NPASS Compound

Natural Product: NPC568159

Natural Product ID	NPC568159
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{R},4~{S},5~{R})-2-[(2~{R},3~{S},4~{S},5~{R})-4-hydroxy-2-(hydroxymethyl)-6-[(4~{S},5'~{S},6~{R},7~{S},9~{S},13~{S},16~{S})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-5-[(3~{R},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxytetrahydropyran-3,4,5-triol
IUPAC Name	(3~{R},4~{S},5~{R})-2-[(2~{R},3~{S},4~{S},5~{R})-4-hydroxy-2-(hydroxymethyl)-6-[(4~{S},5'~{S},6~{R},7~{S},9~{S},13~{S},16~{S})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-5-[(3~{R},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxytetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 129137 0 0 0 0 0 0 0 0999 V2000 11.8207 2.9174 0.0401 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1036 1.9491 -0.8725 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9487 0.6065 -0.2296 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6536 -0.0844 -0.5967 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4634 0.7743 -0.3342 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7555 2.1356 -0.3612 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7416 2.4549 -1.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4812 0.5783 -1.3328 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4366 1.3199 -0.8079 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0853 0.9579 -1.4021 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8966 -0.5075 -0.9802 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5144 -0.9825 -1.1348 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5832 0.1948 -1.4408 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3146 -0.3853 -1.9693 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9198 -1.7011 -1.3758 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5632 -1.8159 -1.3958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2718 -1.0619 -0.3335 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5983 -1.4770 -0.2095 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5266 -0.4989 -0.4915 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4383 -0.9182 -1.4422 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5897 -0.1765 -1.5092 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9449 -0.0744 -2.9989 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1161 -1.4140 -3.4189 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4850 1.1824 -0.8995 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7682 1.7577 -0.8909 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8065 2.9993 -1.4714 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6947 2.9617 -2.5444 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9734 2.5882 -2.1817 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5763 3.7295 -1.3677 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9156 3.5328 -1.0996 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7368 3.8077 -0.0910 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1392 4.8717 0.7043 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3121 4.0740 -0.5315 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4642 4.2959 0.5360 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1389 0.9829 0.5800 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3380 2.0670 0.9437 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3150 -0.2631 0.8049 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0567 -1.3960 1.0422 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7099 -2.0330 2.2272 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3255 -3.3155 1.9269 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3319 -4.1195 1.4598 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6174 -3.4264 1.1547 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5997 -4.4347 1.0160 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1050 -2.4928 2.2110 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5189 -1.3041 1.5659 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9446 -2.1074 3.0979 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8234 -3.0918 4.0776 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6605 -1.0826 1.0114 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8597 -1.0605 1.0429 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4818 -1.9252 0.0178 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0531 -3.3642 0.3750 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9842 -1.9003 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6526 -1.8200 1.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4463 -0.5628 1.4593 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4989 -0.5350 0.3743 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3343 -1.8078 0.4893 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3071 0.7078 0.5769 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7390 0.4789 0.9422 C 0 0 2 0 0 0 0 0 0 0 0 0 8.1155 1.5545 1.9701 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1813 3.1137 0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0216 3.8565 -0.4745 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7372 2.4056 0.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7010 1.8664 -1.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7822 -0.0816 -0.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9898 0.6638 0.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6979 -0.3153 -1.6886 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5854 -1.0156 -0.0347 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7763 3.5661 -1.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4718 1.9845 -2.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6081 2.3964 -0.7868 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3570 1.6315 -0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1904 1.0416 -2.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6134 -1.0472 -1.6738 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4720 -1.5452 -2.1216 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0816 0.7494 -2.2816 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4936 0.9065 -0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4677 0.3625 -1.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4813 -0.5861 -3.0703 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3236 -2.5619 -1.9856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 -1.4897 -2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8621 -2.8952 -1.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3331 0.0187 -0.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1137 0.4737 -0.7734 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4788 -0.6779 -1.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1457 0.4091 -3.5774 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9319 0.3916 -3.1207 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9531 -1.7123 -2.9441 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7488 1.8435 -1.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8334 3.3491 -1.8532 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5585 2.4577 -3.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9888 1.6714 -1.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4171 4.6585 -1.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0061 2.6992 -0.5724 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7881 2.8432 0.4480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7885 4.7173 1.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3374 5.0199 -1.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6126 4.6334 0.1673 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0245 1.0071 1.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0897 2.0600 1.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5994 -0.1178 1.6399 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8981 -1.5101 2.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4807 -5.0300 2.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9637 -4.5609 0.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5533 -2.9561 0.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4630 -4.8991 0.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9632 -2.8861 2.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9396 -1.4739 0.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1429 -1.1585 3.6271 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4395 -3.8374 3.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9959 -2.0353 1.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0638 -0.2765 1.6913 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1401 -0.0097 1.0698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0950 -1.4267 2.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0297 -3.4634 0.4224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4598 -3.6426 1.3782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4583 -4.0919 -0.3399 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2451 -2.9484 -0.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9799 -1.9619 2.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4244 -2.6422 1.4056 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8777 0.3561 1.4297 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9792 -0.6673 2.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2861 -1.6847 -0.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4680 -2.1497 1.5116 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7752 -2.5862 -0.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8178 1.4630 1.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9646 -0.4777 1.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3145 1.6501 2.7148 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2885 2.5315 1.4921 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0424 1.2836 2.5139 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 1 6 7 1 0 5 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 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 24 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 17 48 1 0 48 49 1 0 49 50 1 0 50 51 1 1 50 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 6 55 57 1 0 57 58 1 0 58 59 1 0 7 2 1 0 57 9 1 0 58 5 1 0 55 11 1 0 52 12 1 0 50 15 1 0 37 19 1 0 46 39 1 0 33 26 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 6 3 64 1 0 3 65 1 0 4 66 1 0 4 67 1 0 7 68 1 0 7 69 1 0 9 70 1 1 10 71 1 0 10 72 1 0 11 73 1 0 12 74 1 0 13 75 1 0 13 76 1 0 14 77 1 0 14 78 1 0 15 79 1 0 16 80 1 0 16 81 1 0 17 82 1 6 19 83 1 0 21 84 1 1 22 85 1 0 22 86 1 0 23 87 1 0 24 88 1 6 26 89 1 0 28 90 1 0 28 91 1 0 29 92 1 6 30 93 1 0 31 94 1 1 32 95 1 0 33 96 1 6 34 97 1 0 35 98 1 1 36 99 1 0 37100 1 1 39101 1 0 41102 1 0 41103 1 0 42104 1 6 43105 1 0 44106 1 1 45107 1 0 46108 1 1 47109 1 0 48110 1 0 48111 1 0 49112 1 0 49113 1 0 51114 1 0 51115 1 0 51116 1 0 52117 1 0 53118 1 0 53119 1 0 54120 1 0 54121 1 0 56122 1 0 56123 1 0 56124 1 0 57125 1 0 58126 1 1 59127 1 0 59128 1 0 59129 1 0 M END

Standard InCHIKey	DQIDRINFLSLNGN-CYAFNSHGSA-N
Standard InCHI	InChI=1S/C43H70O16/c1-19-7-12-43(54-16-19)20(2)30-28(59-43)14-25-23-6-5-21-13-22(8-10-41(21,3)24(23)9-11-42(25,30)4)55-40-37(58-39-34(50)32(48)27(46)18-53-39)35(51)36(29(15-44)56-40)57-38-33(49)31(47)26(45)17-52-38/h19-40,44-51H,5-18H2,1-4H3/t19-,20-,21?,22-,23?,24?,25?,26+,27+,28-,29+,30?,31-,32-,33+,34+,35-,36+,37+,38?,39?,40?,41-,42-,43+/m0/s1
SMILES	C[C@H]1CC[C@@]2(OC1)O[C@H]1CC3C4CCC5C[C@@H](OC6O[C@H](CO)[C@@H](OC7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6OC6OC[C@@H](O)[C@H](O)[C@H]6O)CC[C@]5(C)C4CC[C@]3(C)C1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	842.47	Volume:	815.919 ? Van der Waals volume.
Dense:	1.033	LogP:	1.747 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.726 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.313 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.164	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.613	Fsp³:	1.0
MCE-18:	225.256 ? 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:	0.624	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.023 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.162	Promiscuous compounds:	0.008

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.157	MDCK Permeability:	-5.034
Pgp-inhibitor:	0.0	Pgp-substrate:	0.857
PAMPA:	0.999 ? 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):	0.0
20% Bioavailability (F20%):	0.003	30% Bioavailability (F30%):	0.164
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.124
Plasma Protein Binding (PPB):	64.465%	Volume Distribution (VD):	-0.42
Fu:	28.829% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.021
BSEP inhibitor:	0.94

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.309	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.176 ? 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):

0.135

Half-life (T1/2):

3.923

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.292
Human Hepatotoxicity (H-HT):	0.756	Drug-induced Liver Injury (DILI):	0.599
AMES Toxicity:	0.246	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.303	Skin Sensitization:	1.0
Carcinogencity:	0.159	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.997
Hematotoxicity:	0.006	Drug-induced Nephrotoxicity:	0.731
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.197
A549 Cytotoxicity:	0.12	Hek293 Cytotoxicity:	0.512
BCF:	1.858 ? 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:	3.847 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.326 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.465 ? 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
NPO43764	Asparagus stipularis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38398569]
NPO43764	Asparagus stipularis	Species	Asparagaceae	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

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

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 NPC568159 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	27145
0.1-0.2	20225
0.2-0.3	2018
0.3-0.4	258
0.4-0.5	85
0.5-0.6	64
0.6-0.7	40
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8778	High Similarity	NPC471464
0.8488	Intermediate Similarity	NPC19400
0.8202	Intermediate Similarity	NPC6295
0.8085	Intermediate Similarity	NPC128572
0.8046	Intermediate Similarity	NPC250393
0.7634	Intermediate Similarity	NPC160426
0.7553	Intermediate Similarity	NPC475351
0.7419	Intermediate Similarity	NPC485595
0.74	Intermediate Similarity	NPC475333
0.74	Intermediate Similarity	NPC475625
0.74	Intermediate Similarity	NPC224098
0.74	Intermediate Similarity	NPC208383
0.7273	Intermediate Similarity	NPC97700
0.7273	Intermediate Similarity	NPC30856
0.7111	Intermediate Similarity	NPC297348
0.7111	Intermediate Similarity	NPC249204
0.7111	Intermediate Similarity	NPC48339
0.7111	Intermediate Similarity	NPC141769
0.7111	Intermediate Similarity	NPC477547
0.7097	Intermediate Similarity	NPC211354
0.7021	Intermediate Similarity	NPC264101
0.699	Remote Similarity	NPC232037
0.6957	Remote Similarity	NPC477451
0.6947	Remote Similarity	NPC107962
0.6923	Remote Similarity	NPC325828
0.6923	Remote Similarity	NPC177834
0.69	Remote Similarity	NPC274200
0.6869	Remote Similarity	NPC475643
0.6809	Remote Similarity	NPC206003
0.6809	Remote Similarity	NPC473610
0.6804	Remote Similarity	NPC195297
0.6792	Remote Similarity	NPC132080
0.6789	Remote Similarity	NPC480556
0.67	Remote Similarity	NPC470433
0.67	Remote Similarity	NPC46190
0.67	Remote Similarity	NPC171073
0.6571	Remote Similarity	NPC116756
0.6569	Remote Similarity	NPC51172
0.6569	Remote Similarity	NPC49032
0.6562	Remote Similarity	NPC107188
0.6514	Remote Similarity	NPC232054
0.6505	Remote Similarity	NPC480555
0.6505	Remote Similarity	NPC150372
0.6381	Remote Similarity	NPC475319
0.6321	Remote Similarity	NPC269297
0.6321	Remote Similarity	NPC222202
0.6316	Remote Similarity	NPC234352
0.6275	Remote Similarity	NPC473601
0.6226	Remote Similarity	NPC115165
0.6182	Remote Similarity	NPC233433
0.6161	Remote Similarity	NPC470866
0.6154	Remote Similarity	NPC248746
0.6147	Remote Similarity	NPC480554
0.6132	Remote Similarity	NPC184617
0.6091	Remote Similarity	NPC476112
0.6091	Remote Similarity	NPC307534
0.6055	Remote Similarity	NPC194207
0.6055	Remote Similarity	NPC22779
0.6036	Remote Similarity	NPC480553
0.6022	Remote Similarity	NPC481418
0.6	Remote Similarity	NPC224314
0.5965	Remote Similarity	NPC94086
0.5965	Remote Similarity	NPC473817
0.5962	Remote Similarity	NPC202898
0.5882	Remote Similarity	NPC125324
0.5849	Remote Similarity	NPC92890
0.5818	Remote Similarity	NPC32361
0.5816	Remote Similarity	NPC294686
0.5812	Remote Similarity	NPC220836
0.5794	Remote Similarity	NPC42171
0.5784	Remote Similarity	NPC215408
0.576	Remote Similarity	NPC329807
0.5714	Remote Similarity	NPC470864
0.57	Remote Similarity	NPC222731
0.5699	Remote Similarity	NPC88962
0.5676	Remote Similarity	NPC473518
0.5625	Remote Similarity	NPC232611
0.5625	Remote Similarity	NPC481189
0.5581	Remote Similarity	NPC329727
0.5575	Remote Similarity	NPC108072
0.551	Remote Similarity	NPC485594
0.5472	Remote Similarity	NPC113044
0.5472	Remote Similarity	NPC283829
0.5472	Remote Similarity	NPC161676
0.5455	Remote Similarity	NPC151134
0.5431	Remote Similarity	NPC31896
0.5429	Remote Similarity	NPC470432
0.5429	Remote Similarity	NPC230507
0.5417	Remote Similarity	NPC477808
0.5413	Remote Similarity	NPC477809
0.5405	Remote Similarity	NPC98018
0.5405	Remote Similarity	NPC284104
0.5405	Remote Similarity	NPC103616
0.5391	Remote Similarity	NPC83137
0.5321	Remote Similarity	NPC602423
0.5304	Remote Similarity	NPC249265
0.5268	Remote Similarity	NPC294129
0.5243	Remote Similarity	NPC312678
0.5243	Remote Similarity	NPC253268
0.5225	Remote Similarity	NPC300557
0.5196	Remote Similarity	NPC291203
0.5196	Remote Similarity	NPC485591
0.5196	Remote Similarity	NPC217205
0.5191	Remote Similarity	NPC329820
0.5172	Remote Similarity	NPC48463
0.5172	Remote Similarity	NPC248944
0.5172	Remote Similarity	NPC7479
0.5172	Remote Similarity	NPC257296
0.5156	Remote Similarity	NPC330026
0.5152	Remote Similarity	NPC24960
0.5149	Remote Similarity	NPC181845
0.5149	Remote Similarity	NPC481423
0.513	Remote Similarity	NPC13193
0.5122	Remote Similarity	NPC210569
0.5096	Remote Similarity	NPC474399
0.5094	Remote Similarity	NPC485590
0.5093	Remote Similarity	NPC141433
0.5093	Remote Similarity	NPC70204
0.5085	Remote Similarity	NPC84111
0.5085	Remote Similarity	NPC287483
0.5085	Remote Similarity	NPC470865
0.5082	Remote Similarity	NPC473505
0.5051	Remote Similarity	NPC473774
0.5051	Remote Similarity	NPC481419
0.5051	Remote Similarity	NPC481417

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC568159 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7766
0.1-0.2	1319
0.2-0.3	52
0.3-0.4	8
0.4-0.5	1
0.5-0.6	3
0.6-0.7	1
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
0.6923	Remote Similarity	NPD8171	Phase 2
0.5882	Remote Similarity	NPD8170	Phase 2
0.5172	Remote Similarity	NPD6928	Phase 2
0.5102	Remote Similarity	NPD7991	Discontinued

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