NPASS Compound

Natural Product: NPC305981

Natural Product ID	NPC305981
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Glucopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Alpha-L-Arabinopyranosyl]Olean-12-Ene-28-O-[Alpha-L-Rhamnopyranosyl(1->4)-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl]Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-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
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501032
PubChem CID	21603407
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 2D 201211 0 0 0 0 0 0 0 0999 V2000 12.4472 -7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6972 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 -3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0586 -2.1469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5586 -2.1469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 -9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0105 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -10.5705 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12 1 1 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 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 6 24 29 1 1 24 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 1 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 38 40 1 0 37 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 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 53 69 1 0 46 70 1 0 45 71 1 0 17 72 1 0 17 73 1 0 10 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 75 78 1 0 74 79 1 0 5 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 86 87 1 0 86 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 89 92 1 0 88 93 1 0 81 94 1 0 80 95 1 0 82 3 1 0 90 84 1 0 76 8 1 0 27 14 1 0 38 32 1 0 47 42 1 0 55 49 1 0 65 58 1 0 19 14 1 0 25 20 1 0 33 23 1 0 1 96 1 0 2 97 1 0 2 98 1 0 3 99 1 6 5100 1 6 7101 1 0 7102 1 0 8103 1 6 10104 1 6 15105 1 0 15106 1 0 16107 1 0 16108 1 0 18109 1 0 18110 1 0 19111 1 1 21112 1 0 22113 1 0 22114 1 0 23115 1 6 26116 1 0 26117 1 0 27118 1 0 27119 1 0 28120 1 0 28121 1 0 28122 1 0 29123 1 0 29124 1 0 29125 1 0 30126 1 0 30127 1 0 31128 1 0 31129 1 0 32130 1 6 34131 1 0 34132 1 0 34133 1 0 35134 1 0 35135 1 0 36136 1 0 36137 1 0 37138 1 6 39139 1 0 39140 1 0 39141 1 0 40142 1 0 40143 1 0 40144 1 0 42145 1 1 44146 1 0 44147 1 0 45148 1 1 46149 1 1 47150 1 6 49151 1 1 51152 1 6 52153 1 0 52154 1 0 52155 1 0 53156 1 1 54157 1 6 55158 1 6 56159 1 0 58160 1 6 60161 1 6 61162 1 0 61163 1 0 62164 1 0 63165 1 1 64166 1 6 65167 1 1 66168 1 0 67169 1 0 68170 1 0 69171 1 0 70172 1 0 71173 1 0 72174 1 0 72175 1 0 72176 1 0 73177 1 0 73178 1 0 73179 1 0 74180 1 1 75181 1 6 76182 1 1 77183 1 0 78184 1 0 79185 1 0 80186 1 1 81187 1 6 82188 1 1 84189 1 1 86190 1 6 87191 1 0 87192 1 0 87193 1 0 88194 1 1 89195 1 6 90196 1 6 91197 1 0 92198 1 0 93199 1 0 94200 1 0 95201 1 0 M END

Standard InCHIKey	AGNAAINECZAUIZ-TZKIKZJCSA-N
Standard InCHI	InChI=1S/C65H106O30/c1-25-36(69)41(74)45(78)54(86-25)92-50-31(22-67)89-53(48(81)44(50)77)85-24-32-40(73)43(76)47(80)56(90-32)95-59(83)65-18-16-60(3,4)20-28(65)27-10-11-34-62(7)14-13-35(61(5,6)33(62)12-15-64(34,9)63(27,8)17-19-65)91-58-52(38(71)29(68)23-84-58)94-57-49(82)51(37(70)26(2)87-57)93-55-46(79)42(75)39(72)30(21-66)88-55/h10,25-26,28-58,66-82H,11-24H2,1-9H3/t25-,26-,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	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CCC(C[C@H]4C4=CC[C@H]5[C@@]([C@@]4(CC3)C)(C)CC[C@@H]3[C@]5(C)CC[C@@H](C3(C)C)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)O)O)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1366.68	Volume:	1297.108 ? Van der Waals volume.
Dense:	1.054	LogP:	0.527 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.328 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.504 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	63.0
TPSA:	471.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	30.0
H-Bond Donor:	17.0	Rings:	11.0
Heavy Atoms:	30.0

MedChem Properties

QED Drug-Likeness Score:	0.043	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.669	Fsp³:	0.954
MCE-18:	239.717 ? 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:	0.761	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.385	Promiscuous compounds:	0.071

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.101	MDCK Permeability:	-4.92
Pgp-inhibitor:	0.0	Pgp-substrate:	0.777
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%):	0.945	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.001
Plasma Protein Binding (PPB):	60.489%	Volume Distribution (VD):	-0.283
Fu:	19.036% ? 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:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.192
HLM stability:	0.009 ? 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):

-1.363

Half-life (T1/2):

5.001

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.734	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.993	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.003	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.78	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.311	RPMI-8226 Immunitoxicity:	0.574
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.323
BCF:	1.47 ? 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:	3.634 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.124 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.23 ? 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
NPO33015	trevesia palmata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757708]

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	2

Activity Type	# Activity
Cell line	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
NPT71	Cell line	HEK293	Homo sapiens	IC50	=	520.0	nM	PMID[25682561]
NPT3470	Cell line	WEHI-164	Mus musculus	IC50	=	1800.0	nM	PMID[25682561]

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 NPC305981 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	25715
0.1-0.2	20340
0.2-0.3	2502
0.3-0.4	667
0.4-0.5	372
0.5-0.6	75
0.6-0.7	58
0.7-0.8	0
0.8-0.85	12
0.85-0.9	9
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC261506
0.9909	High Similarity	NPC4328
0.9817	High Similarity	NPC41061
0.9817	High Similarity	NPC227551
0.9464	High Similarity	NPC236638
0.9464	High Similarity	NPC294453
0.9266	High Similarity	NPC135904
0.9211	High Similarity	NPC298034
0.9211	High Similarity	NPC71065
0.9204	High Similarity	NPC43550
0.9138	High Similarity	NPC250247
0.9083	High Similarity	NPC79643
0.8991	High Similarity	NPC60557
0.8991	High Similarity	NPC67857
0.8793	High Similarity	NPC202828
0.8793	High Similarity	NPC119592
0.875	High Similarity	NPC123199
0.8684	High Similarity	NPC481080
0.8649	High Similarity	NPC475287
0.8571	High Similarity	NPC220160
0.8547	High Similarity	NPC65105
0.8376	Intermediate Similarity	NPC110633
0.8319	Intermediate Similarity	NPC76972
0.8319	Intermediate Similarity	NPC469782
0.8319	Intermediate Similarity	NPC204414
0.8214	Intermediate Similarity	NPC481078
0.819	Intermediate Similarity	NPC475160
0.819	Intermediate Similarity	NPC473714
0.8167	Intermediate Similarity	NPC481081
0.8165	Intermediate Similarity	NPC63159
0.8136	Intermediate Similarity	NPC476068
0.8083	Intermediate Similarity	NPC293330
0.8017	Intermediate Similarity	NPC136768
0.7966	Intermediate Similarity	NPC488560
0.7965	Intermediate Similarity	NPC295823
0.7965	Intermediate Similarity	NPC174720
0.7965	Intermediate Similarity	NPC475467
0.789	Intermediate Similarity	NPC112352
0.7863	Intermediate Similarity	NPC165204
0.7851	Intermediate Similarity	NPC258617
0.7714	Intermediate Similarity	NPC469778
0.7681	Intermediate Similarity	NPC469776
0.7643	Intermediate Similarity	NPC32723
0.7589	Intermediate Similarity	NPC481323
0.7583	Intermediate Similarity	NPC100639
0.7483	Intermediate Similarity	NPC135334
0.7466	Intermediate Similarity	NPC295941
0.7431	Intermediate Similarity	NPC481324
0.7398	Intermediate Similarity	NPC57484
0.7355	Intermediate Similarity	NPC155410
0.735	Intermediate Similarity	NPC241909
0.7304	Intermediate Similarity	NPC475504
0.7222	Intermediate Similarity	NPC161717
0.7183	Intermediate Similarity	NPC469775
0.7182	Intermediate Similarity	NPC48499
0.7153	Intermediate Similarity	NPC469774
0.7143	Intermediate Similarity	NPC469777
0.7132	Intermediate Similarity	NPC224381
0.7119	Intermediate Similarity	NPC481079
0.7069	Intermediate Similarity	NPC148417
0.7054	Intermediate Similarity	NPC70809
0.7049	Intermediate Similarity	NPC192600
0.7043	Intermediate Similarity	NPC104071
0.7008	Intermediate Similarity	NPC475514
0.7007	Intermediate Similarity	NPC100925
0.7	Intermediate Similarity	NPC469772
0.6983	Remote Similarity	NPC102439
0.6983	Remote Similarity	NPC46665
0.6908	Remote Similarity	NPC469773
0.68	Remote Similarity	NPC251263
0.6746	Remote Similarity	NPC470218
0.6724	Remote Similarity	NPC469946
0.6667	Remote Similarity	NPC219180
0.6667	Remote Similarity	NPC480422
0.661	Remote Similarity	NPC160415
0.6555	Remote Similarity	NPC480475
0.6525	Remote Similarity	NPC223301
0.6525	Remote Similarity	NPC171544
0.6496	Remote Similarity	NPC295371
0.6475	Remote Similarity	NPC104372
0.6466	Remote Similarity	NPC475516
0.6446	Remote Similarity	NPC297263
0.6434	Remote Similarity	NPC54636
0.6417	Remote Similarity	NPC473459
0.6406	Remote Similarity	NPC475209
0.6341	Remote Similarity	NPC114484
0.6328	Remote Similarity	NPC133818
0.6325	Remote Similarity	NPC235405
0.632	Remote Similarity	NPC31838
0.632	Remote Similarity	NPC187290
0.6311	Remote Similarity	NPC222580
0.629	Remote Similarity	NPC301449
0.629	Remote Similarity	NPC601290
0.6288	Remote Similarity	NPC286457
0.6281	Remote Similarity	NPC10607
0.6281	Remote Similarity	NPC251768
0.6271	Remote Similarity	NPC249848
0.6271	Remote Similarity	NPC107966
0.624	Remote Similarity	NPC80986
0.623	Remote Similarity	NPC475591
0.623	Remote Similarity	NPC236870
0.623	Remote Similarity	NPC235438
0.6207	Remote Similarity	NPC29069
0.6198	Remote Similarity	NPC30735
0.616	Remote Similarity	NPC324875
0.616	Remote Similarity	NPC292677
0.6159	Remote Similarity	NPC102505
0.6159	Remote Similarity	NPC488514
0.6148	Remote Similarity	NPC164389
0.6138	Remote Similarity	NPC472268
0.6116	Remote Similarity	NPC192791
0.6107	Remote Similarity	NPC471550
0.6107	Remote Similarity	NPC191827
0.6103	Remote Similarity	NPC302543
0.609	Remote Similarity	NPC21691
0.6074	Remote Similarity	NPC471385
0.6069	Remote Similarity	NPC297950
0.6045	Remote Similarity	NPC13998
0.6033	Remote Similarity	NPC161674
0.6016	Remote Similarity	NPC159309
0.6016	Remote Similarity	NPC86222
0.6015	Remote Similarity	NPC85154
0.6	Remote Similarity	NPC150400
0.6	Remote Similarity	NPC470876
0.5985	Remote Similarity	NPC309223
0.5984	Remote Similarity	NPC480473
0.5984	Remote Similarity	NPC480474
0.5983	Remote Similarity	NPC214484
0.595	Remote Similarity	NPC39211
0.5938	Remote Similarity	NPC104137
0.5938	Remote Similarity	NPC475486
0.5938	Remote Similarity	NPC26626
0.5935	Remote Similarity	NPC309714
0.5915	Remote Similarity	NPC33012
0.5909	Remote Similarity	NPC166422
0.5887	Remote Similarity	NPC101744
0.5887	Remote Similarity	NPC173859
0.5887	Remote Similarity	NPC148603
0.5878	Remote Similarity	NPC123522
0.5868	Remote Similarity	NPC473373
0.5862	Remote Similarity	NPC489208
0.5847	Remote Similarity	NPC90856
0.5845	Remote Similarity	NPC8524
0.5844	Remote Similarity	NPC472269
0.584	Remote Similarity	NPC68175
0.5833	Remote Similarity	NPC470911
0.5827	Remote Similarity	NPC281148
0.5809	Remote Similarity	NPC473452
0.5809	Remote Similarity	NPC480418
0.5794	Remote Similarity	NPC609763
0.5793	Remote Similarity	NPC475368
0.5789	Remote Similarity	NPC480419
0.5778	Remote Similarity	NPC4749
0.5772	Remote Similarity	NPC263756
0.5772	Remote Similarity	NPC213674
0.5769	Remote Similarity	NPC75287
0.5746	Remote Similarity	NPC283417
0.5746	Remote Similarity	NPC200049
0.5714	Remote Similarity	NPC471384
0.5704	Remote Similarity	NPC480417
0.5703	Remote Similarity	NPC276093
0.5694	Remote Similarity	NPC477464
0.5692	Remote Similarity	NPC36831
0.5664	Remote Similarity	NPC489209
0.5645	Remote Similarity	NPC76497
0.5635	Remote Similarity	NPC40775
0.5635	Remote Similarity	NPC488526
0.5629	Remote Similarity	NPC45606
0.5625	Remote Similarity	NPC134835
0.5593	Remote Similarity	NPC128925
0.5573	Remote Similarity	NPC473826
0.5565	Remote Similarity	NPC470512
0.5565	Remote Similarity	NPC157868
0.5564	Remote Similarity	NPC268184
0.5556	Remote Similarity	NPC309907
0.5547	Remote Similarity	NPC481082
0.5547	Remote Similarity	NPC164419
0.553	Remote Similarity	NPC470915
0.552	Remote Similarity	NPC473343
0.5496	Remote Similarity	NPC96641
0.5496	Remote Similarity	NPC163183
0.549	Remote Similarity	NPC220838
0.5484	Remote Similarity	NPC173583
0.5481	Remote Similarity	NPC475899
0.5481	Remote Similarity	NPC323341
0.5478	Remote Similarity	NPC23020
0.5474	Remote Similarity	NPC47995
0.5462	Remote Similarity	NPC73318
0.5449	Remote Similarity	NPC478559
0.5449	Remote Similarity	NPC478560
0.5431	Remote Similarity	NPC237503
0.5426	Remote Similarity	NPC257468
0.5391	Remote Similarity	NPC167383
0.5385	Remote Similarity	NPC469821
0.5379	Remote Similarity	NPC187618
0.5379	Remote Similarity	NPC69811
0.536	Remote Similarity	NPC58448
0.536	Remote Similarity	NPC127056
0.5352	Remote Similarity	NPC135849

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7882
0.1-0.2	1211
0.2-0.3	50
0.3-0.4	7
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