NPASS Compound

Natural Product: NPC51947

Natural Product ID	NPC51947
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	23-Hydroxy-3Beta-[(O-Beta-D-Glucopyranosyl-(1->4)-Alpha-L-Arabinopyranosyl)Oxy]Lup-20(29)-En-28-Oic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500243
PubChem CID	11592978
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 120126 0 0 0 0 0 0 0 0999 V2000 -7.5449 0.5001 3.4082 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9149 0.2572 2.1576 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5864 -1.0316 1.8562 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6644 1.2518 1.0784 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0226 1.4964 0.4107 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8441 1.0039 -1.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3891 1.2344 -1.2466 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8036 0.4705 -2.3818 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3195 0.4147 -2.3855 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6996 0.2124 -1.0484 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8527 -1.2721 -0.7151 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3594 1.0403 0.0530 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7529 0.8209 1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2573 0.8035 1.4407 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6819 0.1044 0.2714 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1689 -0.0432 0.2878 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4636 1.2577 0.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7992 -0.8662 1.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6335 -1.2549 1.5827 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3517 -1.2960 0.2314 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4387 -1.6412 -0.8722 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1178 -1.5090 -2.2140 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1793 -3.1662 -0.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3652 -3.8657 -0.8712 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -0.8878 -0.9181 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0934 -0.0899 -2.1660 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5905 0.1246 -2.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2270 0.6359 -1.0177 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2024 2.1488 -1.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1466 -0.1677 0.0745 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4926 -0.3593 0.1954 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3597 0.1881 -0.8729 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6753 -0.6102 -0.8006 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1465 -0.5211 0.6287 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3013 0.5130 1.3694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9721 0.1902 1.4159 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4631 -0.1057 0.6122 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3298 -0.9424 1.2928 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4401 -1.5210 0.5038 C 0 0 1 0 0 0 0 0 0 0 0 0 10.6306 -0.6164 0.3042 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9393 0.2136 1.5030 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6842 0.7223 2.1819 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1238 1.8164 1.3405 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9903 2.4160 1.8804 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8025 -0.2854 2.4032 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7132 -0.4839 2.4401 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4796 0.1996 -0.8184 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9129 -2.6485 1.2108 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5428 0.0144 -1.6938 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9127 0.0567 -2.1700 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8056 0.6356 0.0428 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0827 2.6744 -1.3677 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5540 3.1723 -2.4116 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3543 3.5728 -0.3461 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0488 1.4521 3.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7260 -0.2241 4.2015 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5820 -1.3046 0.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6535 -1.0326 2.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1063 -1.8843 2.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2594 2.1807 1.5277 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2965 2.5531 0.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8285 0.9147 0.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4123 1.7194 -1.6608 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1500 -0.0338 -1.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2561 -0.5620 -2.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1403 0.9101 -3.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9393 1.2615 -2.9731 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0402 -0.4964 -2.9998 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0421 -1.8806 -1.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0140 -1.4614 0.3455 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7910 -1.6486 -1.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3401 2.1087 -0.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 1.6644 2.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1808 -0.0920 1.8440 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8683 1.7996 1.6660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0031 0.1818 2.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0428 -0.9689 0.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1212 1.5833 -0.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2155 1.3217 1.2923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1688 2.1196 0.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4815 -1.7426 1.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0186 -0.2901 2.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2422 -0.5573 2.2196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6819 -2.2319 2.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0834 -2.1476 0.3756 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5846 -2.1378 -2.9927 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1297 -1.9969 -2.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2653 -0.4858 -2.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6127 -3.4841 -1.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1784 -3.3129 0.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1576 -4.7967 -1.1057 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6623 -1.6805 -0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5327 0.8406 -2.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8288 -0.6880 -3.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0306 -0.8291 -2.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7586 0.8644 -3.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3864 2.6405 -0.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2107 2.4209 -1.5344 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9511 2.5671 -1.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7012 -1.4486 0.3285 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5850 1.2771 -0.7465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4142 -1.6411 -1.1036 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0009 -1.4720 1.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6790 0.4691 2.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5218 1.5453 1.0406 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7017 -1.8025 1.7137 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1517 -1.8861 -0.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4951 -1.2896 0.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5787 1.0668 1.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0073 1.2165 3.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8990 2.6501 1.3160 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9649 1.5824 0.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0834 3.3610 2.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7685 -1.4428 2.1977 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1559 0.0049 -1.5140 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6426 -2.5906 2.1743 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9450 -0.7357 -2.2370 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1926 -0.8278 -2.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9240 -0.4510 -0.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6779 4.3035 -0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 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 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 40 47 1 0 39 48 1 0 33 49 1 0 32 50 1 0 12 51 1 0 7 52 1 6 52 53 2 0 52 54 1 0 51 4 1 0 51 7 1 0 28 10 1 0 36 31 1 0 45 38 1 0 28 15 1 0 25 16 1 0 1 55 1 0 1 56 1 0 3 57 1 0 3 58 1 0 3 59 1 0 4 60 1 1 5 61 1 0 5 62 1 0 6 63 1 0 6 64 1 0 8 65 1 0 8 66 1 0 9 67 1 0 9 68 1 0 11 69 1 0 11 70 1 0 11 71 1 0 12 72 1 6 13 73 1 0 13 74 1 0 14 75 1 0 14 76 1 0 15 77 1 1 17 78 1 0 17 79 1 0 17 80 1 0 18 81 1 0 18 82 1 0 19 83 1 0 19 84 1 0 20 85 1 1 22 86 1 0 22 87 1 0 22 88 1 0 23 89 1 0 23 90 1 0 24 91 1 0 25 92 1 6 26 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 29 97 1 0 29 98 1 0 29 99 1 0 31100 1 1 32101 1 1 33102 1 6 34103 1 1 35104 1 0 35105 1 0 38106 1 1 39107 1 6 40108 1 6 41109 1 6 42110 1 1 43111 1 0 43112 1 0 44113 1 0 46114 1 0 47115 1 0 48116 1 0 49117 1 0 50118 1 0 51119 1 6 54120 1 0 M END

Standard InCHIKey	JCANRUGQLLZCME-OIQDTBJDSA-N
Standard InCHI	InChI=1S/C41H66O13/c1-20(2)21-9-14-41(36(49)50)16-15-39(5)22(28(21)41)7-8-26-37(3)12-11-27(38(4,19-43)25(37)10-13-40(26,39)6)54-34-32(47)30(45)24(18-51-34)53-35-33(48)31(46)29(44)23(17-42)52-35/h21-35,42-48H,1,7-19H2,2-6H3,(H,49,50)/t21-,22+,23+,24-,25+,26+,27-,28+,29+,30-,31-,32+,33+,34-,35-,37-,38-,39+,40+,41-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	766.45	Volume:	766.797 ? Van der Waals volume.
Dense:	1.0	LogP:	1.836 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.445 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.78 ? 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:	0.132	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.843	Fsp³:	0.927
MCE-18:	147.595 ? 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:	0.914	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:	0.187	Promiscuous compounds:	0.175

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.081	MDCK Permeability:	-5.246
Pgp-inhibitor:	0.0	Pgp-substrate:	0.061
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):	0.001
20% Bioavailability (F20%):	0.052	30% Bioavailability (F30%):	0.678
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123	MRP1:	0.859
Plasma Protein Binding (PPB):	82.581%	Volume Distribution (VD):	-0.469
Fu:	11.949% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.773	BCRP inhibitor:	0.047
BSEP inhibitor:	0.001

ADMET: Metabolism

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

0.486

Half-life (T1/2):

2.087

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.847	Drug-induced Liver Injury (DILI):	0.954
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.738	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.058
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.987
Hematotoxicity:	0.725	Drug-induced Nephrotoxicity:	0.95
Genotoxicity:	0.448	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.505	Hek293 Cytotoxicity:	0.266
BCF:	0.867 ? 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:	3.396 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.757 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.956 ? 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
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[15473660]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730260]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24360605]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	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
ED50	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[20122767]

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 NPC51947 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	19959
0.1-0.2	23938
0.2-0.3	4403
0.3-0.4	1319
0.4-0.5	200
0.5-0.6	28
0.6-0.7	6
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
0.7826	Intermediate Similarity	NPC240734
0.7188	Intermediate Similarity	NPC204392
0.7041	Intermediate Similarity	NPC91838
0.6556	Remote Similarity	NPC88744
0.6471	Remote Similarity	NPC275668
0.6392	Remote Similarity	NPC136877
0.6327	Remote Similarity	NPC488205
0.617	Remote Similarity	NPC224414
0.602	Remote Similarity	NPC488208
0.5743	Remote Similarity	NPC11035
0.5728	Remote Similarity	NPC488207
0.5648	Remote Similarity	NPC488206
0.5595	Remote Similarity	NPC488164
0.5595	Remote Similarity	NPC264005
0.5579	Remote Similarity	NPC203974
0.5517	Remote Similarity	NPC160506
0.5476	Remote Similarity	NPC264317
0.5476	Remote Similarity	NPC294438
0.5465	Remote Similarity	NPC4309
0.5437	Remote Similarity	NPC80640
0.5361	Remote Similarity	NPC57362
0.5349	Remote Similarity	NPC271974
0.5349	Remote Similarity	NPC247312
0.5281	Remote Similarity	NPC478841
0.5281	Remote Similarity	NPC488166
0.5263	Remote Similarity	NPC473844
0.5258	Remote Similarity	NPC204407
0.5229	Remote Similarity	NPC473383
0.5182	Remote Similarity	NPC473405
0.5172	Remote Similarity	NPC201655
0.5149	Remote Similarity	NPC228190
0.5135	Remote Similarity	NPC146563
0.5114	Remote Similarity	NPC16377
0.5098	Remote Similarity	NPC284807
0.5096	Remote Similarity	NPC270667
0.5047	Remote Similarity	NPC473373
0.5045	Remote Similarity	NPC139044

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5876
0.1-0.2	3161
0.2-0.3	98
0.3-0.4	12
0.4-0.5	0
0.5-0.6	3
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
0.5517	Remote Similarity	NPD8035	Phase 2
0.5476	Remote Similarity	NPD7520	Phase 1
0.54	Remote Similarity	NPD8034	Phase 2

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