NPASS Compound

Natural Product: NPC486101

Natural Product ID	NPC486101
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IXFCBPYFIQTJAP-YGFSCBLISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	132566268
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

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 79 84 0 0 0 0 0 0 0 0999 V2000 5.6775 -3.2358 2.1301 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3638 -2.1035 1.5722 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7439 -1.3816 0.5649 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5003 -1.7308 0.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8546 -1.0163 -0.9154 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5571 0.0561 -1.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8226 0.4166 -0.9380 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4256 -0.3000 0.0520 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6695 0.2676 0.3308 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9791 1.0970 -0.7804 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6919 1.4300 -1.2766 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5217 -1.4329 -1.3974 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7998 -0.3160 -2.0399 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5031 -0.7412 -2.7029 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5459 -0.0700 -2.1068 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0077 0.9978 -1.4814 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8379 1.8017 -0.6142 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2044 2.9318 -0.0645 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8701 3.7890 0.7817 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1882 3.5343 1.0966 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8424 2.4443 0.5827 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1336 1.5927 -0.2742 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8205 0.5183 -0.7621 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9481 -0.6842 -0.0846 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3729 -0.9481 0.3882 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8910 -2.2788 -0.1776 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9928 -3.3514 0.4011 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5687 -2.8896 0.1099 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8173 -4.0677 -0.4496 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4168 -4.5030 -1.6189 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5750 -1.8201 -0.7917 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2599 -3.4050 1.7667 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7479 -2.3016 -1.5725 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4593 -1.0755 1.7693 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1863 2.1932 0.9101 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2193 2.7553 0.0842 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8894 4.3908 1.9535 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8496 4.1031 3.3331 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2868 4.9127 1.3483 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0619 5.1843 1.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2100 0.3832 -0.7961 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9470 -0.7693 0.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7367 -1.8348 -0.3157 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2994 -3.7237 2.8897 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4103 -3.9786 1.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7332 -2.8250 2.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9654 -2.5848 0.5044 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1784 0.6770 -2.1865 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5939 0.5901 -1.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5431 1.9781 -0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6918 -2.2464 -2.1251 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3633 0.3785 -2.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4020 -1.8453 -2.7019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5907 -0.4200 -3.7817 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 1.7284 -2.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8211 3.1516 -0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3321 -0.6677 0.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0963 -0.1994 0.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9220 -2.4273 0.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2011 -4.3405 -0.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1537 -2.5552 1.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7722 -3.7623 -0.6693 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8600 -4.8857 0.3002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8456 -5.4060 -1.4956 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2051 -3.2826 1.9789 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1811 -1.5068 -1.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8882 -0.4329 2.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0274 3.8539 -0.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1018 2.2648 -0.9046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1858 2.5212 0.5505 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9023 3.5710 3.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9599 5.0220 3.9552 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6862 3.4084 3.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2416 5.1282 -0.0489 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7455 4.5009 1.5871 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2666 6.2583 1.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9040 1.1431 -0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0984 -1.0971 -0.0417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0586 -0.5306 1.1631 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 9 10 1 0 10 11 1 0 5 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 21 35 1 0 35 36 1 0 20 37 1 0 37 38 1 0 19 39 1 0 39 40 1 0 16 41 1 0 41 42 1 0 42 43 1 0 8 3 1 0 43 12 1 0 11 7 1 0 41 13 1 0 22 17 1 0 31 24 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 6 48 1 0 10 49 1 0 10 50 1 0 12 51 1 6 13 52 1 6 14 53 1 0 14 54 1 0 16 55 1 6 18 56 1 0 24 57 1 1 25 58 1 6 26 59 1 6 27 60 1 6 28 61 1 1 29 62 1 0 29 63 1 0 30 64 1 0 32 65 1 0 33 66 1 0 34 67 1 0 36 68 1 0 36 69 1 0 36 70 1 0 38 71 1 0 38 72 1 0 38 73 1 0 40 74 1 0 40 75 1 0 40 76 1 0 41 77 1 1 42 78 1 0 42 79 1 0 M END

Standard InCHIKey	IXFCBPYFIQTJAP-YGFSCBLISA-N
Standard InCHI	InChI=1S/C29H36O14/c1-34-16-5-12(6-18-26(16)41-11-40-18)23-14-9-39-24(15(14)10-38-23)13-7-17(35-2)27(36-3)28(37-4)25(13)43-29-22(33)21(32)20(31)19(8-30)42-29/h5-7,14-15,19-24,29-33H,8-11H2,1-4H3/t14-,15-,19+,20+,21-,22+,23+,24-,29-/m0/s1
SMILES	COc1cc(cc2c1OCO2)[C@@H]1[C@H]2CO[C@@H](c3cc(c(c(c3O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)OC)OC)OC)[C@H]2CO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.21	Volume:	566.046 ? Van der Waals volume.
Dense:	1.074	LogP:	0.333 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.923 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.962 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	173.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.313	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.826	Fsp³:	0.586
MCE-18:	126.783 ? 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:	0.573	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.142 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.092 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.06	Promiscuous compounds:	0.104

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.68	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.0	Pgp-substrate:	0.01
PAMPA:	0.262 ? 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%):	0.009	30% Bioavailability (F30%):	0.054
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117	MRP1:	0.401
Plasma Protein Binding (PPB):	80.592%	Volume Distribution (VD):	-0.245
Fu:	20.59% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.441

ADMET: Metabolism

CYP1A2-inhibitor:	0.437	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.28
CYP3A4-inhibitor:	0.894	CYP3A4-substrate:	0.274
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.07
HLM stability:	0.419 ? 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):

2.556

Half-life (T1/2):

3.708

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.884	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.882	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.079	Skin Sensitization:	0.998
Carcinogencity:	0.37	Eye Corrosion:	0.0
Eye Irritation:	0.121	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.115	Ototoxicity:	0.916
Hematotoxicity:	0.734	Drug-induced Nephrotoxicity:	0.913
Genotoxicity:	0.831	RPMI-8226 Immunitoxicity:	0.314
A549 Cytotoxicity:	0.258	Hek293 Cytotoxicity:	0.311
BCF:	1.029 ? 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:	3.357 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.293 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.043 ? 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
NPO40374	Terminalia citrina	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27110635]
NPO40374	Terminalia citrina	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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	3
Inhibition	1

Activity Type	# Activity
Cell line	4

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
NPT83	Cell line	MCF7	Homo sapiens	Activity	<	0.01	uM	PMID[27110635]
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	0.6	uM	PMID[27110635]
NPT396	Cell line	T47D	Homo sapiens	Activity	=	5.6	uM	PMID[27110635]
NPT83	Cell line	MCF7	Homo sapiens	Inhibition	>	50.0	%	PMID[27110635]

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 NPC486101 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	24509
0.1-0.2	22135
0.2-0.3	2596
0.3-0.4	495
0.4-0.5	88
0.5-0.6	10
0.6-0.7	10
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC486100
0.8769	High Similarity	NPC486104
0.8592	High Similarity	NPC486098
0.8209	Intermediate Similarity	NPC486102
0.8108	Intermediate Similarity	NPC486099
0.7612	Intermediate Similarity	NPC486107
0.75	Intermediate Similarity	NPC486103
0.7273	Intermediate Similarity	NPC95392
0.7273	Intermediate Similarity	NPC84013
0.7273	Intermediate Similarity	NPC55715
0.7273	Intermediate Similarity	NPC35877
0.7162	Intermediate Similarity	NPC486109
0.7162	Intermediate Similarity	NPC486108
0.7067	Intermediate Similarity	NPC486105
0.6914	Remote Similarity	NPC486097
0.6575	Remote Similarity	NPC216129
0.6575	Remote Similarity	NPC130449
0.6575	Remote Similarity	NPC248132
0.6494	Remote Similarity	NPC486106
0.625	Remote Similarity	NPC276753
0.625	Remote Similarity	NPC205796
0.6234	Remote Similarity	NPC51328
0.6234	Remote Similarity	NPC55158
0.6164	Remote Similarity	NPC246947
0.5823	Remote Similarity	NPC286235
0.5714	Remote Similarity	NPC186316
0.5556	Remote Similarity	NPC38041
0.5556	Remote Similarity	NPC22150
0.5556	Remote Similarity	NPC279298
0.5385	Remote Similarity	NPC148893
0.5385	Remote Similarity	NPC25333
0.5385	Remote Similarity	NPC49235
0.507	Remote Similarity	NPC185071
0.5055	Remote Similarity	NPC222531

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC486101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6194
0.1-0.2	2874
0.2-0.3	74
0.3-0.4	8
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