NPASS Compound

Natural Product: NPC308191

Natural Product ID	NPC308191
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DOSPRDHNGNPKKJ-BYPUAWAASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2430127
PubChem CID	56841025
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002875] Tigliane and ingenane diterpenoids

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 100103 0 0 0 0 0 0 0 0999 V2000 13.0414 1.4541 -0.7955 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7679 0.0401 -0.2894 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4904 -0.4990 -0.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2453 -1.8988 -0.4494 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0342 -2.4809 -1.0857 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7760 -1.6455 -0.8185 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5296 -1.5603 0.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3702 -0.7987 1.1290 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9808 -1.1611 0.8952 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4422 -1.2775 -0.4688 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9388 -1.5917 -0.4558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1176 -0.5520 0.2141 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6207 -0.8562 0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1067 -0.9715 -1.1761 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3685 -1.2608 -1.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1190 -0.1419 -0.6305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6229 0.9233 -0.1865 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5196 -0.1880 -0.5010 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2687 0.8324 0.0548 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2472 1.4582 -0.8778 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4783 1.0293 -0.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4612 0.0973 0.4941 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8013 -1.2374 -0.0278 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3927 -1.4870 -1.4531 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3210 -1.3453 -0.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0767 -0.1860 -0.4807 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2532 1.0471 0.1825 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5119 1.4015 1.4221 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5837 2.5879 1.2379 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2748 2.7071 1.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7264 4.0558 1.1321 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7007 4.8994 0.6435 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3796 1.6628 2.0204 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2073 0.4216 1.1685 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6264 -0.5839 1.9046 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6823 1.3506 3.3431 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5015 0.2930 1.5786 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4889 -0.4231 2.5076 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4047 0.1365 0.1737 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5991 0.4358 -0.7526 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8236 -0.4038 1.4852 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8140 2.4176 -1.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8284 1.3694 -1.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4262 2.0869 0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1099 1.8769 -1.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5815 0.0387 0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6240 -0.6129 -0.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6748 0.1885 -0.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6253 -0.5286 -2.0626 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2319 -1.8732 0.6563 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1458 -2.5511 -0.6848 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1178 -2.5682 -2.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8678 -3.5186 -0.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9599 -2.0442 -1.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9510 -0.6053 -1.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4932 -1.1296 1.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5261 -2.5972 1.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5184 0.3023 0.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4942 -0.7080 2.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3586 -0.3241 1.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7062 -2.0615 1.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9276 -2.1791 -0.9666 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6652 -0.3756 -1.0572 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8208 -2.5901 -0.0372 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6697 -1.6368 -1.5346 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2890 0.4722 -0.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -0.5076 1.3020 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1639 -0.0138 0.7655 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5281 -1.8147 0.7865 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3548 -0.0069 -1.6953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6983 -1.7427 -1.7199 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5612 -2.2270 -0.7231 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6889 -1.2970 -2.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5918 1.6766 0.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3070 1.3777 -1.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4056 -2.0735 0.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3796 -1.9012 -1.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4878 -0.6111 -2.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0747 -2.2730 -1.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5915 -1.7538 0.9648 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5537 -2.2202 -0.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1603 -0.1479 -1.6177 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4538 1.9841 -0.4274 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1313 1.5086 2.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0597 3.4647 0.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8345 3.9571 0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3880 4.4721 2.1288 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2713 5.6635 0.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3624 2.1596 2.0811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1560 -1.3830 2.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9604 0.7492 3.6583 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9765 1.4343 -0.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2498 0.3366 -1.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3158 -0.3835 -0.6015 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0570 0.4867 2.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8321 -0.9057 1.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1189 -1.0007 2.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0001 3.0292 -1.5226 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3671 1.8045 -2.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6628 3.0272 -2.3084 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 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 22 21 1 6 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 30 33 1 0 33 34 1 0 34 35 1 1 33 36 1 0 28 37 1 0 37 38 2 0 27 39 1 0 39 40 1 0 39 41 1 0 20 42 1 0 34 19 1 0 37 22 1 0 34 22 1 0 39 26 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 6 55 1 0 7 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 10 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 19 74 1 1 21 75 1 0 23 76 1 1 24 77 1 0 24 78 1 0 24 79 1 0 25 80 1 0 25 81 1 0 26 82 1 6 27 83 1 6 28 84 1 1 29 85 1 0 31 86 1 0 31 87 1 0 32 88 1 0 33 89 1 1 35 90 1 0 36 91 1 0 40 92 1 0 40 93 1 0 40 94 1 0 41 95 1 0 41 96 1 0 41 97 1 0 42 98 1 0 42 99 1 0 42100 1 0 M END

Standard InCHIKey	DOSPRDHNGNPKKJ-BYPUAWAASA-N
Standard InCHI	InChI=1S/C36H58O6/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-29(38)42-33-24(2)22-35-25(3)20-28-30(34(28,4)5)27(32(35)40)21-26(23-37)31(39)36(33,35)41/h21-22,25,27-28,30-31,33,37,39,41H,6-20,23H2,1-5H3/t25-,27+,28-,30+,31-,33+,35+,36+/m1/s1
SMILES	CCCCCCCCCCCCCCCC(=O)O[C@H]1C(=C[C@]23[C@H](C)C[C@@H]4[C@H]([C@H](C=C(CO)[C@H]([C@]13O)O)C2=O)C4(C)C)C

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
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542364]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15165157]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	bark	n.a.	n.a.	PMID[21627109]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[21627109]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[24660966]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29148766]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30817151]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184480]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4235	Thymus magnus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1000	Thymus transcaucasicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10833	Heteromma simplicifolium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO520	Euphorbia lathyris	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5571	Jacobaea arnautorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4494	Ecbolium linneanum	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8283	Pseudophegopteris subaurita	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10733	Plantago uniflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2462	Machilus robusta	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10036	Bruguiera cylindrica	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9866	Symphytum tuberosum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10479	Ophiocoma echinata	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3940	Erioderma chilense	Species	Pannariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO299	Euphorbia ebracteolata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10959	Kalanchoe marmorata	Species	Crassulaceae	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
EC50	4
IC50	1
CC50	1

Activity Type	# Activity
Cell line	1
Individual protein	1
Organism	1
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT881	Individual protein	Protein kinase C delta	Homo sapiens	EC50	=	4.7	nM	PMID[23993332]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT25	Cell line	MT4	Homo sapiens	CC50	=	26300.0	nM	PMID[31184480]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	4.1	nM	PMID[31184480]
NPT2	Others	Unspecified	n.a.	EC50	=	7.3	nM	PMID[23993332]
NPT2	Others	Unspecified	n.a.	EC50	=	8.4	nM	PMID[23993332]
NPT2	Others	Unspecified	n.a.	EC50	=	28.0	nM	PMID[23993332]

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 NPC308191 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	16691
0.1-0.2	29518
0.2-0.3	3520
0.3-0.4	86
0.4-0.5	12
0.5-0.6	16
0.6-0.7	5
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC38423
0.9818	High Similarity	NPC607683
0.9167	High Similarity	NPC482240
0.9167	High Similarity	NPC482239
0.7869	Intermediate Similarity	NPC257240
0.7463	Intermediate Similarity	NPC46269
0.7463	Intermediate Similarity	NPC106395
0.746	Intermediate Similarity	NPC267734
0.746	Intermediate Similarity	NPC482241
0.6562	Remote Similarity	NPC600642
0.6462	Remote Similarity	NPC482234
0.6462	Remote Similarity	NPC303053
0.6438	Remote Similarity	NPC607157
0.6197	Remote Similarity	NPC47951
0.5789	Remote Similarity	NPC67290
0.5789	Remote Similarity	NPC133677
0.5658	Remote Similarity	NPC482242
0.5658	Remote Similarity	NPC482243
0.56	Remote Similarity	NPC138757
0.5556	Remote Similarity	NPC261341
0.5405	Remote Similarity	NPC609657
0.5395	Remote Similarity	NPC138303
0.5278	Remote Similarity	NPC473488
0.5278	Remote Similarity	NPC92898
0.5278	Remote Similarity	NPC31883
0.5278	Remote Similarity	NPC179891
0.527	Remote Similarity	NPC482235
0.527	Remote Similarity	NPC479252
0.5063	Remote Similarity	NPC134131
0.5063	Remote Similarity	NPC25043

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC308191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6395
0.1-0.2	2675
0.2-0.3	75
0.3-0.4	4
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
0.7869	Intermediate Similarity	NPD6371	Phase 4

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