NPASS Compound

Natural Product: NPC482301

Natural Product ID	NPC482301
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PQNNHWCHNOPKGC-PSLQACODSA-N
IUPAC Name	n.a.
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 84 86 0 0 0 0 0 0 0 0999 V2000 3.4050 0.3639 -3.5657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8330 -0.2366 -2.2430 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2958 0.7543 -1.2243 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9810 0.4760 -0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3964 1.5650 0.8206 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5981 2.2296 0.1190 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9717 0.9109 2.0498 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3693 2.5759 1.0612 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4460 3.5861 0.3183 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2723 2.5446 2.0634 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2316 1.5280 1.6408 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5057 1.7689 0.4074 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4731 2.9130 -0.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3779 0.6699 -0.1364 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2127 -0.6552 -0.2280 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6289 -1.8020 0.2746 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3043 -2.9647 -0.1186 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4957 -4.2355 -0.3012 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9519 -2.5194 -1.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4267 -1.1035 -1.6471 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3827 -0.2944 -2.4234 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8851 0.3999 -3.3236 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7876 -1.2668 -2.3421 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7433 -1.6984 -3.6473 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3321 -1.9591 -4.2489 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9839 -1.8943 -4.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 -2.0222 -0.4147 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9819 -2.1892 0.3522 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9327 -2.1370 1.6193 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2999 -2.4295 -0.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6617 0.7312 0.4422 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8028 1.1343 -0.2139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6226 1.4615 -1.4246 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1195 1.1901 0.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1828 1.6143 -0.3622 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4639 1.6823 0.1915 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6965 1.3297 1.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6285 0.9064 2.2724 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3770 0.8494 1.6993 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2577 1.3999 2.7088 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1006 0.2977 3.4824 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7974 -0.7129 3.3283 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9529 0.3146 4.5541 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8177 2.0710 3.2985 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4048 0.7991 -3.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4162 -0.4773 -4.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7544 1.1729 -3.9255 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3153 -1.1936 -2.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0450 1.8138 -1.4010 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2284 -0.5575 0.0634 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1549 2.7994 0.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2470 1.4549 -0.3028 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2314 2.9079 -0.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0488 1.5470 2.9272 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0216 0.5746 1.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4505 -0.0694 2.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8657 3.5329 2.2698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7690 0.5432 1.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9747 3.8061 0.1192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0867 3.0665 -1.1546 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5548 1.0053 -1.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1952 -0.7676 0.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7268 -1.7684 1.3620 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0307 -3.1455 0.6956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2194 -5.0610 -0.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0704 -4.4318 0.6299 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1644 -4.1519 -1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0452 -2.5255 -1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6966 -3.1884 -2.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7910 -1.2680 -4.0281 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7816 -1.4989 -5.4933 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2431 -2.9566 -4.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8266 -3.2959 0.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9481 -1.5474 -0.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2076 -2.5838 -1.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1022 1.9101 -1.3965 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3233 2.0103 -0.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6908 1.3810 1.9445 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8368 0.6372 3.2974 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5641 0.5127 2.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2106 -0.7550 4.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5406 0.7262 5.4975 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8825 0.7882 4.2166 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7432 1.1064 3.3491 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 1 0 5 7 1 0 5 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 20 23 1 6 23 24 1 0 24 25 2 0 24 26 1 0 16 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 14 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 11 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 10 44 1 0 21 2 1 0 39 34 1 0 20 15 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 1 3 49 1 0 4 50 1 0 6 51 1 0 6 52 1 0 6 53 1 0 7 54 1 0 7 55 1 0 7 56 1 0 10 57 1 1 11 58 1 6 13 59 1 0 13 60 1 0 14 61 1 6 15 62 1 1 16 63 1 1 17 64 1 1 18 65 1 0 18 66 1 0 18 67 1 0 19 68 1 0 19 69 1 0 26 70 1 0 26 71 1 0 26 72 1 0 30 73 1 0 30 74 1 0 30 75 1 0 35 76 1 0 36 77 1 0 37 78 1 0 38 79 1 0 39 80 1 0 43 81 1 0 43 82 1 0 43 83 1 0 44 84 1 0 M END

Standard InCHIKey	PQNNHWCHNOPKGC-PSLQACODSA-N
Standard InCHI	InChI=1S/C33H40O11/c1-17-14-15-32(7,8)30(39)25(37)28(42-21(5)35)19(3)27(43-31(40)23-12-10-9-11-13-23)24-26(41-20(4)34)18(2)16-33(24,29(17)38)44-22(6)36/h9-15,17-18,24-28,37H,3,16H2,1-2,4-8H3/b15-14+/t17-,18-,24+,25+,26-,27-,28-,33+/m0/s1
SMILES	C[C@H]1/C=C/C(C)(C)C(=O)[C@@H]([C@H](C(=C)[C@@H]([C@H]2[C@H]([C@@H](C)C[C@@]2(C1=O)OC(=O)C)OC(=O)C)OC(=O)c1ccccc1)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	612.26	Volume:	621.346 ? Van der Waals volume.
Dense:	0.985	LogP:	2.258 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.561 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.139 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	159.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.295	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.527	Fsp³:	0.515
MCE-18:	102.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.918	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.029 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.071 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.156

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.386	MDCK Permeability:	-4.778
Pgp-inhibitor:	1.0	Pgp-substrate:	0.051
PAMPA:	0.833 ? 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%):	0.972	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	85.257%	Volume Distribution (VD):	0.02
Fu:	15.647% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.013
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.687	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.988 ? 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):

4.288

Half-life (T1/2):

0.666

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.08
Human Hepatotoxicity (H-HT):	0.329	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.514	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.185	Skin Sensitization:	0.995
Carcinogencity:	0.415	Eye Corrosion:	0.0
Eye Irritation:	0.111	Respiratory Toxicity:	0.076
Drug-induced Neurotoxicity:	0.261	Ototoxicity:	0.327
Hematotoxicity:	0.314	Drug-induced Nephrotoxicity:	0.873
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.25
A549 Cytotoxicity:	0.673	Hek293 Cytotoxicity:	0.429
BCF:	0.602 ? 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:	3.501 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.393 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.75 ? 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
NPO40845	Euphorbia glomerulans	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30860373]

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
Ratio IC50	1
IC50	3

Activity Type	# Activity
Cell line	2
Individual protein	2

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	Ratio IC50	=	3.0	n.a.	PMID[30860373]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	IC50	=	21600.0	nM	PMID[30860373]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[30860373]

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 NPC482301 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	7600
0.1-0.2	38101
0.2-0.3	3522
0.3-0.4	515
0.4-0.5	86
0.5-0.6	18
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC482302
0.8378	Intermediate Similarity	NPC482310
0.7368	Intermediate Similarity	NPC482307
0.7273	Intermediate Similarity	NPC482314
0.7215	Intermediate Similarity	NPC205389
0.7125	Intermediate Similarity	NPC482252
0.6835	Remote Similarity	NPC86772
0.675	Remote Similarity	NPC290833
0.675	Remote Similarity	NPC482249
0.6582	Remote Similarity	NPC482313
0.65	Remote Similarity	NPC482308
0.642	Remote Similarity	NPC482300
0.642	Remote Similarity	NPC482315
0.6341	Remote Similarity	NPC265459
0.6341	Remote Similarity	NPC482265
0.5952	Remote Similarity	NPC475262
0.5952	Remote Similarity	NPC482304
0.5814	Remote Similarity	NPC482272
0.5652	Remote Similarity	NPC482258
0.5632	Remote Similarity	NPC482268
0.5632	Remote Similarity	NPC482269
0.5517	Remote Similarity	NPC482251
0.5402	Remote Similarity	NPC82467
0.5402	Remote Similarity	NPC482270
0.5357	Remote Similarity	NPC196683
0.5333	Remote Similarity	NPC482253
0.5326	Remote Similarity	NPC482250
0.5169	Remote Similarity	NPC482347
0.5155	Remote Similarity	NPC482261
0.5155	Remote Similarity	NPC482262
0.5111	Remote Similarity	NPC482267
0.5063	Remote Similarity	NPC105725
0.5057	Remote Similarity	NPC473497

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC482301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3537
0.1-0.2	5461
0.2-0.3	145
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