NPASS Compound

Natural Product: NPC285253

Natural Product ID	NPC285253
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KQGDHYQRJRGMDG-CYMACDCKSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3613720
PubChem CID	21637632
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 122129 0 0 0 0 0 0 0 0999 V2000 9.6013 -1.7587 -1.9607 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6226 -2.6861 -1.5735 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7583 -2.1467 -0.4635 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1330 -0.9805 -0.9359 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5049 -0.2986 0.1140 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6470 0.6465 -0.4299 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0358 1.9446 -0.1110 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9763 2.6906 0.6489 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5941 3.8272 1.2172 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8015 3.0704 -0.1867 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0585 3.4331 -1.4855 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0851 2.8582 -2.1483 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3643 2.7343 -1.3588 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3605 2.0878 -2.0468 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6889 1.4880 -2.6427 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8994 2.0044 -0.2490 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 2.2988 0.3202 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5853 2.4611 -0.7104 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0041 1.2209 -1.2564 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3400 0.1765 -0.1840 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0956 0.7574 1.1687 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2389 1.3885 1.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0606 2.1829 2.7145 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3314 0.3856 1.6799 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4573 -0.1636 2.2712 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9605 -0.3383 2.2371 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4805 -0.7028 0.8704 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8405 0.0027 -0.2538 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3157 -0.5889 -1.5246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5468 -1.0593 -1.5606 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5094 -1.0512 -0.4302 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9736 -0.3618 0.7957 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0957 1.1299 0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7407 -0.8586 1.9895 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2180 -0.7170 1.7201 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5869 -1.4087 0.4594 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8967 -0.7866 -0.7666 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4518 0.5103 -1.0675 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8772 0.2894 -1.6106 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9395 0.4915 -3.0936 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8555 1.2910 -0.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3845 -1.0785 -1.2665 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0191 -1.5100 0.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8162 -2.7093 0.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5899 -2.4249 -0.0659 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9143 -1.3765 2.7605 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2333 -2.1907 0.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4418 -1.0403 -0.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8635 -1.2520 1.0657 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4471 -2.5349 0.3430 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7405 -3.1924 -0.0989 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2715 -3.9547 0.9625 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6182 -2.2437 -0.7354 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7505 -1.6446 2.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9208 -1.2828 -1.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2042 -3.5427 -1.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0431 -3.0665 -2.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4106 -1.9300 0.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3171 0.2292 0.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9486 1.8601 0.5394 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7027 2.0430 1.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9391 4.2931 1.8228 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3047 3.9320 0.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3167 3.4450 -3.1044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7136 3.7436 -1.0614 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1291 2.6711 -2.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9602 0.9620 -2.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5670 0.8091 -2.7574 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1906 1.5720 -3.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 3.3437 0.7442 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2100 3.0847 -0.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0202 3.0604 -1.5363 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7223 0.8144 -2.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8866 1.5108 -1.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 1.6162 1.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4087 1.5974 3.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6798 3.0933 2.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0108 2.5220 2.8265 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9798 0.7965 2.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9944 0.2404 0.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9383 -0.5595 2.1101 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 -1.1475 2.2734 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2243 0.3414 3.2463 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1870 -1.1991 2.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4092 0.5305 2.7066 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2091 1.0782 -0.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6714 -0.6390 -2.4142 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9009 -1.4924 -2.4901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2275 1.6674 1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1791 1.5690 -0.2325 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9412 1.5009 1.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5143 -0.1378 2.8299 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4494 -1.8416 2.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5382 0.3256 1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1791 -1.4959 -1.6014 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8835 0.9780 -1.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5550 1.2551 -0.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5469 -0.3297 -3.6914 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9794 0.8020 -3.3687 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3090 1.4023 -3.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2692 2.1991 -0.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1436 0.8497 0.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7068 1.4604 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1427 -1.8529 -2.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5131 -1.0171 -1.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6941 -0.9929 0.8837 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3275 -2.5937 0.2053 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3530 -3.3591 -0.3234 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8441 -3.2614 1.3741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3655 -2.0738 3.1709 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8797 -2.7734 1.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1977 -2.3639 1.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1834 -2.5813 -0.2644 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3322 -0.7970 -1.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1375 -1.7580 -1.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8674 -1.6147 0.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9632 -0.8609 1.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9552 -3.1722 1.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5203 -3.9098 -0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 -3.9810 1.7043 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0444 -3.0158 -0.9706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0607 -0.8682 2.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 10 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 22 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 6 32 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 39 41 1 0 39 42 1 0 42 43 1 0 36 44 1 1 44 45 1 0 35 46 1 0 27 47 1 6 20 48 1 6 5 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 51 3 1 0 13 7 1 0 22 17 1 0 32 27 1 0 43 36 1 0 28 20 1 0 31 45 1 1 37 31 1 0 1 55 1 0 2 56 1 0 2 57 1 0 3 58 1 1 5 59 1 1 7 60 1 1 8 61 1 1 9 62 1 0 10 63 1 1 12 64 1 6 13 65 1 1 14 66 1 0 15 67 1 0 15 68 1 0 15 69 1 0 17 70 1 1 18 71 1 0 18 72 1 0 19 73 1 0 19 74 1 0 21 75 1 1 23 76 1 0 23 77 1 0 23 78 1 0 24 79 1 0 24 80 1 0 24 81 1 0 25 82 1 0 25 83 1 0 26 84 1 0 26 85 1 0 28 86 1 6 29 87 1 0 30 88 1 0 33 89 1 0 33 90 1 0 33 91 1 0 34 92 1 0 34 93 1 0 35 94 1 6 37 95 1 6 38 96 1 0 38 97 1 0 40 98 1 0 40 99 1 0 40100 1 0 41101 1 0 41102 1 0 41103 1 0 42104 1 0 42105 1 0 43106 1 0 43107 1 0 44108 1 0 44109 1 0 46110 1 0 47111 1 0 47112 1 0 47113 1 0 48114 1 0 48115 1 0 48116 1 0 49117 1 1 50118 1 1 51119 1 6 52120 1 0 53121 1 0 54122 1 0 M END

Standard InCHIKey	KQGDHYQRJRGMDG-CYMACDCKSA-N
Standard InCHI	InChI=1S/C42H68O12/c1-21-28(45)33(54-34-31(48)30(47)29(46)22(19-43)52-34)32(49)35(51-21)53-27-11-12-38(6)23(37(27,4)5)9-13-39(7)24(38)10-14-42-25-17-36(2,3)15-16-41(25,20-50-42)26(44)18-40(39,42)8/h10,14,21-35,43-49H,9,11-13,15-20H2,1-8H3/t21-,22-,23+,24-,25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,38+,39-,40+,41-,42+/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@@H]2O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3C=C[C@]34[C@@]2(C)C[C@@H]([C@@]2([C@H]4CC(C)(C)CC2)CO3)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	764.47	Volume:	769.382 ? Van der Waals volume.
Dense:	0.994	LogP:	1.615 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.158 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.78 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	41.0
TPSA:	187.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	8.0
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:	7.155	Fsp³:	0.952
MCE-18:	225.366 ? 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:	0.881	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.201	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.031	MDCK Permeability:	-5.071
Pgp-inhibitor:	0.062	Pgp-substrate:	0.119
PAMPA:	0.98 ? 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):	0.019
20% Bioavailability (F20%):	0.199	30% Bioavailability (F30%):	0.95
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.031
Plasma Protein Binding (PPB):	80.328%	Volume Distribution (VD):	-0.427
Fu:	17.437% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.03
BSEP inhibitor:	0.883

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.038	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.743
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.957
HLM stability:	0.877 ? 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):

0.943

Half-life (T1/2):

3.674

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.171
Human Hepatotoxicity (H-HT):	0.344	Drug-induced Liver Injury (DILI):	0.452
AMES Toxicity:	0.688	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.124	Skin Sensitization:	0.998
Carcinogencity:	0.136	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.042
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.991
Hematotoxicity:	0.143	Drug-induced Nephrotoxicity:	0.667
Genotoxicity:	0.064	RPMI-8226 Immunitoxicity:	0.186
A549 Cytotoxicity:	0.064	Hek293 Cytotoxicity:	0.319
BCF:	1.881 ? 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:	3.995 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.503 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.774 ? 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
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21983	Bupleurum polyclonum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3915	Bupleurum rockii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21983	Bupleurum polyclonum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3915	Bupleurum rockii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20248	Bupleurum marginatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3107	Bupleurum falcatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Inhibition	1
CC50	1

Activity Type	# Activity
Cell line	6
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
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[26259802]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	20530.0	nM	PMID[26259802]
NPT1872	Cell line	Bcap37	Homo sapiens	IC50	=	15420.0	nM	PMID[26259802]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	21290.0	nM	PMID[26259802]
NPT2615	Cell line	HEK-293T	Homo sapiens	Inhibition	=	44.83	%	PMID[28314599]
NPT2615	Cell line	HEK-293T	Homo sapiens	CC50	=	2850.0	nM	PMID[28314599]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	16690.0	nM	PMID[26259802]

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 NPC285253 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	25374
0.1-0.2	21100
0.2-0.3	2553
0.3-0.4	656
0.4-0.5	140
0.5-0.6	18
0.6-0.7	1
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC180459
0.9059	High Similarity	NPC195116
0.9059	High Similarity	NPC221110
0.8652	High Similarity	NPC473128
0.8261	Intermediate Similarity	NPC600293
0.8191	Intermediate Similarity	NPC476305
0.7684	Intermediate Similarity	NPC40133
0.7684	Intermediate Similarity	NPC49413
0.7579	Intermediate Similarity	NPC157474
0.7419	Intermediate Similarity	NPC290608
0.7356	Intermediate Similarity	NPC38376
0.7356	Intermediate Similarity	NPC80210
0.7216	Intermediate Similarity	NPC44298
0.7083	Intermediate Similarity	NPC473130
0.7083	Intermediate Similarity	NPC110494
0.6923	Remote Similarity	NPC473125
0.5728	Remote Similarity	NPC203354
0.5682	Remote Similarity	NPC92885
0.5619	Remote Similarity	NPC18724
0.5505	Remote Similarity	NPC171741
0.5495	Remote Similarity	NPC253611
0.5495	Remote Similarity	NPC488782
0.5462	Remote Similarity	NPC189575
0.534	Remote Similarity	NPC109792
0.534	Remote Similarity	NPC57065
0.534	Remote Similarity	NPC54521
0.531	Remote Similarity	NPC77717
0.5285	Remote Similarity	NPC471424
0.5189	Remote Similarity	NPC473127
0.5189	Remote Similarity	NPC110656
0.5143	Remote Similarity	NPC162354
0.5135	Remote Similarity	NPC323231
0.5124	Remote Similarity	NPC471425
0.5085	Remote Similarity	NPC209798

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC285253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7712
0.1-0.2	1381
0.2-0.3	53
0.3-0.4	4
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