NPASS Compound

Natural Product: NPC51099

Natural Product ID	NPC51099
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2'oacetylpolygalacin D2
IUPAC Name	[(2S,3R,4S,5S)-3-[(2S,3R,4S,5S,6S)-4-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-3-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	2'Oacetylpolygalacin D2
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1641867
PubChem CID	53317705
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 -7.4743 -1.0354 1.9397 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7003 0.0187 0.8765 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0967 0.5726 0.9214 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2499 1.5424 -0.2352 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2445 2.6485 -0.0164 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8623 1.9918 0.0579 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8211 1.0968 1.1309 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6458 1.3451 -1.1500 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5885 1.9870 -1.7987 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9531 2.4384 -3.1716 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7129 2.9083 -3.8952 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7407 1.7570 -3.9776 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0983 0.6922 -3.1983 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4471 1.0010 -1.8878 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3226 1.5534 -1.2308 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6775 0.8744 -0.2673 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1264 -0.2986 0.0132 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4855 1.3011 0.5437 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9746 2.4787 1.3551 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2436 3.7519 1.1552 C 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3339 1.9851 -0.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3948 0.3583 2.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3870 0.1653 0.6992 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2353 -0.9381 1.9165 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5877 -2.5513 3.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4071 -3.0742 3.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0835 -1.5165 4.6551 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0357 -0.9516 5.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7720 -1.9613 0.7224 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4880 -2.0841 -1.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0179 -3.7516 -2.6043 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1601 -4.6026 -1.0180 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4432 -6.1922 -2.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7983 -3.8670 -0.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8166 -5.4213 -0.7395 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7980 -4.2829 -3.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9235 -0.6409 -2.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0074 1.3260 3.1196 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 18 16 1 6 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 6 35 37 1 0 37 38 1 0 35 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 6 42 44 1 0 44 45 1 1 44 46 1 0 46 47 1 0 47 48 1 0 34 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 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 65 66 1 0 64 67 1 0 63 68 1 0 62 69 1 0 61 70 1 0 51 71 1 0 33 72 1 0 11 73 1 0 10 74 1 0 5 75 1 0 4 76 1 0 76 77 1 0 77 78 2 0 77 79 1 0 3 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 84 87 1 0 83 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 91 94 1 0 94 95 1 0 91 96 1 6 90 97 1 0 82 98 1 0 7 2 1 0 14 9 1 0 25 18 1 0 44 26 1 0 57 50 1 0 67 60 1 0 86 81 1 0 95 89 1 0 47 18 1 0 42 29 1 0 39 30 1 0 1 99 1 0 1100 1 0 1101 1 0 2102 1 6 3103 1 1 4104 1 6 5105 1 6 6106 1 1 9107 1 1 10108 1 6 11109 1 6 12110 1 0 12111 1 0 14112 1 1 19113 1 0 19114 1 0 20115 1 0 20116 1 0 22117 1 0 22118 1 0 22119 1 0 23120 1 0 23121 1 0 23122 1 0 24123 1 0 24124 1 0 25125 1 6 27126 1 0 28127 1 0 28128 1 0 29129 1 1 31130 1 0 31131 1 0 31132 1 0 32133 1 0 32134 1 0 33135 1 1 34136 1 1 36137 1 0 36138 1 0 36139 1 0 37140 1 0 37141 1 0 38142 1 0 39143 1 1 40144 1 0 40145 1 0 41146 1 0 41147 1 0 43148 1 0 43149 1 0 43150 1 0 45151 1 0 45152 1 0 45153 1 0 46154 1 0 46155 1 0 47156 1 1 48157 1 0 50158 1 1 51159 1 6 52160 1 1 53161 1 6 54162 1 1 55163 1 0 55164 1 0 56165 1 0 58166 1 0 60167 1 1 61168 1 6 62169 1 1 63170 1 6 64171 1 1 65172 1 0 65173 1 0 66174 1 0 68175 1 0 69176 1 0 70177 1 0 71178 1 0 72179 1 0 73180 1 0 74181 1 0 75182 1 0 79183 1 0 79184 1 0 79185 1 0 81186 1 1 82187 1 6 83188 1 1 84189 1 1 85190 1 0 85191 1 0 87192 1 0 89193 1 1 90194 1 1 92195 1 0 92196 1 0 93197 1 0 94198 1 0 94199 1 0 96200 1 0 97201 1 0 98202 1 0 M END

Standard InCHIKey	QIHODHJJXXXEHU-CPNNXQAESA-N
Standard InCHI	InChI=1S/C65H104O33/c1-25-45(93-52-42(80)46(31(73)21-86-52)94-57-50(83)64(85,23-69)24-88-57)48(90-26(2)70)44(82)54(89-25)96-49-37(75)30(72)20-87-56(49)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)97-55-43(81)47(39(77)33(19-67)92-55)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	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](CO[C@H]1OC(=O)[C@]12CCC(C)(C)C[C@H]1C1=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O[C@H]1[C@@H]([C@@](CO)(CO1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1412.65	Volume:	1320.843 ? Van der Waals volume.
Dense:	1.07	LogP:	-1.156 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.395 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.668 ? 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:	7.978	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:	0.666	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.316	Promiscuous compounds:	0.502

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.188	MDCK Permeability:	-4.896
Pgp-inhibitor:	0.0	Pgp-substrate:	0.993
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):	0.388
20% Bioavailability (F20%):	0.055	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.018
Plasma Protein Binding (PPB):	51.22%	Volume Distribution (VD):	-0.445
Fu:	30.183% ? 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:	0.0
HLM stability:	0.205 ? 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):

-1.151

Half-life (T1/2):

4.284

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.838	Drug-induced Liver Injury (DILI):	0.926
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.032	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.846	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.135	RPMI-8226 Immunitoxicity:	0.311
A549 Cytotoxicity:	0.983	Hek293 Cytotoxicity:	0.637
BCF:	0.468 ? 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:	3.269 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.942 ? 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[19006373]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	3400.0	nM	PMID[20939516]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	5900.0	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 NPC51099 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	25482
0.1-0.2	20999
0.2-0.3	2497
0.3-0.4	534
0.4-0.5	263
0.5-0.6	51
0.6-0.7	16
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
0.9739	High Similarity	NPC142151
0.9083	High Similarity	NPC68767
0.9076	High Similarity	NPC267694
0.879	High Similarity	NPC275225
0.875	High Similarity	NPC144644
0.875	High Similarity	NPC170407
0.8548	High Similarity	NPC153673
0.8468	Intermediate Similarity	NPC293031
0.8145	Intermediate Similarity	NPC37860
0.7969	Intermediate Similarity	NPC110385
0.7786	Intermediate Similarity	NPC480421
0.6923	Remote Similarity	NPC237191
0.6846	Remote Similarity	NPC85154
0.6746	Remote Similarity	NPC815
0.637	Remote Similarity	NPC473452
0.637	Remote Similarity	NPC480418
0.625	Remote Similarity	NPC13998
0.6224	Remote Similarity	NPC33012
0.6154	Remote Similarity	NPC104137
0.6154	Remote Similarity	NPC26626
0.6154	Remote Similarity	NPC8524
0.6154	Remote Similarity	NPC480422
0.6116	Remote Similarity	NPC475208
0.6084	Remote Similarity	NPC489209
0.6045	Remote Similarity	NPC475899
0.6026	Remote Similarity	NPC475394
0.6014	Remote Similarity	NPC286457
0.5984	Remote Similarity	NPC164389
0.5968	Remote Similarity	NPC150400
0.5956	Remote Similarity	NPC480423
0.5948	Remote Similarity	NPC475584
0.5948	Remote Similarity	NPC475152
0.5946	Remote Similarity	NPC489208
0.5935	Remote Similarity	NPC485563
0.5903	Remote Similarity	NPC480417
0.5793	Remote Similarity	NPC102505
0.5793	Remote Similarity	NPC488514
0.5745	Remote Similarity	NPC475514
0.5683	Remote Similarity	NPC471577
0.566	Remote Similarity	NPC23020
0.5655	Remote Similarity	NPC220160
0.5625	Remote Similarity	NPC309223
0.5625	Remote Similarity	NPC302543
0.5603	Remote Similarity	NPC473386
0.5597	Remote Similarity	NPC69811
0.5591	Remote Similarity	NPC480420
0.5562	Remote Similarity	NPC476113
0.5532	Remote Similarity	NPC4749
0.553	Remote Similarity	NPC488517
0.5507	Remote Similarity	NPC123522
0.55	Remote Similarity	NPC283417
0.55	Remote Similarity	NPC200049
0.5493	Remote Similarity	NPC21691
0.5442	Remote Similarity	NPC482010
0.5417	Remote Similarity	NPC471580
0.5414	Remote Similarity	NPC475504
0.5412	Remote Similarity	NPC488513
0.5397	Remote Similarity	NPC1046
0.5385	Remote Similarity	NPC475527
0.538	Remote Similarity	NPC475892
0.5374	Remote Similarity	NPC70809
0.5369	Remote Similarity	NPC478825
0.5366	Remote Similarity	NPC472270
0.5366	Remote Similarity	NPC112492
0.531	Remote Similarity	NPC470876
0.5195	Remote Similarity	NPC478822
0.518	Remote Similarity	NPC11242
0.517	Remote Similarity	NPC293330
0.5149	Remote Similarity	NPC488526
0.5149	Remote Similarity	NPC305267
0.5137	Remote Similarity	NPC473645
0.5108	Remote Similarity	NPC481078
0.5105	Remote Similarity	NPC480419
0.5101	Remote Similarity	NPC33068
0.5101	Remote Similarity	NPC476991
0.5065	Remote Similarity	NPC485562
0.5036	Remote Similarity	NPC64715
0.5033	Remote Similarity	NPC51564

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC51099 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7865
0.1-0.2	1256
0.2-0.3	28
0.3-0.4	1
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