NPASS Compound

Natural Product: NPC121648

Natural Product ID	NPC121648
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YNBYFOIDLBTOMW-IPTBNLQOSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11331683
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 123128 0 0 0 0 0 0 0 0999 V2000 -0.9766 -4.9896 1.5906 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3988 -5.3770 1.2184 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4639 -4.6553 1.4977 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5018 -3.3638 2.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0904 -2.1996 1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 -1.7689 0.2630 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3535 -2.8720 -0.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0244 -1.3425 0.7281 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2712 -0.2103 1.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8317 0.8109 1.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7960 0.1035 0.7080 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4295 -0.9974 1.5296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8346 -0.6022 -0.2731 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6152 -1.3940 -1.2538 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8641 -0.7385 -1.7809 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6561 -0.0403 -0.7463 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9562 0.5272 -1.2320 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8156 1.5650 -2.3003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7024 -0.6473 -1.8855 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1504 -0.3437 -2.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7722 0.0429 -0.7862 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1291 1.2575 -0.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7210 1.3779 1.2413 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4868 2.5116 -0.8929 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6766 1.0007 -0.0111 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9272 2.1610 0.5852 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5427 1.7594 1.0168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7961 0.9641 -0.0006 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0855 1.9169 -0.9198 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1555 0.2452 -0.9834 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8098 -1.5359 -2.4163 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9192 -0.5915 -0.2665 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2313 -0.6333 -0.6148 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5291 -0.1754 -2.0034 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1299 1.2690 -2.2387 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0370 1.9544 -0.8894 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1794 1.4333 -0.0618 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4066 2.2731 1.1767 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4695 1.8137 1.9401 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6896 1.8291 1.3181 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6623 2.7291 2.0972 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7964 3.0432 1.1509 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3983 1.7109 0.7290 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3584 0.7143 0.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3227 0.5805 1.2615 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1701 1.9893 -0.4192 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7553 3.7933 1.7955 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0152 3.8518 2.5624 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 0.1622 0.3466 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0763 3.3392 -1.0347 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9111 1.3573 -2.8933 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8820 -0.3815 -2.3345 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5758 -6.6619 0.4836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4651 -4.3558 0.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5991 -5.9267 1.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0680 -4.5036 2.5772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4407 -5.0618 1.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0626 -3.5906 3.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4640 -3.1845 2.5800 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1542 -1.3593 2.2511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1557 -2.5330 1.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1526 -3.6468 -0.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3981 -3.4102 -0.8245 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6153 -2.4867 -1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4858 -2.2068 1.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2446 -0.5813 2.7622 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2171 0.2997 1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3402 1.0133 2.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4695 1.7803 1.2231 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5566 -1.9440 0.9669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3982 -0.7357 1.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7749 -1.2471 2.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1929 0.1034 -0.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8309 -2.4336 -0.9236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6807 -0.1427 -2.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5095 -1.5915 -2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9551 -0.8148 0.0093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2279 1.1078 -3.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8431 1.7036 -2.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4603 2.5364 -1.9768 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6044 -1.5554 -1.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2423 -0.7385 -2.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6330 -1.3105 -2.4024 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3668 0.3632 -2.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6938 -0.8290 -0.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8071 1.2444 1.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3038 0.5796 1.8882 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5184 2.4005 1.6431 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0030 2.2227 -1.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6543 3.2029 -1.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2686 3.1183 -0.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5836 0.1628 0.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8627 3.0441 -0.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4823 2.4625 1.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9796 2.7236 1.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5874 1.2932 2.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4396 2.9805 -0.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9893 1.9760 -0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2123 1.7019 -1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5045 -0.3693 -1.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3802 -1.7612 -3.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7324 -1.6341 -0.4674 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9464 -0.7745 -2.7237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8938 1.8123 -2.8296 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0821 1.7157 -0.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0955 1.5184 -0.6875 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5068 2.2181 1.8432 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5351 3.3500 0.9422 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7015 2.2136 0.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0771 2.0975 2.9060 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3960 3.5432 0.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1176 1.3427 1.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8423 -0.2308 0.0807 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8917 1.0911 -0.6194 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8280 1.5339 -1.2188 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6171 4.7498 1.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3900 3.5428 3.2776 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3035 3.6068 -1.9719 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9590 2.0558 -3.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2177 -1.0620 -1.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4915 -6.5299 -0.6162 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2443 -7.3610 0.7764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5704 -7.0652 0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 14 31 1 0 6 32 1 6 32 33 1 0 33 34 1 0 34 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 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 37 49 1 0 36 50 1 0 35 51 1 0 34 52 1 0 2 53 1 0 13 8 1 0 28 16 1 0 49 33 1 0 28 11 1 0 45 40 1 0 25 17 1 0 1 54 1 0 1 55 1 0 1 56 1 0 3 57 1 0 4 58 1 0 4 59 1 0 5 60 1 0 5 61 1 0 7 62 1 0 7 63 1 0 7 64 1 0 8 65 1 1 9 66 1 0 9 67 1 0 10 68 1 0 10 69 1 0 12 70 1 0 12 71 1 0 12 72 1 0 13 73 1 6 14 74 1 1 15 75 1 0 15 76 1 0 16 77 1 1 18 78 1 0 18 79 1 0 18 80 1 0 19 81 1 0 19 82 1 0 20 83 1 0 20 84 1 0 21 85 1 1 23 86 1 0 23 87 1 0 23 88 1 0 24 89 1 0 24 90 1 0 24 91 1 0 25 92 1 1 26 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 29 97 1 0 29 98 1 0 29 99 1 0 30100 1 0 31101 1 0 33102 1 6 34103 1 6 35104 1 6 36105 1 1 37106 1 6 38107 1 0 38108 1 0 40109 1 6 41110 1 1 42111 1 6 43112 1 1 44113 1 0 44114 1 0 46115 1 0 47116 1 0 48117 1 0 50118 1 0 51119 1 0 52120 1 0 53121 1 0 53122 1 0 53123 1 0 M END

Standard InCHIKey	YNBYFOIDLBTOMW-IPTBNLQOSA-N
Standard InCHI	InChI=1S/C41H70O12/c1-21(2)10-9-14-41(8,53-36-34(49)32(47)31(46)25(52-36)20-51-35-33(48)30(45)24(43)19-50-35)22-11-16-40(7)29(22)23(42)18-27-38(5)15-13-28(44)37(3,4)26(38)12-17-39(27,40)6/h10,22-36,42-49H,9,11-20H2,1-8H3/t22-,23+,24+,25+,26-,27+,28-,29-,30-,31+,32-,33+,34+,35-,36-,38-,39+,40+,41-/m0/s1
SMILES	CC(=CCC[C@@](C)([C@H]1CC[C@]2(C)[C@@H]1[C@@H](C[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	754.49	Volume:	769.199 ? Van der Waals volume.
Dense:	0.981	LogP:	3.34 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.546 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.023 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	33.0
TPSA:	198.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.161	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.876	Fsp³:	0.951
MCE-18:	131.075 ? 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:	0.843	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:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.185	Promiscuous compounds:	0.213

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.004	MDCK Permeability:	-5.121
Pgp-inhibitor:	0.001	Pgp-substrate:	0.91
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):	0.044
20% Bioavailability (F20%):	0.482	30% Bioavailability (F30%):	0.595
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.363	MRP1:	0.769
Plasma Protein Binding (PPB):	77.121%	Volume Distribution (VD):	-0.459
Fu:	14.624% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.021
BSEP inhibitor:	0.02

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.85	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.005	CYP3A4-substrate:	0.833
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.956
HLM stability:	0.022 ? 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):

1.122

Half-life (T1/2):

2.366

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.069
Human Hepatotoxicity (H-HT):	0.446	Drug-induced Liver Injury (DILI):	0.113
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.039	Skin Sensitization:	1.0
Carcinogencity:	0.114	Eye Corrosion:	0.0
Eye Irritation:	0.056	Respiratory Toxicity:	0.057
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.979
Hematotoxicity:	0.386	Drug-induced Nephrotoxicity:	0.957
Genotoxicity:	0.03	RPMI-8226 Immunitoxicity:	0.184
A549 Cytotoxicity:	0.819	Hek293 Cytotoxicity:	0.394
BCF:	1.61 ? 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:	3.737 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.228 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.478 ? 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
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17560738]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2015.01.015]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12055308]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448045]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26774486]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37770099]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29353	Benzoin praecox	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	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 NPC121648 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	20980
0.1-0.2	23882
0.2-0.3	4392
0.3-0.4	517
0.4-0.5	46
0.5-0.6	22
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC131479
0.7532	Intermediate Similarity	NPC66654
0.7234	Intermediate Similarity	NPC6931
0.7209	Intermediate Similarity	NPC213190
0.7097	Intermediate Similarity	NPC14946
0.7097	Intermediate Similarity	NPC63368
0.7045	Intermediate Similarity	NPC152584
0.6915	Remote Similarity	NPC159005
0.6897	Remote Similarity	NPC69737
0.6842	Remote Similarity	NPC246124
0.6701	Remote Similarity	NPC180183
0.6526	Remote Similarity	NPC160816
0.6383	Remote Similarity	NPC208650
0.6353	Remote Similarity	NPC160734
0.625	Remote Similarity	NPC220427
0.6207	Remote Similarity	NPC114874
0.6047	Remote Similarity	NPC31907
0.5882	Remote Similarity	NPC135369
0.5841	Remote Similarity	NPC488293
0.5789	Remote Similarity	NPC127801
0.5745	Remote Similarity	NPC207845
0.5699	Remote Similarity	NPC208477
0.5684	Remote Similarity	NPC472719
0.5657	Remote Similarity	NPC476360
0.5657	Remote Similarity	NPC476361
0.56	Remote Similarity	NPC65167
0.5556	Remote Similarity	NPC208594
0.5556	Remote Similarity	NPC146868
0.5556	Remote Similarity	NPC309425
0.5556	Remote Similarity	NPC146652
0.5514	Remote Similarity	NPC241381
0.5505	Remote Similarity	NPC488294
0.5495	Remote Similarity	NPC157659
0.5474	Remote Similarity	NPC181467
0.5408	Remote Similarity	NPC472717
0.5217	Remote Similarity	NPC488291
0.5204	Remote Similarity	NPC269627
0.5192	Remote Similarity	NPC305418
0.5052	Remote Similarity	NPC473199

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121648 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7618
0.1-0.2	1471
0.2-0.3	59
0.3-0.4	2
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