NPASS Compound

Natural Product: NPC478065

Natural Product ID	NPC478065
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	butyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aR,9S,12aS,14aR,14bR)-9-[(2E)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
IUPAC Name	butyl (2S,3S,4S,5R,6R)-6-[[(3S,6aR,6bS,7R,8S,8aR,9S,12aS,14aR,14bR)-9-[(2E)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44575724
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 180187 0 0 0 0 0 0 0 0999 V2000 -7.3548 -3.5086 4.0655 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7790 -4.9343 3.9677 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8134 -5.3002 3.0048 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6385 -5.2560 1.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2187 -4.0648 0.9995 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9714 -3.5691 0.9302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9881 -4.1997 1.3768 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6923 -2.2245 0.3011 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3895 -2.0918 -0.9977 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6878 -1.0673 -1.8691 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9581 -0.0569 -1.0093 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9254 -0.8015 -0.1587 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3565 -2.0285 0.2341 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6998 -0.9280 -0.8477 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6737 -0.2477 -0.1911 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9187 -1.2706 0.6511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5215 -0.9467 0.9639 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2603 -0.5975 -0.2917 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6086 -0.1115 0.2116 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1615 -0.9950 1.2941 C 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0 0 0 -8.1845 2.4046 -0.5317 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4765 3.8498 -0.3254 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6623 4.4779 0.7527 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2356 3.9425 0.7224 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3168 2.5765 0.9699 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4762 4.6870 1.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4439 6.0434 1.4638 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7158 5.8451 0.6673 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8223 3.9157 0.1220 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4212 1.9957 -1.8461 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7545 -1.7444 -2.6454 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7058 -1.6151 -0.8814 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6471 -2.4287 -1.4666 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7350 -2.7384 -0.5120 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8735 -1.8609 -0.9181 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3970 -1.2400 -2.1862 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2290 -1.8309 -2.5900 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4813 -1.3784 -3.2370 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6321 -0.7750 -2.7782 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0730 -0.8989 0.0940 O 0 0 0 0 0 0 0 0 0 0 0 0 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4.1387 -0.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9398 4.5498 2.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4244 4.3456 1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4653 6.6503 2.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3360 6.1848 1.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8995 3.6109 1.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2802 2.4417 -2.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2038 -2.1205 -3.4645 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1080 -3.3153 -1.8679 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4126 -2.4957 0.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8279 -2.4215 -1.0216 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2290 -0.1347 -2.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6998 -2.4679 -3.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1820 -0.8741 -4.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3150 -1.4523 -2.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4926 -1.3869 0.8592 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2931 -4.5653 -0.9571 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 2 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 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 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 32 39 1 6 31 40 1 1 30 41 1 0 29 42 1 0 28 43 1 6 43 44 1 0 27 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 0 49 50 1 0 49 51 1 0 51 52 1 0 52 53 1 0 53 54 2 3 54 55 1 0 54 56 1 0 25 57 1 0 25 58 1 0 18 59 1 6 11 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 65 67 1 0 67 68 1 0 64 69 1 0 63 70 1 0 62 71 1 0 10 72 1 0 9 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 77 79 1 0 79 80 1 0 76 81 1 0 75 82 1 0 13 8 1 0 36 15 1 0 35 18 1 0 32 19 1 0 31 22 1 0 28 23 1 0 66 61 1 0 78 74 1 0 1 83 1 0 1 84 1 0 1 85 1 0 2 86 1 0 2 87 1 0 3 88 1 0 3 89 1 0 4 90 1 0 4 91 1 0 8 92 1 1 9 93 1 6 10 94 1 6 11 95 1 6 12 96 1 1 15 97 1 1 16 98 1 0 16 99 1 0 17100 1 0 17101 1 0 19102 1 1 20103 1 0 20104 1 0 21105 1 0 23106 1 1 24107 1 0 24108 1 0 26109 1 0 26110 1 0 27111 1 1 29112 1 6 30113 1 6 33114 1 0 33115 1 0 34116 1 0 34117 1 0 35118 1 0 37119 1 0 37120 1 0 37121 1 0 38122 1 0 38123 1 0 38124 1 0 39125 1 0 39126 1 0 39127 1 0 40128 1 0 40129 1 0 40130 1 0 41131 1 0 42132 1 0 43133 1 0 43134 1 0 44135 1 0 48136 1 0 50137 1 0 50138 1 0 50139 1 0 51140 1 0 51141 1 0 52142 1 0 52143 1 0 53144 1 0 55145 1 0 55146 1 0 55147 1 0 56148 1 0 56149 1 0 56150 1 0 57151 1 0 57152 1 0 57153 1 0 58154 1 0 58155 1 0 58156 1 0 59157 1 0 59158 1 0 59159 1 0 61160 1 6 62161 1 1 63162 1 6 64163 1 1 65164 1 6 67165 1 0 67166 1 0 68167 1 0 69168 1 0 70169 1 0 71170 1 0 72171 1 0 74172 1 6 75173 1 1 76174 1 6 77175 1 1 79176 1 0 79177 1 0 80178 1 0 81179 1 0 82180 1 0 M END

Standard InCHIKey	KEDJBUGHODJQAX-JCHISVDESA-N
Standard InCHI	InChI=1S/C61H98O21/c1-12-13-23-75-52(74)49-47(80-53-44(69)42(67)35(28-63)77-53)46(71)48(81-54-45(70)43(68)41(66)34(27-62)76-54)55(82-49)79-38-20-21-58(9)36(57(38,7)8)19-22-59(10)37(58)18-17-32-33-25-56(5,6)26-39(61(33,29-64)51(73)50(72)60(32,59)11)78-40(65)24-31(4)16-14-15-30(2)3/h15,17,24,33-39,41-51,53-55,62-64,66-73H,12-14,16,18-23,25-29H2,1-11H3/b31-24+/t33-,34+,35-,36?,37+,38-,39-,41+,42-,43-,44+,45+,46-,47-,48+,49-,50-,51+,53-,54-,55+,58-,59+,60-,61+/m0/s1
SMILES	CCCCOC(=O)[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC=C5[C@@H]6CC(C[C@@H]([C@@]6([C@@H]([C@@H]([C@]5([C@@]4(CCC3C2(C)C)C)C)O)O)CO)OC(=O)/C=C(\C)/CCC=C(C)C)(C)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H](O8)CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1166.66	Volume:	1166.572 ? Van der Waals volume.
Dense:	1.0	LogP:	4.254 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.365 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.924 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	47.0
TPSA:	330.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.031	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.031	Fsp³:	0.869
MCE-18:	176.561 ? 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:	0.953	Fluc inhibitor:	0.002 ? 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:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.193	Promiscuous compounds:	0.307

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.393	MDCK Permeability:	-5.145
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.914 ? 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%):	0.461	30% Bioavailability (F30%):	0.922
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.226	MRP1:	0.449
Plasma Protein Binding (PPB):	85.439%	Volume Distribution (VD):	-0.333
Fu:	8.094% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.338

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.113	CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.952
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.995
HLM stability:	1.0 ? 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):

0.118

Half-life (T1/2):

2.977

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.379	Drug-induced Liver Injury (DILI):	0.961
AMES Toxicity:	0.814	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.077	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.998
Hematotoxicity:	0.762	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.079	RPMI-8226 Immunitoxicity:	0.424
A549 Cytotoxicity:	0.971	Hek293 Cytotoxicity:	0.732
BCF:	1.402 ? 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:	4.174 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.966 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.019 ? 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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	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
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	4.04	ug/ml	PMID[15620235]

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 NPC478065 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	22480
0.1-0.2	23257
0.2-0.3	3037
0.3-0.4	748
0.4-0.5	276
0.5-0.6	42
0.6-0.7	9
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301639
0.8448	Intermediate Similarity	NPC173435
0.8448	Intermediate Similarity	NPC172374
0.8448	Intermediate Similarity	NPC478064
0.7881	Intermediate Similarity	NPC329993
0.7563	Intermediate Similarity	NPC134914
0.6977	Remote Similarity	NPC69425
0.6885	Remote Similarity	NPC264566
0.6667	Remote Similarity	NPC478066
0.6378	Remote Similarity	NPC475167
0.6311	Remote Similarity	NPC609281
0.6016	Remote Similarity	NPC477075
0.6	Remote Similarity	NPC329923
0.6	Remote Similarity	NPC475281
0.6	Remote Similarity	NPC295408
0.5985	Remote Similarity	NPC225791
0.5985	Remote Similarity	NPC262796
0.5985	Remote Similarity	NPC45346
0.5935	Remote Similarity	NPC470914
0.5896	Remote Similarity	NPC475377
0.5896	Remote Similarity	NPC476074
0.5865	Remote Similarity	NPC475513
0.5802	Remote Similarity	NPC470912
0.5748	Remote Similarity	NPC606553
0.5691	Remote Similarity	NPC235438
0.5682	Remote Similarity	NPC277212
0.5682	Remote Similarity	NPC30279
0.5645	Remote Similarity	NPC470913
0.5639	Remote Similarity	NPC71391
0.5636	Remote Similarity	NPC474190
0.5564	Remote Similarity	NPC473918
0.5563	Remote Similarity	NPC150893
0.5538	Remote Similarity	NPC610461
0.552	Remote Similarity	NPC222580
0.5469	Remote Similarity	NPC80986
0.5426	Remote Similarity	NPC329976
0.542	Remote Similarity	NPC610204
0.5391	Remote Similarity	NPC606145
0.5349	Remote Similarity	NPC477078
0.5319	Remote Similarity	NPC484063
0.5319	Remote Similarity	NPC484064
0.5303	Remote Similarity	NPC607904
0.5267	Remote Similarity	NPC62725
0.5252	Remote Similarity	NPC484833
0.5191	Remote Similarity	NPC31838
0.5185	Remote Similarity	NPC609305
0.5161	Remote Similarity	NPC39211
0.5149	Remote Similarity	NPC1314
0.5149	Remote Similarity	NPC273878
0.5145	Remote Similarity	NPC178264
0.5145	Remote Similarity	NPC473755
0.5109	Remote Similarity	NPC46823
0.5072	Remote Similarity	NPC192765
0.504	Remote Similarity	NPC603026
0.5038	Remote Similarity	NPC605294
0.5035	Remote Similarity	NPC484059
0.5035	Remote Similarity	NPC484060

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC478065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7483
0.1-0.2	1612
0.2-0.3	53
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