NPASS Compound

Natural Product: NPC275225

Natural Product ID	NPC275225
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3''o-Acetylpolygalacin D2
IUPAC Name	[(2S,3R,4S,5S)-3-[(2S,3R,4R,5R,6S)-3-acetyloxy-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl] (4aR,5R,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-10-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	3'O-Acetylpolygalacin D2
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1641868
PubChem CID	53321794
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 202212 0 0 0 0 0 0 0 0999 V2000 11.1320 -1.3608 1.4400 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5865 -2.3247 0.5526 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8497 -1.8303 -0.8353 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8164 -1.3134 -1.5307 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3081 -0.0815 -1.1053 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3735 -0.3799 -0.1489 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0393 -0.2700 -0.5757 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5400 -1.6763 -0.7889 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4100 -2.5428 -0.1097 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1234 -1.9390 -0.5687 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5198 -1.2437 0.6406 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8750 0.2103 0.5858 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3039 0.5667 0.4005 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0494 0.7331 1.7119 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2766 1.9809 -0.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5288 2.4833 -0.4307 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2401 0.9393 1.7385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7342 0.9142 1.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1790 -0.4279 1.2344 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0277 -1.3362 0.4086 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4960 -2.7273 0.5576 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0418 -2.6895 0.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3071 -1.6199 0.1460 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8591 -0.2742 0.4519 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0539 0.6190 -0.7182 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8669 0.3927 1.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4802 0.5761 0.8083 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9623 -0.5275 -0.1057 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1371 -1.7409 -0.1791 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4369 -2.6166 -1.3265 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -2.0048 -2.6194 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5703 -3.0905 -3.4154 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2435 -1.4976 -3.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8534 -0.8857 -2.4148 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3697 0.1035 -1.4252 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2996 -0.9858 0.4712 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7467 -0.3298 1.4404 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0051 -2.0529 -0.0098 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2337 -2.4108 0.5955 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1029 -3.6216 1.2729 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0033 -4.5873 0.9177 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0780 -4.7786 -0.5856 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4042 -3.5116 -1.3055 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3335 -2.3428 -0.3957 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5860 -2.1410 0.1996 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1579 -0.9310 -0.0846 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3536 -0.1613 1.0869 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6354 -0.3804 1.6244 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6096 0.0980 3.0539 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6756 0.3491 0.8044 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2761 0.2044 -0.6722 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4852 -1.1117 -0.7460 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2820 -1.4507 -2.1147 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9257 -2.5468 -2.6924 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6933 -3.2100 -1.9283 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7569 -2.9513 -4.1024 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5050 1.2703 -1.0675 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8955 -0.2577 0.9719 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8778 0.5719 1.4693 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.2882 0.1082 2.7115 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.2726 -0.8551 2.5044 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5653 -0.1594 2.2092 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.2873 1.0680 1.3356 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.0503 0.7078 0.5240 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.7362 1.6546 -0.4296 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.3692 1.3004 0.5097 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.8929 2.5408 0.7696 C 0 0 2 0 0 0 0 0 0 0 0 0 -17.2546 2.4769 1.1275 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.6379 3.8201 1.1214 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.9629 4.4792 -0.0353 C 0 0 2 0 0 0 0 0 0 0 0 0 -16.0027 3.3914 -0.5023 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.7732 3.9345 -0.8678 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.1897 5.5624 0.3687 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.9249 4.8608 -1.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.7562 5.8649 -0.6513 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.1578 0.1870 3.4170 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6405 -3.3552 -2.4736 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9099 -5.3665 -1.0771 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6129 1.7993 0.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7839 -1.0573 2.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0023 -1.9598 1.8514 C 0 0 0 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0 0 0 7.0665 -2.3271 1.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9872 -1.4166 2.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4425 -2.9089 2.0158 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9789 1.3954 0.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3223 1.0490 -1.5063 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6987 -1.2801 0.0426 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1709 -1.2776 -2.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4541 2.1588 -0.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7226 1.8962 -0.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 17.9932 0.6695 0.9079 H 0 0 0 0 0 0 0 0 0 0 0 0 18.6829 2.3546 0.7262 H 0 0 0 0 0 0 0 0 0 0 0 0 18.4508 2.3389 2.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0102 4.0468 1.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7319 4.4549 -0.6016 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1874 3.0682 2.0842 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7556 4.2481 -0.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 15.1761 6.1731 0.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 16.8130 3.7812 -1.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1263 2.8454 -1.2462 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 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 12 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 2 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 34 35 1 0 28 36 1 1 36 37 2 0 36 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 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 2 0 54 56 1 0 51 57 1 0 50 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 70 73 1 1 70 74 1 0 74 75 1 0 62 76 1 0 43 77 1 0 42 78 1 0 27 79 1 0 19 80 1 1 11 81 1 1 5 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 83 86 1 0 86 87 1 0 87 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 89 92 1 0 92 93 1 0 93 94 1 0 94 95 1 0 93 96 1 0 92 97 1 0 82 98 1 0 84 3 1 0 94 87 1 0 13 7 1 0 24 19 1 0 35 28 1 0 44 39 1 0 52 46 1 0 64 59 1 0 71 67 1 0 20 11 1 0 29 23 1 0 1 99 1 0 2100 1 0 2101 1 0 3102 1 6 5103 1 6 7104 1 6 8105 1 6 9106 1 0 10107 1 0 10108 1 0 12109 1 6 14110 1 0 14111 1 0 14112 1 0 15113 1 0 15114 1 0 16115 1 0 17116 1 0 17117 1 0 18118 1 0 18119 1 0 20120 1 6 21121 1 0 21122 1 0 22123 1 0 25124 1 0 25125 1 0 25126 1 0 26127 1 0 26128 1 0 27129 1 1 29130 1 1 30131 1 0 30132 1 0 32133 1 0 32134 1 0 32135 1 0 33136 1 0 33137 1 0 33138 1 0 34139 1 0 34140 1 0 35141 1 0 35142 1 0 39143 1 1 41144 1 0 41145 1 0 42146 1 1 43147 1 6 44148 1 6 46149 1 6 48150 1 1 49151 1 0 49152 1 0 49153 1 0 50154 1 1 51155 1 6 52156 1 1 56157 1 0 56158 1 0 56159 1 0 57160 1 0 59161 1 1 61162 1 0 61163 1 0 62164 1 6 63165 1 1 64166 1 6 65167 1 0 67168 1 1 69169 1 0 69170 1 0 71171 1 6 72172 1 0 73173 1 0 74174 1 0 74175 1 0 75176 1 0 76177 1 0 77178 1 0 78179 1 0 79180 1 0 80181 1 0 80182 1 0 80183 1 0 81184 1 0 81185 1 0 81186 1 0 82187 1 1 83188 1 6 84189 1 1 85190 1 0 87191 1 6 89192 1 6 90193 1 0 90194 1 0 91195 1 0 92196 1 1 93197 1 6 94198 1 1 95199 1 0 96200 1 0 97201 1 0 98202 1 0 M END

Standard InCHIKey	GASXVTWMSSHPAL-QALSBQOCSA-N
Standard InCHI	InChI=1S/C65H104O33/c1-25-45(93-52-43(81)46(31(73)21-86-52)94-57-50(83)64(85,23-69)24-88-57)42(80)49(90-26(2)70)56(89-25)96-48-37(75)30(72)20-87-55(48)98-58(84)65-14-13-59(3,4)15-28(65)27-9-10-35-60(5)16-29(71)51(61(6,22-68)34(60)11-12-62(35,7)63(27,8)17-36(65)74)97-54-44(82)47(39(77)33(19-67)92-54)95-53-41(79)40(78)38(76)32(18-66)91-53/h9,25,28-57,66-69,71-83,85H,10-24H2,1-8H3/t25-,28-,29-,30-,31+,32+,33+,34+,35+,36+,37-,38+,39+,40-,41+,42+,43+,44+,45-,46-,47-,48+,49+,50-,51-,52-,53-,54-,55-,56-,57-,60-,61-,62+,63+,64+,65+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2OC[C@@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2OC(=O)C)O)O[C@@H]2OC[C@H]([C@@H]([C@H]2O)O[C@@H]2OC[C@]([C@H]2O)(O)CO)O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1412.65	Volume:	1320.843 ? Van der Waals volume.
Dense:	1.07	LogP:	-1.054 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.399 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.813 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	63.0
TPSA:	518.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	33.0
H-Bond Donor:	18.0	Rings:	11.0
Heavy Atoms:	33.0

MedChem Properties

QED Drug-Likeness Score:	0.037	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.981	Fsp³:	0.938
MCE-18:	244.444 ? 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:	0.667	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.337	Promiscuous compounds:	0.554

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.145	MDCK Permeability:	-4.905
Pgp-inhibitor:	0.0	Pgp-substrate:	0.995
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):	0.182
20% Bioavailability (F20%):	0.03	30% Bioavailability (F30%):	0.99
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.017
Plasma Protein Binding (PPB):	51.483%	Volume Distribution (VD):	-0.454
Fu:	30.129% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.0

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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.048 ? 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):

-1.243

Half-life (T1/2):

4.237

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.886	Drug-induced Liver Injury (DILI):	0.954
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.035	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.869	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.27	RPMI-8226 Immunitoxicity:	0.336
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.655
BCF:	0.464 ? 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:	3.268 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.938 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.794 ? 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
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[17851435]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	root	n.a.	PMID[20939516]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29808	Platycodon grandiflorum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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	4

Activity Type	# Activity
Cell line	1
Non-molecular	3

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
NPT148	Cell line	HCT-15	Homo sapiens	IC50	=	3600.0	nM	PMID[12137465]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[20939516]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3300.0	nM	PMID[20939516]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	5800.0	nM	PMID[20939516]

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 NPC275225 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	25975
0.1-0.2	20731
0.2-0.3	2332
0.3-0.4	499
0.4-0.5	242
0.5-0.6	52
0.6-0.7	10
0.7-0.8	0
0.8-0.85	2
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC153673
0.9098	High Similarity	NPC110385
0.9016	High Similarity	NPC68767
0.879	High Similarity	NPC51099
0.8689	High Similarity	NPC144644
0.8689	High Similarity	NPC170407
0.8548	High Similarity	NPC142151
0.8413	Intermediate Similarity	NPC293031
0.8095	Intermediate Similarity	NPC37860
0.7969	Intermediate Similarity	NPC267694
0.7101	Intermediate Similarity	NPC480421
0.7023	Intermediate Similarity	NPC237191
0.6906	Remote Similarity	NPC33012
0.6835	Remote Similarity	NPC8524
0.6818	Remote Similarity	NPC85154
0.6719	Remote Similarity	NPC815
0.6258	Remote Similarity	NPC23020
0.6232	Remote Similarity	NPC13998
0.6136	Remote Similarity	NPC104137
0.6136	Remote Similarity	NPC26626
0.6115	Remote Similarity	NPC473452
0.6013	Remote Similarity	NPC475394
0.5968	Remote Similarity	NPC475208
0.5935	Remote Similarity	NPC475584
0.5935	Remote Similarity	NPC475152
0.5846	Remote Similarity	NPC164389
0.5827	Remote Similarity	NPC480423
0.5827	Remote Similarity	NPC150400
0.5823	Remote Similarity	NPC485563
0.5797	Remote Similarity	NPC475899
0.5782	Remote Similarity	NPC102505
0.5782	Remote Similarity	NPC488514
0.5775	Remote Similarity	NPC480418
0.5775	Remote Similarity	NPC286457
0.5734	Remote Similarity	NPC475514
0.5674	Remote Similarity	NPC471577
0.5646	Remote Similarity	NPC220160
0.5616	Remote Similarity	NPC309223
0.56	Remote Similarity	NPC480422
0.5594	Remote Similarity	NPC473386
0.5586	Remote Similarity	NPC293330
0.5556	Remote Similarity	NPC476113
0.5533	Remote Similarity	NPC489209
0.5517	Remote Similarity	NPC470876
0.551	Remote Similarity	NPC302543
0.5474	Remote Similarity	NPC69811
0.5462	Remote Similarity	NPC480420
0.5436	Remote Similarity	NPC482010
0.5419	Remote Similarity	NPC489208
0.5411	Remote Similarity	NPC471580
0.5407	Remote Similarity	NPC488517
0.538	Remote Similarity	NPC475527
0.5375	Remote Similarity	NPC475892
0.5369	Remote Similarity	NPC70809
0.5364	Remote Similarity	NPC480417
0.5364	Remote Similarity	NPC478825
0.5361	Remote Similarity	NPC472270
0.5361	Remote Similarity	NPC112492
0.5347	Remote Similarity	NPC484546
0.5318	Remote Similarity	NPC488513
0.531	Remote Similarity	NPC4749
0.5294	Remote Similarity	NPC475504
0.5282	Remote Similarity	NPC123522
0.5278	Remote Similarity	NPC283417
0.5278	Remote Similarity	NPC200049
0.5274	Remote Similarity	NPC21691
0.5271	Remote Similarity	NPC1046
0.5099	Remote Similarity	NPC33068
0.5068	Remote Similarity	NPC471550
0.5068	Remote Similarity	NPC57484
0.5068	Remote Similarity	NPC484545
0.5064	Remote Similarity	NPC477464
0.5036	Remote Similarity	NPC488526
0.5036	Remote Similarity	NPC305267

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7893
0.1-0.2	1227
0.2-0.3	30
0.3-0.4	0
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