NPASS Compound

Natural Product: NPC470477

Natural Product ID	NPC470477
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BSAJSBIMAAMTCW-KMOKQNOLSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2047209
PubChem CID	21603506
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 144152 0 0 0 0 0 0 0 0999 V2000 -10.8089 1.2472 -2.6226 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6806 0.2585 -2.4370 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9216 -0.9415 -3.3104 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5902 -1.4329 -3.8350 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5199 -1.3468 -2.7548 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3900 0.0904 -2.2336 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4527 0.8001 -2.7341 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2753 0.0631 -0.8688 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0537 0.5543 -0.3889 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4044 1.6724 0.5887 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3959 1.1077 1.5660 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0823 -0.2507 2.0789 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5181 -1.1107 1.1705 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4643 -0.5575 0.4535 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4157 -0.1609 1.2544 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2316 -0.8398 0.9800 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8534 -1.5667 2.2533 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6393 -0.5955 3.3542 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0011 0.6941 2.9712 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1488 1.0966 1.6917 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0831 0.0969 0.7299 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8265 -0.4869 0.8767 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0419 -0.2122 -0.1776 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1509 0.7261 0.2432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2719 0.0733 0.9674 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6222 -1.3117 0.4856 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9990 -1.6584 -0.8199 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5169 -1.4066 -0.9148 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1672 -1.2367 -2.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2804 -2.6310 -0.5106 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6701 -1.0392 -2.0030 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0368 -0.4614 -1.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7972 -1.4005 -0.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1237 -1.5562 0.4867 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7687 -0.8144 1.6354 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6303 0.3031 1.2687 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3439 0.2875 0.1508 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2279 -0.9002 -0.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8161 -0.7450 -2.0631 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0109 0.7153 -2.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0230 1.1279 -1.4014 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2290 1.4601 -0.1726 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2169 1.7048 0.9468 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1936 2.7573 0.5910 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8465 2.5916 -0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8774 2.2700 -1.8489 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6560 1.8244 -2.9426 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6302 4.1651 0.6463 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3269 2.7125 1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8045 -0.1324 -1.2443 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8575 -0.3196 -0.5450 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1983 -1.1440 -2.0079 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0119 -2.0163 0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9191 -2.7643 -1.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0713 -2.2623 1.5673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3488 1.8094 3.8874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7030 2.9041 3.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 1.6817 5.2718 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6482 2.8099 6.0469 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8696 -0.3203 3.9481 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7727 -2.5649 2.5678 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3891 -0.8771 2.5519 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1966 -2.1083 3.1517 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6982 1.1097 1.0521 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9883 2.7496 -0.0721 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3222 -1.7641 -3.3039 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7190 -2.7757 -4.1585 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7669 -0.6419 -4.3914 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6162 0.9820 -1.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4593 2.2696 -2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2199 1.2186 -3.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7071 -0.0766 -1.3771 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4475 -1.7623 -2.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2848 -0.8769 -4.7477 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8269 -2.0468 -1.9501 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4453 0.5186 -2.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3877 0.8809 -1.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4927 1.9539 1.1496 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4195 1.8052 2.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4386 -0.1905 2.9883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1038 -1.3518 -0.2483 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3637 -1.5656 0.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9053 -2.1020 2.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0298 -1.1105 4.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8877 0.5439 3.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1338 0.6310 -0.2486 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5774 0.4382 -0.8736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6837 1.4968 0.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5242 1.2709 -0.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1553 0.7592 0.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0086 0.0835 2.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1057 -2.7793 -0.9357 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8915 -1.6009 -2.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7868 -1.8428 -3.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 -0.1555 -2.6795 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3610 -2.4818 -0.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 -2.8745 0.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0095 -3.5141 -1.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1018 -0.2070 -2.4764 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7995 -1.7925 -2.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0334 0.5472 -1.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5531 -0.4014 -2.7126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2689 -2.6505 0.7622 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 -1.4935 2.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9762 -0.4686 2.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7063 1.1790 1.9089 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3595 -1.3426 -2.8436 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4555 0.7243 -3.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1353 1.3390 -2.3244 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6710 2.3779 -0.3441 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7514 0.7790 1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6383 2.0356 1.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3127 3.5790 -1.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6909 1.8642 -0.7161 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2629 3.1251 -2.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4008 2.4486 -3.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3641 4.3834 1.6933 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7867 4.2901 -0.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4705 4.8503 0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9448 2.5209 2.6457 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9922 1.8499 1.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9612 3.6213 1.5532 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6373 -1.6155 0.8349 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3543 -2.7698 0.4383 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7085 -2.5228 -0.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5794 -2.7353 -2.5574 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3756 -3.5337 -0.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9653 -3.1381 -1.5390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2094 -1.8401 2.0970 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9848 -3.2862 1.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8617 -2.3281 2.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5362 3.3359 5.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9516 2.4640 7.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 3.5355 6.1426 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8055 -0.2764 4.9341 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9931 -2.5759 3.5148 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0092 -1.0334 1.6459 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9601 -0.1748 3.1944 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4782 -2.5769 2.6582 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3333 1.6214 1.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9093 3.5520 0.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3520 -1.7886 -4.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6592 -3.0514 -4.1265 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3174 -0.0507 -5.0616 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 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 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 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 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 44 48 1 0 44 49 1 0 41 50 1 0 50 51 2 0 50 52 1 0 38 53 1 0 33 54 1 0 26 55 1 0 19 56 1 0 56 57 2 0 56 58 1 0 58 59 1 0 18 60 1 0 17 61 1 0 12 62 1 0 62 63 1 0 11 64 1 0 10 65 1 0 5 66 1 0 4 67 1 0 3 68 1 0 7 2 1 0 14 9 1 0 21 16 1 0 28 23 1 0 34 26 1 0 38 33 1 0 42 37 1 0 52 39 1 0 46 41 1 0 1 69 1 0 1 70 1 0 1 71 1 0 2 72 1 0 3 73 1 0 4 74 1 0 5 75 1 0 6 76 1 0 9 77 1 0 10 78 1 0 11 79 1 0 12 80 1 0 14 81 1 0 16 82 1 0 17 83 1 0 18 84 1 0 19 85 1 0 21 86 1 0 23 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 25 91 1 0 27 92 1 0 29 93 1 0 29 94 1 0 29 95 1 0 30 96 1 0 30 97 1 0 30 98 1 0 31 99 1 0 31100 1 0 32101 1 0 32102 1 0 34103 1 0 35104 1 0 35105 1 0 36106 1 0 39107 1 0 40108 1 0 40109 1 0 42110 1 0 43111 1 0 43112 1 0 45113 1 0 45114 1 0 46115 1 0 47116 1 0 48117 1 0 48118 1 0 48119 1 0 49120 1 0 49121 1 0 49122 1 0 53123 1 0 53124 1 0 53125 1 0 54126 1 0 54127 1 0 54128 1 0 55129 1 0 55130 1 0 55131 1 0 59132 1 0 59133 1 0 59134 1 0 60135 1 0 61136 1 0 62137 1 0 62138 1 0 63139 1 0 64140 1 0 65141 1 0 66142 1 0 67143 1 0 68144 1 0 M END

Standard InCHIKey	BSAJSBIMAAMTCW-KMOKQNOLSA-N
Standard InCHI	InChI=1S/C49H76O19/c1-20-29(52)31(54)35(58)40(62-20)67-37-32(55)30(53)23(19-50)63-41(37)68-38-34(57)33(56)36(39(59)61-9)66-42(38)64-27-13-14-46(6)24(45(27,4)5)12-15-47(7)25(46)11-10-21-22-16-44(2,3)17-26(51)49(22)18-28(48(21,47)8)65-43(49)60/h10,20,22-38,40-42,50-58H,11-19H2,1-9H3/t20-,22-,23+,24-,25+,26-,27-,28+,29-,30+,31+,32-,33-,34-,35+,36-,37+,38+,40-,41-,42+,46-,47+,48-,49-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(C8CC9(C7CC(CC9O)(C)C)C(=O)O8)C)C)C)C(=O)OC)O)O)CO)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
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	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
IC50	1
Inhibition	1

Activity Type	# Activity
Cell line	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
NPT521	Cell line	RBL-2H3	Rattus norvegicus	IC50	>	200000.0	nM	PMID[19318257]
NPT521	Cell line	RBL-2H3	Rattus norvegicus	Inhibition	=	40.3	%	DrugMatrix in vivo data: Pathology

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 NPC470477 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	21113
0.1-0.2	24132
0.2-0.3	3381
0.3-0.4	745
0.4-0.5	407
0.5-0.6	68
0.6-0.7	4
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	Natural Product ID
0.6339	Remote Similarity	NPC162574
0.6154	Remote Similarity	NPC207738
0.6106	Remote Similarity	NPC164389
0.6	Remote Similarity	NPC297263
0.595	Remote Similarity	NPC123522
0.5776	Remote Similarity	NPC105800
0.5726	Remote Similarity	NPC222580
0.5726	Remote Similarity	NPC470913
0.5703	Remote Similarity	NPC470876
0.561	Remote Similarity	NPC610204
0.561	Remote Similarity	NPC610461
0.5583	Remote Similarity	NPC486564
0.5575	Remote Similarity	NPC25605
0.5565	Remote Similarity	NPC469946
0.5546	Remote Similarity	NPC486563
0.5538	Remote Similarity	NPC484059
0.5538	Remote Similarity	NPC484060
0.5517	Remote Similarity	NPC112352
0.55	Remote Similarity	NPC236657
0.55	Remote Similarity	NPC78034
0.5495	Remote Similarity	NPC214484
0.5492	Remote Similarity	NPC31838
0.5462	Remote Similarity	NPC123796
0.5455	Remote Similarity	NPC481079
0.5455	Remote Similarity	NPC606145
0.5446	Remote Similarity	NPC1046
0.5426	Remote Similarity	NPC484061
0.5426	Remote Similarity	NPC484062
0.5424	Remote Similarity	NPC232237
0.5417	Remote Similarity	NPC64715
0.5373	Remote Similarity	NPC484063
0.5373	Remote Similarity	NPC484064
0.536	Remote Similarity	NPC607904
0.5308	Remote Similarity	NPC21691
0.5294	Remote Similarity	NPC10607
0.5294	Remote Similarity	NPC148603
0.5294	Remote Similarity	NPC2370
0.5294	Remote Similarity	NPC480475
0.5289	Remote Similarity	NPC95437
0.5271	Remote Similarity	NPC277212
0.5271	Remote Similarity	NPC30279
0.5267	Remote Similarity	NPC286457
0.5254	Remote Similarity	NPC223301
0.5254	Remote Similarity	NPC171544
0.5246	Remote Similarity	NPC114692
0.5242	Remote Similarity	NPC104137
0.5242	Remote Similarity	NPC26626
0.5242	Remote Similarity	NPC609281
0.5207	Remote Similarity	NPC131469
0.5194	Remote Similarity	NPC471550
0.5175	Remote Similarity	NPC164194
0.5167	Remote Similarity	NPC488526
0.5159	Remote Similarity	NPC172365
0.5154	Remote Similarity	NPC470912
0.5126	Remote Similarity	NPC469945
0.5124	Remote Similarity	NPC118440
0.512	Remote Similarity	NPC36831
0.5118	Remote Similarity	NPC268184
0.5113	Remote Similarity	NPC225791
0.5103	Remote Similarity	NPC329893
0.5086	Remote Similarity	NPC12288
0.5083	Remote Similarity	NPC480947
0.5083	Remote Similarity	NPC160415
0.5079	Remote Similarity	NPC470915
0.5078	Remote Similarity	NPC151543
0.5041	Remote Similarity	NPC173859
0.5041	Remote Similarity	NPC302887
0.5041	Remote Similarity	NPC46665
0.504	Remote Similarity	NPC120116
0.504	Remote Similarity	NPC160452
0.5036	Remote Similarity	NPC220160
0.5034	Remote Similarity	NPC329878

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7288
0.1-0.2	1810
0.2-0.3	47
0.3-0.4	5
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