NPASS Compound

Natural Product: NPC262286

Natural Product ID	NPC262286
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cowaxanthone
IUPAC Name	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,6-trihydroxy-7-methoxyxanthen-9-one
Synonyms	Cowaxanthone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517161
PubChem CID	10386850
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003517] 2-prenylated xanthones

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 56 58 0 0 0 0 0 0 0 0999 V2000 -8.4632 0.9695 -2.6077 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3606 0.8721 -1.1989 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1698 0.6305 -0.5244 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9919 0.4692 -1.1781 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8386 0.2328 -0.4750 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8654 0.1582 0.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0915 0.3276 1.5627 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2423 0.5637 0.8468 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4656 0.7333 1.5218 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7914 -0.0641 1.6279 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6218 -0.2253 1.0614 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5121 -0.1626 -0.3203 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 0.0659 -1.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5505 0.1276 -2.3603 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2594 -0.3318 -0.9131 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2030 -0.2595 -2.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1459 -0.5589 -0.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2600 -0.6238 1.2466 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4844 -0.4581 1.8294 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8999 -0.8573 1.9676 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1841 -0.7098 -0.8052 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2340 -0.3728 0.1983 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1618 -1.2450 0.5534 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1446 -0.7864 1.5638 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5607 -0.8092 1.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8359 0.0463 -0.0780 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6418 1.0944 -0.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8504 1.8880 -1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3153 1.4905 1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2072 -2.5945 -0.0215 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7407 0.3282 -3.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5006 0.6003 -2.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3080 2.0173 -2.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8998 0.5130 -2.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1045 0.2672 2.6574 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1960 0.0507 1.3848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6635 0.4540 -2.7432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5935 -0.5042 2.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9833 -0.5417 2.9124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3705 -1.7257 -1.1803 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2621 -0.0126 -1.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1928 0.6326 0.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8567 0.1882 2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0763 -1.5138 2.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7908 -1.8817 0.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2882 -0.5819 1.8875 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3408 -0.1973 -1.0382 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8923 1.8562 -1.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6303 2.9559 -1.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1204 1.5832 -2.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8408 0.6809 1.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4931 1.8861 1.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0774 2.2796 0.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9758 -3.2216 0.4510 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4590 -2.5778 -1.1124 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2469 -3.1454 0.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 6 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 12 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 3 27 28 1 0 27 29 1 0 23 30 1 0 8 3 1 0 19 11 1 0 13 5 1 0 1 31 1 0 1 32 1 0 1 33 1 0 4 34 1 0 7 35 1 0 9 36 1 0 16 37 1 0 19 38 1 0 20 39 1 0 21 40 1 0 21 41 1 0 22 42 1 0 24 43 1 0 24 44 1 0 25 45 1 0 25 46 1 0 26 47 1 0 28 48 1 0 28 49 1 0 28 50 1 0 29 51 1 0 29 52 1 0 29 53 1 0 30 54 1 0 30 55 1 0 30 56 1 0 M END

Standard InCHIKey	VEGUCVDYIMCIAZ-RIYZIHGNSA-N
Standard InCHI	InChI=1S/C24H26O6/c1-13(2)6-5-7-14(3)8-9-15-17(25)11-21-22(23(15)27)24(28)16-10-20(29-4)18(26)12-19(16)30-21/h6,8,10-12,25-27H,5,7,9H2,1-4H3/b14-8+
SMILES	COc1cc2c(cc1O)oc1c(c2=O)c(O)c(c(c1)O)C/C=C(/CCC=C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	410.17	Volume:	427.004 ? Van der Waals volume.
Dense:	0.961	LogP:	5.934 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.086 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.655 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	19.0
TPSA:	100.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.376	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.945	Fsp³:	0.292
MCE-18:	21.0 ? 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:	0.879	Fluc inhibitor:	0.596 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.987 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.755 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.188	Promiscuous compounds:	0.099

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044	MDCK Permeability:	-4.666
Pgp-inhibitor:	0.995	Pgp-substrate:	0.022
PAMPA:	0.005 ? 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):	0.014
20% Bioavailability (F20%):	0.169	30% Bioavailability (F30%):	0.691
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.864
Plasma Protein Binding (PPB):	96.815%	Volume Distribution (VD):	-0.01
Fu:	3.126% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.892
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.009	CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.687	CYP2C19-substrate:	0.231
CYP2C9-inhibitor:	0.61	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.891	CYP2D6-substrate:	0.727
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.881
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.948 ? 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):

1.922

Half-life (T1/2):

1.502

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.56
Human Hepatotoxicity (H-HT):	0.649	Drug-induced Liver Injury (DILI):	0.872
AMES Toxicity:	0.327	Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.699	Skin Sensitization:	0.934
Carcinogencity:	0.622	Eye Corrosion:	0.013
Eye Irritation:	0.971	Respiratory Toxicity:	0.956
Drug-induced Neurotoxicity:	0.051	Ototoxicity:	0.207
Hematotoxicity:	0.181	Drug-induced Nephrotoxicity:	0.136
Genotoxicity:	0.886	RPMI-8226 Immunitoxicity:	0.141
A549 Cytotoxicity:	0.472	Hek293 Cytotoxicity:	0.631
BCF:	2.061 ? 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:	5.028 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.377 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.929 ? 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
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608849]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	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	5
IC50	4
Activity	4
MIC	6

Activity Type	# Activity
Cell line	5
Organism	7
Others	6
Protein family	1

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[12608849]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[12608849]
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	15750.0	nM	PMID[30684866]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.5	ug.mL-1	PMID[19299148]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	64.0	ug.mL-1	PMID[25651042]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[25651042]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[25651042]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT2	Others	Unspecified	n.a.	Inhibition	=	0.0	%	PMID[12608849]
NPT2	Others	Unspecified	n.a.	Inhibition	=	40.6	%	PMID[12608849]
NPT2	Others	Unspecified	n.a.	Inhibition	=	76.6	%	PMID[12608849]
NPT2	Others	Unspecified	n.a.	Inhibition	=	97.5	%	PMID[12608849]
NPT2	Others	Unspecified	n.a.	IC50	=	398.0	molar ratio	PMID[12608849]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	64.0	ug.mL-1	PMID[25651042]
NPT2	Others	Unspecified	n.a.	Inhibition	>	100.0	%	PMID[25651042]
NPT28736	Protein family	Alpha-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	44000.0	nM	PMID[30282319]

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 NPC262286 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	19591
0.1-0.2	26390
0.2-0.3	3384
0.3-0.4	412
0.4-0.5	52
0.5-0.6	20
0.6-0.7	5
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	Natural Product ID
0.726	Intermediate Similarity	NPC40491
0.726	Intermediate Similarity	NPC278052
0.6795	Remote Similarity	NPC7483
0.6795	Remote Similarity	NPC74766
0.6486	Remote Similarity	NPC227337
0.6301	Remote Similarity	NPC68093
0.6267	Remote Similarity	NPC236796
0.5974	Remote Similarity	NPC320359
0.589	Remote Similarity	NPC228785
0.5854	Remote Similarity	NPC488441
0.5753	Remote Similarity	NPC488548
0.5679	Remote Similarity	NPC133392
0.5679	Remote Similarity	NPC472448
0.5676	Remote Similarity	NPC602307
0.557	Remote Similarity	NPC61010
0.5542	Remote Similarity	NPC479155
0.55	Remote Similarity	NPC300727
0.5443	Remote Similarity	NPC25152
0.5342	Remote Similarity	NPC186397
0.525	Remote Similarity	NPC37684
0.525	Remote Similarity	NPC212932
0.5185	Remote Similarity	NPC310349
0.5128	Remote Similarity	NPC217677
0.5114	Remote Similarity	NPC39091
0.5063	Remote Similarity	NPC236132
0.5059	Remote Similarity	NPC206153
0.5059	Remote Similarity	NPC271629

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC262286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3729
0.1-0.2	5359
0.2-0.3	61
0.3-0.4	1
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