NPASS Compound

Natural Product: NPC6923

Natural Product ID	NPC6923
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	4-[2,4-Dihydroxy-6-(2-Oxoheptyl)Benzoyl]Oxy-2-Hydroxy-6-Pentylbenzoic Acid
IUPAC Name	4-[2,4-dihydroxy-6-(2-oxoheptyl)benzoyl]oxy-2-hydroxy-6-pentylbenzoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3770253
PubChem CID	591238
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

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 66 67 0 0 0 0 0 0 0 0999 V2000 8.6550 -1.5527 -1.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6273 -2.6373 -1.1367 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5471 -2.5670 -0.1195 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7195 -1.3054 -0.1705 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6141 -1.3442 0.8748 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8127 -0.0801 0.7865 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6418 -0.1153 0.0214 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8639 0.9913 -0.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3100 2.1616 0.4251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4477 2.2073 1.1734 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2502 1.0678 1.3820 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4317 1.1641 2.1899 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1715 0.2048 2.4374 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8204 2.3945 2.7598 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9006 3.3801 1.7865 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7100 0.9542 -0.9407 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4605 1.6342 -0.7258 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5391 2.3915 0.2645 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6054 1.4760 -1.6544 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5883 0.5652 -1.4373 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6049 -0.2271 -0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8144 -1.1014 -0.1302 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8661 -2.0788 -0.8559 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9677 -0.8280 0.7551 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1081 -1.7802 0.5249 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3061 -1.4623 1.3930 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8257 -0.0635 1.1097 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0269 0.1770 1.9915 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5923 0.4172 -2.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6536 1.1489 -3.5485 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6478 2.0708 -3.7522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 2.2317 -2.8252 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6623 3.1647 -3.0651 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6929 0.9439 -4.4521 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3717 -0.6675 -1.6974 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5758 -1.9672 -1.6028 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9122 -1.2884 -0.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2572 -2.7308 -2.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1977 -3.5977 -0.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0084 -2.7040 0.8844 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8744 -3.4395 -0.2564 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2913 -0.3790 -0.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2188 -1.3311 -1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9155 -2.2015 0.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0020 -1.5365 1.8790 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3511 -1.0547 -0.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7045 3.0507 0.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8312 2.5870 2.8380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2508 4.1385 1.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6646 0.4488 0.7029 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6816 -0.8274 -0.0470 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2387 0.2229 0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6504 -0.9888 1.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4408 -1.6539 -0.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8674 -2.8342 0.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1401 -2.1664 1.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0833 -1.5137 2.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1212 0.0995 0.0745 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0386 0.6726 1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5720 -0.7849 2.2257 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7038 0.6762 2.9326 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7365 0.8475 1.4574 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3512 -0.2952 -2.2012 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6879 2.6511 -4.6735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1647 3.3183 -2.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8652 1.6464 -5.1536 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 12 13 2 0 12 14 1 0 10 15 1 0 8 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 20 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 30 34 1 0 11 6 1 0 32 19 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 7 46 1 0 9 47 1 0 14 48 1 0 15 49 1 0 21 50 1 0 21 51 1 0 24 52 1 0 24 53 1 0 25 54 1 0 25 55 1 0 26 56 1 0 26 57 1 0 27 58 1 0 27 59 1 0 28 60 1 0 28 61 1 0 28 62 1 0 29 63 1 0 31 64 1 0 33 65 1 0 34 66 1 0 M END

Standard InCHIKey	VZPLPGICHZXOCQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C26H32O8/c1-3-5-7-9-16-13-20(15-22(30)23(16)25(31)32)34-26(33)24-17(12-19(28)14-21(24)29)11-18(27)10-8-6-4-2/h12-15,28-30H,3-11H2,1-2H3,(H,31,32)
SMILES	CCCCCc1cc(cc(c1C(=O)O)O)OC(=O)c1c(CC(=O)CCCCC)cc(cc1O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.21	Volume:	487.733 ? Van der Waals volume.
Dense:	0.968	LogP:	6.262 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.458 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.604 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	15.0
TPSA:	141.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.178	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.78	Fsp³:	0.423
MCE-18:	17.0 ? 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:	0.57	Fluc inhibitor:	0.488 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.222 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.686 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.279	Promiscuous compounds:	0.288

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032	MDCK Permeability:	-4.751
Pgp-inhibitor:	0.089	Pgp-substrate:	0.011
PAMPA:	0.629 ? 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):	0.015
20% Bioavailability (F20%):	0.491	30% Bioavailability (F30%):	0.591
50% Bioavailability (F50%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.914
Plasma Protein Binding (PPB):	97.879%	Volume Distribution (VD):	-0.183
Fu:	1.556% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.055
OATP1B3 inhibitor:	0.812	BCRP inhibitor:	0.072
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.005	CYP2C19-substrate:	0.984
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.182	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.14
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? 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):

0.808

Half-life (T1/2):

1.515

ADMET: Toxicity

hERG Blockers:	0.162	hERG Blockers (10um):	0.391
Human Hepatotoxicity (H-HT):	0.293	Drug-induced Liver Injury (DILI):	0.422
AMES Toxicity:	0.025	Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.179	Skin Sensitization:	0.975
Carcinogencity:	0.02	Eye Corrosion:	0.463
Eye Irritation:	0.991	Respiratory Toxicity:	0.982
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.356
Hematotoxicity:	0.099	Drug-induced Nephrotoxicity:	0.619
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.647	Hek293 Cytotoxicity:	0.221
BCF:	1.298 ? 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:	4.319 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.486 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.419 ? 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
NPO8465	Maesa indica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4891	Lentinellus ursinus	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7203	Lindera lucida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5847	Moghania faginea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4334	Garcinia griffithii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4517	Laggera tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8465	Maesa indica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4334	Garcinia griffithii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4334	Garcinia griffithii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8465	Maesa indica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1286	Parmelia furfuracea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4517	Laggera tomentosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6552	Astrocasia phyllanthoides	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4334	Garcinia griffithii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4891	Lentinellus ursinus	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3334	Dicranum japonicum	Species	Dicranaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6307	Salix lasiolepis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7203	Lindera lucida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8465	Maesa indica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9084	Rumex confertus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24532	Ula pilosa	Species	Pediciidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5847	Moghania faginea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9731	Roccella fuciformis	Species	Roccellaceae	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
IC50	3

Activity Type	# Activity
Individual protein	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	IC50	>	30000.0	nM	DOI[10.1039/C5MD00278H]
NPT956	Individual protein	Prostaglandin E synthase	Homo sapiens	IC50	=	1150.0	nM	DOI[10.1039/C5MD00278H]
NPT956	Individual protein	Prostaglandin E synthase	Homo sapiens	IC50	=	400.0	nM	PMID[29329790]

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 NPC6923 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	20535
0.1-0.2	27451
0.2-0.3	1745
0.3-0.4	96
0.4-0.5	16
0.5-0.6	7
0.6-0.7	2
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
0.8209	Intermediate Similarity	NPC606753
0.7971	Intermediate Similarity	NPC604559
0.7639	Intermediate Similarity	NPC309979
0.7297	Intermediate Similarity	NPC307780
0.7101	Intermediate Similarity	NPC602325
0.6575	Remote Similarity	NPC237208
0.6053	Remote Similarity	NPC134621
0.56	Remote Similarity	NPC66404
0.5479	Remote Similarity	NPC603370
0.5476	Remote Similarity	NPC93739
0.5467	Remote Similarity	NPC29577
0.5278	Remote Similarity	NPC105648
0.5119	Remote Similarity	NPC284007
0.5067	Remote Similarity	NPC12305

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC6923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3692
0.1-0.2	5343
0.2-0.3	115
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