NPASS Compound

Natural Product: NPC239019

Natural Product ID	NPC239019
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tannin Analogue
IUPAC Name	[(2R,3R,4S,5R,6R)-6-hydroxy-3,4,5-tris[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500292
PubChem CID	13888120
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins

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 84 88 0 0 0 0 0 0 0 0999 V2000 0.8013 -3.8562 0.1811 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8080 -2.4906 -0.0711 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8642 -1.9372 0.6105 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0537 -0.5811 0.3287 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2993 -0.1006 0.9853 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3951 -0.8206 0.5131 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8244 -0.8905 -0.7918 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1904 -0.2582 -1.6552 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0025 -1.7014 -1.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6738 -2.3853 -0.1182 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7820 -3.1562 -0.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4373 -3.8340 0.6464 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2643 -3.2689 -1.6608 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5932 -2.5829 -2.6617 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4831 -1.8129 -2.3937 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0428 -2.6683 -3.9654 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3908 -4.0472 -1.9489 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8073 0.1249 0.8797 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3241 -0.3437 -0.0180 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4896 -1.8293 0.3276 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6114 -2.3876 -0.2563 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6352 -2.8985 0.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4693 -2.8168 1.7886 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8373 -3.4971 -0.0364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0544 -3.6067 -1.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2058 -4.1791 -1.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3982 -4.2765 -3.2622 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1651 -4.6542 -1.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9782 -4.5595 0.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8066 -3.9772 0.8123 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9676 -5.0495 1.1558 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3430 -5.2396 -1.5403 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4949 0.3786 0.1247 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0321 1.0228 -0.9800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4085 0.9096 -2.0714 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2648 1.8026 -0.9015 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7647 2.4272 -2.0207 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9322 3.1698 -1.9631 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4529 3.8033 -3.0654 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6310 3.3041 -0.7713 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1376 2.6839 0.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9575 1.9362 0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7822 2.7706 1.5856 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7987 4.0372 -0.6784 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9504 1.5010 0.9285 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8929 2.2766 2.0700 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6946 1.6890 3.1561 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0490 3.7224 2.0753 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9691 4.3749 3.2879 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1012 5.7233 3.4012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0180 6.3570 4.6239 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3227 6.4549 2.2573 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4049 5.8058 1.0286 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2712 4.4400 0.9125 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6289 6.5793 -0.1002 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4566 7.8255 2.3749 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 -4.3125 -0.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9639 -2.3269 -1.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0473 -0.4804 -0.7623 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2146 -0.2909 2.0778 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4030 0.9998 0.8558 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3085 -2.3085 0.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2899 -3.4021 1.0051 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9581 -1.2776 -3.1693 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5510 -1.8657 -4.3262 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6448 -4.8009 -1.3499 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6321 -0.3488 1.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0789 -0.3274 -1.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5183 -1.8463 1.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3208 -3.2437 -2.0965 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3091 -4.4608 -3.6622 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7189 -3.9323 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7825 -5.0722 2.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1369 -5.3354 -0.9190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2147 2.3199 -2.9531 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5443 4.8168 -3.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5594 1.4429 1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7932 2.9014 1.5762 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2577 4.4690 -1.4653 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7930 3.8204 4.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9931 5.8950 5.5084 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3293 3.9112 -0.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1990 7.4051 -0.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7569 8.2378 3.2489 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 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 11 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 13 17 1 0 4 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 26 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 28 32 1 0 19 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 38 40 2 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 18 45 1 0 45 46 1 0 46 47 2 0 46 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 50 52 2 0 52 53 1 0 53 54 2 0 53 55 1 0 52 56 1 0 20 2 1 0 30 24 1 0 42 36 1 0 54 48 1 0 15 9 1 0 1 57 1 0 2 58 1 6 4 59 1 6 5 60 1 0 5 61 1 0 10 62 1 0 12 63 1 0 15 64 1 0 16 65 1 0 17 66 1 0 18 67 1 1 19 68 1 6 20 69 1 1 25 70 1 0 27 71 1 0 30 72 1 0 31 73 1 0 32 74 1 0 37 75 1 0 39 76 1 0 42 77 1 0 43 78 1 0 44 79 1 0 49 80 1 0 51 81 1 0 54 82 1 0 55 83 1 0 56 84 1 0 M END

Standard InCHIKey	RJINLRBSXMOGAQ-UEKZKNBCSA-N
Standard InCHI	InChI=1S/C34H28O22/c35-14-1-10(2-15(36)23(14)43)30(47)52-9-22-27(54-31(48)11-3-16(37)24(44)17(38)4-11)28(55-32(49)12-5-18(39)25(45)19(40)6-12)29(34(51)53-22)56-33(50)13-7-20(41)26(46)21(42)8-13/h1-8,22,27-29,34-46,51H,9H2/t22-,27-,28+,29-,34-/m1/s1
SMILES	O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	788.11	Volume:	705.039 ? Van der Waals volume.
Dense:	1.118	LogP:	0.583 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.393 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.49 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	34.0
TPSA:	377.42 ? Topological Polar Surface Area.	H-Bond Acceptor:	22.0
H-Bond Donor:	13.0	Rings:	5.0
Heavy Atoms:	22.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.515	Fsp³:	0.176
MCE-18:	130.0 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.967	Fluc inhibitor:	0.129 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.237 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.649 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.65	Promiscuous compounds:	0.99

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.517	MDCK Permeability:	-4.677
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
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):	0.0
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	69.753%	Volume Distribution (VD):	-0.215
Fu:	18.699% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.994
BSEP inhibitor:	0.032

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.027 ? 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):

7.342

Half-life (T1/2):

3.462

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.995
Human Hepatotoxicity (H-HT):	0.013	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.643	Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.893	Skin Sensitization:	1.0
Carcinogencity:	0.056	Eye Corrosion:	0.0
Eye Irritation:	0.989	Respiratory Toxicity:	0.027
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.195
BCF:	0.337 ? 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:	3.332 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.214 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.156 ? 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
NPO33051	mango tree	n.a.	n.a.	n.a.	stem bark	n.a.	n.a.	PMID[24613627]

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	5
Phorbol displacement	1
Inhibition	2
ED50	5
Activity	1

Activity Type	# Activity
Individual protein	2
Cell line	6
Protein family	2
Single protein	2
Non-molecular	1
Organism	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3084	Individual protein	Neuraminidase	Influenza A virus	Inhibition	=	81.7	%	DrugMatrix in vivo data: Pathology
NPT3084	Individual protein	Neuraminidase	Influenza A virus	IC50	=	9200.0	nM	PMID[17980607]
NPT316	Protein family	Protein kinase C (PKC)	Homo sapiens	IC50	=	82000.0	nM	PMID[10998351]
NPT727	Protein family	Protein kinase C, PKC; classical/novel	Homo sapiens	Phorbol displacement	<=	50.0	uM	DOI[10.1016/S0960-894X(01)81072-6]
NPT24971	Single protein	Genome polyprotein	Coxsackievirus B3 (strain Nancy)	Inhibition	=	100.0	%	PMID[24613627]
NPT24971	Single protein	Genome polyprotein	Coxsackievirus B3 (strain Nancy)	IC50	=	2000.0	nM	PMID[24613627]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT672	Cell line	TE-671	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[24809953]
NPT180	Cell line	HCT-8	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[19902967]
NPT81	Cell line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[26003344]
NPT91	Cell line	KB	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[19245261]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	151400.0	nM	Open TG-GATES in vivo data: Biochemistry
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	240500.0	nM	PMID[18195064]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	10.0	ug ml-1	PMID[1431932]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	-5.2	mmHg	PMID[25630222]

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 NPC239019 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	21036
0.1-0.2	27611
0.2-0.3	1013
0.3-0.4	118
0.4-0.5	49
0.5-0.6	22
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
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	NPC247629
0.7925	Intermediate Similarity	NPC175793
0.7925	Intermediate Similarity	NPC159913
0.6981	Remote Similarity	NPC31034
0.6531	Remote Similarity	NPC610546
0.5926	Remote Similarity	NPC482667
0.5818	Remote Similarity	NPC114791
0.5818	Remote Similarity	NPC104222
0.5818	Remote Similarity	NPC210501
0.5818	Remote Similarity	NPC318826
0.5818	Remote Similarity	NPC141331
0.5517	Remote Similarity	NPC283806
0.5517	Remote Similarity	NPC238419
0.5493	Remote Similarity	NPC237202
0.5484	Remote Similarity	NPC488888
0.5472	Remote Similarity	NPC226738
0.5455	Remote Similarity	NPC229036
0.5455	Remote Similarity	NPC603485
0.5385	Remote Similarity	NPC269046
0.5357	Remote Similarity	NPC142528
0.5345	Remote Similarity	NPC205037
0.5345	Remote Similarity	NPC3746
0.5263	Remote Similarity	NPC44260
0.5263	Remote Similarity	NPC120621
0.525	Remote Similarity	NPC483711
0.5091	Remote Similarity	NPC225036
0.5088	Remote Similarity	NPC75945

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC239019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5307
0.1-0.2	3811
0.2-0.3	29
0.3-0.4	2
0.4-0.5	1
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