NPASS Compound

Natural Product: NPC174336

Natural Product ID	NPC174336
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Avicin D
IUPAC Name	[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5S,6S)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-3-[(2E,6R)-6-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-5-[(2E,6R)-6-hydroxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy-6-methyloxan-2-yl]oxy-2-(hydroxymethyl)-6-methylocta-2,7-dienoyl]oxy-5-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms	avicin D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508651
PubChem CID	44566777
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

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-4.3483 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5889 -0.9220 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5209 0.3563 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5796 -0.0948 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6700 -3.2059 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8202 -2.2210 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4786 -14.4891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9270 -14.7385 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9095 -16.4578 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2086 -17.2078 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6105 -15.7078 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1595 -17.7569 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -16.1230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4681 -14.3109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1858 3.3118 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8406 0.4756 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 2.3251 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9877 2.5158 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9875 2.8547 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5942 4.2726 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -0.7860 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1007 -1.9703 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 -4.5264 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4681 -6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8164 -2.9048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0548 -3.0758 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0198 1.5699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5861 2.5581 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0891 0.9054 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6382 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6237 -1.2889 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2872 -3.5623 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7356 -3.8116 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8226 -4.2601 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0332 -4.2229 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.3354 -2.9329 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6186 -1.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.5730 -1.7162 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8179 0.3589 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.8458 -5.7092 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3607 -6.7551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0372 -4.8613 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2997 -7.4356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8354 -7.8157 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.6544 -4.8613 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5634 -0.8086 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.0664 0.9512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8478 3.8161 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9169 3.6096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0529 3.0999 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7507 5.3912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8729 1.7894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7741 3.9252 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.2291 3.5959 0.0000 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 1 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 1 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 37 40 1 6 37 41 1 0 33 42 1 0 42 43 1 0 19 44 1 0 44 45 2 0 19 46 1 0 15 47 1 0 47 48 1 0 11 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 57 61 1 6 56 62 1 1 56 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 1 66 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 71 73 1 0 70 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 82 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 93 94 1 0 92 95 1 0 91 96 1 0 85 97 1 0 84 98 1 0 77 99 1 0 99100 1 0 100101 1 0 101102 1 0 102103 2 3 103104 1 0 103105 1 0 100106 1 0 99107 1 0 49108 1 0 49109 1 0 5110 1 0 110111 1 0 111112 1 0 112113 1 0 111114 1 0 110115 1 0 115116 1 0 116117 1 0 117118 1 0 118119 1 0 118120 1 0 120121 1 0 121122 1 0 122123 1 0 121124 1 0 124125 1 0 125126 1 0 126127 1 0 127128 1 0 128129 1 0 127130 1 0 130131 1 0 131132 1 0 132133 1 0 131134 1 0 130135 1 0 120136 1 0 136137 1 0 137138 1 0 138139 1 0 139140 1 0 140141 1 0 141142 1 0 140143 1 0 139144 1 0 144145 1 0 112 3 1 0 122116 1 0 132125 1 0 141137 1 0 59 9 1 0 71 65 1 0 101 75 1 0 51 9 1 0 57 52 1 0 86 80 1 0 93 88 1 0 27 21 1 0 66 55 1 0 1146 1 0 2147 1 0 2148 1 0 3149 1 6 5150 1 6 10151 1 0 10152 1 0 11153 1 6 16154 1 0 17155 1 0 17156 1 0 18157 1 0 18158 1 0 21159 1 6 23160 1 6 24161 1 0 24162 1 0 24163 1 0 25164 1 1 26165 1 6 27166 1 1 28167 1 0 29168 1 0 34169 1 0 35170 1 0 35171 1 0 36172 1 0 36173 1 0 38174 1 0 39175 1 0 39176 1 0 40177 1 0 41178 1 0 41179 1 0 41180 1 0 42181 1 0 42182 1 0 43183 1 0 44184 1 0 45185 1 0 45186 1 0 46187 1 0 46188 1 0 46189 1 0 47190 1 0 47191 1 0 48192 1 0 50193 1 0 50194 1 0 51195 1 1 53196 1 0 54197 1 0 54198 1 0 55199 1 6 58200 1 0 58201 1 0 59202 1 1 60203 1 0 61204 1 0 61205 1 0 61206 1 0 62207 1 0 62208 1 0 62209 1 0 63210 1 0 63211 1 0 64212 1 0 64213 1 0 65214 1 6 67215 1 0 67216 1 0 67217 1 0 68218 1 0 68219 1 0 69220 1 0 69221 1 0 70222 1 6 72223 1 0 72224 1 0 72225 1 0 73226 1 0 73227 1 0 73228 1 0 75229 1 6 77230 1 6 78231 1 0 78232 1 0 80233 1 1 82234 1 1 83235 1 0 83236 1 0 83237 1 0 84238 1 1 85239 1 1 86240 1 6 88241 1 1 90242 1 0 90243 1 0 91244 1 6 92245 1 1 93246 1 6 94247 1 0 95248 1 0 96249 1 0 97250 1 0 98251 1 0 99252 1 1 100253 1 6 101254 1 1 104255 1 0 105256 1 0 105257 1 0 105258 1 0 106259 1 0 107260 1 0 108261 1 0 108262 1 0 108263 1 0 109264 1 0 109265 1 0 109266 1 0 110267 1 1 111268 1 6 112269 1 1 113270 1 0 114271 1 0 116272 1 1 118273 1 6 119274 1 0 119275 1 0 119276 1 0 120277 1 1 121278 1 6 122279 1 6 123280 1 0 125281 1 1 127282 1 1 128283 1 0 128284 1 0 129285 1 0 130286 1 6 131287 1 1 132288 1 6 133289 1 0 134290 1 0 135291 1 0 137292 1 6 139293 1 1 140294 1 6 141295 1 1 142296 1 0 143297 1 0 144298 1 0 144299 1 0 145300 1 0 M END

Standard InCHIKey	HKEDBKXRDHFCFB-LUAQNYIXSA-N
Standard InCHI	InChI=1S/C98H155NO46/c1-16-93(11,127)26-18-20-45(34-101)81(125)139-75-41(4)132-87(73(122)69(75)118)145-94(12,17-2)27-19-21-44(33-100)80(124)137-57-32-98(90(126)144-89-79(68(117)62(111)50(36-103)135-89)143-86-74(123)77(141-85-72(121)66(115)61(110)49(35-102)133-85)76(42(5)131-86)140-84-71(120)63(112)51(37-104)134-84)47(30-91(57,7)8)46-22-23-54-95(13)28-25-56(92(9,10)53(95)24-29-96(54,14)97(46,15)31-55(98)107)138-82-58(99-43(6)105)65(114)64(113)52(136-82)39-129-88-78(67(116)59(108)40(3)130-88)142-83-70(119)60(109)48(106)38-128-83/h16-17,20-22,40-42,47-79,82-89,100-104,106-123,127H,1-2,18-19,23-39H2,3-15H3,(H,99,105)/b44-21+,45-20+/t40-,41-,42+,47+,48-,49-,50-,51+,52-,53+,54-,55-,56+,57+,58-,59+,60+,61-,62-,63+,64-,65-,66+,67+,68+,69-,70-,71-,72-,73-,74-,75-,76+,77+,78-,79-,82+,83+,84+,85+,86+,87+,88-,89+,93+,94+,95+,96-,97-,98-/m1/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23C[C@H](OC(=O)/C(=C/CC[C@@](O[C@@H]4O[C@H](C)[C@H]([C@@H]([C@H]4O)O)OC(=O)/C(=C/CC[C@](C=C)(O)C)/CO)(C=C)C)/CO)C(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(C[C@H]2O)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](C)[C@@H]([C@@H]([C@H]3O[C@@H]3OC[C@H]([C@@H]([C@H]3O)O)O)O)O)[C@H]([C@@H]([C@H]2N=C(O)C)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](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[C@@H]1O[C@H]([C@@H]([C@H]1O)O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	2081.98	Volume:	1983.948 ? Van der Waals volume.
Dense:	1.049	LogP:	0.036 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.003 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.985 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	38.0	Rigid Bonds:	81.0
TPSA:	735.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	47.0
H-Bond Donor:	25.0	Rings:	13.0
Heavy Atoms:	47.0

MedChem Properties

QED Drug-Likeness Score:	0.005	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	8.759	Fsp³:	0.857
MCE-18:	301.912 ? 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:	0.731	Fluc inhibitor:	0.004 ? 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:	0.325	Promiscuous compounds:	0.581

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.281	MDCK Permeability:	-4.816
Pgp-inhibitor:	0.0	Pgp-substrate:	0.361
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):	0.999
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	51.229%	Volume Distribution (VD):	-0.269
Fu:	21.794% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
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:	0.063
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):

-2.094

Half-life (T1/2):

5.492

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.812	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.597
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.616
BCF:	0.013 ? 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:	3.587 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.059 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.535 ? 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
NPO29529	Acacia victoriae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828461]
NPO29529	Acacia victoriae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2067	Acacia victoria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29529	Acacia victoriae	Species	Fabaceae	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
IC50	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
NPT15	Cell line	Jurkat	Homo sapiens	IC50	=	0.58	ug.mL-1	PMID[12828461]

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 NPC174336 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	26280
0.1-0.2	20825
0.2-0.3	1912
0.3-0.4	551
0.4-0.5	220
0.5-0.6	28
0.6-0.7	10
0.7-0.8	0
0.8-0.85	8
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC187497
0.9128	High Similarity	NPC100612
0.9122	High Similarity	NPC113620
0.8889	High Similarity	NPC265699
0.8733	High Similarity	NPC475444
0.8733	High Similarity	NPC473679
0.84	Intermediate Similarity	NPC196874
0.8228	Intermediate Similarity	NPC319719
0.8182	Intermediate Similarity	NPC222951
0.8101	Intermediate Similarity	NPC322904
0.8092	Intermediate Similarity	NPC233223
0.8092	Intermediate Similarity	NPC183816
0.8067	Intermediate Similarity	NPC484830
0.8026	Intermediate Similarity	NPC484829
0.7937	Intermediate Similarity	NPC324933
0.7922	Intermediate Similarity	NPC300655
0.7885	Intermediate Similarity	NPC311178
0.7867	Intermediate Similarity	NPC475177
0.7677	Intermediate Similarity	NPC329878
0.7636	Intermediate Similarity	NPC488201
0.7628	Intermediate Similarity	NPC43589
0.7438	Intermediate Similarity	NPC478559
0.7438	Intermediate Similarity	NPC478560
0.7436	Intermediate Similarity	NPC329893
0.7365	Intermediate Similarity	NPC488204
0.7333	Intermediate Similarity	NPC488620
0.7262	Intermediate Similarity	NPC488202
0.7152	Intermediate Similarity	NPC484831
0.7081	Intermediate Similarity	NPC220838
0.7	Intermediate Similarity	NPC488203
0.6867	Remote Similarity	NPC488618
0.686	Remote Similarity	NPC488200
0.6826	Remote Similarity	NPC488619
0.681	Remote Similarity	NPC45606
0.6727	Remote Similarity	NPC13989
0.6376	Remote Similarity	NPC172365
0.6301	Remote Similarity	NPC482013
0.6173	Remote Similarity	NPC489209
0.6145	Remote Similarity	NPC489208
0.6133	Remote Similarity	NPC207738
0.5882	Remote Similarity	NPC210729
0.5882	Remote Similarity	NPC82931
0.5876	Remote Similarity	NPC23020
0.5866	Remote Similarity	NPC472270
0.5866	Remote Similarity	NPC112492
0.5806	Remote Similarity	NPC488513
0.5583	Remote Similarity	NPC470876
0.557	Remote Similarity	NPC123522
0.5543	Remote Similarity	NPC472268
0.5526	Remote Similarity	NPC105800
0.5521	Remote Similarity	NPC286457
0.5325	Remote Similarity	NPC482010
0.5298	Remote Similarity	NPC309223
0.5263	Remote Similarity	NPC102505
0.5263	Remote Similarity	NPC488514
0.522	Remote Similarity	NPC104137
0.522	Remote Similarity	NPC26626
0.5172	Remote Similarity	NPC33012
0.5161	Remote Similarity	NPC472269
0.515	Remote Similarity	NPC473452
0.514	Remote Similarity	NPC297950
0.5122	Remote Similarity	NPC603137
0.512	Remote Similarity	NPC85154
0.5115	Remote Similarity	NPC8524
0.5064	Remote Similarity	NPC232237
0.5061	Remote Similarity	NPC243680
0.5058	Remote Similarity	NPC220160
0.5049	Remote Similarity	NPC475649

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC174336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7664
0.1-0.2	1459
0.2-0.3	27
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