote Similarity	NPC2370
0.5851	Remote Similarity	NPC488520
0.5846	Remote Similarity	NPC275225
0.5818	Remote Similarity	NPC192791
0.5818	Remote Similarity	NPC223301
0.5818	Remote Similarity	NPC171544
0.5814	Remote Similarity	NPC480422
0.5812	Remote Similarity	NPC185466
0.581	Remote Similarity	NPC90856
0.5794	Remote Similarity	NPC70809
0.5789	Remote Similarity	NPC104372
0.5789	Remote Similarity	NPC114484
0.5776	Remote Similarity	NPC36831
0.5776	Remote Similarity	NPC187290
0.5772	Remote Similarity	NPC488308
0.5763	Remote Similarity	NPC76972
0.5763	Remote Similarity	NPC469782
0.5763	Remote Similarity	NPC204414
0.5748	Remote Similarity	NPC484063
0.5748	Remote Similarity	NPC224381
0.5748	Remote Similarity	NPC484064
0.5741	Remote Similarity	NPC235405
0.5739	Remote Similarity	NPC324875
0.5739	Remote Similarity	NPC292677
0.5729	Remote Similarity	NPC488522
0.5726	Remote Similarity	NPC271610
0.5726	Remote Similarity	NPC210729
0.5726	Remote Similarity	NPC312650
0.5726	Remote Similarity	NPC82931
0.5703	Remote Similarity	NPC250247
0.5702	Remote Similarity	NPC475160
0.5702	Remote Similarity	NPC471435
0.5702	Remote Similarity	NPC471434
0.5702	Remote Similarity	NPC471550
0.5702	Remote Similarity	NPC473714
0.5691	Remote Similarity	NPC484061
0.5691	Remote Similarity	NPC484062
0.569	Remote Similarity	NPC187618
0.5688	Remote Similarity	NPC249848
0.5688	Remote Similarity	NPC107966
0.5686	Remote Similarity	NPC48249
0.568	Remote Similarity	NPC293330
0.5678	Remote Similarity	NPC213952
0.5678	Remote Similarity	NPC288205
0.5678	Remote Similarity	NPC51465
0.5664	Remote Similarity	NPC475591
0.5664	Remote Similarity	NPC236870
0.5664	Remote Similarity	NPC235438
0.5662	Remote Similarity	NPC329893
0.5656	Remote Similarity	NPC25663
0.5652	Remote Similarity	NPC233223
0.5652	Remote Similarity	NPC183816
0.5652	Remote Similarity	NPC43589
0.5636	Remote Similarity	NPC295371
0.5635	Remote Similarity	NPC481081
0.563	Remote Similarity	NPC268184
0.5625	Remote Similarity	NPC30735
0.562	Remote Similarity	NPC603137
0.5614	Remote Similarity	NPC488517
0.5612	Remote Similarity	NPC488524
0.561	Remote Similarity	NPC481080
0.5603	Remote Similarity	NPC218954
0.5603	Remote Similarity	NPC485563
0.56	Remote Similarity	NPC258617
0.5593	Remote Similarity	NPC470915
0.5591	Remote Similarity	NPC298034
0.5591	Remote Similarity	NPC71065
0.5588	Remote Similarity	NPC484831
0.5588	Remote Similarity	NPC484830
0.5586	Remote Similarity	NPC161674
0.5583	Remote Similarity	NPC151543
0.558	Remote Similarity	NPC475394
0.558	Remote Similarity	NPC485564
0.558	Remote Similarity	NPC484829
0.5575	Remote Similarity	NPC10607
0.5565	Remote Similarity	NPC476068
0.5565	Remote Similarity	NPC488515
0.5556	Remote Similarity	NPC43550
0.5556	Remote Similarity	NPC480473
0.5556	Remote Similarity	NPC80986
0.5556	Remote Similarity	NPC480474
0.5546	Remote Similarity	NPC475119
0.5546	Remote Similarity	NPC172365
0.5537	Remote Similarity	NPC284449
0.5537	Remote Similarity	NPC475899
0.5537	Remote Similarity	NPC165204
0.5537	Remote Similarity	NPC470911
0.5528	Remote Similarity	NPC488560
0.5526	Remote Similarity	NPC68175
0.5524	Remote Similarity	NPC128925
0.5517	Remote Similarity	NPC472270
0.5517	Remote Similarity	NPC112492

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC164389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7225
0.1-0.2	1862
0.2-0.3	55
0.3-0.4	8
0.4-0.5	0
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