NPASS Compound

Natural Product: NPC86800

Natural Product ID	NPC86800
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JBCGOQGAFRZPEK-NTFYZVRUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1829527
PubChem CID	56640967
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 76 80 0 0 0 0 0 0 0 0999 V2000 -3.2502 0.5567 4.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0256 1.2158 3.0961 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1127 2.4526 2.9414 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7088 0.4493 1.9998 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4699 0.9004 0.7160 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5793 0.3943 -0.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5638 -1.1396 -0.0636 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4883 -1.6513 -1.1178 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2089 -1.7019 -0.0052 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0036 -3.0019 -0.7509 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9283 -3.5863 0.1872 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2877 -2.7229 0.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2073 -1.4597 -0.5802 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1197 -0.7730 -0.5804 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4829 -0.5315 -2.0564 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1117 0.5597 0.1406 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8148 1.5550 -0.8266 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2183 2.4645 -0.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9390 2.3930 0.2866 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4673 3.4663 -1.7838 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4489 4.4042 -1.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2903 5.1144 -2.9731 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2535 4.6281 -3.6429 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2490 3.6414 -2.9436 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2705 -0.6275 -0.1512 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3856 -0.3522 -0.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4294 -0.8841 -2.0730 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4705 0.5091 -0.4631 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5285 0.7713 -1.1967 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6386 1.6134 -0.8019 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6977 1.8160 -1.6571 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7796 2.6219 -1.3036 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7674 3.2187 -0.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7278 3.0386 0.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6613 2.2239 0.4220 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6595 -3.2825 1.5088 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8129 -4.1702 1.7479 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6477 -3.5272 2.6367 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8900 -1.9557 1.3434 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2322 -1.3588 1.1737 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6572 1.2526 5.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9691 -0.2708 4.3067 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3045 0.1008 4.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5833 2.0240 0.7305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5601 0.7519 -1.1902 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5332 0.8013 0.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5058 -1.9452 -0.7148 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1549 -2.5119 -1.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7569 -0.8546 -1.8749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5737 -2.8715 -1.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8389 -3.6956 -0.6926 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7672 -4.6447 0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1456 -3.3347 -0.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5800 -2.4093 1.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5109 -1.7862 -1.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7055 -0.9886 -2.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4602 0.5431 -2.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4162 -1.0101 -2.3431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3491 0.6412 0.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2308 4.6173 -1.0860 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8685 5.9465 -3.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1074 3.0600 -3.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3763 0.9337 0.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5545 0.3014 -2.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7230 1.3541 -2.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6163 2.7913 -1.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6131 3.8523 0.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7468 3.5227 1.7814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8718 2.1117 1.1389 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6883 -4.0485 1.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0958 -4.1107 2.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4560 -5.2323 1.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3238 -2.5587 3.0933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1959 -4.1396 2.2801 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1158 -4.1044 3.4711 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2199 -1.3712 1.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 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 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 13 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 11 36 1 0 36 37 1 0 36 38 1 0 36 39 1 0 7 40 1 1 16 5 1 0 24 20 2 0 35 30 1 0 14 9 1 0 9 39 1 1 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 1 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 11 52 1 6 12 53 1 0 12 54 1 0 13 55 1 6 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 1 21 60 1 0 22 61 1 0 24 62 1 0 28 63 1 0 29 64 1 0 31 65 1 0 32 66 1 0 33 67 1 0 34 68 1 0 35 69 1 0 37 70 1 0 37 71 1 0 37 72 1 0 38 73 1 0 38 74 1 0 38 75 1 0 40 76 1 0 M END

Standard InCHIKey	JBCGOQGAFRZPEK-NTFYZVRUSA-N
Standard InCHI	InChI=1S/C31H36O9/c1-19(32)37-23-17-29(4,35)31-16-22(28(2,3)40-31)15-24(38-25(33)12-11-20-9-7-6-8-10-20)30(31,5)26(23)39-27(34)21-13-14-36-18-21/h6-14,18,22-24,26,35H,15-17H2,1-5H3/b12-11+/t22-,23-,24+,26+,29+,30-,31+/m1/s1
SMILES	CC(=O)O[C@@H]1C[C@@](C)([C@@]23C[C@@H](C[C@@H]([C@]2(C)[C@H]1OC(=O)c1ccoc1)OC(=O)/C=C/c1ccccc1)C(C)(C)O3)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.24	Volume:	557.334 ? Van der Waals volume.
Dense:	0.991	LogP:	4.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.685 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.563 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	121.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.314	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.924	Fsp³:	0.516
MCE-18:	160.851 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.777	Fluc inhibitor:	0.698 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.258 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.36	MDCK Permeability:	-4.812
Pgp-inhibitor:	0.996	Pgp-substrate:	0.127
PAMPA:	0.518 ? 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):	0.001
20% Bioavailability (F20%):	0.919	30% Bioavailability (F30%):	0.96
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148	MRP1:	0.854
Plasma Protein Binding (PPB):	85.25%	Volume Distribution (VD):	0.017
Fu:	15.844% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.841	BCRP inhibitor:	0.027
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.996
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.602 ? 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):

6.119

Half-life (T1/2):

0.907

ADMET: Toxicity

hERG Blockers:	0.228	hERG Blockers (10um):	0.521
Human Hepatotoxicity (H-HT):	0.35	Drug-induced Liver Injury (DILI):	0.859
AMES Toxicity:	0.491	Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.931	Skin Sensitization:	0.973
Carcinogencity:	0.705	Eye Corrosion:	0.0
Eye Irritation:	0.347	Respiratory Toxicity:	0.328
Drug-induced Neurotoxicity:	0.384	Ototoxicity:	0.263
Hematotoxicity:	0.055	Drug-induced Nephrotoxicity:	0.524
Genotoxicity:	0.6	RPMI-8226 Immunitoxicity:	0.104
A549 Cytotoxicity:	0.239	Hek293 Cytotoxicity:	0.468
BCF:	1.014 ? 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:	3.945 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.529 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.084 ? 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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	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
Inhibition	1
Ki	1
Imax	1
Ratio IC50	6
Activity	2

Activity Type	# Activity
Cell line	2
Individual protein	9

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	70.0	%	PMID[25621853]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	570.0	nM	DrugMatrix in vivo data: Hematology
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[21856049]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	1.59	n.a.	PMID[9651160]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	7.77	n.a.	PMID[9651160]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	16.57	n.a.	PMID[21612217]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.89	n.a.	PMID[12762787]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	19.9	n.a.	PMID[25211032]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	83.66	n.a.	PMID[18672316]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	85.95	%	PMID[4851320]
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	100.1	%	PubChem BioAssay data set

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 NPC86800 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	9982
0.1-0.2	36384
0.2-0.3	3063
0.3-0.4	309
0.4-0.5	89
0.5-0.6	20
0.6-0.7	4
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
0.8077	Intermediate Similarity	NPC483878
0.7647	Intermediate Similarity	NPC483873
0.6452	Remote Similarity	NPC483891
0.6322	Remote Similarity	NPC25768
0.625	Remote Similarity	NPC483879
0.6145	Remote Similarity	NPC473889
0.5824	Remote Similarity	NPC483874
0.5714	Remote Similarity	NPC469349
0.5682	Remote Similarity	NPC36021
0.56	Remote Similarity	NPC483880
0.56	Remote Similarity	NPC156941
0.5476	Remote Similarity	NPC37641
0.5476	Remote Similarity	NPC481070
0.5393	Remote Similarity	NPC214550
0.5294	Remote Similarity	NPC114927
0.5248	Remote Similarity	NPC294579
0.5248	Remote Similarity	NPC144779
0.5217	Remote Similarity	NPC488912
0.5217	Remote Similarity	NPC488910
0.5196	Remote Similarity	NPC6981
0.5161	Remote Similarity	NPC472571
0.5158	Remote Similarity	NPC56953
0.5149	Remote Similarity	NPC471980
0.51	Remote Similarity	NPC96801
0.51	Remote Similarity	NPC150698
0.5051	Remote Similarity	NPC294512

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC86800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3067
0.1-0.2	5959
0.2-0.3	124
0.3-0.4	0
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