NPASS Compound

Natural Product: NPC39664

Natural Product ID	NPC39664
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-[(Z)-14-(3,5-Dihydroxyphenyl)Tetradec-10-Enyl]Benzene-1,3-Diol
IUPAC Name	5-[(Z)-14-(3,5-dihydroxyphenyl)tetradec-10-enyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL455348
PubChem CID	10364369
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

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 9.8389 1.3576 0.2546 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6000 0.8271 0.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4471 1.4809 0.1853 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1891 0.9563 0.4826 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9517 1.6468 0.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4322 1.3389 -1.2576 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0454 -0.0917 -1.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9264 -0.5584 -0.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6460 0.2226 -0.8283 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1657 0.1092 -2.2421 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8702 -1.2891 -2.6659 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1757 -1.9756 -1.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5389 -1.2615 -1.9066 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4363 -2.0690 -1.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0515 -1.6414 -0.0204 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9152 -0.2661 0.4736 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2985 0.3832 0.4591 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2665 -0.3454 1.3336 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5918 0.3307 1.2973 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5041 -0.0567 0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7470 0.5548 0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6112 0.0954 -0.7248 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0926 1.5385 1.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1890 1.9356 2.1161 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9565 1.3301 2.1755 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5783 2.9456 2.9915 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1518 -0.2322 1.1557 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3325 -0.8913 1.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5741 -0.3765 1.2366 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2475 -2.1034 2.2146 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4516 0.9949 -0.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4973 2.4233 -0.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1228 2.7334 0.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1733 1.3672 0.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1053 1.6869 -2.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4946 1.9553 -1.3952 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8219 -0.2915 -2.5283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9249 -0.7610 -1.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7624 -1.6334 -0.7783 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1484 -0.4361 0.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7800 1.2685 -0.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8773 -0.2199 -0.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2523 0.7205 -2.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9221 0.5850 -2.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5460 -1.2786 -3.7379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7856 -1.9064 -2.6244 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3054 -3.0394 -2.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1395 -2.0146 -0.7773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3480 -0.2423 -1.6099 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8764 -1.3562 -2.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5924 -3.1160 -1.3802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7170 -2.2944 0.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2667 0.4054 -0.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5878 -0.3233 1.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6588 0.2526 -0.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1799 1.4366 0.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4399 -1.3714 0.9676 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9561 -0.3809 2.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2447 -0.8487 -0.3723 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1955 -0.1088 -1.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0698 1.9969 1.0835 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2357 1.6434 2.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2392 2.7786 3.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2314 -0.7165 1.4366 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4688 -0.9019 1.5337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9428 -2.9022 1.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 21 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 4 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 29 2 1 0 25 19 1 0 1 31 1 0 3 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 20 59 1 0 22 60 1 0 23 61 1 0 25 62 1 0 26 63 1 0 27 64 1 0 29 65 1 0 30 66 1 0 M END

Standard InCHIKey	PFIQXUYXVYYERO-ALCCZGGFSA-N
Standard InCHI	InChI=1S/C26H36O4/c27-23-15-21(16-24(28)19-23)13-11-9-7-5-3-1-2-4-6-8-10-12-14-22-17-25(29)20-26(30)18-22/h5,7,15-20,27-30H,1-4,6,8-14H2/b7-5-
SMILES	Oc1cc(CCCCCCCCC/C=CCCCc2cc(O)cc(c2)O)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.26	Volume:	457.845 ? Van der Waals volume.
Dense:	0.9	LogP:	6.811 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.871 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.884 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	13.0
TPSA:	80.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.46	Fsp³:	0.462
MCE-18:	12.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.952	Fluc inhibitor:	0.436 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.072 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.668	Promiscuous compounds:	0.114

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.114	MDCK Permeability:	-4.72
Pgp-inhibitor:	0.028	Pgp-substrate:	0.001
PAMPA:	0.0 ? 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%):	0.866	30% Bioavailability (F30%):	0.949
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017	MRP1:	0.67
Plasma Protein Binding (PPB):	98.445%	Volume Distribution (VD):	0.39
Fu:	0.878% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.539
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.556
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.68	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.797	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	0.971 ? 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):

2.77

Half-life (T1/2):

1.606

ADMET: Toxicity

hERG Blockers:	0.805	hERG Blockers (10um):	0.918
Human Hepatotoxicity (H-HT):	0.339	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.278	Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.824	Skin Sensitization:	1.0
Carcinogencity:	0.058	Eye Corrosion:	0.86
Eye Irritation:	0.998	Respiratory Toxicity:	0.688
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.118
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.097
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.964	Hek293 Cytotoxicity:	0.988
BCF:	1.536 ? 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:	5.117 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.211 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.858 ? 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
NPO8932	Panopsis rubescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096862]
NPO8932	Panopsis rubescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8932	Panopsis rubescens	Species	Proteaceae	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	2
IC50	2

Activity Type	# Activity
Individual protein	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	98.0	%	PubChem BioAssay data set
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	51.0	%	PMID[22809558]
NPT2216	Individual protein	DNA polymerase beta	Rattus norvegicus	IC50	=	7500.0	nM	PMID[22809558]
NPT4717	Individual protein	Cystathionine beta-synthase	Homo sapiens	IC50	=	7400.0	nM	PMID[30108705]

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 NPC39664 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	31313
0.1-0.2	17083
0.2-0.3	1232
0.3-0.4	130
0.4-0.5	30
0.5-0.6	22
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	8
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC470700
0.9375	High Similarity	NPC54844
0.9375	High Similarity	NPC39097
0.9375	High Similarity	NPC302681
0.9375	High Similarity	NPC118286
0.9375	High Similarity	NPC109691
0.8824	High Similarity	NPC53051
0.8824	High Similarity	NPC24404
0.8824	High Similarity	NPC313030
0.8571	High Similarity	NPC146798
0.8571	High Similarity	NPC222522
0.8571	High Similarity	NPC106396
0.8571	High Similarity	NPC94351
0.8571	High Similarity	NPC168303
0.7895	Intermediate Similarity	NPC71002
0.7895	Intermediate Similarity	NPC10588
0.7895	Intermediate Similarity	NPC302219
0.7895	Intermediate Similarity	NPC242342
0.7895	Intermediate Similarity	NPC249828
0.7895	Intermediate Similarity	NPC85479
0.7692	Intermediate Similarity	NPC72947
0.7632	Intermediate Similarity	NPC166761
0.75	Intermediate Similarity	NPC246056
0.7436	Intermediate Similarity	NPC284011
0.6857	Remote Similarity	NPC294186
0.6857	Remote Similarity	NPC147310
0.6857	Remote Similarity	NPC137415
0.6857	Remote Similarity	NPC166313
0.6857	Remote Similarity	NPC192032
0.6857	Remote Similarity	NPC24407
0.6857	Remote Similarity	NPC11280
0.6667	Remote Similarity	NPC305603
0.6667	Remote Similarity	NPC61033
0.6667	Remote Similarity	NPC127894
0.6667	Remote Similarity	NPC470759
0.6341	Remote Similarity	NPC483454
0.6341	Remote Similarity	NPC162314
0.6316	Remote Similarity	NPC241891
0.6316	Remote Similarity	NPC134829
0.6222	Remote Similarity	NPC470760
0.619	Remote Similarity	NPC94139
0.619	Remote Similarity	NPC147284
0.6122	Remote Similarity	NPC123559
0.6122	Remote Similarity	NPC140521
0.6098	Remote Similarity	NPC232523
0.5952	Remote Similarity	NPC488413
0.5952	Remote Similarity	NPC488412
0.5854	Remote Similarity	NPC55561
0.5814	Remote Similarity	NPC488416
0.5778	Remote Similarity	NPC210497
0.5778	Remote Similarity	NPC192
0.5778	Remote Similarity	NPC219070
0.5714	Remote Similarity	NPC196479
0.5714	Remote Similarity	NPC486908
0.5682	Remote Similarity	NPC158253
0.5682	Remote Similarity	NPC204901
0.561	Remote Similarity	NPC177420
0.54	Remote Similarity	NPC470699
0.5349	Remote Similarity	NPC487734
0.5333	Remote Similarity	NPC114064
0.5319	Remote Similarity	NPC483450
0.5306	Remote Similarity	NPC249836
0.5306	Remote Similarity	NPC15860
0.5227	Remote Similarity	NPC487735
0.5111	Remote Similarity	NPC129373
0.5111	Remote Similarity	NPC115808
0.5106	Remote Similarity	NPC483449

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6961
0.1-0.2	2096
0.2-0.3	86
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