NPASS Compound

Natural Product: NPC473844

Natural Product ID	NPC473844
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	28-O-Beta-D-Glucopyranosylbetulinic Acid 3Beta-O-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL453268
PubChem CID	25209714
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 -9.2921 3.2777 0.0622 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0845 2.7748 -0.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2177 1.9215 -1.6288 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9826 1.4829 -1.9414 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5591 0.2556 -1.5137 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1560 0.4203 -0.1959 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8305 0.3027 0.0235 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1278 1.5916 0.3856 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6633 1.3967 0.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0164 0.2605 0.8365 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8908 -0.9551 0.6782 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3423 -0.7377 0.9771 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6407 -0.4644 2.4192 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0691 -2.0317 0.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2696 -2.1727 1.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0180 -2.4659 0.4808 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0546 -1.3008 0.4237 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7649 -0.0648 0.0353 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0988 1.1372 -0.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0132 0.7201 -1.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8213 -0.4032 -0.8786 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9789 -1.6678 -0.6219 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3042 -2.1647 -1.8817 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9497 -2.7197 -0.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2936 -2.2909 0.2706 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0170 -1.3026 -0.5742 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0132 -0.8231 -1.5994 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8199 0.0647 -2.4088 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1690 -0.6292 -2.4470 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0418 -1.8482 -1.5123 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3549 0.0710 -3.8527 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1069 1.2057 -4.4784 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1768 -1.2170 -4.5904 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6558 -0.2151 0.1984 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3796 1.0068 0.1199 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6783 -0.4853 1.1308 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3043 0.5372 1.8783 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6474 0.5556 1.4355 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1486 1.7984 1.8176 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4296 2.0139 1.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3744 1.0442 1.3147 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3393 1.7782 3.3027 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0331 1.5120 3.9740 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2777 0.3338 3.3485 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9627 0.4442 3.8013 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1655 1.3350 5.3481 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7830 3.0374 3.7043 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5809 -1.2436 1.7945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7960 0.7278 2.2130 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5945 -0.7966 -1.6127 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7724 -0.3494 -0.7409 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2781 0.9138 -1.3468 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8694 0.5810 -2.5875 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2779 -0.1660 0.5448 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0858 -0.9559 -2.9170 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3061 4.2545 -0.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3061 3.5520 -0.4960 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7013 2.0860 0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5768 2.6887 -2.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6978 -0.0076 -2.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3742 0.0431 -0.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4476 2.4282 -0.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3182 1.9680 1.3823 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5328 1.2918 -1.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1711 2.3380 0.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8680 -1.1576 -0.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7463 -0.6614 2.5559 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4699 0.5399 2.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1515 -1.2643 3.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8598 -2.8366 1.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1802 -1.8619 0.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9336 -2.3690 -0.3819 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0737 -2.0836 2.3672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9253 -3.0343 1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4970 -3.3746 0.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3842 -2.7942 -0.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2322 -0.2583 -0.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7335 1.4215 0.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5178 1.9416 -0.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3919 0.4710 -2.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 1.5760 -1.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1082 -0.1037 0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6686 -1.7818 -2.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1676 -3.2799 -1.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9094 -2.0915 -2.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5357 -3.4881 0.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2034 -3.3752 -1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3293 -1.9143 1.3106 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9279 -3.2259 0.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8119 -1.7439 -2.2326 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9085 1.1276 -2.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4385 -1.0370 -3.4231 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9847 0.0404 -2.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7363 -2.7432 -2.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9947 -1.9644 -0.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2236 2.1625 -3.9934 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7784 1.1848 -5.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6190 -2.0740 -4.0845 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6146 -1.1621 -5.6102 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0968 -1.4075 -4.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9074 1.5408 1.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4080 2.5525 1.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1677 1.9208 -0.0321 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8324 3.0472 1.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0543 1.1106 0.5702 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0471 0.9802 3.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3766 2.3960 3.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7083 -0.6266 3.6847 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6352 1.3765 3.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6211 2.1287 5.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6124 3.2265 3.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2032 -0.3769 1.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0704 -2.2311 1.9792 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2049 -1.2556 2.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3751 1.6789 2.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1459 0.0425 3.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7309 1.0659 2.3880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3067 -1.7822 -1.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5148 -1.1798 -0.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0898 1.3157 -0.7061 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6514 1.2624 -3.2779 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4837 -0.9041 1.1599 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6392 -0.3397 -3.5505 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 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 11 15 1 0 15 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 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 2 0 31 33 1 0 26 34 1 1 34 35 2 0 34 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 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 17 48 1 1 10 49 1 1 5 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 50 55 1 0 52 3 1 0 12 7 1 0 22 17 1 0 30 26 1 0 44 37 1 0 18 10 1 0 27 21 1 0 1 56 1 0 2 57 1 0 2 58 1 0 3 59 1 6 5 60 1 6 7 61 1 6 8 62 1 0 8 63 1 0 9 64 1 0 9 65 1 0 11 66 1 6 13 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 14 72 1 0 15 73 1 0 15 74 1 0 16 75 1 0 16 76 1 0 18 77 1 6 19 78 1 0 19 79 1 0 20 80 1 0 20 81 1 0 21 82 1 1 23 83 1 0 23 84 1 0 23 85 1 0 24 86 1 0 24 87 1 0 25 88 1 0 25 89 1 0 27 90 1 6 28 91 1 1 29 92 1 0 29 93 1 0 30 94 1 0 30 95 1 0 32 96 1 0 32 97 1 0 33 98 1 0 33 99 1 0 33100 1 0 37101 1 1 39102 1 1 40103 1 0 40104 1 0 41105 1 0 42106 1 6 43107 1 1 44108 1 6 45109 1 0 46110 1 0 47111 1 0 48112 1 0 48113 1 0 48114 1 0 49115 1 0 49116 1 0 49117 1 0 50118 1 1 51119 1 1 52120 1 1 53121 1 0 54122 1 0 55123 1 0 M END

Standard InCHIKey	MEGZWYPZWAEPFB-QQIJCRMXSA-N
Standard InCHI	InChI=1S/C42H68O13/c1-20(2)21-10-15-42(37(51)55-36-34(50)32(48)30(46)24(19-44)53-36)17-16-40(6)22(28(21)42)8-9-26-39(5)13-12-27(38(3,4)25(39)11-14-41(26,40)7)54-35-33(49)31(47)29(45)23(18-43)52-35/h21-36,43-50H,1,8-19H2,2-7H3/t21-,22+,23+,24+,25-,26+,27-,28+,29+,30+,31-,32-,33+,34+,35-,36-,39-,40+,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@H]3[C@@]2(C)CC[C@@]2([C@@H]3[C@@H](CC2)C(=C)C)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	780.47	Volume:	784.093 ? Van der Waals volume.
Dense:	0.995	LogP:	2.568 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.111 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.141 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	39.0
TPSA:	215.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.106	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.773	Fsp³:	0.929
MCE-18:	149.333 ? 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:	0.961	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.154

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.925	MDCK Permeability:	-5.082
Pgp-inhibitor:	0.001	Pgp-substrate:	0.02
PAMPA:	0.931 ? 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):	0.014
20% Bioavailability (F20%):	0.057	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018	MRP1:	0.268
Plasma Protein Binding (PPB):	79.64%	Volume Distribution (VD):	-0.288
Fu:	13.347% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.012
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.008	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.095	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.113	CYP3A4-substrate:	0.01
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.627
HLM stability:	0.021 ? 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):

0.606

Half-life (T1/2):

2.941

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.797	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.934	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.009	Skin Sensitization:	1.0
Carcinogencity:	0.382	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.996
Hematotoxicity:	0.601	Drug-induced Nephrotoxicity:	0.967
Genotoxicity:	0.455	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.491	Hek293 Cytotoxicity:	0.287
BCF:	1.564 ? 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:	3.733 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.234 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.509 ? 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
NPO33375	eclipata prostrata	Species	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[25443644]
NPO33375	eclipata prostrata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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	8

Activity Type	# Activity
Cell line	8

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	>	100000.0	nM	PMID[12662094]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	100000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	>	200000.0	nM	PMID[20395019]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	200000.0	nM	DrugMatrix in vitro pharmacology data
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	20000.0	nM	PMID[12502328]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	66000.0	nM	PMID[10691704]

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 NPC473844 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	20039
0.1-0.2	24122
0.2-0.3	4265
0.3-0.4	1139
0.4-0.5	241
0.5-0.6	37
0.6-0.7	7
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
0.7253	Intermediate Similarity	NPC470478
0.7125	Intermediate Similarity	NPC94919
0.675	Remote Similarity	NPC240125
0.675	Remote Similarity	NPC91583
0.6386	Remote Similarity	NPC604868
0.6341	Remote Similarity	NPC470312
0.6164	Remote Similarity	NPC98270
0.6122	Remote Similarity	NPC469821
0.6087	Remote Similarity	NPC11035
0.5732	Remote Similarity	NPC473198
0.5658	Remote Similarity	NPC5280
0.5618	Remote Similarity	NPC272242
0.56	Remote Similarity	NPC12774
0.5556	Remote Similarity	NPC287269
0.5521	Remote Similarity	NPC235405
0.5435	Remote Similarity	NPC128925
0.5426	Remote Similarity	NPC204458
0.5426	Remote Similarity	NPC214484
0.5412	Remote Similarity	NPC234287
0.5392	Remote Similarity	NPC146563
0.5357	Remote Similarity	NPC280825
0.5312	Remote Similarity	NPC48499
0.5306	Remote Similarity	NPC58448
0.5306	Remote Similarity	NPC249848
0.5306	Remote Similarity	NPC107966
0.5263	Remote Similarity	NPC90856
0.5263	Remote Similarity	NPC51947
0.5208	Remote Similarity	NPC78046
0.5204	Remote Similarity	NPC475516
0.5181	Remote Similarity	NPC475416
0.5165	Remote Similarity	NPC88744
0.5146	Remote Similarity	NPC148417
0.5132	Remote Similarity	NPC305835
0.5125	Remote Similarity	NPC168231
0.5104	Remote Similarity	NPC470543
0.5104	Remote Similarity	NPC30397
0.51	Remote Similarity	NPC1876
0.51	Remote Similarity	NPC39211
0.5098	Remote Similarity	NPC273962
0.5098	Remote Similarity	NPC30735
0.5098	Remote Similarity	NPC204392
0.5094	Remote Similarity	NPC469823
0.5057	Remote Similarity	NPC88000
0.5057	Remote Similarity	NPC4831
0.5057	Remote Similarity	NPC472023
0.5049	Remote Similarity	NPC40775

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6937
0.1-0.2	2118
0.2-0.3	82
0.3-0.4	12
0.4-0.5	1
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