NPASS Compound

Natural Product: NPC196874

Natural Product ID	NPC196874
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Julibroside J31
IUPAC Name	[(2S,3S,4S,5S,6R)-3-[(2R,3S,4R,5R,6R)-5-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-6-methyl-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,5R,6aS,10S)-10-[(2R,3R,4S,5S,6R)-6-[[(2S,3S,4R,5S,6S)-4,5-dihydroxy-6-methyl-3-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-4,5-dihydroxy-3-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-3-[(2Z)-2-(hydroxymethyl)-6-methyl-6-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyocta-2,7-dienoyl]oxy-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	julibroside J31
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL219125
PubChem CID	44411378
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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-12.0372 -16.6360 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 -11.6209 -14.2098 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8222 3.2736 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 1.0084 2.6978 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9240 3.2148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2291 4.2535 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 7 9 1 0 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 0 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 19 31 1 0 31 32 2 0 19 33 1 0 15 34 1 0 34 35 1 0 11 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 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 44 48 1 6 43 49 1 0 43 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 58 60 1 0 57 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 69 71 1 0 71 72 1 0 72 73 1 0 73 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 79 82 1 0 78 83 1 0 72 84 1 0 71 85 1 0 64 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 95 96 1 0 96 97 1 0 97 98 1 0 96 99 1 0 95100 1 0 87101 1 0 86102 1 0 36103 1 0 36104 1 0 5105 1 0 105106 1 0 106107 1 0 107108 1 0 106109 1 0 105110 1 0 110111 1 0 111112 1 0 112113 1 0 113114 1 0 113115 1 0 115116 1 0 116117 1 0 117118 1 0 116119 1 0 119120 1 0 120121 1 0 121122 1 0 122123 1 0 123124 1 0 122125 1 0 125126 1 0 126127 1 0 127128 1 0 126129 1 0 125130 1 0 115131 1 0 131132 1 0 132133 1 0 133134 1 0 134135 1 0 135136 1 0 136137 1 0 135138 1 0 134139 1 0 139140 1 0 107 3 1 0 117111 1 0 127120 1 0 136132 1 0 46 9 1 0 58 52 1 0 88 62 1 0 97 90 1 0 38 9 1 0 44 39 1 0 73 67 1 0 80 75 1 0 27 21 1 0 53 42 1 0 1141 1 0 2142 1 0 2143 1 0 3144 1 6 5145 1 6 10146 1 0 10147 1 0 11148 1 6 16149 1 0 17150 1 0 17151 1 0 18152 1 0 18153 1 0 21154 1 1 23155 1 1 24156 1 0 24157 1 0 24158 1 0 25159 1 6 26160 1 1 27161 1 6 28162 1 0 29163 1 0 30164 1 0 31165 1 0 32166 1 0 32167 1 0 33168 1 0 33169 1 0 33170 1 0 34171 1 0 34172 1 0 35173 1 0 37174 1 0 37175 1 0 38176 1 0 40177 1 0 41178 1 0 41179 1 0 42180 1 0 45181 1 0 45182 1 0 46183 1 1 47184 1 0 48185 1 0 48186 1 0 48187 1 0 49188 1 0 49189 1 0 49190 1 0 50191 1 0 50192 1 0 51193 1 0 51194 1 0 52195 1 0 54196 1 0 54197 1 0 54198 1 0 55199 1 0 55200 1 0 56201 1 0 56202 1 0 57203 1 6 59204 1 0 59205 1 0 59206 1 0 60207 1 0 60208 1 0 60209 1 0 62210 1 6 64211 1 6 65212 1 0 65213 1 0 67214 1 6 69215 1 6 70216 1 0 70217 1 0 70218 1 0 71219 1 6 72220 1 6 73221 1 1 75222 1 6 77223 1 0 77224 1 0 78225 1 1 79226 1 6 80227 1 1 81228 1 0 82229 1 0 83230 1 0 84231 1 0 85232 1 0 86233 1 1 87234 1 6 88235 1 1 90236 1 0 92237 1 6 93238 1 0 93239 1 0 94240 1 0 95241 1 1 96242 1 6 97243 1 1 98244 1 0 99245 1 0 100246 1 0 101247 1 0 102248 1 0 103249 1 0 103250 1 0 103251 1 0 104252 1 0 104253 1 0 104254 1 0 105255 1 6 106256 1 6 107257 1 1 108258 1 0 109259 1 0 111260 1 6 113261 1 1 114262 1 0 114263 1 0 114264 1 0 115265 1 6 116266 1 1 117267 1 1 118268 1 0 120269 1 6 122270 1 6 123271 1 0 123272 1 0 124273 1 0 125274 1 1 126275 1 6 127276 1 1 128277 1 0 129278 1 0 130279 1 0 132280 1 1 134281 1 6 135282 1 1 136283 1 6 137284 1 0 138285 1 0 139286 1 0 139287 1 0 140288 1 0 M END

Standard InCHIKey	DXEIWTJRTBJALX-DTYQGDICSA-N
Standard InCHI	InChI=1S/C92H148O48/c1-13-88(9,140-81-68(118)58(108)50(100)33(2)124-81)20-14-15-36(26-93)75(120)132-49-25-92(85(121)139-84-74(62(112)55(105)42(29-96)130-84)138-80-69(119)71(135-78-66(116)59(109)53(103)40(27-94)127-78)70(35(4)126-80)134-77-65(115)56(106)43(30-97)129-77)38(23-86(49,5)6)37-16-17-46-89(10)21-19-48(87(7,8)45(89)18-22-90(46,11)91(37,12)24-47(92)99)133-83-73(137-79-67(117)60(110)54(104)41(28-95)128-79)63(113)57(107)44(131-83)32-123-82-72(61(111)51(101)34(3)125-82)136-76-64(114)52(102)39(98)31-122-76/h13,15-16,33-35,38-74,76-84,93-119H,1,14,17-32H2,2-12H3/b36-15-/t33-,34-,35+,38?,39-,40-,41+,42+,43+,44+,45?,46?,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-,76+,77+,78+,79?,80+,81+,82-,83-,84-,88?,89?,90?,91+,92?/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)C23C[C@H](OC(=O)/C(=CCCC(O[C@H]4O[C@@H](C)[C@@H]([C@H]([C@@H]4O)O)O)(C=C)C)/CO)C(CC3C3=CCC4C([C@@]3(C[C@H]2O)C)(C)CCC2C4(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]2OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)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:	2020.91	Volume:	1888.745 ? Van der Waals volume.
Dense:	1.07	LogP:	-1.116 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.151 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.21 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	32.0	Rigid Bonds:	83.0
TPSA:	755.72 ? Topological Polar Surface Area.	H-Bond Acceptor:	48.0
H-Bond Donor:	27.0	Rings:	14.0
Heavy Atoms:	48.0

MedChem Properties

QED Drug-Likeness Score:	0.014	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	8.564	Fsp³:	0.913
MCE-18:	316.364 ? 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:	0.719	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.0 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.088 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.424	Promiscuous compounds:	0.143

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.746	MDCK Permeability:	-4.728
Pgp-inhibitor:	0.0	Pgp-substrate:	0.998
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):	1.0
20% Bioavailability (F20%):	0.981	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):	37.881%	Volume Distribution (VD):	-0.17
Fu:	26.648% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
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:	0.996
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):

-3.837

Half-life (T1/2):

7.967

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.462	Drug-induced Liver Injury (DILI):	0.922
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.162	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.768
A549 Cytotoxicity:	0.974	Hek293 Cytotoxicity:	0.235
BCF:	0.411 ? 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:	3.808 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.074 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.505 ? 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
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12181	Albizia julibrissin	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
Inhibition	9

Activity Type	# Activity
Cell line	9

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
NPT306	Cell line	PC-3	Homo sapiens	Inhibition	=	80.85	%	PMID[16504508]
NPT400	Cell line	MDA-MB-435	Homo sapiens	Inhibition	=	80.41	%	PMID[16504508]
NPT165	Cell line	HeLa	Homo sapiens	Inhibition	=	83.48	%	PMID[16504508]
NPT116	Cell line	HL-60	Homo sapiens	Inhibition	=	39.33	%	PMID[16504508]
NPT547	Cell line	BGC-823	Homo sapiens	Inhibition	=	15.16	%	PMID[16504508]
NPT181	Cell line	Bel-7402	Homo sapiens	Inhibition	=	46.61	%	PMID[16504508]
NPT306	Cell line	PC-3	Homo sapiens	Inhibition	=	94.71	%	PMID[16504508]
NPT181	Cell line	Bel-7402	Homo sapiens	Inhibition	=	44.34	%	PMID[16504508]
NPT165	Cell line	HeLa	Homo sapiens	Inhibition	=	64.33	%	PMID[16504508]

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 NPC196874 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	25988
0.1-0.2	20657
0.2-0.3	2146
0.3-0.4	611
0.4-0.5	359
0.5-0.6	54
0.6-0.7	11
0.7-0.8	0
0.8-0.85	10
0.85-0.9	7
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.947	High Similarity	NPC233223
0.947	High Similarity	NPC183816
0.9398	High Similarity	NPC300655
0.9394	High Similarity	NPC484829
0.9209	High Similarity	NPC100612
0.9149	High Similarity	NPC319719
0.9124	High Similarity	NPC222951
0.9007	High Similarity	NPC322904
0.8929	High Similarity	NPC113620
0.8897	High Similarity	NPC43589
0.8681	High Similarity	NPC324933
0.8643	High Similarity	NPC311178
0.8551	High Similarity	NPC329878
0.8521	High Similarity	NPC475444
0.8521	High Similarity	NPC473679
0.8435	Intermediate Similarity	NPC265699
0.84	Intermediate Similarity	NPC174336
0.8357	Intermediate Similarity	NPC220838
0.8273	Intermediate Similarity	NPC329893
0.8252	Intermediate Similarity	NPC478559
0.8252	Intermediate Similarity	NPC478560
0.8201	Intermediate Similarity	NPC484830
0.8182	Intermediate Similarity	NPC187497
0.8116	Intermediate Similarity	NPC475177
0.8071	Intermediate Similarity	NPC484831
0.7902	Intermediate Similarity	NPC45606
0.7551	Intermediate Similarity	NPC13989
0.7389	Intermediate Similarity	NPC488201
0.7099	Intermediate Similarity	NPC207738
0.7	Intermediate Similarity	NPC488202
0.7	Intermediate Similarity	NPC488204
0.6962	Remote Similarity	NPC488620
0.6626	Remote Similarity	NPC488203
0.6585	Remote Similarity	NPC488200
0.6403	Remote Similarity	NPC123522
0.6331	Remote Similarity	NPC488513
0.6276	Remote Similarity	NPC470876
0.6273	Remote Similarity	NPC488618
0.6269	Remote Similarity	NPC105800
0.6235	Remote Similarity	NPC488619
0.6096	Remote Similarity	NPC286457
0.6028	Remote Similarity	NPC172365
0.5948	Remote Similarity	NPC489209
0.5924	Remote Similarity	NPC489208
0.5904	Remote Similarity	NPC482013
0.5828	Remote Similarity	NPC309223
0.5779	Remote Similarity	NPC102505
0.5779	Remote Similarity	NPC488514
0.5753	Remote Similarity	NPC603137
0.5749	Remote Similarity	NPC23020
0.5725	Remote Similarity	NPC232237
0.5669	Remote Similarity	NPC33012
0.5667	Remote Similarity	NPC473452
0.5664	Remote Similarity	NPC104137
0.5664	Remote Similarity	NPC26626
0.5634	Remote Similarity	NPC481079
0.5605	Remote Similarity	NPC8524
0.5586	Remote Similarity	NPC185466
0.5548	Remote Similarity	NPC220160
0.5517	Remote Similarity	NPC210729
0.5517	Remote Similarity	NPC82931
0.55	Remote Similarity	NPC164389
0.5465	Remote Similarity	NPC472270
0.5465	Remote Similarity	NPC112492
0.5442	Remote Similarity	NPC473824
0.5442	Remote Similarity	NPC610204
0.543	Remote Similarity	NPC85154
0.5423	Remote Similarity	NPC123796
0.535	Remote Similarity	NPC482010
0.5235	Remote Similarity	NPC610461
0.5232	Remote Similarity	NPC609305
0.5223	Remote Similarity	NPC302543
0.521	Remote Similarity	NPC472268
0.5203	Remote Similarity	NPC470915
0.5203	Remote Similarity	NPC606553
0.5197	Remote Similarity	NPC283417
0.5197	Remote Similarity	NPC200049
0.5197	Remote Similarity	NPC475140
0.5195	Remote Similarity	NPC57484
0.5192	Remote Similarity	NPC484059
0.5192	Remote Similarity	NPC484060
0.519	Remote Similarity	NPC70809
0.5161	Remote Similarity	NPC13998
0.5157	Remote Similarity	NPC224381
0.5135	Remote Similarity	NPC609281
0.5125	Remote Similarity	NPC250247
0.5103	Remote Similarity	NPC488517
0.5102	Remote Similarity	NPC606145
0.5099	Remote Similarity	NPC151543
0.5097	Remote Similarity	NPC21691
0.5072	Remote Similarity	NPC1046
0.507	Remote Similarity	NPC469946
0.5061	Remote Similarity	NPC480421
0.5033	Remote Similarity	NPC135904
0.5033	Remote Similarity	NPC607904
0.5032	Remote Similarity	NPC4749

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC196874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8035
0.1-0.2	1083
0.2-0.3	30
0.3-0.4	2
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