NPASS Compound

Natural Product: NPC305793

Natural Product ID	NPC305793
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Isoescin Ia
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8a-(acetyloxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(E)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
Synonyms	isoescin Ia
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500473
PubChem CID	6476032
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 165172 0 0 0 0 0 0 0 0999 V2000 -3.3225 -4.6286 -1.5408 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0848 -5.0325 -2.6289 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3373 -4.1714 -2.6516 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9072 -2.8423 -2.7803 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0482 -2.0565 -2.4256 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6423 -0.8166 -1.9624 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9375 -0.6434 -0.6414 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8434 -0.3835 0.3004 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2289 -1.0087 1.5264 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4642 -0.5871 1.9267 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1309 0.4800 1.1479 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0002 0.4111 -0.3489 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1893 0.2124 -0.9899 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8709 1.7836 1.6254 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9929 2.4061 2.1134 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2491 3.4973 1.2662 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5108 4.0400 1.5029 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6661 5.2014 0.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8979 5.8313 0.6765 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5599 4.6154 2.9038 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2812 3.4787 3.8645 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.8867 2.9481 3.5003 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5812 1.9979 4.4601 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3894 3.8266 5.1880 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7962 5.2014 3.1331 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3945 -1.7375 2.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9319 -2.8873 2.0487 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6964 -1.5491 2.5954 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5690 -0.7503 0.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6082 0.2372 0.3419 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9045 -0.2047 1.6041 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4321 -0.1551 1.5764 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1405 -0.6376 0.2329 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3271 0.3616 -0.7808 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7717 0.7387 -0.7485 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8740 2.2889 -0.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4457 0.4075 -2.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6014 -0.9216 -2.2981 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2352 -0.0479 -2.0941 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7543 0.1791 -2.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4134 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11.6775 0.9664 1.7343 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9502 -0.3086 1.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3195 -0.8320 1.9346 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7508 1.9475 2.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7856 -1.5077 -0.7947 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7484 -1.4519 -1.7088 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9246 -1.5822 -3.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9671 -1.8645 -3.7797 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2510 -1.4037 -3.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7161 0.5285 -2.7263 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7233 -1.8924 -1.3253 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2234 -2.0472 0.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8967 -2.0504 -3.6579 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3395 -3.5123 -3.8609 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1807 -4.4556 -3.8760 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6706 -5.7468 -3.7425 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1212 -3.6426 -5.0013 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0403 -1.2961 -3.5919 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7777 -4.8220 -0.6741 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4796 -4.8664 -3.5410 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3327 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13.8227 -0.2708 2.7511 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6452 1.7420 1.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9946 1.9584 3.1023 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4182 2.9870 1.7660 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3015 -1.6728 0.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2669 -2.5253 -0.8985 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0839 -1.4379 -2.9941 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2960 -0.3952 -4.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3238 -2.1515 -4.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1454 1.0493 -3.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9388 -2.6064 -0.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5624 -1.9120 -2.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8388 -2.2680 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6367 -2.7811 0.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9133 -2.4266 0.8361 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7219 -2.3199 -0.9145 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2721 -1.8130 -4.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9900 -3.7754 -2.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5446 -4.3393 -4.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8786 -6.3511 -3.8937 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6133 -4.1680 -5.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9738 -0.4237 -4.0332 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 11 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 20 25 1 0 10 26 1 0 26 27 2 0 26 28 1 0 8 29 1 0 29 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 1 35 37 1 0 37 38 1 0 34 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 2 0 45 46 1 0 46 47 1 1 46 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 53 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 62 65 1 0 50 66 1 6 66 67 1 0 67 68 1 0 68 69 2 0 68 70 1 0 49 71 1 0 41 72 1 6 33 73 1 6 5 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 75 78 1 0 74 79 1 0 76 3 1 0 12 7 1 0 22 15 1 0 35 30 1 0 46 41 1 0 57 50 1 0 42 33 1 0 51 45 1 0 1 80 1 0 2 81 1 0 2 82 1 0 3 83 1 1 5 84 1 1 7 85 1 1 8 86 1 1 10 87 1 1 11 88 1 6 12 89 1 6 13 90 1 0 15 91 1 1 17 92 1 1 18 93 1 0 18 94 1 0 19 95 1 0 20 96 1 6 21 97 1 6 22 98 1 6 23 99 1 0 24100 1 0 25101 1 0 28102 1 0 30103 1 1 31104 1 0 31105 1 0 32106 1 0 32107 1 0 34108 1 1 36109 1 0 36110 1 0 36111 1 0 37112 1 0 37113 1 0 38114 1 0 39115 1 0 39116 1 0 40117 1 0 40118 1 0 42119 1 1 43120 1 0 43121 1 0 44122 1 0 47123 1 0 47124 1 0 47125 1 0 48126 1 0 48127 1 0 49128 1 6 51129 1 6 52130 1 0 52131 1 0 54132 1 0 54133 1 0 54134 1 0 55135 1 0 55136 1 0 55137 1 0 56138 1 6 57139 1 6 58140 1 0 63141 1 0 64142 1 0 64143 1 0 64144 1 0 65145 1 0 65146 1 0 65147 1 0 66148 1 0 66149 1 0 70150 1 0 70151 1 0 70152 1 0 71153 1 0 72154 1 0 72155 1 0 72156 1 0 73157 1 0 73158 1 0 73159 1 0 74160 1 6 75161 1 1 76162 1 6 77163 1 0 78164 1 0 79165 1 0 M END

Standard InCHIKey	YOSIWGSGLDDTHJ-IVKVKCDBSA-N
Standard InCHI	InChI=1S/C55H86O24/c1-10-23(2)46(71)79-44-43(68)55(22-72-24(3)59)26(17-50(44,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)60)75-49-41(77-48-38(66)36(64)34(62)28(20-57)74-48)39(67)40(42(78-49)45(69)70)76-47-37(65)35(63)33(61)27(19-56)73-47/h10-11,26-44,47-49,56-58,60-68H,12-22H2,1-9H3,(H,69,70)/b23-10+/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)O)O[C@H]2CC[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)[C@H]([C@@H]2O)OC(=O)/C(=C/C)/C)COC(=O)C)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1130.55	Volume:	1089.167 ? Van der Waals volume.
Dense:	1.038	LogP:	0.38 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.724 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.004 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	48.0
TPSA:	388.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	8.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.988	Fsp³:	0.873
MCE-18:	184.893 ? 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:	0.704	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.196	Promiscuous compounds:	0.295

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.287	MDCK Permeability:	-5.156
Pgp-inhibitor:	0.0	Pgp-substrate:	0.127
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):	0.825
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.944
Plasma Protein Binding (PPB):	67.469%	Volume Distribution (VD):	-0.599
Fu:	23.074% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.975	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:	0.008
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):

-0.281

Half-life (T1/2):

3.567

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.678	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.469	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.003
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.956	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.376
A549 Cytotoxicity:	0.992	Hek293 Cytotoxicity:	0.75
BCF:	0.318 ? 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:	3.367 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.339 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.144 ? 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
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[10579862]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15104496]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	seeds	n.a.	n.a.	PMID[25442304]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29234.1	Aesculus chinensis var. wilsonii	Varieties	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29234.1	Aesculus chinensis var. wilsonii	Varieties	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29234	Aesculus chinensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29234	Aesculus chinensis	Species	Sapindaceae	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	1
Activity	2
IC50	2

Activity Type	# Activity
Individual protein	1
Cell line	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual protein	Protease	Human immunodeficiency virus 1	Inhibition	=	39.0	%	PMID[10579862]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell line	U-251	Homo sapiens	Activity	=	61.12	%	PMID[25442304]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	22.61	%	PMID[25442304]
NPT380	Cell line	U-251	Homo sapiens	IC50	=	80360.0	nM	PMID[25442304]
NPT76	Cell line	C6	Rattus norvegicus	IC50	=	54500.0	nM	PMID[25442304]

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 NPC305793 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	21230
0.1-0.2	24065
0.2-0.3	3538
0.3-0.4	695
0.4-0.5	259
0.5-0.6	40
0.6-0.7	9
0.7-0.8	0
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC252289
0.8692	High Similarity	NPC472267
0.8692	High Similarity	NPC115656
0.8304	Intermediate Similarity	NPC269484
0.8304	Intermediate Similarity	NPC97918
0.8108	Intermediate Similarity	NPC252657
0.8108	Intermediate Similarity	NPC88311
0.8018	Intermediate Similarity	NPC107536
0.8018	Intermediate Similarity	NPC280029
0.8018	Intermediate Similarity	NPC9470
0.7719	Intermediate Similarity	NPC1314
0.7719	Intermediate Similarity	NPC273878
0.7686	Intermediate Similarity	NPC476775
0.7603	Intermediate Similarity	NPC11577
0.7603	Intermediate Similarity	NPC141600
0.7387	Intermediate Similarity	NPC611191
0.7008	Intermediate Similarity	NPC476778
0.6953	Remote Similarity	NPC476776
0.672	Remote Similarity	NPC476774
0.6341	Remote Similarity	NPC609119
0.6299	Remote Similarity	NPC82380
0.6299	Remote Similarity	NPC244296
0.6241	Remote Similarity	NPC279915
0.6202	Remote Similarity	NPC476780
0.619	Remote Similarity	NPC603137
0.6167	Remote Similarity	NPC603832
0.5878	Remote Similarity	NPC470518
0.5789	Remote Similarity	NPC271610
0.5769	Remote Similarity	NPC602995
0.5748	Remote Similarity	NPC25998
0.5704	Remote Similarity	NPC476777
0.5597	Remote Similarity	NPC265841
0.5547	Remote Similarity	NPC605294
0.553	Remote Similarity	NPC470218
0.5515	Remote Similarity	NPC476779
0.5448	Remote Similarity	NPC329828
0.542	Remote Similarity	NPC478154
0.5401	Remote Similarity	NPC484059
0.5401	Remote Similarity	NPC484060
0.5401	Remote Similarity	NPC478153
0.5397	Remote Similarity	NPC64715
0.536	Remote Similarity	NPC118440
0.5328	Remote Similarity	NPC312650
0.5312	Remote Similarity	NPC477191
0.5303	Remote Similarity	NPC478155
0.5271	Remote Similarity	NPC187618
0.5255	Remote Similarity	NPC488308
0.5252	Remote Similarity	NPC110700
0.5224	Remote Similarity	NPC609305
0.5221	Remote Similarity	NPC478597
0.5194	Remote Similarity	NPC477079
0.5182	Remote Similarity	NPC484061
0.5182	Remote Similarity	NPC484062
0.5149	Remote Similarity	NPC284449
0.5145	Remote Similarity	NPC478596
0.5116	Remote Similarity	NPC114692
0.5116	Remote Similarity	NPC236657
0.5079	Remote Similarity	NPC605226
0.5078	Remote Similarity	NPC131469
0.5077	Remote Similarity	NPC477076
0.5072	Remote Similarity	NPC178264
0.5039	Remote Similarity	NPC95437
0.5039	Remote Similarity	NPC302887
0.5038	Remote Similarity	NPC477077
0.5038	Remote Similarity	NPC477192
0.5035	Remote Similarity	NPC488309

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305793 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6767
0.1-0.2	2320
0.2-0.3	58
0.3-0.4	5
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