NPASS Compound

Natural Product: NPC473884

Natural Product ID	NPC473884
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ilexoside Xlviii
IUPAC Name	(2R,3R,4R,5S,6S)-6-[[(3S,4R,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms	Ilexoside XLVIII
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL454262
PubChem CID	44566327
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 123129 0 0 0 0 0 0 0 0999 V2000 -8.9502 -2.4939 -4.7021 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6765 -2.5830 -4.1424 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5291 -1.4205 -3.1892 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2842 -1.4088 -2.5658 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2481 -0.3492 -1.6977 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1985 -0.3386 -0.7800 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3031 -0.2107 0.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4447 -0.0946 1.0795 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1181 -0.2050 1.4993 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4851 -1.5787 1.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2002 -1.7913 2.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1602 -0.7357 1.7478 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8220 0.2281 0.8495 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2453 0.5135 -0.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0286 -0.0420 -0.8095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8812 -0.2746 0.4404 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1700 -1.2686 1.2581 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1178 -2.5786 0.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0591 -1.6200 2.4341 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4655 -2.0225 1.9794 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0916 -0.8188 1.2898 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3077 -0.4395 0.0755 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5792 -1.2817 -1.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8228 0.9609 -0.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1060 1.3437 0.2798 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1476 0.2849 0.4600 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5526 -0.9136 1.1783 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0845 -2.1893 0.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1291 -0.8557 2.6050 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7755 0.3283 3.2474 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7888 -0.1206 -0.6545 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1225 0.1674 -0.7823 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9513 -0.9265 -0.7717 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5747 -1.1359 -1.9853 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7031 -1.4671 -3.1027 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1840 -1.6255 -4.2472 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3373 -1.6180 -2.9427 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6135 -0.0562 -2.3084 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0013 1.2470 -1.9158 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4889 1.1333 -1.8320 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0563 2.4511 -1.5269 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3799 2.2029 -2.8612 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7719 -0.2503 -1.5627 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1309 0.8674 1.1344 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1252 2.0833 1.9568 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2688 2.3071 2.8853 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1335 1.1798 3.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6364 -0.1820 2.8784 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7295 2.9367 4.1830 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1929 3.4236 2.3439 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8421 -0.1446 3.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0660 0.9050 -2.5694 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4086 1.0982 -3.2525 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8732 -0.1686 -3.9203 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2838 -0.0899 -3.9941 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3778 2.1358 -4.1881 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8187 2.0239 -1.7973 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9977 -1.8826 -5.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6107 -3.5649 -3.6563 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9496 -2.4354 -4.9656 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3021 -1.5610 -2.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2486 -0.2442 -1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2236 -2.3076 1.6773 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4135 -1.8051 0.1874 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5029 -1.8339 3.1094 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9006 -2.8253 1.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7543 1.2540 -0.9724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1485 -0.9950 -1.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5204 0.6428 -1.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8308 0.7025 0.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0621 -3.4103 1.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7028 -2.8504 -0.1562 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0345 -2.6491 0.0119 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7204 -2.4632 3.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2837 -0.6867 3.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5017 -2.9442 1.4121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0125 -2.1844 2.9153 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8885 0.0214 2.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7365 -1.1292 -1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4379 -0.8571 -1.7457 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8682 -2.3141 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0681 1.7525 -0.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8815 1.0815 -1.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9443 1.8594 1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5683 2.1347 -0.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9300 0.8090 1.0966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1145 -2.3595 0.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2125 -2.1593 -0.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5028 -3.0763 0.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2539 -0.8066 2.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8886 -1.7646 3.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5064 0.7721 3.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3508 0.7140 0.1953 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2406 -2.0526 -1.7851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -1.6565 -3.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8743 -0.0426 -3.3638 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4123 1.5726 -0.9356 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1462 0.9553 -2.8530 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9438 2.5539 -0.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2077 1.9903 -3.3250 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2107 0.6320 -1.4523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5588 1.2506 0.1391 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1676 2.1695 2.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0656 3.0425 1.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1746 1.3571 2.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2699 1.1474 4.3670 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9615 -0.5376 3.6515 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5182 -0.8790 2.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0012 2.2454 4.6255 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6139 2.9669 4.8650 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3413 3.9493 3.9804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5859 4.1728 1.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7909 3.7902 3.1884 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8570 2.8978 1.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5095 -1.0105 3.7335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1415 0.6755 3.1138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7332 0.1995 3.6737 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3078 0.7370 -3.3446 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1849 1.3829 -2.5027 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5359 -0.1709 -4.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6719 -0.1141 -3.0797 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1415 2.9968 -3.7621 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6745 1.7498 -0.8751 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 2 0 9 7 1 6 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 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 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 27 29 1 0 29 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 34 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 13 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 46 50 1 0 12 51 1 1 5 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 54 3 1 0 48 9 1 0 44 9 1 0 17 12 1 0 27 21 1 0 40 32 1 0 22 16 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 5 62 1 1 10 63 1 0 10 64 1 0 11 65 1 0 11 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 1 18 71 1 0 18 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 20 76 1 0 20 77 1 0 21 78 1 1 23 79 1 0 23 80 1 0 23 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 1 28 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 29 91 1 0 30 92 1 0 32 93 1 1 34 94 1 1 37 95 1 0 38 96 1 6 39 97 1 1 40 98 1 6 41 99 1 0 42100 1 0 43101 1 0 44102 1 6 45103 1 0 45104 1 0 47105 1 0 47106 1 0 48107 1 0 48108 1 0 49109 1 0 49110 1 0 49111 1 0 50112 1 0 50113 1 0 50114 1 0 51115 1 0 51116 1 0 51117 1 0 52118 1 6 53119 1 1 54120 1 6 55121 1 0 56122 1 0 57123 1 0 M END

Standard InCHIKey	RZQHWSDMLZHIRN-ISEAIKIGSA-N
Standard InCHI	InChI=1S/C42H66O15/c1-37(2)13-15-42(36(53)57-34-30(49)27(46)26(45)22(18-43)54-34)16-14-40(5)20(21(42)17-37)7-8-24-38(3)11-10-25(39(4,19-44)23(38)9-12-41(24,40)6)55-35-31(50)28(47)29(48)32(56-35)33(51)52/h7,21-32,34-35,43-50H,8-19H2,1-6H3,(H,51,52)/t21-,22+,23+,24+,25-,26+,27-,28+,29+,30+,31-,32+,34-,35-,38-,39-,40+,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@]23CC[C@@]4(C(=CC[C@H]5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H]([C@@]4(C)CO)O[C@H]4O[C@@H](C(=O)O)[C@@H]([C@H]([C@@H]4O)O)O)[C@@H]3CC(CC2)(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	810.44	Volume:	799.037 ? Van der Waals volume.
Dense:	1.014	LogP:	1.64 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.32 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.401 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	40.0
TPSA:	253.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.887	Fsp³:	0.905
MCE-18:	154.0 ? 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:	0.913	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.113

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.202	MDCK Permeability:	-5.131
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.051
20% Bioavailability (F20%):	0.231	30% Bioavailability (F30%):	0.797
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241	MRP1:	0.386
Plasma Protein Binding (PPB):	73.615%	Volume Distribution (VD):	-0.405
Fu:	18.783% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.161	BCRP inhibitor:	0.001
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.012	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	0.034
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.86
HLM stability:	0.006 ? 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):

0.042

Half-life (T1/2):

3.029

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.597	Drug-induced Liver Injury (DILI):	0.842
AMES Toxicity:	0.632	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.066	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.994
Hematotoxicity:	0.561	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.411	RPMI-8226 Immunitoxicity:	0.126
A549 Cytotoxicity:	0.261	Hek293 Cytotoxicity:	0.068
BCF:	0.63 ? 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:	3.591 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.369 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.384 ? 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]

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	3

Activity Type	# Activity
Individual protein	3

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	=	64.3	%	DOI[10.1039/C4MD00091A]
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	36.5	%	PMID[20092289]
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	15.7	%	PMID[18443127]

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 NPC473884 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	19272
0.1-0.2	25520
0.2-0.3	3753
0.3-0.4	790
0.4-0.5	314
0.5-0.6	138
0.6-0.7	41
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC157868
0.8889	High Similarity	NPC242840
0.8495	Intermediate Similarity	NPC11551
0.8172	Intermediate Similarity	NPC475171
0.7732	Intermediate Similarity	NPC251768
0.7732	Intermediate Similarity	NPC159309
0.7732	Intermediate Similarity	NPC86222
0.7576	Intermediate Similarity	NPC31193
0.7551	Intermediate Similarity	NPC40775
0.7526	Intermediate Similarity	NPC75417
0.7426	Intermediate Similarity	NPC114484
0.7353	Intermediate Similarity	NPC301449
0.7353	Intermediate Similarity	NPC601290
0.7347	Intermediate Similarity	NPC192791
0.73	Intermediate Similarity	NPC475591
0.73	Intermediate Similarity	NPC236870
0.7143	Intermediate Similarity	NPC295371
0.7087	Intermediate Similarity	NPC281148
0.7065	Intermediate Similarity	NPC224121
0.7021	Intermediate Similarity	NPC209894
0.6923	Remote Similarity	NPC237503
0.6889	Remote Similarity	NPC167383
0.6887	Remote Similarity	NPC187290
0.6875	Remote Similarity	NPC214484
0.6768	Remote Similarity	NPC235405
0.6735	Remote Similarity	NPC48499
0.67	Remote Similarity	NPC249848
0.67	Remote Similarity	NPC107966
0.66	Remote Similarity	NPC475516
0.6535	Remote Similarity	NPC473373
0.6495	Remote Similarity	NPC480937
0.6471	Remote Similarity	NPC39211
0.6466	Remote Similarity	NPC258617
0.6442	Remote Similarity	NPC30735
0.6373	Remote Similarity	NPC150400
0.6364	Remote Similarity	NPC90856
0.6355	Remote Similarity	NPC64715
0.6346	Remote Similarity	NPC223301
0.6346	Remote Similarity	NPC171544
0.6321	Remote Similarity	NPC235438
0.6321	Remote Similarity	NPC118440
0.6316	Remote Similarity	NPC470218
0.63	Remote Similarity	NPC29069
0.625	Remote Similarity	NPC469946
0.6224	Remote Similarity	NPC256798
0.62	Remote Similarity	NPC189884
0.62	Remote Similarity	NPC138334
0.619	Remote Similarity	NPC112352
0.6147	Remote Similarity	NPC114692
0.6132	Remote Similarity	NPC309714
0.6075	Remote Similarity	NPC10607
0.6075	Remote Similarity	NPC46665
0.6071	Remote Similarity	NPC11242
0.6058	Remote Similarity	NPC482748
0.6055	Remote Similarity	NPC95437
0.6042	Remote Similarity	NPC204407
0.6036	Remote Similarity	NPC187618
0.6036	Remote Similarity	NPC241909
0.6019	Remote Similarity	NPC63159
0.6	Remote Similarity	NPC236657
0.6	Remote Similarity	NPC104372
0.5979	Remote Similarity	NPC306746
0.5979	Remote Similarity	NPC199457
0.5963	Remote Similarity	NPC222580
0.5963	Remote Similarity	NPC475504
0.5963	Remote Similarity	NPC131469
0.5963	Remote Similarity	NPC297263
0.5918	Remote Similarity	NPC68419
0.5897	Remote Similarity	NPC100639
0.5893	Remote Similarity	NPC120116
0.5893	Remote Similarity	NPC480474
0.5859	Remote Similarity	NPC286347
0.5842	Remote Similarity	NPC294112
0.581	Remote Similarity	NPC139894
0.5776	Remote Similarity	NPC192600
0.5758	Remote Similarity	NPC604133
0.5752	Remote Similarity	NPC480473
0.5752	Remote Similarity	NPC80986
0.5702	Remote Similarity	NPC31838
0.5702	Remote Similarity	NPC481078
0.569	Remote Similarity	NPC76972
0.569	Remote Similarity	NPC313110
0.569	Remote Similarity	NPC469782
0.569	Remote Similarity	NPC204414
0.5676	Remote Similarity	NPC609763
0.5676	Remote Similarity	NPC611191
0.5667	Remote Similarity	NPC4749
0.5664	Remote Similarity	NPC481079
0.5664	Remote Similarity	NPC218954
0.5657	Remote Similarity	NPC57362
0.5648	Remote Similarity	NPC473343
0.562	Remote Similarity	NPC21691
0.561	Remote Similarity	NPC293330
0.561	Remote Similarity	NPC65105
0.5588	Remote Similarity	NPC128925
0.5577	Remote Similarity	NPC204458
0.5575	Remote Similarity	NPC247315
0.5575	Remote Similarity	NPC482728
0.5566	Remote Similarity	NPC136877
0.5556	Remote Similarity	NPC472949
0.5546	Remote Similarity	NPC155410
0.5524	Remote Similarity	NPC270667
0.5524	Remote Similarity	NPC1046
0.552	Remote Similarity	NPC298034
0.552	Remote Similarity	NPC71065
0.5508	Remote Similarity	NPC79643
0.55	Remote Similarity	NPC475160
0.55	Remote Similarity	NPC283417
0.55	Remote Similarity	NPC471550
0.55	Remote Similarity	NPC37739
0.55	Remote Similarity	NPC200049
0.55	Remote Similarity	NPC473714
0.55	Remote Similarity	NPC606107
0.5495	Remote Similarity	NPC44716
0.5495	Remote Similarity	NPC473459
0.5495	Remote Similarity	NPC480475
0.5481	Remote Similarity	NPC47063
0.5481	Remote Similarity	NPC480943
0.5478	Remote Similarity	NPC295823
0.5478	Remote Similarity	NPC174720
0.5478	Remote Similarity	NPC481030
0.5478	Remote Similarity	NPC475467
0.5472	Remote Similarity	NPC475208
0.5464	Remote Similarity	NPC191763
0.5455	Remote Similarity	NPC46388
0.5455	Remote Similarity	NPC475368
0.5429	Remote Similarity	NPC473481
0.5429	Remote Similarity	NPC480938
0.5417	Remote Similarity	NPC135904
0.5417	Remote Similarity	NPC123199
0.541	Remote Similarity	NPC481080
0.5405	Remote Similarity	NPC109588
0.5385	Remote Similarity	NPC75287
0.5377	Remote Similarity	NPC78046
0.5372	Remote Similarity	NPC191827
0.537	Remote Similarity	NPC309780
0.537	Remote Similarity	NPC59804
0.5366	Remote Similarity	NPC476068
0.5357	Remote Similarity	NPC102439
0.5351	Remote Similarity	NPC302887
0.5333	Remote Similarity	NPC475899
0.5321	Remote Similarity	NPC58448
0.5294	Remote Similarity	NPC137917
0.5283	Remote Similarity	NPC269095
0.5278	Remote Similarity	NPC603870
0.5268	Remote Similarity	NPC104071
0.5248	Remote Similarity	NPC116794
0.5243	Remote Similarity	NPC271138
0.5243	Remote Similarity	NPC110139
0.5243	Remote Similarity	NPC108709
0.5229	Remote Similarity	NPC108748
0.5225	Remote Similarity	NPC22956
0.5214	Remote Similarity	NPC160452
0.521	Remote Similarity	NPC213952
0.5197	Remote Similarity	NPC202828
0.5197	Remote Similarity	NPC119592
0.5196	Remote Similarity	NPC28198
0.5196	Remote Similarity	NPC476123
0.5189	Remote Similarity	NPC195132
0.5185	Remote Similarity	NPC179434
0.5167	Remote Similarity	NPC60557
0.5167	Remote Similarity	NPC67857
0.5161	Remote Similarity	NPC487505
0.5161	Remote Similarity	NPC82380
0.5161	Remote Similarity	NPC244296
0.5159	Remote Similarity	NPC41061
0.5159	Remote Similarity	NPC227551
0.5156	Remote Similarity	NPC302543
0.5149	Remote Similarity	NPC605954
0.5146	Remote Similarity	NPC310014
0.5146	Remote Similarity	NPC269315
0.5138	Remote Similarity	NPC12288
0.5118	Remote Similarity	NPC43550
0.5096	Remote Similarity	NPC31839
0.5096	Remote Similarity	NPC102914
0.5089	Remote Similarity	NPC263756
0.5089	Remote Similarity	NPC213674
0.5086	Remote Similarity	NPC603832
0.5085	Remote Similarity	NPC96641
0.5085	Remote Similarity	NPC163183
0.5083	Remote Similarity	NPC472267
0.5083	Remote Similarity	NPC107536
0.5083	Remote Similarity	NPC115656
0.5083	Remote Similarity	NPC280029
0.5083	Remote Similarity	NPC9470
0.5082	Remote Similarity	NPC481031
0.5081	Remote Similarity	NPC47995
0.5081	Remote Similarity	NPC488560
0.5078	Remote Similarity	NPC305981
0.5078	Remote Similarity	NPC481081
0.5048	Remote Similarity	NPC220984
0.5045	Remote Similarity	NPC173583
0.5043	Remote Similarity	NPC139044
0.5041	Remote Similarity	NPC475287
0.5041	Remote Similarity	NPC252657
0.5041	Remote Similarity	NPC88311
0.5041	Remote Similarity	NPC470476
0.5039	Remote Similarity	NPC261506
0.5039	Remote Similarity	NPC4328

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6300
0.1-0.2	2771
0.2-0.3	73
0.3-0.4	4
0.4-0.5	2
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