NPASS Compound

Natural Product: NPC470876

Natural Product ID	NPC470876
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Helianthoside 3
IUPAC Name	[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(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] (4aR,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-5-hydroxy-10-[(2R,3R,4S,5S,6R)-4-hydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]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	Helianthoside 3
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL227302
PubChem CID	44423117
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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13 1 0 13 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 1 0 21 23 1 0 20 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 2 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 37 38 1 0 38 39 1 0 37 40 1 0 37 41 1 0 34 42 1 0 42 43 2 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 48 53 1 0 47 54 1 0 46 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 60 62 1 0 59 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 68 70 1 0 70 71 1 0 67 72 1 0 66 73 1 0 65 74 1 0 58 75 1 0 57 76 1 0 33 77 1 0 31 78 1 0 26 79 1 0 19 80 1 0 12 81 1 0 81 82 1 0 11 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 88 89 1 0 87 90 1 0 86 91 1 0 85 92 1 0 10 93 1 0 5 94 1 0 4 95 1 0 3 96 1 0 7 2 1 0 69 64 1 0 89 84 1 0 14 9 1 0 21 16 1 0 27 19 1 0 31 26 1 0 35 30 1 0 39 34 1 0 50 45 1 0 61 56 1 0 1 97 1 0 1 98 1 0 1 99 1 0 2100 1 0 3101 1 0 4102 1 0 5103 1 0 6104 1 0 9105 1 0 10106 1 0 11107 1 0 12108 1 0 14109 1 0 16110 1 0 17111 1 0 17112 1 0 18113 1 0 18114 1 0 20115 1 0 22116 1 0 22117 1 0 22118 1 0 23119 1 0 23120 1 0 23121 1 0 24122 1 0 24123 1 0 25124 1 0 25125 1 0 27126 1 0 28127 1 0 28128 1 0 29129 1 0 32130 1 0 32131 1 0 33132 1 0 35133 1 0 36134 1 0 36135 1 0 38136 1 0 38137 1 0 39138 1 0 39139 1 0 40140 1 0 40141 1 0 40142 1 0 41143 1 0 41144 1 0 41145 1 0 45146 1 0 46147 1 0 47148 1 0 48149 1 0 49150 1 0 51151 1 0 51152 1 0 52153 1 0 53154 1 0 54155 1 0 56156 1 0 57157 1 0 58158 1 0 59159 1 0 60160 1 0 62161 1 0 62162 1 0 62163 1 0 64164 1 0 65165 1 0 66166 1 0 67167 1 0 68168 1 0 70169 1 0 70170 1 0 71171 1 0 72172 1 0 73173 1 0 74174 1 0 75175 1 0 76176 1 0 77177 1 0 78178 1 0 78179 1 0 78180 1 0 79181 1 0 79182 1 0 79183 1 0 80184 1 0 80185 1 0 80186 1 0 81187 1 0 81188 1 0 82189 1 0 84190 1 0 85191 1 0 86192 1 0 87193 1 0 88194 1 0 88195 1 0 90196 1 0 91197 1 0 92198 1 0 93199 1 0 94200 1 0 95201 1 0 96202 1 0 M END

Standard InCHIKey	AYYLWNDUOGPVDY-XARGMJFBSA-N
Standard InCHI	InChI=1S/C65H106O31/c1-24-36(71)40(75)45(80)54(86-24)95-52-48(83)50(93-53-44(79)37(72)28(69)23-85-53)31(22-68)90-57(52)91-35-13-14-62(7)32(61(35,5)6)12-15-63(8)33(62)11-10-26-27-18-60(3,4)16-17-65(27,34(70)19-64(26,63)9)59(84)96-58-51(42(77)39(74)30(21-67)89-58)94-55-47(82)43(78)49(25(2)87-55)92-56-46(81)41(76)38(73)29(20-66)88-56/h10,24-25,27-58,66-83H,11-23H2,1-9H3/t24-,25-,27-,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-,58-,62-,63+,64+,65+/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(C(C(OC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CC(C7(C6CC(CC7)(C)C)C(=O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)OC1C(C(C(C(O1)CO)O)O)O)O)O)O)C)C)C)CO)OC1C(C(C(CO1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1382.67	Volume:	1305.899 ? Van der Waals volume.
Dense:	1.059	LogP:	-1.086 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.138 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.929 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	63.0
TPSA:	491.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	31.0
H-Bond Donor:	18.0	Rings:	11.0
Heavy Atoms:	31.0

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:	7.751	Fsp³:	0.954
MCE-18:	242.504 ? 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:	0.003	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.329 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.427	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.403	MDCK Permeability:	-4.866
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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%):	0.92	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	13.293%	Volume Distribution (VD):	-0.448
Fu:	36.736% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.015	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.934	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	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:	0.0 ? 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):

-1.32

Half-life (T1/2):

5.188

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.172
Human Hepatotoxicity (H-HT):	0.315	Drug-induced Liver Injury (DILI):	0.364
AMES Toxicity:	0.476	Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.054	Skin Sensitization:	0.003
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.336	Ototoxicity:	1.0
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.01
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.131
A549 Cytotoxicity:	0.015	Hek293 Cytotoxicity:	0.869
BCF:	0.67 ? 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:	4.173 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.572 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.413 ? 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
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	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
ID50	1
Ratio	1

Activity Type	# Activity
Organism	2

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	156.0	nmol	PMID[17682106]
NPT32	Organism	Mus musculus	Mus musculus	Ratio	=	73.0	%	PMID[16513348]

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 NPC470876 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	24595
0.1-0.2	21286
0.2-0.3	2577
0.3-0.4	764
0.4-0.5	363
0.5-0.6	124
0.6-0.7	60
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.807	Intermediate Similarity	NPC123522
0.8051	Intermediate Similarity	NPC286457
0.8036	Intermediate Similarity	NPC104137
0.8036	Intermediate Similarity	NPC26626
0.7966	Intermediate Similarity	NPC57484
0.7459	Intermediate Similarity	NPC473452
0.7438	Intermediate Similarity	NPC85154
0.7411	Intermediate Similarity	NPC164389
0.7231	Intermediate Similarity	NPC33012
0.7222	Intermediate Similarity	NPC309223
0.7209	Intermediate Similarity	NPC489209
0.7154	Intermediate Similarity	NPC8524
0.7109	Intermediate Similarity	NPC220160
0.7	Intermediate Similarity	NPC102505
0.7	Intermediate Similarity	NPC488514
0.6917	Remote Similarity	NPC815
0.6909	Remote Similarity	NPC1046
0.6889	Remote Similarity	NPC489208
0.6812	Remote Similarity	NPC329893
0.6692	Remote Similarity	NPC302543
0.6641	Remote Similarity	NPC13998
0.6591	Remote Similarity	NPC482010
0.6587	Remote Similarity	NPC283417
0.6587	Remote Similarity	NPC200049
0.6552	Remote Similarity	NPC469946
0.6529	Remote Similarity	NPC481079
0.6462	Remote Similarity	NPC475514
0.6423	Remote Similarity	NPC207738
0.637	Remote Similarity	NPC478559
0.637	Remote Similarity	NPC478560
0.6364	Remote Similarity	NPC64715
0.6327	Remote Similarity	NPC222951
0.6308	Remote Similarity	NPC21691
0.6303	Remote Similarity	NPC30289
0.6296	Remote Similarity	NPC250247
0.6284	Remote Similarity	NPC23020
0.6276	Remote Similarity	NPC300655
0.6276	Remote Similarity	NPC196874
0.6269	Remote Similarity	NPC70809
0.625	Remote Similarity	NPC135904
0.6231	Remote Similarity	NPC4749
0.6183	Remote Similarity	NPC473386
0.617	Remote Similarity	NPC475177
0.6154	Remote Similarity	NPC484830
0.6149	Remote Similarity	NPC311178
0.6142	Remote Similarity	NPC610204
0.6138	Remote Similarity	NPC329878
0.6124	Remote Similarity	NPC603137
0.6116	Remote Similarity	NPC488526
0.6096	Remote Similarity	NPC233223
0.6096	Remote Similarity	NPC183816
0.6096	Remote Similarity	NPC43589
0.6083	Remote Similarity	NPC112352
0.608	Remote Similarity	NPC295823
0.608	Remote Similarity	NPC174720
0.608	Remote Similarity	NPC475467
0.6078	Remote Similarity	NPC322904
0.6063	Remote Similarity	NPC185466
0.6061	Remote Similarity	NPC237191
0.6054	Remote Similarity	NPC13989
0.6042	Remote Similarity	NPC484831
0.6033	Remote Similarity	NPC117714
0.6031	Remote Similarity	NPC471577
0.6027	Remote Similarity	NPC484829
0.6016	Remote Similarity	NPC60557
0.6016	Remote Similarity	NPC475287
0.6016	Remote Similarity	NPC67857
0.6016	Remote Similarity	NPC123796
0.6016	Remote Similarity	NPC297263
0.6	Remote Similarity	NPC236638
0.6	Remote Similarity	NPC294453
0.6	Remote Similarity	NPC305981
0.6	Remote Similarity	NPC319719
0.6	Remote Similarity	NPC76497
0.6	Remote Similarity	NPC213674
0.5985	Remote Similarity	NPC224381
0.5984	Remote Similarity	NPC11242
0.5956	Remote Similarity	NPC261506
0.5956	Remote Similarity	NPC4328
0.5956	Remote Similarity	NPC144644
0.5956	Remote Similarity	NPC37860
0.5956	Remote Similarity	NPC170407
0.5954	Remote Similarity	NPC480423
0.5948	Remote Similarity	NPC472270
0.5948	Remote Similarity	NPC112492
0.5926	Remote Similarity	NPC43550
0.5906	Remote Similarity	NPC31838
0.5906	Remote Similarity	NPC481078
0.5899	Remote Similarity	NPC68767
0.5899	Remote Similarity	NPC293031
0.5894	Remote Similarity	NPC488618
0.5865	Remote Similarity	NPC481080
0.586	Remote Similarity	NPC265699
0.5855	Remote Similarity	NPC475444
0.5855	Remote Similarity	NPC473679
0.5855	Remote Similarity	NPC488619
0.5854	Remote Similarity	NPC305267
0.5852	Remote Similarity	NPC471580
0.5852	Remote Similarity	NPC41061
0.5852	Remote Similarity	NPC227551
0.5847	Remote Similarity	NPC475208
0.5833	Remote Similarity	NPC324933
0.5828	Remote Similarity	NPC485563
0.5806	Remote Similarity	NPC105800
0.5806	Remote Similarity	NPC100612
0.5769	Remote Similarity	NPC300419
0.5769	Remote Similarity	NPC607904
0.5769	Remote Similarity	NPC610461
0.5758	Remote Similarity	NPC475209
0.5748	Remote Similarity	NPC606145
0.5743	Remote Similarity	NPC124828
0.5738	Remote Similarity	NPC263756
0.5735	Remote Similarity	NPC258617
0.5714	Remote Similarity	NPC302887
0.5703	Remote Similarity	NPC160452
0.5703	Remote Similarity	NPC470477
0.5703	Remote Similarity	NPC69811
0.5693	Remote Similarity	NPC484059
0.5693	Remote Similarity	NPC484060
0.5677	Remote Similarity	NPC113620
0.5672	Remote Similarity	NPC488560
0.5667	Remote Similarity	NPC220838
0.5659	Remote Similarity	NPC609281
0.5652	Remote Similarity	NPC136768
0.5643	Remote Similarity	NPC482011
0.5639	Remote Similarity	NPC123199
0.5634	Remote Similarity	NPC110385
0.5634	Remote Similarity	NPC153673
0.5625	Remote Similarity	NPC301449
0.5625	Remote Similarity	NPC601290
0.5606	Remote Similarity	NPC151543
0.56	Remote Similarity	NPC46665
0.5597	Remote Similarity	NPC475160
0.5597	Remote Similarity	NPC473714
0.559	Remote Similarity	NPC488201
0.5583	Remote Similarity	NPC174336
0.5581	Remote Similarity	NPC241909
0.5574	Remote Similarity	NPC480420
0.557	Remote Similarity	NPC488620
0.5556	Remote Similarity	NPC63159
0.5546	Remote Similarity	NPC238935
0.554	Remote Similarity	NPC202828
0.554	Remote Similarity	NPC119592
0.554	Remote Similarity	NPC481081
0.5538	Remote Similarity	NPC36831
0.5538	Remote Similarity	NPC187290
0.5532	Remote Similarity	NPC484063
0.5532	Remote Similarity	NPC484064
0.553	Remote Similarity	NPC76972
0.553	Remote Similarity	NPC469782
0.553	Remote Similarity	NPC204414
0.5517	Remote Similarity	NPC275225
0.5517	Remote Similarity	NPC480421
0.5512	Remote Similarity	NPC222580
0.55	Remote Similarity	NPC298034
0.55	Remote Similarity	NPC71065
0.5497	Remote Similarity	NPC45606
0.5497	Remote Similarity	NPC475394
0.5489	Remote Similarity	NPC79643
0.5481	Remote Similarity	NPC475140
0.5476	Remote Similarity	NPC232237
0.5476	Remote Similarity	NPC148603
0.5476	Remote Similarity	NPC480475
0.5474	Remote Similarity	NPC476068
0.5474	Remote Similarity	NPC484061
0.5474	Remote Similarity	NPC484062
0.5468	Remote Similarity	NPC293330
0.5468	Remote Similarity	NPC65105
0.5462	Remote Similarity	NPC488209
0.5449	Remote Similarity	NPC187497
0.5448	Remote Similarity	NPC485562
0.5448	Remote Similarity	NPC477464
0.5435	Remote Similarity	NPC265841
0.5435	Remote Similarity	NPC110633
0.5432	Remote Similarity	NPC488204
0.5425	Remote Similarity	NPC475584
0.5425	Remote Similarity	NPC475152
0.5414	Remote Similarity	NPC473824
0.5414	Remote Similarity	NPC268184
0.5407	Remote Similarity	NPC609305
0.5403	Remote Similarity	NPC488561
0.5379	Remote Similarity	NPC470915
0.5379	Remote Similarity	NPC606553
0.5364	Remote Similarity	NPC472268
0.5354	Remote Similarity	NPC2370
0.5349	Remote Similarity	NPC471435
0.5349	Remote Similarity	NPC471434
0.5344	Remote Similarity	NPC488564
0.5338	Remote Similarity	NPC172365
0.5333	Remote Similarity	NPC165204
0.5315	Remote Similarity	NPC142151
0.5315	Remote Similarity	NPC267694
0.531	Remote Similarity	NPC51099
0.5298	Remote Similarity	NPC297950
0.5298	Remote Similarity	NPC40085
0.5294	Remote Similarity	NPC257211
0.528	Remote Similarity	NPC469778
0.5276	Remote Similarity	NPC160415
0.5255	Remote Similarity	NPC100639

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7796
0.1-0.2	1304
0.2-0.3	44
0.3-0.4	6
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