NPASS Compound

Natural Product: NPC481082

Natural Product ID	NPC481082
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QDYPTQWAAOGCJD-KJAMEOKDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	46888055
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 135142 0 0 0 0 0 0 0 0999 V2000 5.9050 0.8097 2.4063 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7411 0.8541 0.9246 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0539 0.3572 0.3024 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7164 0.0626 -1.1419 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8100 -1.1541 -1.1209 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0021 -1.1613 0.1661 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6360 0.1604 0.4438 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9437 -2.0238 0.1063 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9891 -2.9774 1.0741 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1679 -4.4071 0.5366 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6387 -5.3836 1.5980 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7647 -4.8355 2.9779 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2447 -3.5693 3.1836 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7920 -3.0583 1.9811 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0308 -1.9228 2.0605 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7055 -2.0971 1.6575 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1581 -1.8504 2.8385 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5709 -1.4792 2.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6757 -0.3377 1.5500 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9597 0.8174 2.1990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0497 -0.9021 0.3382 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3664 -0.0984 -0.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8591 -0.3853 -1.1505 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5901 0.2973 -0.0180 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4995 1.7889 -0.2985 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1220 -0.0989 1.3406 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7170 0.9213 2.2993 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0892 1.2805 1.9412 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7614 0.8711 0.8573 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1433 1.2810 0.5713 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5713 2.5775 1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0461 2.7819 0.9297 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8005 3.1069 2.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3341 3.9443 0.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7269 1.5692 0.3640 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0863 1.1245 -0.9072 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5672 1.2142 -0.8448 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0731 -0.0461 -1.5574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5774 -0.0359 -1.4743 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0546 -0.0718 -0.0846 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3088 -1.4644 0.4604 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1751 2.3340 -1.7188 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5137 3.3344 -1.4503 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6223 2.2515 -3.0621 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4034 -1.2557 0.4478 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7187 -2.1160 -0.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3444 -0.0851 0.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4928 -6.5084 1.5299 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5362 -4.6297 0.4464 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6222 -2.2787 -1.2325 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7970 -0.0959 -1.9715 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8486 0.8551 -2.9713 C 0 0 1 0 0 0 0 0 0 0 0 0 9.2089 1.4950 -3.0707 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9629 2.8761 -3.6854 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9671 2.6452 -4.8022 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9145 1.2149 -5.2358 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6087 0.3038 -4.2573 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7175 3.2015 -4.5391 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1317 3.4508 -4.1295 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9087 1.5529 -1.8927 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9528 1.3869 0.4741 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6848 0.0462 2.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3273 1.8080 2.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9479 0.6164 2.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6248 1.9130 0.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4532 -0.5306 0.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1166 0.9332 -1.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1019 -1.1150 -1.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6836 -1.5047 0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8898 -2.7544 1.7186 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6056 -4.5927 -0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6433 -5.7817 1.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8276 -4.8865 3.3199 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1807 -5.5419 3.6430 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1022 -3.8491 1.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6015 -3.1910 1.3783 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3402 -1.1626 3.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2004 -2.8198 3.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1488 -2.3583 2.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0113 -1.1056 3.5292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8892 1.7280 1.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4396 0.9803 3.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0620 0.4819 2.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5739 -1.9052 0.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7526 -0.2654 -1.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3480 0.9850 -0.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 -1.4748 -1.1825 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1769 0.0748 -2.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4304 2.3407 -0.0891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6963 2.3042 0.2170 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3295 1.9646 -1.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6581 -1.0553 1.6104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0557 1.8145 2.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6849 0.4987 3.3196 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6157 1.9408 2.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7818 0.4970 1.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0207 3.4122 0.7496 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4806 2.5611 2.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0959 2.8858 3.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7416 2.5646 2.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9942 4.1958 2.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1963 4.5796 0.3662 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7038 3.5693 -0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5059 4.6407 -0.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7687 1.9110 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8949 0.7590 1.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5103 1.6740 -1.7746 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4203 0.0563 -1.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5756 -0.9547 -1.2506 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3196 0.1264 -2.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2460 -1.0052 -1.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1812 0.7536 -2.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2413 -1.8386 -0.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5384 -2.1977 0.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6096 -1.4538 1.5418 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4067 2.9868 -3.7248 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5187 -1.6586 -1.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1634 -2.1960 -1.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9793 -3.1573 -0.4884 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8465 0.8967 0.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0458 -0.0778 1.2780 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0580 -0.1404 -0.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0014 -7.3609 1.6202 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8898 -5.2733 1.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6230 -2.6138 -2.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0092 1.6002 -2.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8419 0.9303 -3.8209 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5168 3.4820 -2.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3610 3.2223 -5.6800 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8821 0.9839 -5.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1423 1.1600 -6.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8784 3.9490 -3.9069 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7271 3.6709 -3.3729 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1697 0.6509 -1.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4871 1.2815 1.3113 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 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 1 37 42 1 6 42 43 2 0 42 44 1 0 21 45 1 0 45 46 1 0 45 47 1 0 11 48 1 0 10 49 1 0 5 50 1 0 4 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 55 58 1 0 54 59 1 0 53 60 1 0 3 61 1 0 7 2 1 0 14 9 1 0 45 16 1 0 57 52 1 0 26 19 1 0 40 29 1 0 40 24 1 0 37 30 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 6 3 66 1 1 4 67 1 6 5 68 1 6 6 69 1 1 9 70 1 1 10 71 1 6 11 72 1 6 12 73 1 0 12 74 1 0 14 75 1 6 16 76 1 6 17 77 1 0 17 78 1 0 18 79 1 0 18 80 1 0 20 81 1 0 20 82 1 0 20 83 1 0 21 84 1 6 22 85 1 0 22 86 1 0 23 87 1 0 23 88 1 0 25 89 1 0 25 90 1 0 25 91 1 0 26 92 1 1 27 93 1 0 27 94 1 0 28 95 1 0 30 96 1 1 31 97 1 0 31 98 1 0 33 99 1 0 33100 1 0 33101 1 0 34102 1 0 34103 1 0 34104 1 0 35105 1 0 35106 1 0 36107 1 0 36108 1 0 38109 1 0 38110 1 0 39111 1 0 39112 1 0 41113 1 0 41114 1 0 41115 1 0 44116 1 0 46117 1 0 46118 1 0 46119 1 0 47120 1 0 47121 1 0 47122 1 0 48123 1 0 49124 1 0 50125 1 0 52126 1 1 53127 1 6 54128 1 1 55129 1 6 56130 1 0 56131 1 0 58132 1 0 59133 1 0 60134 1 0 61135 1 0 M END

Standard InCHIKey	QDYPTQWAAOGCJD-KJAMEOKDSA-N
Standard InCHI	InChI=1S/C46H74O15/c1-22-30(49)35(60-37-33(52)31(50)25(47)20-56-37)34(53)38(58-22)61-36-32(51)26(48)21-57-39(36)59-29-12-13-43(6)27(42(29,4)5)11-14-45(8)28(43)10-9-23-24-19-41(2,3)15-17-46(24,40(54)55)18-16-44(23,45)7/h9,22,24-39,47-53H,10-21H2,1-8H3,(H,54,55)/t22-,24+,25+,26-,27-,28+,29-,30-,31-,32-,33+,34+,35+,36+,37-,38-,39-,43-,44+,45+,46-/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]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	866.5	Volume:	862.301 ? Van der Waals volume.
Dense:	1.005	LogP:	2.62 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.104 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.187 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	45.0
TPSA:	234.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	8.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.136	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.139	Fsp³:	0.935
MCE-18:	169.978 ? 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:	0.948	Fluc inhibitor:	0.0 ? 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:	0.191	Promiscuous compounds:	0.123

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.995	MDCK Permeability:	-5.191
Pgp-inhibitor:	0.0	Pgp-substrate:	0.011
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):	0.021
20% Bioavailability (F20%):	0.036	30% Bioavailability (F30%):	0.471
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063	MRP1:	0.055
Plasma Protein Binding (PPB):	75.089%	Volume Distribution (VD):	-0.452
Fu:	16.737% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.045
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.971
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.0 ? 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):

0.002

Half-life (T1/2):

3.082

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.031
Human Hepatotoxicity (H-HT):	0.71	Drug-induced Liver Injury (DILI):	0.925
AMES Toxicity:	0.612	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.029	Skin Sensitization:	0.999
Carcinogencity:	0.116	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.076
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.991
Hematotoxicity:	0.516	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.076	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.361	Hek293 Cytotoxicity:	0.367
BCF:	1.718 ? 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:	4.144 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.749 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.958 ? 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
NPO2435	Cephalaria scoparia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384364]
NPO2435	Cephalaria scoparia	Species	Caprifoliaceae	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
MIC	8

Activity Type	# Activity
Organism	8

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
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	32.0	ug.mL-1	PMID[20384364]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	64.0	ug.mL-1	PMID[20384364]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	16.0	ug.mL-1	PMID[20384364]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	16.0	ug.mL-1	PMID[20384364]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[20384364]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	16.0	ug.mL-1	PMID[20384364]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16.0	ug.mL-1	PMID[20384364]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	16.0	ug.mL-1	PMID[20384364]

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 NPC481082 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	23459
0.1-0.2	22710
0.2-0.3	2394
0.3-0.4	770
0.4-0.5	365
0.5-0.6	91
0.6-0.7	32
0.7-0.8	0
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC164419
0.8866	High Similarity	NPC324875
0.8866	High Similarity	NPC292677
0.8365	Intermediate Similarity	NPC166422
0.8365	Intermediate Similarity	NPC219180
0.8298	Intermediate Similarity	NPC56713
0.82	Intermediate Similarity	NPC276093
0.819	Intermediate Similarity	NPC251263
0.7838	Intermediate Similarity	NPC161717
0.7835	Intermediate Similarity	NPC127056
0.78	Intermediate Similarity	NPC104400
0.78	Intermediate Similarity	NPC10320
0.7757	Intermediate Similarity	NPC323341
0.7755	Intermediate Similarity	NPC488561
0.7692	Intermediate Similarity	NPC283849
0.7619	Intermediate Similarity	NPC475486
0.76	Intermediate Similarity	NPC469945
0.7593	Intermediate Similarity	NPC133818
0.7551	Intermediate Similarity	NPC174679
0.7551	Intermediate Similarity	NPC279554
0.74	Intermediate Similarity	NPC6377
0.74	Intermediate Similarity	NPC208381
0.7383	Intermediate Similarity	NPC280941
0.7383	Intermediate Similarity	NPC235772
0.7232	Intermediate Similarity	NPC54636
0.7217	Intermediate Similarity	NPC471385
0.72	Intermediate Similarity	NPC59804
0.7184	Intermediate Similarity	NPC114304
0.7117	Intermediate Similarity	NPC471384
0.7075	Intermediate Similarity	NPC79718
0.6981	Remote Similarity	NPC257468
0.6947	Remote Similarity	NPC28198
0.6947	Remote Similarity	NPC476123
0.6863	Remote Similarity	NPC25605
0.6822	Remote Similarity	NPC73829
0.6735	Remote Similarity	NPC100383
0.6733	Remote Similarity	NPC164194
0.6667	Remote Similarity	NPC481078
0.6667	Remote Similarity	NPC80843
0.6636	Remote Similarity	NPC180550
0.6636	Remote Similarity	NPC35405
0.6635	Remote Similarity	NPC114441
0.6606	Remote Similarity	NPC488515
0.6571	Remote Similarity	NPC472949
0.6429	Remote Similarity	NPC488564
0.6429	Remote Similarity	NPC488209
0.6429	Remote Similarity	NPC606107
0.6422	Remote Similarity	NPC139044
0.6422	Remote Similarity	NPC471383
0.6408	Remote Similarity	NPC270667
0.6404	Remote Similarity	NPC288205
0.6404	Remote Similarity	NPC51465
0.64	Remote Similarity	NPC242611
0.6325	Remote Similarity	NPC123199
0.6321	Remote Similarity	NPC109079
0.6286	Remote Similarity	NPC12288
0.6204	Remote Similarity	NPC22956
0.6195	Remote Similarity	NPC323359
0.6161	Remote Similarity	NPC119794
0.6139	Remote Similarity	NPC286347
0.6033	Remote Similarity	NPC488211
0.6017	Remote Similarity	NPC79643
0.5963	Remote Similarity	NPC488516
0.5932	Remote Similarity	NPC475287
0.5929	Remote Similarity	NPC275668
0.5929	Remote Similarity	NPC475504
0.592	Remote Similarity	NPC236638
0.592	Remote Similarity	NPC294453
0.5897	Remote Similarity	NPC62725
0.5847	Remote Similarity	NPC476992
0.5842	Remote Similarity	NPC204407
0.5833	Remote Similarity	NPC136877
0.581	Remote Similarity	NPC284807
0.5781	Remote Similarity	NPC488212
0.578	Remote Similarity	NPC475296
0.5776	Remote Similarity	NPC75318
0.5755	Remote Similarity	NPC191410
0.5745	Remote Similarity	NPC120840
0.5739	Remote Similarity	NPC484832
0.5714	Remote Similarity	NPC475119
0.569	Remote Similarity	NPC37134
0.568	Remote Similarity	NPC110633
0.5667	Remote Similarity	NPC200788
0.5645	Remote Similarity	NPC4749
0.5636	Remote Similarity	NPC474589
0.5635	Remote Similarity	NPC41061
0.5635	Remote Similarity	NPC227551
0.562	Remote Similarity	NPC40085
0.5577	Remote Similarity	NPC177246
0.5547	Remote Similarity	NPC202828
0.5547	Remote Similarity	NPC119592
0.5547	Remote Similarity	NPC305981
0.5537	Remote Similarity	NPC473824
0.5505	Remote Similarity	NPC127853
0.5504	Remote Similarity	NPC261506
0.5504	Remote Similarity	NPC4328
0.5447	Remote Similarity	NPC243680
0.5446	Remote Similarity	NPC480424
0.5439	Remote Similarity	NPC112352
0.5431	Remote Similarity	NPC258885
0.5431	Remote Similarity	NPC91838
0.5429	Remote Similarity	NPC264270
0.5426	Remote Similarity	NPC481081
0.5426	Remote Similarity	NPC111466
0.542	Remote Similarity	NPC220160
0.5413	Remote Similarity	NPC475472
0.5385	Remote Similarity	NPC302543
0.5379	Remote Similarity	NPC250247
0.5378	Remote Similarity	NPC301449
0.5378	Remote Similarity	NPC291903
0.5378	Remote Similarity	NPC601290
0.5377	Remote Similarity	NPC31839
0.537	Remote Similarity	NPC294112
0.537	Remote Similarity	NPC473538
0.536	Remote Similarity	NPC283417
0.536	Remote Similarity	NPC200049
0.536	Remote Similarity	NPC475140
0.5354	Remote Similarity	NPC21691
0.525	Remote Similarity	NPC218954
0.5246	Remote Similarity	NPC480939
0.5231	Remote Similarity	NPC293330
0.5217	Remote Similarity	NPC263756
0.5217	Remote Similarity	NPC213674
0.5217	Remote Similarity	NPC469946
0.5214	Remote Similarity	NPC488526
0.5207	Remote Similarity	NPC187618
0.5194	Remote Similarity	NPC265841
0.5194	Remote Similarity	NPC488308
0.5191	Remote Similarity	NPC136768
0.5169	Remote Similarity	NPC63159
0.5167	Remote Similarity	NPC145899
0.5156	Remote Similarity	NPC481080
0.5154	Remote Similarity	NPC312650
0.5152	Remote Similarity	NPC298034
0.5152	Remote Similarity	NPC71065
0.5135	Remote Similarity	NPC475611
0.5118	Remote Similarity	NPC191827
0.5116	Remote Similarity	NPC57484
0.5104	Remote Similarity	NPC480946
0.5104	Remote Similarity	NPC130577
0.5104	Remote Similarity	NPC142415
0.5104	Remote Similarity	NPC102683
0.5088	Remote Similarity	NPC309780
0.5085	Remote Similarity	NPC164389
0.5075	Remote Similarity	NPC224381
0.5075	Remote Similarity	NPC488309
0.5041	Remote Similarity	NPC187290
0.504	Remote Similarity	NPC60557
0.504	Remote Similarity	NPC313110
0.504	Remote Similarity	NPC67857
0.5039	Remote Similarity	NPC85154
0.5039	Remote Similarity	NPC71391
0.5038	Remote Similarity	NPC271610

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC481082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6888
0.1-0.2	2219
0.2-0.3	36
0.3-0.4	5
0.4-0.5	1
0.5-0.6	1
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
0.5221	Remote Similarity	NPD8295	Clinical (unspecified phase)

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