NPASS Compound

Natural Product: NPC486549

Natural Product ID	NPC486549
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QJTSRUOQQNGNIN-BHKGFAFJSA-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] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

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 68 71 0 0 0 0 0 0 0 0999 V2000 8.2819 3.2352 -0.7934 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8722 1.9614 -0.6746 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2158 0.8478 -0.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9023 0.9290 0.2583 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2694 -0.1808 0.7538 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9475 -1.3709 0.8215 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -1.4216 0.3892 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9186 -0.3323 -0.1134 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2384 -0.3946 -0.5488 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8477 -0.1072 1.2209 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8997 -0.4120 0.0785 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4744 -0.3305 0.5783 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3332 -1.6782 1.2962 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3165 -2.5251 0.7294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0271 -1.8445 -0.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6298 -2.4070 -1.1909 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5060 -0.2470 -0.5318 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9572 -0.2743 -1.7115 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0734 -0.1360 -0.3407 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8156 -0.0689 -1.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1923 0.0402 -1.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6963 0.0834 0.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7892 0.0149 1.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4346 -0.0923 0.9370 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2486 0.0548 2.4666 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3502 -0.0127 3.5375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0333 0.1895 0.4406 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1134 0.2711 -0.4229 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0766 -0.9139 -0.2533 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0427 -0.8137 -1.4100 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6898 0.5185 -1.4598 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8450 1.6676 -1.0519 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7745 2.7234 -0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7957 3.0643 -1.3101 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8785 1.3981 -0.1241 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1117 0.7404 -2.7883 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0421 -1.8065 -1.2887 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4006 -2.1116 -0.2309 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7804 3.4717 0.1827 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0914 3.9638 -1.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5018 3.1964 -1.5716 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3717 1.8949 0.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4798 -2.2772 1.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8177 -2.3533 0.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4617 -0.8813 -1.4080 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6475 0.9023 1.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7106 -0.8254 2.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0385 0.2526 -0.7722 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4128 0.5103 1.2695 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5194 -1.4839 2.3605 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3442 -2.1435 1.0936 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4490 -0.1006 -2.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8720 0.0914 -1.9946 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2338 -0.1412 1.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6798 0.8921 3.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8509 -0.0428 4.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6602 -0.8938 3.4643 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8206 0.2448 -1.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6243 -0.7040 0.6937 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4409 -0.9943 -2.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6386 0.4701 -0.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3548 2.1896 -1.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2120 3.5744 -0.0484 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2476 2.2104 0.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5806 2.4646 -1.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0649 -0.0885 -3.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1196 -2.0946 -0.3414 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4258 -2.4387 0.7168 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 5 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 12 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 22 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 30 37 1 0 29 38 1 0 8 3 1 0 15 11 1 0 24 19 1 0 35 28 1 0 1 39 1 0 1 40 1 0 1 41 1 0 4 42 1 0 6 43 1 0 7 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 6 12 49 1 1 13 50 1 0 13 51 1 0 20 52 1 0 21 53 1 0 24 54 1 0 26 55 1 0 26 56 1 0 26 57 1 0 28 58 1 6 29 59 1 1 30 60 1 6 31 61 1 1 32 62 1 6 33 63 1 0 33 64 1 0 34 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 M END

Standard InCHIKey	QJTSRUOQQNGNIN-BHKGFAFJSA-N
Standard InCHI	InChI=1S/C26H30O12/c1-34-18-8-12(3-5-16(18)28)7-14-15(11-36-25(14)33)21(29)13-4-6-17(19(9-13)35-2)37-26-24(32)23(31)22(30)20(10-27)38-26/h3-6,8-9,14-15,20,22-24,26-28,30-32H,7,10-11H2,1-2H3/t14-,15+,20-,22-,23+,24-,26-/m1/s1
SMILES	COc1cc(ccc1O)C[C@@H]1[C@H](COC1=O)C(=O)c1ccc(c(c1)OC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.17	Volume:	508.417 ? Van der Waals volume.
Dense:	1.051	LogP:	-0.647 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.166 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.151 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	25.0
TPSA:	181.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.211	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.245	Fsp³:	0.462
MCE-18:	92.368 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.612	Fluc inhibitor:	0.07 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.118 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.57 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.076	Promiscuous compounds:	0.211

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.931	MDCK Permeability:	-5.077
Pgp-inhibitor:	0.001	Pgp-substrate:	0.3
PAMPA:	0.644 ? 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):	0.078
20% Bioavailability (F20%):	0.357	30% Bioavailability (F30%):	0.92
50% Bioavailability (F50%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.22
Plasma Protein Binding (PPB):	70.088%	Volume Distribution (VD):	-0.417
Fu:	28.952% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.123

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.974	CYP2C19-substrate:	0.016
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.74	CYP3A4-substrate:	0.118
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.968
HLM stability:	0.054 ? 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):

2.712

Half-life (T1/2):

4.064

ADMET: Toxicity

hERG Blockers:	0.035	hERG Blockers (10um):	0.161
Human Hepatotoxicity (H-HT):	0.934	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.959	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.056	Skin Sensitization:	1.0
Carcinogencity:	0.393	Eye Corrosion:	0.0
Eye Irritation:	0.122	Respiratory Toxicity:	0.012
Drug-induced Neurotoxicity:	0.047	Ototoxicity:	0.97
Hematotoxicity:	0.677	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	0.965	RPMI-8226 Immunitoxicity:	0.206
A549 Cytotoxicity:	0.291	Hek293 Cytotoxicity:	0.508
BCF:	0.466 ? 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:	3.164 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.834 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.951 ? 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
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10571166]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700070]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30232882]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6409	Eutrema japonicum	Species	Brassicaceae	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
Activity	2
IC50	5

Activity Type	# Activity
Cell line	7

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
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	122.1	%	PMID[27700070]
NPT76	Cell line	C6	Rattus norvegicus	Activity	=	100.9	%	PMID[27700070]
NPT34	Cell line	BV-2	Mus musculus	IC50	>	50000.0	nM	PMID[27700070]
NPT457	Cell line	BT-549	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT81	Cell line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]
NPT147	Cell line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[27700070]

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 NPC486549 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	12528
0.1-0.2	31848
0.2-0.3	4264
0.3-0.4	1019
0.4-0.5	151
0.5-0.6	32
0.6-0.7	7
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
0.7821	Intermediate Similarity	NPC299706
0.7821	Intermediate Similarity	NPC115466
0.7821	Intermediate Similarity	NPC61604
0.7654	Intermediate Similarity	NPC486546
0.7317	Intermediate Similarity	NPC486548
0.6905	Remote Similarity	NPC486547
0.6747	Remote Similarity	NPC245615
0.6588	Remote Similarity	NPC163635
0.6582	Remote Similarity	NPC158635
0.6582	Remote Similarity	NPC229882
0.6301	Remote Similarity	NPC102908
0.6207	Remote Similarity	NPC185307
0.5977	Remote Similarity	NPC486545
0.5955	Remote Similarity	NPC470235
0.5843	Remote Similarity	NPC470950
0.5778	Remote Similarity	NPC283995
0.5696	Remote Similarity	NPC278961
0.5696	Remote Similarity	NPC113680
0.5647	Remote Similarity	NPC38041
0.5647	Remote Similarity	NPC22150
0.5604	Remote Similarity	NPC129417
0.5495	Remote Similarity	NPC478055
0.5341	Remote Similarity	NPC38699
0.5287	Remote Similarity	NPC18979
0.5287	Remote Similarity	NPC147596
0.5275	Remote Similarity	NPC39657
0.5256	Remote Similarity	NPC210015
0.519	Remote Similarity	NPC300776
0.519	Remote Similarity	NPC176814
0.519	Remote Similarity	NPC4982
0.519	Remote Similarity	NPC606629
0.5176	Remote Similarity	NPC148273
0.5161	Remote Similarity	NPC46092
0.5128	Remote Similarity	NPC472024
0.5128	Remote Similarity	NPC270849
0.5128	Remote Similarity	NPC205054
0.5125	Remote Similarity	NPC100675
0.5125	Remote Similarity	NPC601691
0.5114	Remote Similarity	NPC279298
0.5106	Remote Similarity	NPC112861
0.5063	Remote Similarity	NPC26653
0.5063	Remote Similarity	NPC80600
0.5056	Remote Similarity	NPC471063
0.5055	Remote Similarity	NPC44452

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3371
0.1-0.2	5612
0.2-0.3	153
0.3-0.4	14
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