NPASS Compound

Natural Product: NPC306991

Natural Product ID	NPC306991
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BMZJWILIQLATMQ-VHQVREFHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102403269
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 133139 0 0 0 0 0 0 0 0999 V2000 8.4879 -0.1600 -4.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9075 -0.6636 -2.8930 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4342 0.5498 -2.1197 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8210 0.2692 -0.8036 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5675 -0.5367 -0.8152 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6594 -1.7056 -1.2021 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3543 0.1467 -0.3540 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2247 -0.4907 -0.2433 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9488 -1.9297 -0.5417 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7965 -2.8771 -0.4970 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5119 -2.0751 -0.9009 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 -0.6473 -0.8175 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4489 -0.5939 -0.3872 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2787 -0.5934 -1.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6333 -0.0424 -1.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0603 0.4950 -0.3388 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4370 1.0060 -0.2328 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9324 1.3092 1.1206 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9246 1.8362 2.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5369 1.9242 1.5144 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1758 0.6169 0.8312 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3155 -0.5458 1.7588 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7520 0.6710 0.3019 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1990 1.1447 1.3481 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5767 1.2686 0.6313 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9237 -0.0748 0.2501 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6740 -0.9765 1.4881 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7293 0.3104 1.7113 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0120 0.6921 1.9615 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9809 -0.2198 1.2456 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8518 -1.6354 1.8045 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1154 -1.6317 3.2892 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3270 -0.5482 3.9384 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8987 -1.0157 4.2591 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9639 -2.2511 4.9367 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2749 0.6359 3.3027 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4642 -1.4733 3.6025 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5455 -2.0469 1.5690 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2977 0.2060 1.4530 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9511 0.4036 0.2468 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2396 -0.3621 0.2227 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.1376 -0.0092 -0.9097 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.1889 1.4621 -1.1402 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8228 2.1145 -1.0319 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9597 1.7905 -2.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2454 1.7786 0.1780 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9781 2.0845 -0.1502 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8917 -0.7563 -2.0650 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0349 -1.7410 0.3140 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3668 1.6035 -0.0588 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8939 -1.3851 -2.0561 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9947 -0.7862 -1.5910 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0220 -0.3509 -2.3326 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3705 1.1228 -2.1679 C 0 0 1 0 0 0 0 0 0 0 0 0 11.6776 1.4150 -0.7063 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2367 0.1590 -0.0475 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0217 -0.5480 -1.1280 C 0 0 1 0 0 0 0 0 0 0 0 0 13.8084 -1.6549 -0.4189 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6788 -1.0858 0.5275 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1806 -1.1255 -2.0251 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0481 0.4912 1.0407 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5786 1.9280 -0.0413 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4106 1.4885 -3.0181 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0695 0.7608 -4.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6232 0.0592 -4.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0619 -0.9386 -4.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0381 -1.3086 -3.1856 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7729 1.1261 -2.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3147 1.1996 -1.9483 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5369 -0.3995 -0.1836 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7786 1.1773 -0.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3846 -2.4749 -1.9284 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9709 -2.7091 -0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1952 -0.1291 -1.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7396 -1.5194 0.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3167 -1.5903 -2.1532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7774 0.0885 -2.4146 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3240 -0.1026 -2.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1559 0.3879 -0.8350 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4182 1.9790 -0.8302 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6921 2.1606 0.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9263 1.3062 3.0554 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1813 2.9094 2.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8449 2.0781 2.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4441 2.7570 0.8148 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4632 -1.5097 1.2125 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4687 -0.5910 2.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2245 -0.4828 2.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7545 1.4826 -0.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0427 2.2117 1.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2503 0.5940 2.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 1.9797 -0.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2389 1.6688 1.4103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0119 -0.3882 2.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3390 -1.8689 1.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6352 -1.2555 1.5989 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2306 1.7335 1.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8194 -0.2829 0.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5668 -2.3104 1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7458 -2.6025 3.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7931 -0.3410 4.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3588 -0.2408 4.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3144 -1.2267 3.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0700 -2.6743 4.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6291 -2.0462 4.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5721 -2.7796 0.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3673 0.1604 -0.6465 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7757 -0.0885 1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1902 -0.3099 -0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5815 1.6852 -2.1484 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9788 3.2116 -1.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0244 2.5991 -3.0094 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3523 0.8724 -2.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8846 1.6833 -1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8178 3.0680 -0.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6824 -1.1963 -2.4353 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6794 -2.2577 -0.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5955 1.8894 0.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2143 2.0209 -0.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5026 2.1533 -0.5397 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3625 -1.9304 -1.1918 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2543 -2.3290 -2.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8755 -0.5340 -3.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5019 1.7175 -2.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4831 2.1713 -0.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3947 -0.4885 0.2606 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7265 0.1504 -1.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0828 -2.2648 0.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3674 -2.2703 -1.1253 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2792 -1.7289 0.9267 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6477 0.0898 1.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4355 1.3231 0.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9826 2.2123 -2.6111 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 2 0 5 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 18 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 30 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 44 46 1 0 43 47 1 0 42 48 1 0 41 49 1 0 7 50 1 0 2 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 55 62 1 0 54 63 1 0 26 8 1 0 36 29 1 0 46 40 1 0 60 53 1 0 26 12 1 0 23 13 1 0 21 16 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 6 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 11 72 1 0 11 73 1 0 12 74 1 6 13 75 1 1 14 76 1 0 14 77 1 0 15 78 1 0 17 79 1 0 17 80 1 0 18 81 1 6 19 82 1 0 19 83 1 0 20 84 1 0 20 85 1 0 22 86 1 0 22 87 1 0 22 88 1 0 23 89 1 6 24 90 1 0 24 91 1 0 25 92 1 0 25 93 1 0 27 94 1 0 27 95 1 0 27 96 1 0 29 97 1 6 30 98 1 6 31 99 1 6 32100 1 1 33101 1 1 34102 1 0 34103 1 0 35104 1 0 37105 1 0 38106 1 0 40107 1 6 41108 1 1 42109 1 1 43110 1 6 44111 1 1 45112 1 0 45113 1 0 45114 1 0 47115 1 0 48116 1 0 49117 1 0 50118 1 0 50119 1 0 50120 1 0 51121 1 0 51122 1 0 53123 1 6 54124 1 6 55125 1 6 56126 1 1 57127 1 6 58128 1 0 58129 1 0 59130 1 0 61131 1 0 62132 1 0 63133 1 0 M END

Standard InCHIKey	BMZJWILIQLATMQ-VHQVREFHSA-N
Standard InCHI	InChI=1S/C45H70O18/c1-19(18-58-41-38(56)36(54)33(51)29(16-46)61-41)6-9-27(48)20(2)31-28(49)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)60-43-40(37(55)34(52)30(17-47)62-43)63-42-39(57)35(53)32(50)21(3)59-42/h7,19,21,23-26,29-30,32-43,46-47,50-57H,6,8-18H2,1-5H3/b31-20+/t19-,21+,23+,24-,25+,26+,29-,30-,32+,33-,34-,35-,36+,37+,38-,39-,40-,41-,42+,43-,44+,45+/m1/s1
SMILES	C[C@H](CCC(=O)/C(=C/1C(=O)C[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)/C)CO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	898.46	Volume:	874.659 ? Van der Waals volume.
Dense:	1.027	LogP:	1.066 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.946 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.926 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	41.0
TPSA:	291.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.081	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.251	Fsp³:	0.867
MCE-18:	138.667 ? 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:	0.829	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.192	Promiscuous compounds:	0.333

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.456	MDCK Permeability:	-5.142
Pgp-inhibitor:	0.0	Pgp-substrate:	0.405
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):	0.086
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.008
Plasma Protein Binding (PPB):	72.782%	Volume Distribution (VD):	-0.345
Fu:	20.442% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.019
BSEP inhibitor:	0.003

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.03	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.72	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.153 ? 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):

0.371

Half-life (T1/2):

2.553

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.023
Human Hepatotoxicity (H-HT):	0.703	Drug-induced Liver Injury (DILI):	0.868
AMES Toxicity:	0.935	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.06	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.476	Drug-induced Nephrotoxicity:	0.92
Genotoxicity:	0.084	RPMI-8226 Immunitoxicity:	0.175
A549 Cytotoxicity:	0.724	Hek293 Cytotoxicity:	0.446
BCF:	0.629 ? 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:	3.34 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.949 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.004 ? 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
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32870000]
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16818	Trillium tschonoskii	Species	Melanthiaceae	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
FC	2

Activity Type	# Activity
Cell line	1
Others	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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	12700.0	nM	PMID[28454671]
NPT2	Others	Unspecified	n.a.	FC	=	1.0	n.a.	PMID[32870000]
NPT2	Others	Unspecified	n.a.	FC	=	5.7	n.a.	PMID[32870000]

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 NPC306991 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	20648
0.1-0.2	24459
0.2-0.3	3486
0.3-0.4	1095
0.4-0.5	105
0.5-0.6	47
0.6-0.7	11
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
0.7684	Intermediate Similarity	NPC486388
0.697	Remote Similarity	NPC98696
0.6381	Remote Similarity	NPC475182
0.6311	Remote Similarity	NPC40440
0.6275	Remote Similarity	NPC113044
0.6275	Remote Similarity	NPC283829
0.6275	Remote Similarity	NPC470748
0.6275	Remote Similarity	NPC161676
0.6091	Remote Similarity	NPC197003
0.6019	Remote Similarity	NPC73243
0.6019	Remote Similarity	NPC244086
0.6019	Remote Similarity	NPC84956
0.5962	Remote Similarity	NPC305423
0.5909	Remote Similarity	NPC486386
0.5909	Remote Similarity	NPC247037
0.5872	Remote Similarity	NPC102016
0.5872	Remote Similarity	NPC95051
0.5862	Remote Similarity	NPC190939
0.5841	Remote Similarity	NPC23808
0.5841	Remote Similarity	NPC486383
0.5841	Remote Similarity	NPC87998
0.5804	Remote Similarity	NPC194207
0.5804	Remote Similarity	NPC22779
0.5804	Remote Similarity	NPC254255
0.5752	Remote Similarity	NPC249265
0.5739	Remote Similarity	NPC308140
0.5714	Remote Similarity	NPC13193
0.5714	Remote Similarity	NPC165439
0.566	Remote Similarity	NPC600116
0.5614	Remote Similarity	NPC218571
0.5614	Remote Similarity	NPC487615
0.5577	Remote Similarity	NPC600456
0.5575	Remote Similarity	NPC309278
0.5556	Remote Similarity	NPC232054
0.5556	Remote Similarity	NPC197231
0.5495	Remote Similarity	NPC480555
0.5495	Remote Similarity	NPC150372
0.5463	Remote Similarity	NPC19888
0.5455	Remote Similarity	NPC477809
0.5446	Remote Similarity	NPC272015
0.5354	Remote Similarity	NPC242748
0.5327	Remote Similarity	NPC94272
0.5268	Remote Similarity	NPC300557
0.5268	Remote Similarity	NPC124677
0.5254	Remote Similarity	NPC480553
0.5225	Remote Similarity	NPC470433
0.5225	Remote Similarity	NPC46190
0.5225	Remote Similarity	NPC171073
0.5172	Remote Similarity	NPC475333
0.5172	Remote Similarity	NPC224098
0.5172	Remote Similarity	NPC208383
0.5138	Remote Similarity	NPC141433
0.5093	Remote Similarity	NPC485601
0.5089	Remote Similarity	NPC602423
0.5086	Remote Similarity	NPC269297
0.5086	Remote Similarity	NPC222202
0.5085	Remote Similarity	NPC480554
0.5049	Remote Similarity	NPC181845
0.5041	Remote Similarity	NPC480556

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC306991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6997
0.1-0.2	2033
0.2-0.3	105
0.3-0.4	12
0.4-0.5	3
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