NPASS Compound

Natural Product: NPC515242

Natural Product ID	NPC515242
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,5,7-trihydroxy-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
IUPAC Name	3,5,7-trihydroxy-2-[4-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxyphenyl]chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 51 54 0 0 0 0 0 0 0 0999 V2000 -5.4267 2.4516 -1.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8838 1.2098 -0.5695 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5089 0.2454 -1.4870 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7167 -0.7191 -0.8365 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7089 -0.0214 -0.1671 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3522 -0.1578 -0.3051 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5565 0.6580 0.4794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7906 0.5576 0.3763 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4144 -0.3458 -0.4992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8516 -0.4029 -0.5609 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -1.2229 -1.3562 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9841 -2.1282 -2.2282 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9551 -1.1827 -1.3238 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6133 -1.9474 -2.0655 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5950 -0.3091 -0.4827 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9642 -0.2743 -0.4554 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7147 -1.1091 -1.2652 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5677 0.6181 0.4040 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8341 1.4559 1.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4328 2.3514 2.0790 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4571 1.3920 1.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8123 0.5056 0.3078 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5213 0.4209 0.2318 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6011 -1.1331 -1.2561 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7891 -1.0439 -1.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5741 -1.4779 0.1869 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7648 -2.4555 0.7480 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0332 -0.4545 1.1936 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7400 -0.9908 2.2419 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8535 0.5709 0.4048 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4798 1.4766 1.2228 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9878 2.2507 -2.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6061 3.1773 -1.3347 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1430 2.9124 -0.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9821 1.4817 0.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3658 -1.4668 -1.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 1.3726 1.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4184 1.1953 0.9895 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1390 -3.1053 -2.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9469 -2.0239 -0.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6570 0.6793 0.4582 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2672 2.8697 1.8357 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8568 2.0441 1.7938 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9669 -1.8628 -1.9626 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3899 -1.7056 -1.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4435 -1.8606 -0.3472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4951 -2.2198 1.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1146 0.1058 1.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0946 -1.4037 2.8655 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5636 -0.0404 -0.2115 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3574 1.0626 1.4971 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 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 19 21 1 0 21 22 2 0 22 23 1 0 9 24 1 0 24 25 2 0 4 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 2 1 0 25 6 1 0 23 10 1 0 22 15 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 1 4 36 1 6 7 37 1 0 8 38 1 0 12 39 1 0 17 40 1 0 18 41 1 0 20 42 1 0 21 43 1 0 24 44 1 0 25 45 1 0 26 46 1 6 27 47 1 0 28 48 1 1 29 49 1 0 30 50 1 6 31 51 1 0 M END

Standard InCHIKey	KTZDZZQLJUYTES-PCCJGUQWSA-N
Standard InCHI	InChI=1S/C21H20O10/c1-8-15(24)17(26)19(28)21(29-8)30-11-4-2-9(3-5-11)20-18(27)16(25)14-12(23)6-10(22)7-13(14)31-20/h2-8,15,17,19,21-24,26-28H,1H3/t8-,15-,17+,19-,21-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC=C(C3=C(O)C(=O)C4=C(O)C=C(O)C=C4O3)C=C2)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.11	Volume:	404.357 ? Van der Waals volume.
Dense:	1.069	LogP:	1.418 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.598 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.415 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	170.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.348	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.869	Fsp³:	0.286
MCE-18:	87.63 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.614	Fluc inhibitor:	0.423 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.911 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.887 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.229	Promiscuous compounds:	0.55

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.19	MDCK Permeability:	-5.103
Pgp-inhibitor:	0.005	Pgp-substrate:	0.366
PAMPA:	0.978 ? 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):	0.072
20% Bioavailability (F20%):	0.015	30% Bioavailability (F30%):	0.706
50% Bioavailability (F50%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.358
Plasma Protein Binding (PPB):	93.291%	Volume Distribution (VD):	-0.358
Fu:	3.618% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.976
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.903
BSEP inhibitor:	0.454

ADMET: Metabolism

CYP1A2-inhibitor:	0.088	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.014
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.937 ? 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):

2.73

Half-life (T1/2):

3.949

ADMET: Toxicity

hERG Blockers:	0.059	hERG Blockers (10um):	0.405
Human Hepatotoxicity (H-HT):	0.349	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.811	Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.422	Skin Sensitization:	0.401
Carcinogencity:	0.234	Eye Corrosion:	0.001
Eye Irritation:	0.902	Respiratory Toxicity:	0.215
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.687
Hematotoxicity:	0.057	Drug-induced Nephrotoxicity:	0.215
Genotoxicity:	0.928	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.205	Hek293 Cytotoxicity:	0.502
BCF:	0.953 ? 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:	3.748 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.771 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.321 ? 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
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844943]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16394535]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379417]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4087921]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8991954]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8991954]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20003	Phyllanthus niruri	Species	Phyllanthaceae	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

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

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 NPC515242 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	15210
0.1-0.2	30716
0.2-0.3	2785
0.3-0.4	677
0.4-0.5	322
0.5-0.6	111
0.6-0.7	28
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8267	Intermediate Similarity	NPC187379
0.7176	Intermediate Similarity	NPC287889
0.7162	Intermediate Similarity	NPC108831
0.7162	Intermediate Similarity	NPC182634
0.7105	Intermediate Similarity	NPC21100
0.7051	Intermediate Similarity	NPC136761
0.6711	Remote Similarity	NPC254306
0.6711	Remote Similarity	NPC238376
0.6582	Remote Similarity	NPC219904
0.6579	Remote Similarity	NPC111929
0.6579	Remote Similarity	NPC320283
0.6579	Remote Similarity	NPC41121
0.6515	Remote Similarity	NPC241838
0.65	Remote Similarity	NPC197285
0.6494	Remote Similarity	NPC127546
0.6494	Remote Similarity	NPC57625
0.6494	Remote Similarity	NPC173637
0.6494	Remote Similarity	NPC317489
0.6494	Remote Similarity	NPC223424
0.6494	Remote Similarity	NPC143851
0.6494	Remote Similarity	NPC600591
0.641	Remote Similarity	NPC64305
0.6364	Remote Similarity	NPC135599
0.6364	Remote Similarity	NPC73855
0.6364	Remote Similarity	NPC113968
0.6364	Remote Similarity	NPC328940
0.6364	Remote Similarity	NPC277174
0.6364	Remote Similarity	NPC606877
0.6282	Remote Similarity	NPC476405
0.6203	Remote Similarity	NPC265530
0.6049	Remote Similarity	NPC472459
0.6024	Remote Similarity	NPC223747
0.6	Remote Similarity	NPC323593
0.6	Remote Similarity	NPC203500
0.5867	Remote Similarity	NPC268668
0.5806	Remote Similarity	NPC135358
0.5783	Remote Similarity	NPC285197
0.5714	Remote Similarity	NPC473327
0.5714	Remote Similarity	NPC486578
0.5682	Remote Similarity	NPC173582
0.5682	Remote Similarity	NPC265885
0.5682	Remote Similarity	NPC181465
0.5682	Remote Similarity	NPC215710
0.5682	Remote Similarity	NPC67105
0.5682	Remote Similarity	NPC473438
0.5682	Remote Similarity	NPC253788
0.5647	Remote Similarity	NPC88023
0.5647	Remote Similarity	NPC309025
0.5634	Remote Similarity	NPC54394
0.5634	Remote Similarity	NPC159103
0.5618	Remote Similarity	NPC203259
0.5618	Remote Similarity	NPC33054
0.5618	Remote Similarity	NPC176740
0.5618	Remote Similarity	NPC471725
0.5618	Remote Similarity	NPC134532
0.5618	Remote Similarity	NPC602582
0.561	Remote Similarity	NPC156457
0.561	Remote Similarity	NPC277205
0.561	Remote Similarity	NPC37919
0.5595	Remote Similarity	NPC191306
0.5595	Remote Similarity	NPC60735
0.5595	Remote Similarity	NPC26230
0.5529	Remote Similarity	NPC120099
0.5529	Remote Similarity	NPC609478
0.5517	Remote Similarity	NPC116864
0.5517	Remote Similarity	NPC244776
0.5506	Remote Similarity	NPC39834
0.5506	Remote Similarity	NPC227508
0.55	Remote Similarity	NPC171821
0.5488	Remote Similarity	NPC77672
0.5488	Remote Similarity	NPC133671
0.5488	Remote Similarity	NPC135391
0.5488	Remote Similarity	NPC78263
0.5488	Remote Similarity	NPC250069
0.5426	Remote Similarity	NPC477629
0.5422	Remote Similarity	NPC145038
0.5422	Remote Similarity	NPC56077
0.5422	Remote Similarity	NPC281131
0.5422	Remote Similarity	NPC253662
0.5422	Remote Similarity	NPC179950
0.5422	Remote Similarity	NPC88789
0.5422	Remote Similarity	NPC491374
0.5412	Remote Similarity	NPC307938
0.5412	Remote Similarity	NPC175107
0.5402	Remote Similarity	NPC476215
0.5373	Remote Similarity	NPC116775
0.5373	Remote Similarity	NPC187432
0.5366	Remote Similarity	NPC331652
0.5366	Remote Similarity	NPC160515
0.5357	Remote Similarity	NPC46420
0.5357	Remote Similarity	NPC84265
0.5341	Remote Similarity	NPC95866
0.5341	Remote Similarity	NPC477848
0.5301	Remote Similarity	NPC19388
0.5301	Remote Similarity	NPC240431
0.5301	Remote Similarity	NPC249281
0.5301	Remote Similarity	NPC55786
0.5294	Remote Similarity	NPC138540
0.5281	Remote Similarity	NPC278419
0.5281	Remote Similarity	NPC179198
0.5275	Remote Similarity	NPC605592
0.5263	Remote Similarity	NPC476472
0.5263	Remote Similarity	NPC294815
0.5263	Remote Similarity	NPC16194
0.5263	Remote Similarity	NPC76831
0.5238	Remote Similarity	NPC282987
0.5238	Remote Similarity	NPC609879
0.5233	Remote Similarity	NPC611303
0.5227	Remote Similarity	NPC601586
0.5222	Remote Similarity	NPC609888
0.5217	Remote Similarity	NPC179271
0.5217	Remote Similarity	NPC131745
0.5211	Remote Similarity	NPC219330
0.5176	Remote Similarity	NPC271692
0.5172	Remote Similarity	NPC601710
0.5169	Remote Similarity	NPC4390
0.5165	Remote Similarity	NPC163242
0.5165	Remote Similarity	NPC272068
0.5161	Remote Similarity	NPC153755
0.5139	Remote Similarity	NPC50403
0.5139	Remote Similarity	NPC28274
0.5122	Remote Similarity	NPC288084
0.5119	Remote Similarity	NPC19709
0.5116	Remote Similarity	NPC216496
0.5116	Remote Similarity	NPC325555
0.5116	Remote Similarity	NPC226304
0.5116	Remote Similarity	NPC117260
0.5109	Remote Similarity	NPC155877
0.5106	Remote Similarity	NPC12013
0.5106	Remote Similarity	NPC11432
0.5106	Remote Similarity	NPC477613
0.5104	Remote Similarity	NPC80068
0.5104	Remote Similarity	NPC89127
0.5102	Remote Similarity	NPC244875
0.5072	Remote Similarity	NPC20791
0.5067	Remote Similarity	NPC125062
0.506	Remote Similarity	NPC67037
0.506	Remote Similarity	NPC255615
0.5059	Remote Similarity	NPC158674
0.5057	Remote Similarity	NPC159579
0.5056	Remote Similarity	NPC203050
0.5056	Remote Similarity	NPC225434
0.5055	Remote Similarity	NPC471079
0.5054	Remote Similarity	NPC129264
0.5053	Remote Similarity	NPC122467

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC515242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4253
0.1-0.2	4817
0.2-0.3	64
0.3-0.4	8
0.4-0.5	6
0.5-0.6	2
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
0.5618	Remote Similarity	NPD6797	Phase 2
0.5072	Remote Similarity	NPD1512	Phase 3

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