NPASS Compound

Natural Product: NPC267637

Natural Product ID	NPC267637
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Anagalligenone-3-O-[Beta-D-Xylopyranosyl(1->2)-Beta-D-Glucopyranosyl(1->4)-Alpha-L-Arabinopyranoside]
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2420027
PubChem CID	72375912
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 137145 0 0 0 0 0 0 0 0999 V2000 10.7914 0.5986 2.2176 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2825 -0.0923 0.9646 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4068 -1.5773 1.0282 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9547 0.5386 -0.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2610 0.4072 -1.5198 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7949 0.4848 -1.5157 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0950 -0.3012 -2.5851 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9975 -0.8599 -2.0165 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8705 -0.4437 -0.6742 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2142 -1.6028 0.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7660 -1.8085 -0.3734 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0401 -0.5261 -0.2699 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5251 -0.6058 -0.3398 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9885 -1.1907 -1.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0507 -1.5000 0.7897 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5684 -1.5870 0.8829 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1747 -0.2853 0.6226 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6704 0.9096 0.5655 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0215 2.0488 -0.1969 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7262 1.4666 2.0179 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5311 1.7838 2.4603 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0537 0.7735 0.0050 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3962 1.7035 -1.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9174 1.8297 -1.1605 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6427 0.5260 -1.1463 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6956 0.0807 -2.5699 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0413 0.8100 -0.5656 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9325 1.1853 0.8798 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7269 1.9503 -1.2707 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1937 1.8082 -1.3850 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8919 2.7907 -1.3698 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0972 -0.4400 -0.4185 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4034 -0.6318 0.0112 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2842 0.4086 -0.6205 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6595 -0.2374 -0.9671 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9869 -1.0472 0.2376 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9927 -2.2116 0.3270 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8679 -1.9014 -0.4195 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2794 -1.4793 0.3995 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8109 -1.1446 1.6407 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1197 -0.4634 1.4891 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6027 -0.1690 2.9108 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9985 -1.5251 3.4629 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1106 -2.6153 2.9706 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8500 -3.7019 2.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0618 -4.0323 2.7390 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9382 -2.2887 2.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0707 -1.4892 4.8460 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5390 0.8005 3.0205 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9711 0.6993 0.7389 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8052 0.7227 -0.3938 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7222 1.8980 -0.4368 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.4153 1.9263 -1.8038 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3695 1.9243 -2.8834 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5875 0.6277 -2.7095 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9743 0.7022 -1.4822 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9506 1.9220 -4.1356 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2113 3.0758 -1.8668 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7568 1.8266 0.4877 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3778 -1.0294 -2.0898 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5731 1.4158 0.3320 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2755 -0.3254 -0.3083 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7911 0.3274 0.8700 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4548 0.0745 3.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8921 0.7201 2.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3621 1.6300 2.2861 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5147 -2.0624 1.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2904 -1.8108 1.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6569 -1.9878 0.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9932 0.1555 -0.3210 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0592 1.6423 0.0115 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6580 1.2030 -2.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5853 -0.5508 -1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8899 0.2706 -3.5015 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7960 -1.1353 -2.8839 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7506 -2.5243 -0.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3811 -1.6352 1.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6363 -2.3699 -1.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3783 -2.4966 0.4378 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1985 -0.2204 0.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1436 -1.9267 -1.4149 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7136 -1.8240 -2.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5710 -0.4887 -2.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3837 -2.5726 0.6398 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4759 -1.1934 1.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3662 -1.9738 1.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0935 -2.3623 0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8600 -0.2275 1.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4307 3.0196 0.2243 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1837 1.9841 -1.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0599 2.1415 -0.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1406 0.6336 2.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4077 2.3337 2.0650 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7762 2.7237 2.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7316 1.1113 0.8532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0577 2.7631 -0.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9765 1.4661 -2.0935 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2510 2.5871 -0.4289 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0976 2.3608 -2.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4217 0.6327 -3.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6984 0.3459 -3.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -0.9648 -2.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6665 2.0031 1.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0239 0.3112 1.5834 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9806 1.6601 1.1930 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3414 2.1726 -2.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5423 2.9076 -0.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4906 -0.6475 1.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8928 0.8826 -1.5170 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3374 0.5828 -1.1803 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7328 -0.4382 1.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4560 -3.1697 0.0222 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6490 -2.3635 1.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0971 -0.4978 2.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8766 -1.0899 0.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6848 0.1526 3.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0340 -1.7171 3.0971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8178 -3.1899 3.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2406 -4.6505 2.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9244 -3.4211 1.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7420 -4.2957 2.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4899 -2.2205 5.2048 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2721 1.5731 3.6055 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3965 -0.2089 -0.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2034 2.8671 -0.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0439 1.0188 -1.9065 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7183 2.8029 -2.7207 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2680 -0.2248 -2.7349 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7745 0.5525 -3.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7884 1.4049 -4.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1069 2.8083 -2.1305 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7246 2.5196 1.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0392 -0.7774 -2.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0701 2.1356 -0.1448 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7558 -1.3274 -0.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3840 0.1123 1.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9111 1.4410 0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 6 5 1 6 6 7 1 0 7 8 1 0 9 8 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 18 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 25 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 2 0 17 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 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 44 47 1 0 43 48 1 0 42 49 1 0 41 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 59 1 0 35 60 1 0 34 61 1 0 9 62 1 0 62 63 1 0 63 2 1 0 62 6 1 0 30 6 1 0 38 33 1 0 47 40 1 0 56 51 1 0 27 9 1 0 25 12 1 0 22 13 1 0 1 64 1 0 1 65 1 0 1 66 1 0 3 67 1 0 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 5 72 1 0 5 73 1 0 7 74 1 0 7 75 1 0 10 76 1 0 10 77 1 0 11 78 1 0 11 79 1 0 12 80 1 1 14 81 1 0 14 82 1 0 14 83 1 0 15 84 1 0 15 85 1 0 16 86 1 0 16 87 1 0 17 88 1 1 19 89 1 0 19 90 1 0 19 91 1 0 20 92 1 0 20 93 1 0 21 94 1 0 22 95 1 1 23 96 1 0 23 97 1 0 24 98 1 0 24 99 1 0 26100 1 0 26101 1 0 26102 1 0 28103 1 0 28104 1 0 28105 1 0 29106 1 0 29107 1 0 33108 1 1 34109 1 6 35110 1 6 36111 1 1 37112 1 0 37113 1 0 40114 1 1 41115 1 6 42116 1 1 43117 1 6 44118 1 1 45119 1 0 45120 1 0 46121 1 0 48122 1 0 49123 1 0 51124 1 6 52125 1 1 53126 1 6 54127 1 6 55128 1 0 55129 1 0 57130 1 0 58131 1 0 59132 1 0 60133 1 0 61134 1 0 62135 1 6 63136 1 0 63137 1 0 M END

Standard InCHIKey	IYIIGIDPFTYYCU-ISLMCVPPSA-N
Standard InCHI	InChI=1S/C46H74O17/c1-40(2)13-14-45-21-59-46(27(45)15-40)12-8-26-41(3)10-9-29(42(4,20-48)25(41)7-11-43(26,5)44(46,6)16-28(45)50)62-37-35(56)32(53)24(19-58-37)61-39-36(33(54)31(52)23(17-47)60-39)63-38-34(55)30(51)22(49)18-57-38/h22-27,29-39,47-49,51-56H,7-21H2,1-6H3/t22-,23-,24+,25-,26-,27-,29+,30+,31-,32+,33+,34-,35-,36-,37+,38+,39+,41+,42+,43-,44+,45-,46+/m1/s1
SMILES	CC1(C)CC[C@@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@@H]([C@@](C)(CO)[C@@H]6CC[C@@]5(C)[C@]4(C)CC3=O)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O)O)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	898.49	Volume:	873.961 ? Van der Waals volume.
Dense:	1.028	LogP:	1.082 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.931 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.724 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	48.0
TPSA:	263.75 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.598	Fsp³:	0.978
MCE-18:	251.67 ? 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:	0.927	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.158	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.207	MDCK Permeability:	-5.235
Pgp-inhibitor:	0.0	Pgp-substrate:	0.193
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):	0.006
20% Bioavailability (F20%):	0.148	30% Bioavailability (F30%):	0.286
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892	MRP1:	0.049
Plasma Protein Binding (PPB):	75.999%	Volume Distribution (VD):	-0.429
Fu:	15.577% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.806	BCRP inhibitor:	0.152
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.017	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.004	CYP3A4-substrate:	0.786
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.056 ? 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):

0.216

Half-life (T1/2):

2.253

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.662
AMES Toxicity:	0.968	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.174	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.996
Hematotoxicity:	0.731	Drug-induced Nephrotoxicity:	0.981
Genotoxicity:	0.174	RPMI-8226 Immunitoxicity:	0.175
A549 Cytotoxicity:	0.775	Hek293 Cytotoxicity:	0.444
BCF:	1.211 ? 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:	3.522 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.015 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.094 ? 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
NPO33016	lysimachia parvifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23911853]
NPO33016	lysimachia parvifolia	Species	Primulaceae	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	6

Activity Type	# Activity
Cell line	5
Non-molecular	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
NPT2015	Cell line	U-266	Homo sapiens	IC50	=	10370.0	nM	PMID[16124784]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	10260.0	nM	PMID[17008103]
NPT515	Cell line	SGC-7901	Homo sapiens	IC50	=	9240.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	10880.0	nM	PMID[16038541]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	8870.0	nM	PMID[20970223]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	9140.0	nM	PMID[23911853]

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 NPC267637 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	22765
0.1-0.2	23562
0.2-0.3	2690
0.3-0.4	719
0.4-0.5	86
0.5-0.6	21
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8191	Intermediate Similarity	NPC80640
0.7889	Intermediate Similarity	NPC80417
0.7788	Intermediate Similarity	NPC273189
0.7429	Intermediate Similarity	NPC87393
0.7184	Intermediate Similarity	NPC323231
0.7037	Intermediate Similarity	NPC184805
0.6696	Remote Similarity	NPC66513
0.6667	Remote Similarity	NPC119628
0.6486	Remote Similarity	NPC471373
0.633	Remote Similarity	NPC171741
0.6281	Remote Similarity	NPC471430
0.6228	Remote Similarity	NPC475630
0.6174	Remote Similarity	NPC471374
0.6106	Remote Similarity	NPC77717
0.5877	Remote Similarity	NPC158367
0.5826	Remote Similarity	NPC470623
0.5785	Remote Similarity	NPC470622
0.5678	Remote Similarity	NPC138219
0.5678	Remote Similarity	NPC475234
0.563	Remote Similarity	NPC473688
0.563	Remote Similarity	NPC471375
0.5583	Remote Similarity	NPC51579
0.547	Remote Similarity	NPC253611
0.547	Remote Similarity	NPC488782
0.5455	Remote Similarity	NPC209798
0.531	Remote Similarity	NPC473130
0.5238	Remote Similarity	NPC471425
0.5208	Remote Similarity	NPC50658
0.5197	Remote Similarity	NPC189575
0.5175	Remote Similarity	NPC18724
0.5154	Remote Similarity	NPC471426
0.5079	Remote Similarity	NPC205129
0.5077	Remote Similarity	NPC106701
0.5041	Remote Similarity	NPC267238
0.5039	Remote Similarity	NPC262567

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC267637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7080
0.1-0.2	2040
0.2-0.3	27
0.3-0.4	3
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