NPASS Compound

Natural Product: NPC80297

Natural Product ID	NPC80297
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Epiglochidiol
IUPAC Name	(1R,3aR,5aR,5bR,7aS,9S,11R,11aR,11bS,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-9,11-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581953
PubChem CID	488250
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 82 86 0 0 0 0 0 0 0 0999 V2000 5.0980 -2.5139 2.8683 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3154 -1.3700 2.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0560 -0.3473 3.0405 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9201 -1.5317 0.8415 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2518 -1.5784 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2326 -0.2704 -0.7482 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7732 -0.2691 -1.1409 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1312 -0.4405 0.2449 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6785 -0.7749 -0.0677 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9477 -1.3762 1.0527 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4280 -0.8964 1.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0708 -0.0202 0.3470 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3891 0.0513 -0.9878 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0474 0.4597 -0.6550 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0621 1.6102 0.3555 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7799 0.9613 -1.8561 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2653 1.0094 -1.6917 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3894 -1.2281 -1.7519 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0231 1.0988 -1.8708 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 0.9081 -1.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0553 0.9945 -0.5497 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5962 -0.1781 0.2457 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0385 -1.5094 -0.1842 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1235 0.0469 1.6711 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3183 -0.6868 1.8634 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4731 1.4778 1.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6202 1.9536 1.0271 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4553 1.4237 -0.4056 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6123 2.6703 -1.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5612 0.5322 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8519 1.5760 1.5474 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5382 -1.4459 -2.0360 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8539 -3.4731 2.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1603 -2.2961 2.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9413 -2.5692 3.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3998 -0.3410 4.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5038 0.5318 2.7249 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4094 -2.5205 0.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2185 -2.4677 -0.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1209 -1.6559 0.7110 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8891 -0.4435 -1.6072 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5170 0.5545 -0.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2237 0.5321 0.7586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7405 -1.5056 -0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5861 -1.2943 1.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9240 -2.5021 0.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1084 -1.7833 1.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4178 -0.4008 2.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9973 1.0444 0.7427 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0670 2.1174 0.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3429 2.4020 0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0137 1.2655 1.3875 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4535 2.0376 -1.9884 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5519 0.4750 -2.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6173 1.8640 -1.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7238 1.1658 -2.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1565 -2.1342 -1.2016 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3510 -1.3203 -2.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3690 -1.1578 -2.5824 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8422 2.1281 -1.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6402 0.9504 -2.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9098 1.8072 -2.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8459 0.0432 -2.5245 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4822 1.8844 -0.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2513 -2.3180 -0.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8604 -1.9228 0.4762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4232 -1.6168 -1.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4432 -0.3056 2.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5287 -0.6334 2.8209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8601 1.5243 2.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6063 2.1409 1.8946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5852 3.0604 1.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5172 3.1926 -0.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7121 3.2884 -1.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9174 2.2929 -2.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4631 0.8404 -0.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9284 0.6791 -1.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4662 -0.5351 -0.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5168 2.2811 1.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4341 -2.4124 -1.5365 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4747 -1.5423 -2.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7366 -1.2882 -2.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 1 14 16 1 0 16 17 1 0 13 18 1 6 13 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 7 32 1 6 8 4 1 0 14 9 1 0 28 21 1 0 17 7 1 0 22 12 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 4 38 1 1 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 1 9 44 1 6 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 1 15 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 1 23 65 1 0 23 66 1 0 23 67 1 0 24 68 1 1 25 69 1 0 26 70 1 0 26 71 1 0 27 72 1 6 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	SWEUJTWPRYKNNX-AXLUDCLJSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-28(6)20(25(19)27)9-10-22-29(28,7)14-12-21-26(3,4)23(31)17-24(32)30(21,22)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22-,23-,24+,25+,27+,28+,29+,30-/m0/s1
SMILES	CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)[C@H](O)C[C@@H](C1(C)C)O)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
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	Tanzania	n.a.	PMID[11430019]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12027753]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502337]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16557460]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	root	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17960072]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26221771]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15518	Streptomyces netropsis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10723	Penicillium viridicatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11182	Hylocereus undatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6313	Phormidium sp	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1358	Iris pallida	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3588	Crucianella maritima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1019	Citrus hybr	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15769	Solidago chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11182	Hylocereus undatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10723	Penicillium viridicatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3835	Reticulitermes flavipes	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5923	Bidens cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11321	Zanthoxylum rigidifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24527	Plazia daphnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25151	Euphorbia cheiradenia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7153	Astragalus trigonus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8483	Pteris cristata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9688	Gynura bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8278	Perenniporia ochroleuca	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15518	Streptomyces netropsis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2309	Achillea micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO783	Pholiota squarrosa	Species	Strophariaceae	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
Inhibition	1

Activity Type	# Activity
Organism	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
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[25927586]

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 NPC80297 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	28001
0.1-0.2	19569
0.2-0.3	1999
0.3-0.4	209
0.4-0.5	49
0.5-0.6	17
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475727
1.0	High Similarity	NPC116119
0.78	Intermediate Similarity	NPC472742
0.74	Intermediate Similarity	NPC475679
0.6863	Remote Similarity	NPC192638
0.6863	Remote Similarity	NPC25511
0.6863	Remote Similarity	NPC600137
0.6852	Remote Similarity	NPC57469
0.6604	Remote Similarity	NPC202540
0.6111	Remote Similarity	NPC102708
0.5965	Remote Similarity	NPC269396
0.5893	Remote Similarity	NPC248830
0.5893	Remote Similarity	NPC212241
0.5741	Remote Similarity	NPC35652
0.5439	Remote Similarity	NPC240235
0.5439	Remote Similarity	NPC14112
0.5424	Remote Similarity	NPC74595
0.5424	Remote Similarity	NPC264665
0.5345	Remote Similarity	NPC231256
0.5345	Remote Similarity	NPC178383
0.5263	Remote Similarity	NPC43300
0.5254	Remote Similarity	NPC93662
0.5172	Remote Similarity	NPC301226
0.5167	Remote Similarity	NPC305835
0.5167	Remote Similarity	NPC246956
0.5161	Remote Similarity	NPC471900
0.5085	Remote Similarity	NPC293803

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC80297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7876
0.1-0.2	1239
0.2-0.3	34
0.3-0.4	1
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