NPASS Compound

Natural Product: NPC252104

Natural Product ID	NPC252104
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VBWLFPXNVMBQCR-HJMNTHRUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	21580243
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 3.0462 1.1307 0.3984 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1806 -0.0057 -0.0151 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6742 -0.5034 -1.3692 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7452 0.3021 -0.1698 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4352 1.1011 -1.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0093 0.7687 -1.7081 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9424 0.9684 -0.5797 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3011 2.4343 -0.6050 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4362 0.5102 0.7910 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4013 0.9103 1.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8033 0.3759 1.5969 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2115 0.6652 0.2125 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4902 0.1066 -0.2617 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2593 -0.2293 -1.7454 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8786 0.2912 -2.0770 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1853 0.1105 -0.7749 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9391 -1.3498 -0.6080 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7007 0.9777 -0.2218 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5596 2.2482 -1.0098 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2096 1.3117 1.1524 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7015 1.5440 0.8286 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8859 0.3985 -0.1404 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1343 0.4653 -0.9501 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1312 1.5831 -1.9622 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2215 -0.8332 -1.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2497 0.6021 -0.1514 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7403 0.2713 -0.8571 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6184 1.0719 2.4916 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0012 0.7695 1.0584 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2995 2.1976 1.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4929 -0.0660 2.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1777 -1.3501 1.8292 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3817 -1.1934 0.9250 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4888 -0.9504 1.6928 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4547 -1.9183 1.6181 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8559 -1.4930 1.3655 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8271 -2.2384 2.2736 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4354 -3.6452 2.5707 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9473 -3.8726 2.6025 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6023 -4.8789 3.6825 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2260 -5.0417 3.7051 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3595 -2.6410 2.8374 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0638 -4.5632 1.6944 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9079 -1.5811 3.5267 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2181 -1.5233 0.0465 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6662 -0.3963 -0.5433 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0281 -0.6247 -1.1547 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5887 0.7784 -1.4113 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4923 1.7655 -1.6616 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2112 1.1947 -2.1516 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1884 1.2260 -3.6605 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5305 2.4906 -4.1452 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8714 -0.0531 -1.6787 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3153 2.6379 -0.5598 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4889 0.7084 -2.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8858 -1.3924 -0.4246 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2111 1.0807 1.5172 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0759 1.1055 -0.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6571 2.1274 0.1603 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0598 0.3292 -1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8521 -1.0344 -1.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4858 -1.2508 -1.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2669 -0.7189 -0.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6021 2.1875 -1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0541 0.7636 -2.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2842 1.4538 -2.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0041 -0.2450 -2.1440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4169 3.0428 -0.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0971 2.6727 -1.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5797 2.8795 0.3371 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5069 -0.6247 0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1220 0.4104 2.8212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4766 1.9638 2.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8922 -0.6873 1.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2528 1.7632 0.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7579 -0.8570 0.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4000 -1.2996 -1.9264 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9573 0.3060 -2.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8370 1.2450 -2.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4434 -0.4565 -2.8059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9093 -1.6595 -0.9118 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1253 -1.7791 0.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5869 -1.9623 -1.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3089 2.3564 -1.8354 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7581 3.0980 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5270 2.4263 -1.3721 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1851 0.4498 1.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8642 2.2622 1.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3306 1.4410 1.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8671 2.5225 0.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9709 -0.5236 0.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1584 1.7369 -2.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5056 1.2760 -2.8397 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8015 2.5523 -1.5404 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9903 -1.7073 -1.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3981 -0.7568 -2.5232 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1532 -0.9072 -2.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1217 1.3494 0.4709 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1211 1.5307 3.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4265 2.8914 0.6048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1940 2.2459 2.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5424 2.5434 2.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3451 -0.3310 2.8758 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2814 0.4899 2.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3882 -1.9870 2.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4176 -1.9192 1.2415 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4288 -2.1056 0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1267 -2.6737 0.8726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9637 -0.4386 1.6934 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8553 -2.2439 1.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8195 -3.9620 3.5863 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6110 -4.3219 1.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1432 -5.8053 3.4478 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9240 -4.4689 4.6651 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8050 -4.2863 3.2367 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0125 -4.6926 1.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5361 -0.8067 3.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7477 0.4870 0.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9208 -1.0560 -2.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1585 1.1176 -0.5018 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8888 2.4528 -2.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3943 1.9064 -1.8287 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9133 0.5018 -4.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1864 0.9453 -4.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3116 3.2143 -3.4998 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6866 3.3383 -0.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3561 -0.1389 -2.9744 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7608 -2.3316 -0.7056 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 1 7 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 1 13 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 23 26 1 0 22 27 1 0 11 28 1 0 9 29 1 0 29 30 1 1 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 37 44 1 0 36 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 33 2 1 0 42 35 1 0 53 46 1 0 29 4 1 0 16 7 1 0 27 18 1 0 16 12 1 0 1 57 1 0 1 58 1 0 1 59 1 0 3 60 1 0 3 61 1 0 3 62 1 0 4 63 1 6 5 64 1 0 5 65 1 0 6 66 1 0 6 67 1 0 8 68 1 0 8 69 1 0 8 70 1 0 9 71 1 6 10 72 1 0 10 73 1 0 11 74 1 1 12 75 1 1 13 76 1 1 14 77 1 0 14 78 1 0 15 79 1 0 15 80 1 0 17 81 1 0 17 82 1 0 17 83 1 0 19 84 1 0 19 85 1 0 19 86 1 0 20 87 1 0 20 88 1 0 21 89 1 0 21 90 1 0 22 91 1 1 24 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 25 97 1 0 26 98 1 0 28 99 1 0 30100 1 0 30101 1 0 30102 1 0 31103 1 0 31104 1 0 32105 1 0 32106 1 0 33107 1 6 35108 1 6 36109 1 1 37110 1 6 38111 1 1 39112 1 6 40113 1 0 40114 1 0 41115 1 0 43116 1 0 44117 1 0 46118 1 1 47119 1 6 48120 1 1 49121 1 6 50122 1 1 51123 1 0 51124 1 0 52125 1 0 54126 1 0 55127 1 0 56128 1 0 M END

Standard InCHIKey	VBWLFPXNVMBQCR-HJMNTHRUSA-N
Standard InCHI	InChI=1S/C42H72O14/c1-37(2)24-10-15-40(6)25(17-21(45)28-20(9-14-41(28,40)7)42(8)16-12-27(56-42)38(3,4)51)39(24,5)13-11-26(37)54-36-34(32(49)30(47)23(19-44)53-36)55-35-33(50)31(48)29(46)22(18-43)52-35/h20-36,43-51H,9-19H2,1-8H3/t20-,21+,22+,23+,24-,25+,26-,27-,28-,29+,30+,31-,32-,33+,34+,35-,36-,39-,40+,41+,42-/m0/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](C[C@H]([C@@H]4[C@H](CC[C@@]34C)[C@]3(C)CC[C@@H](C(C)(C)O)O3)O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	800.49	Volume:	798.156 ? Van der Waals volume.
Dense:	1.003	LogP:	1.743 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.402 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.076 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	37.0
TPSA:	228.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.935	Fsp³:	1.0
MCE-18:	153.333 ? 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:	0.866	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.248	Promiscuous compounds:	0.209

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.281	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.009	Pgp-substrate:	0.042
PAMPA:	0.97 ? 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):	0.039
20% Bioavailability (F20%):	0.074	30% Bioavailability (F30%):	0.935
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041	MRP1:	0.313
Plasma Protein Binding (PPB):	75.506%	Volume Distribution (VD):	-0.462
Fu:	18.78% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.011

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.988	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.023	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.273
HLM stability:	0.026 ? 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):

0.558

Half-life (T1/2):

2.48

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.018
Human Hepatotoxicity (H-HT):	0.723	Drug-induced Liver Injury (DILI):	0.736
AMES Toxicity:	0.951	Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	1.0
Carcinogencity:	0.383	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.996
Hematotoxicity:	0.708	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	0.654	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.827	Hek293 Cytotoxicity:	0.573
BCF:	1.048 ? 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:	3.285 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.464 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.669 ? 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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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]
NPO11990	Coleostephus myconis	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]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	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]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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 NPC252104 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	25985
0.1-0.2	20017
0.2-0.3	2855
0.3-0.4	778
0.4-0.5	153
0.5-0.6	36
0.6-0.7	26
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	Natural Product ID
0.7654	Intermediate Similarity	NPC208477
0.7284	Intermediate Similarity	NPC252253
0.7073	Intermediate Similarity	NPC472897
0.7073	Intermediate Similarity	NPC472896
0.7024	Intermediate Similarity	NPC229801
0.6988	Remote Similarity	NPC8039
0.6988	Remote Similarity	NPC120123
0.6966	Remote Similarity	NPC208650
0.6813	Remote Similarity	NPC220427
0.6747	Remote Similarity	NPC159036
0.6706	Remote Similarity	NPC472987
0.6596	Remote Similarity	NPC14946
0.6596	Remote Similarity	NPC63368
0.6591	Remote Similarity	NPC307167
0.6588	Remote Similarity	NPC312553
0.6463	Remote Similarity	NPC31907
0.6421	Remote Similarity	NPC159005
0.6404	Remote Similarity	NPC269627
0.6392	Remote Similarity	NPC135369
0.6364	Remote Similarity	NPC181467
0.6265	Remote Similarity	NPC82955
0.6139	Remote Similarity	NPC241381
0.6133	Remote Similarity	NPC477285
0.6087	Remote Similarity	NPC210759
0.6023	Remote Similarity	NPC45959
0.6019	Remote Similarity	NPC488292
0.6019	Remote Similarity	NPC146868
0.6	Remote Similarity	NPC472988
0.6	Remote Similarity	NPC139271
0.6	Remote Similarity	NPC69737
0.6	Remote Similarity	NPC38217
0.5978	Remote Similarity	NPC194842
0.5978	Remote Similarity	NPC472715
0.5833	Remote Similarity	NPC88000
0.5833	Remote Similarity	NPC4831
0.5833	Remote Similarity	NPC472023
0.5816	Remote Similarity	NPC305418
0.581	Remote Similarity	NPC488294
0.5806	Remote Similarity	NPC276758
0.5789	Remote Similarity	NPC234160
0.5783	Remote Similarity	NPC473198
0.5778	Remote Similarity	NPC165033
0.5778	Remote Similarity	NPC273879
0.5638	Remote Similarity	NPC304011
0.5636	Remote Similarity	NPC488291
0.5612	Remote Similarity	NPC65167
0.56	Remote Similarity	NPC64081
0.5595	Remote Similarity	NPC280825
0.5545	Remote Similarity	NPC246124
0.549	Remote Similarity	NPC472718
0.5465	Remote Similarity	NPC234287
0.5435	Remote Similarity	NPC16573
0.5333	Remote Similarity	NPC157659
0.5312	Remote Similarity	NPC236753
0.5312	Remote Similarity	NPC127801
0.5304	Remote Similarity	NPC488293
0.53	Remote Similarity	NPC237071
0.53	Remote Similarity	NPC238796
0.5275	Remote Similarity	NPC611039
0.5238	Remote Similarity	NPC472716
0.5172	Remote Similarity	NPC66654
0.5158	Remote Similarity	NPC488576
0.5104	Remote Similarity	NPC488575
0.5104	Remote Similarity	NPC488574
0.5102	Remote Similarity	NPC488577
0.51	Remote Similarity	NPC208594
0.5057	Remote Similarity	NPC76486

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7799
0.1-0.2	1285
0.2-0.3	63
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data