NPASS Compound

Natural Product: NPC179434

Natural Product ID	NPC179434
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ilekudinoside C
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylate
Synonyms	Ilekudinoside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501236
PubChem CID	21635823
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 121127 0 0 0 0 0 0 0 0999 V2000 3.1085 -4.7204 -1.5876 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7427 -3.4384 -2.0366 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0721 -3.1486 -1.3766 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8092 -2.9772 0.0757 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8533 -1.8514 0.4053 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0343 -2.3199 1.5630 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9374 -1.3759 1.8873 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9648 -1.2556 0.7006 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4070 -2.6476 0.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7613 -0.7660 -0.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3189 0.2053 -1.1887 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0323 0.9027 -1.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8623 0.1397 -0.1294 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2133 0.7728 0.0789 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1969 2.1834 0.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8403 0.7769 -1.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2827 1.1232 -1.3304 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1347 0.4457 -0.3170 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5011 0.1553 0.9868 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7998 1.2301 2.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1825 -1.1190 1.5184 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9138 -2.0994 0.5346 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0380 -0.1558 0.9079 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3724 -0.2834 2.2446 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1174 -1.1347 1.9627 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1645 -0.3401 1.0997 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4143 0.7489 1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2502 1.2607 -0.1034 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4302 0.7101 -0.5317 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4376 0.6162 0.5900 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4336 1.7650 0.3839 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2198 1.3894 -0.8785 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1940 0.9549 -1.9001 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9504 1.4926 -1.5916 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9748 2.4652 -1.3106 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7590 2.9401 0.1163 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2043 -0.5575 0.4195 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7622 0.7716 -2.6178 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1237 -1.3241 -0.7676 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8893 -2.2327 -1.9274 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0400 -1.4505 -3.2462 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7356 -0.7620 0.9456 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6518 -0.3129 2.0899 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6938 -0.2487 0.0833 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5855 0.7884 0.4910 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9952 0.2625 0.3228 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9188 1.2957 -0.2882 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6128 2.6865 0.2074 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1426 2.9617 0.0844 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9391 4.0855 -0.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5923 4.4216 -1.0232 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4262 1.8561 -0.3861 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0833 2.8006 1.5132 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8752 1.2976 -1.6714 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5124 -0.0973 1.5658 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9314 -4.8312 -0.5253 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1793 -4.8468 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7968 -5.5463 -1.8949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0199 -3.6376 -3.1195 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4812 -2.2478 -1.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7549 -3.9844 -1.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4501 -3.9510 0.4870 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8164 -2.8479 0.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7248 -2.3218 2.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7215 -3.3792 1.4837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3654 -0.4062 2.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3350 -1.8229 2.7184 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4454 -2.7159 -0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1851 -3.0148 1.5766 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1632 -3.3789 0.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9465 0.5704 -2.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2151 1.9481 -0.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4025 0.9564 -2.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1105 -0.8111 -0.7020 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2714 2.7436 0.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.7905 0.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4611 2.3317 1.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2997 1.6131 -1.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6449 -0.1973 -1.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4589 2.2393 -1.2919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5519 -0.4885 -0.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8163 1.0310 2.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8577 2.2355 1.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1091 1.1532 2.8912 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7576 -1.4819 2.4473 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2596 -0.9770 1.6342 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4401 -2.8695 0.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9662 -1.1695 0.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0166 0.6517 2.6771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9231 -0.8244 3.0063 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5609 -2.0088 1.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6867 -1.4488 2.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6359 0.2741 2.9575 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2687 1.5724 2.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3237 1.2195 1.5288 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3108 -0.3006 -0.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0124 0.6669 1.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0951 1.8942 1.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8724 0.5288 -0.5820 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5333 1.2676 -2.9087 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0710 -0.1498 -1.9319 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2295 3.0714 -0.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2280 3.4850 -0.5827 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7255 -0.7364 1.2417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4994 1.3622 -2.9013 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7651 -0.4822 -1.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8181 -2.5925 -1.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5859 -2.0832 -4.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0868 -1.1502 -3.6753 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7528 -0.6175 -3.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3826 1.0813 1.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0378 -0.6371 -0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9517 1.0547 0.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2329 3.3847 -0.4142 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7301 3.2901 1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3372 3.8115 -1.9077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4971 5.0007 -0.6020 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4101 5.2593 -0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3402 2.7512 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5326 0.4502 -2.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -0.6175 1.4006 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 6 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 19 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 18 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 17 38 1 0 10 39 1 0 39 40 1 0 40 41 1 0 5 42 1 1 42 43 2 0 42 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 49 52 1 0 48 53 1 0 47 54 1 0 46 55 1 0 40 2 1 0 52 45 1 0 39 5 1 0 26 8 1 0 34 29 1 0 26 13 1 0 23 14 1 0 1 56 1 0 1 57 1 0 1 58 1 0 2 59 1 6 3 60 1 0 3 61 1 0 4 62 1 0 4 63 1 0 6 64 1 0 6 65 1 0 7 66 1 0 7 67 1 0 9 68 1 0 9 69 1 0 9 70 1 0 11 71 1 0 12 72 1 0 12 73 1 0 13 74 1 6 15 75 1 0 15 76 1 0 15 77 1 0 16 78 1 0 16 79 1 0 17 80 1 1 18 81 1 6 20 82 1 0 20 83 1 0 20 84 1 0 21 85 1 0 21 86 1 0 22 87 1 0 23 88 1 6 24 89 1 0 24 90 1 0 25 91 1 0 25 92 1 0 27 93 1 0 27 94 1 0 27 95 1 0 29 96 1 6 30 97 1 1 31 98 1 1 32 99 1 1 33100 1 0 33101 1 0 35102 1 0 36103 1 0 37104 1 0 38105 1 0 39106 1 6 40107 1 1 41108 1 0 41109 1 0 41110 1 0 45111 1 1 46112 1 6 47113 1 6 48114 1 6 49115 1 1 50116 1 0 50117 1 0 51118 1 0 53119 1 0 54120 1 0 55121 1 0 M END

Standard InCHIKey	JEUZHXDEBVXESF-SMFLOBOHSA-N
Standard InCHI	InChI=1S/C41H66O14/c1-19-9-12-41(36(51)55-35-32(50)30(48)29(47)24(16-42)53-35)14-13-39(5)21(27(41)20(19)2)7-8-26-37(3)15-22(44)33(54-34-31(49)28(46)23(45)17-52-34)38(4,18-43)25(37)10-11-40(26,39)6/h7,19-20,22-35,42-50H,8-18H2,1-6H3/t19-,20+,22-,23+,24-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40-,41+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)O)[C@@H]2[C@H]1C)C(=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:	782.45	Volume:	775.587 ? Van der Waals volume.
Dense:	1.009	LogP:	2.073 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.571 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.801 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	39.0
TPSA:	236.06 ? 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:	0.103	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.992	Fsp³:	0.927
MCE-18:	149.013 ? 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:	0.757	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.087 ? 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:	0.147	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.254	MDCK Permeability:	-5.127
Pgp-inhibitor:	0.0	Pgp-substrate:	0.608
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):	0.265
20% Bioavailability (F20%):	0.732	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905	MRP1:	0.08
Plasma Protein Binding (PPB):	70.549%	Volume Distribution (VD):	-0.408
Fu:	20.29% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.077
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.078
HLM stability:	0.02 ? 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):

0.442

Half-life (T1/2):

2.38

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.707	Drug-induced Liver Injury (DILI):	0.851
AMES Toxicity:	0.911	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.349	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.995
Hematotoxicity:	0.779	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	0.634	RPMI-8226 Immunitoxicity:	0.111
A549 Cytotoxicity:	0.801	Hek293 Cytotoxicity:	0.303
BCF:	1.045 ? 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:	3.436 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.862 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.091 ? 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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	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
Inhibition	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	35.5	%	PMID[10479318]

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 NPC179434 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	21700
0.1-0.2	23253
0.2-0.3	3605
0.3-0.4	926
0.4-0.5	277
0.5-0.6	71
0.6-0.7	15
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
0.7802	Intermediate Similarity	NPC139894
0.7386	Intermediate Similarity	NPC110139
0.7386	Intermediate Similarity	NPC108709
0.6848	Remote Similarity	NPC256798
0.6809	Remote Similarity	NPC189884
0.6809	Remote Similarity	NPC138334
0.6667	Remote Similarity	NPC473343
0.65	Remote Similarity	NPC475171
0.6465	Remote Similarity	NPC150400
0.6458	Remote Similarity	NPC90856
0.64	Remote Similarity	NPC295371
0.6327	Remote Similarity	NPC475208
0.6316	Remote Similarity	NPC128925
0.6289	Remote Similarity	NPC204458
0.6216	Remote Similarity	NPC475899
0.6132	Remote Similarity	NPC134835
0.6061	Remote Similarity	NPC78046
0.6	Remote Similarity	NPC101744
0.5865	Remote Similarity	NPC469946
0.5833	Remote Similarity	NPC68419
0.5789	Remote Similarity	NPC116794
0.5773	Remote Similarity	NPC271138
0.5773	Remote Similarity	NPC102914
0.5743	Remote Similarity	NPC127853
0.5729	Remote Similarity	NPC37739
0.57	Remote Similarity	NPC195132
0.5699	Remote Similarity	NPC191763
0.5684	Remote Similarity	NPC46388
0.5684	Remote Similarity	NPC605954
0.5673	Remote Similarity	NPC473373
0.567	Remote Similarity	NPC7870
0.567	Remote Similarity	NPC310014
0.567	Remote Similarity	NPC269315
0.567	Remote Similarity	NPC75747
0.5625	Remote Similarity	NPC237503
0.5596	Remote Similarity	NPC297263
0.5588	Remote Similarity	NPC29069
0.5579	Remote Similarity	NPC167383
0.5575	Remote Similarity	NPC815
0.5567	Remote Similarity	NPC479080
0.5566	Remote Similarity	NPC471547
0.5556	Remote Similarity	NPC473401
0.5556	Remote Similarity	NPC220984
0.5545	Remote Similarity	NPC601659
0.5524	Remote Similarity	NPC480420
0.551	Remote Similarity	NPC137917
0.5495	Remote Similarity	NPC73318
0.5487	Remote Similarity	NPC31838
0.5463	Remote Similarity	NPC471548
0.5463	Remote Similarity	NPC309714
0.5455	Remote Similarity	NPC488517
0.5446	Remote Similarity	NPC301449
0.5446	Remote Similarity	NPC601290
0.5437	Remote Similarity	NPC1046
0.5413	Remote Similarity	NPC473383
0.5398	Remote Similarity	NPC481030
0.5398	Remote Similarity	NPC241909
0.5392	Remote Similarity	NPC47063
0.5385	Remote Similarity	NPC48499
0.5364	Remote Similarity	NPC63159
0.5351	Remote Similarity	NPC481078
0.5321	Remote Similarity	NPC109588
0.5321	Remote Similarity	NPC160415
0.531	Remote Similarity	NPC481079
0.5243	Remote Similarity	NPC161434
0.5234	Remote Similarity	NPC58448
0.5229	Remote Similarity	NPC112352
0.5217	Remote Similarity	NPC187290
0.521	Remote Similarity	NPC123199
0.52	Remote Similarity	NPC144644
0.52	Remote Similarity	NPC170407
0.5192	Remote Similarity	NPC269095
0.5185	Remote Similarity	NPC473884
0.514	Remote Similarity	NPC475516
0.5135	Remote Similarity	NPC480475
0.5126	Remote Similarity	NPC481031
0.5122	Remote Similarity	NPC480418
0.5118	Remote Similarity	NPC142151
0.5114	Remote Similarity	NPC40552
0.5111	Remote Similarity	NPC307335
0.5111	Remote Similarity	NPC74855
0.51	Remote Similarity	NPC306746
0.5083	Remote Similarity	NPC480419
0.505	Remote Similarity	NPC177246
0.505	Remote Similarity	NPC604133
0.5048	Remote Similarity	NPC214484
0.5046	Remote Similarity	NPC39211
0.5041	Remote Similarity	NPC471550
0.5039	Remote Similarity	NPC68767

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC179434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7268
0.1-0.2	1825
0.2-0.3	51
0.3-0.4	6
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