NPASS Compound

Natural Product: NPC269532

Natural Product ID	NPC269532
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DZVSPONQDHAPDF-RTQWZQBFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24897390
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 128134 0 0 0 0 0 0 0 0999 V2000 1.6903 -0.2344 -5.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5949 -0.1941 -3.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4985 0.8598 -3.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9276 -1.5873 -3.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3873 -1.9839 -1.7647 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5882 -1.0173 -0.9795 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5259 -1.7023 -0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7545 -1.9426 -1.0525 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5274 -0.6851 -1.4032 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7820 -0.7691 -2.9089 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4304 0.3605 -1.2692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6774 1.4904 -0.6434 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9291 1.9452 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0103 1.0028 -0.2752 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0950 1.1851 0.7933 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6164 0.9595 2.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3853 2.7147 0.7617 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6212 3.0234 1.6042 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8282 2.2673 1.1911 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5695 0.7610 1.0672 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6563 0.0626 2.3720 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7386 0.2598 0.2536 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7439 -1.1128 0.0527 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3257 0.5780 0.2532 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2462 -0.7094 -0.4674 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0305 -0.7738 -1.4142 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7376 -0.4027 -0.6210 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8628 -1.4269 0.5021 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8011 2.3990 2.1764 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1710 3.1768 1.6055 S 0 0 0 0 0 0 0 0 0 0 0 0 -10.2993 4.4735 2.3713 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3597 2.3369 1.9697 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0738 3.4735 -0.0404 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0663 0.0787 -1.7978 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1126 -0.0370 -3.2510 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4810 -0.4284 0.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4233 0.8206 0.1984 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3405 -1.1126 0.8661 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1301 -0.4482 1.8333 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9467 -0.9428 3.2277 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7933 -2.1792 3.4002 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3838 -2.6615 2.1116 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1727 -1.5290 1.4794 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4953 -1.8480 0.0224 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2004 -0.8433 -0.5720 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4346 -0.5812 -0.0274 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4982 -0.6892 -1.0694 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8469 -0.2188 -0.6421 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6965 1.0995 0.0958 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6405 0.9627 1.1892 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5966 2.1748 2.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8428 2.4541 2.6305 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4038 0.6639 0.6280 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9156 1.4126 0.6729 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6258 -0.0382 -1.7859 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6361 -2.0720 -1.3484 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4742 -0.3521 1.4677 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3175 -3.6595 2.4484 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0363 -3.1982 3.9871 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4332 0.0740 4.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6794 -0.7378 -5.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7592 0.7704 -5.5120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9147 -0.8845 -5.5180 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4210 0.8099 -3.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0761 1.8598 -3.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8823 0.8642 -2.1004 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -2.2723 -3.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0231 -1.7949 -3.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2517 -2.3837 -1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7619 -2.9211 -1.9008 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1887 -2.7089 0.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7128 -1.1018 0.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3535 -2.7654 -0.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3413 -2.4270 -1.9973 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8542 -0.8292 -3.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4267 0.1215 -3.4606 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4032 -1.7452 -3.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7868 2.1841 -0.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7729 2.1749 1.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1180 2.9419 -0.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5478 1.4484 -1.1830 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5373 0.5998 2.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4346 1.8999 2.7813 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1834 0.3504 2.8501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5159 3.0654 -0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5767 3.2163 1.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4097 2.8687 2.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8102 4.1046 1.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2338 2.7070 0.2599 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7353 -0.2363 2.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1221 -0.8797 2.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4642 0.7976 3.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7089 0.4755 0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8389 0.8149 -0.7065 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4330 -1.2745 -0.6549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5711 1.2891 -0.6335 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0955 -0.7241 -1.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4148 -1.6209 0.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0298 -1.7989 -1.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2488 0.0254 -2.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7415 -1.2524 1.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0031 -1.5266 1.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1838 -2.4240 0.0517 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3991 4.4054 -0.1840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5834 0.9851 -1.5861 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 0.9014 -3.7470 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3075 -0.8725 -3.7925 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7939 0.6394 1.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8799 -1.0961 3.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6311 -1.9605 4.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6712 -3.1354 1.4323 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1108 -1.4518 2.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6044 -2.0860 -0.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1308 -2.7733 0.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6489 -1.3092 0.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1788 -0.2326 -2.0497 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2982 -0.9890 0.0177 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3844 1.8991 -0.5760 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9391 0.0967 1.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8828 2.0576 2.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2078 3.0816 1.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0537 3.4358 2.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3620 0.6766 1.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0144 0.8613 -1.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9537 -2.1427 -2.2880 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2187 -3.4569 2.1318 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5550 -4.0304 3.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6284 -0.2740 4.9836 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 20 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 19 29 1 0 29 30 1 0 30 31 2 0 30 32 2 0 30 33 1 0 11 34 1 0 34 35 1 0 6 36 1 1 36 37 2 0 36 38 1 0 38 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 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 43 57 1 0 42 58 1 0 41 59 1 0 40 60 1 0 35 2 1 0 57 39 1 0 34 6 1 0 53 46 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 61 1 0 1 62 1 0 1 63 1 0 3 64 1 0 3 65 1 0 3 66 1 0 4 67 1 0 4 68 1 0 5 69 1 0 5 70 1 0 7 71 1 0 7 72 1 0 8 73 1 0 8 74 1 0 10 75 1 0 10 76 1 0 10 77 1 0 12 78 1 0 13 79 1 0 13 80 1 0 14 81 1 6 16 82 1 0 16 83 1 0 16 84 1 0 17 85 1 0 17 86 1 0 18 87 1 0 18 88 1 0 19 89 1 6 21 90 1 0 21 91 1 0 21 92 1 0 22 93 1 0 22 94 1 0 23 95 1 0 24 96 1 6 25 97 1 0 25 98 1 0 26 99 1 0 26100 1 0 28101 1 0 28102 1 0 28103 1 0 33104 1 0 34105 1 1 35106 1 0 35107 1 0 39108 1 1 40109 1 1 41110 1 1 42111 1 6 43112 1 1 44113 1 0 44114 1 0 46115 1 1 47116 1 6 48117 1 1 49118 1 6 50119 1 1 51120 1 0 51121 1 0 52122 1 0 54123 1 0 55124 1 0 56125 1 0 58126 1 0 59127 1 0 60128 1 0 M END

Standard InCHIKey	DZVSPONQDHAPDF-RTQWZQBFSA-N
Standard InCHI	InChI=1S/C42H68O17S/c1-37(2)13-15-42(36(51)58-35-33(50)31(48)29(46)24(57-35)19-55-34-32(49)30(47)28(45)23(18-43)56-34)16-14-40(5)21(22(42)17-37)7-8-26-38(3)11-10-27(59-60(52,53)54)39(4,20-44)25(38)9-12-41(26,40)6/h7,22-35,43-50H,8-20H2,1-6H3,(H,52,53,54)/t22-,23+,24+,25+,26+,27-,28+,29+,30-,31-,32+,33+,34+,35-,38-,39-,40+,41+,42-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)OS(=O)(=O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	876.42	Volume:	837.763 ? Van der Waals volume.
Dense:	1.046	LogP:	0.756 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.971 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.367 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	41.0
TPSA:	279.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.026	Fsp³:	0.929
MCE-18:	158.963 ? 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:	0.967	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.135	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.18	MDCK Permeability:	-5.153
Pgp-inhibitor:	0.001	Pgp-substrate:	0.001
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):	0.294
20% Bioavailability (F20%):	0.621	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.571	MRP1:	0.069
Plasma Protein Binding (PPB):	65.432%	Volume Distribution (VD):	-0.671
Fu:	29.165% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.054
BSEP inhibitor:	0.4

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.105
HLM stability:	0.042 ? 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):

0.341

Half-life (T1/2):

2.4

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.721	Drug-induced Liver Injury (DILI):	0.959
AMES Toxicity:	0.921	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	1.0
Carcinogencity:	0.16	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.995
Hematotoxicity:	0.421	Drug-induced Nephrotoxicity:	0.926
Genotoxicity:	0.866	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.188	Hek293 Cytotoxicity:	0.169
BCF:	0.558 ? 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:	3.629 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.553 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.536 ? 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
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18442289]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24757	Meryta denhamii	Species	Araliaceae	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

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 NPC269532 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	20203
0.1-0.2	24249
0.2-0.3	4036
0.3-0.4	898
0.4-0.5	294
0.5-0.6	95
0.6-0.7	72
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
0.8	Intermediate Similarity	NPC295371
0.7766	Intermediate Similarity	NPC48499
0.766	Intermediate Similarity	NPC29069
0.7172	Intermediate Similarity	NPC473373
0.7087	Intermediate Similarity	NPC63159
0.6931	Remote Similarity	NPC473884
0.6759	Remote Similarity	NPC241909
0.6726	Remote Similarity	NPC100639
0.6726	Remote Similarity	NPC470218
0.6702	Remote Similarity	NPC237503
0.6699	Remote Similarity	NPC473343
0.6667	Remote Similarity	NPC167383
0.6667	Remote Similarity	NPC473459
0.6633	Remote Similarity	NPC209894
0.6571	Remote Similarity	NPC109588
0.6518	Remote Similarity	NPC76972
0.6518	Remote Similarity	NPC469782
0.6518	Remote Similarity	NPC204414
0.6509	Remote Similarity	NPC251768
0.6509	Remote Similarity	NPC102439
0.6505	Remote Similarity	NPC150400
0.646	Remote Similarity	NPC192600
0.646	Remote Similarity	NPC79643
0.6442	Remote Similarity	NPC157868
0.6441	Remote Similarity	NPC258617
0.6415	Remote Similarity	NPC104071
0.6415	Remote Similarity	NPC309714
0.6389	Remote Similarity	NPC609763
0.6387	Remote Similarity	NPC65105
0.6381	Remote Similarity	NPC469946
0.6364	Remote Similarity	NPC301449
0.6364	Remote Similarity	NPC601290
0.6348	Remote Similarity	NPC155410
0.6348	Remote Similarity	NPC135904
0.6348	Remote Similarity	NPC123199
0.6337	Remote Similarity	NPC214484
0.6321	Remote Similarity	NPC192791
0.6321	Remote Similarity	NPC242840
0.6306	Remote Similarity	NPC295823
0.6306	Remote Similarity	NPC174720
0.6306	Remote Similarity	NPC475467
0.6293	Remote Similarity	NPC475160
0.6293	Remote Similarity	NPC473714
0.6286	Remote Similarity	NPC39211
0.6281	Remote Similarity	NPC298034
0.6281	Remote Similarity	NPC71065
0.625	Remote Similarity	NPC475516
0.6216	Remote Similarity	NPC481079
0.6204	Remote Similarity	NPC40775
0.6204	Remote Similarity	NPC159309
0.6204	Remote Similarity	NPC11551
0.6204	Remote Similarity	NPC86222
0.6186	Remote Similarity	NPC481080
0.6176	Remote Similarity	NPC90856
0.6168	Remote Similarity	NPC112352
0.6161	Remote Similarity	NPC480474
0.6147	Remote Similarity	NPC475591
0.6147	Remote Similarity	NPC236870
0.6116	Remote Similarity	NPC293330
0.6106	Remote Similarity	NPC187290
0.6095	Remote Similarity	NPC235405
0.6095	Remote Similarity	NPC139894
0.6091	Remote Similarity	NPC222580
0.6091	Remote Similarity	NPC297263
0.6087	Remote Similarity	NPC60557
0.6087	Remote Similarity	NPC67857
0.604	Remote Similarity	NPC256798
0.6038	Remote Similarity	NPC249848
0.6038	Remote Similarity	NPC107966
0.6033	Remote Similarity	NPC41061
0.6033	Remote Similarity	NPC227551
0.6019	Remote Similarity	NPC223301
0.6019	Remote Similarity	NPC171544
0.6018	Remote Similarity	NPC480473
0.6	Remote Similarity	NPC476068
0.6	Remote Similarity	NPC136877
0.6	Remote Similarity	NPC235438
0.5984	Remote Similarity	NPC43550
0.5982	Remote Similarity	NPC281148
0.5982	Remote Similarity	NPC104372
0.5982	Remote Similarity	NPC114484
0.5965	Remote Similarity	NPC31838
0.5963	Remote Similarity	NPC30735
0.5935	Remote Similarity	NPC202828
0.5935	Remote Similarity	NPC119592
0.5935	Remote Similarity	NPC305981
0.5935	Remote Similarity	NPC481081
0.5909	Remote Similarity	NPC46665
0.5887	Remote Similarity	NPC261506
0.5887	Remote Similarity	NPC4328
0.5882	Remote Similarity	NPC191827
0.5865	Remote Similarity	NPC189884
0.5865	Remote Similarity	NPC138334
0.5833	Remote Similarity	NPC488560
0.5826	Remote Similarity	NPC481078
0.5804	Remote Similarity	NPC475504
0.58	Remote Similarity	NPC306746
0.58	Remote Similarity	NPC199457
0.578	Remote Similarity	NPC471547
0.5776	Remote Similarity	NPC75287
0.5766	Remote Similarity	NPC10607
0.5748	Remote Similarity	NPC250247
0.5743	Remote Similarity	NPC68419
0.5739	Remote Similarity	NPC80986
0.5714	Remote Similarity	NPC148417
0.5676	Remote Similarity	NPC471548
0.5664	Remote Similarity	NPC31193
0.5636	Remote Similarity	NPC475171
0.5625	Remote Similarity	NPC473401
0.5603	Remote Similarity	NPC481030
0.5588	Remote Similarity	NPC604133
0.5577	Remote Similarity	NPC128925
0.5556	Remote Similarity	NPC236638
0.5556	Remote Similarity	NPC294453
0.5487	Remote Similarity	NPC305267
0.5487	Remote Similarity	NPC480475
0.5463	Remote Similarity	NPC475208
0.5463	Remote Similarity	NPC179434
0.5455	Remote Similarity	NPC191763
0.5455	Remote Similarity	NPC475899
0.5421	Remote Similarity	NPC204458
0.537	Remote Similarity	NPC78046
0.5351	Remote Similarity	NPC101744
0.5351	Remote Similarity	NPC473383
0.5349	Remote Similarity	NPC70809
0.5345	Remote Similarity	NPC64715
0.534	Remote Similarity	NPC37739
0.5328	Remote Similarity	NPC165204
0.5327	Remote Similarity	NPC47063
0.5315	Remote Similarity	NPC173583
0.5312	Remote Similarity	NPC135849
0.531	Remote Similarity	NPC75417
0.5294	Remote Similarity	NPC46388
0.5288	Remote Similarity	NPC137917
0.5278	Remote Similarity	NPC269095
0.5268	Remote Similarity	NPC470512
0.5243	Remote Similarity	NPC204407
0.5243	Remote Similarity	NPC116794
0.5242	Remote Similarity	NPC471550
0.5229	Remote Similarity	NPC1046
0.521	Remote Similarity	NPC96641
0.521	Remote Similarity	NPC163183
0.5203	Remote Similarity	NPC481031
0.52	Remote Similarity	NPC25663
0.5197	Remote Similarity	NPC480418
0.5179	Remote Similarity	NPC480420
0.5172	Remote Similarity	NPC139044
0.5172	Remote Similarity	NPC470515
0.5161	Remote Similarity	NPC480419
0.5146	Remote Similarity	NPC605954
0.5124	Remote Similarity	NPC11242
0.5118	Remote Similarity	NPC57484
0.5094	Remote Similarity	NPC271138
0.5094	Remote Similarity	NPC102914
0.5094	Remote Similarity	NPC110139
0.5094	Remote Similarity	NPC108709
0.5093	Remote Similarity	NPC284807
0.5089	Remote Similarity	NPC59804
0.5088	Remote Similarity	NPC263756
0.5088	Remote Similarity	NPC213674
0.5086	Remote Similarity	NPC173859
0.5086	Remote Similarity	NPC148603
0.5085	Remote Similarity	NPC134835
0.5085	Remote Similarity	NPC119794
0.5083	Remote Similarity	NPC187618
0.5047	Remote Similarity	NPC220984
0.5044	Remote Similarity	NPC58448
0.5043	Remote Similarity	NPC118440
0.5042	Remote Similarity	NPC73318
0.5041	Remote Similarity	NPC475287
0.5041	Remote Similarity	NPC300419
0.5039	Remote Similarity	NPC475514

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC269532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6491
0.1-0.2	2592
0.2-0.3	60
0.3-0.4	7
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