NPASS Compound

Natural Product: NPC80534

Natural Product ID	NPC80534
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Notabilisin A
IUPAC Name	2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]-5,7-dihydroxy-3-methoxychromen-4-one
Synonyms	Notabilisin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1808152
PubChem CID	53363478
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

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 61 63 0 0 0 0 0 0 0 0999 V2000 6.3050 1.3401 1.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7234 0.1981 1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8405 -0.6941 0.5915 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3799 -0.5555 0.8769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6069 -0.4021 -0.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1523 -0.2611 -0.1855 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2847 -1.1543 -0.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1708 -1.1108 -0.5090 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9714 -0.8990 -1.7387 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3122 -0.6519 -1.6808 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1107 -0.6022 -2.8388 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5633 -0.7961 -4.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2152 -1.0386 -4.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4416 -1.0875 -3.0011 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9008 -1.3331 -3.1594 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6230 -1.2372 -5.3960 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0181 -0.2337 -0.4690 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5421 0.8089 0.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2568 1.1784 1.4287 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 2.1150 2.1490 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3967 0.4585 1.7163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1426 0.7780 2.8326 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2866 0.0833 3.1491 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7431 -0.9754 2.3543 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9997 -1.2888 1.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8348 -0.5793 0.9286 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1336 -0.8807 -0.1229 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9043 -1.6653 2.6928 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6801 1.8378 3.6222 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4034 1.5235 -0.0449 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4227 2.6764 -0.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 0.8563 0.6212 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1677 0.0288 0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6696 1.0284 2.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1821 1.9137 2.2603 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6670 2.0363 1.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1806 -1.5223 -0.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9871 -1.4593 1.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2439 0.3053 1.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0291 0.4815 -0.9701 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8483 -1.2906 -1.0455 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7698 -1.9577 -1.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4078 -2.2610 -0.3060 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5434 -0.6862 0.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1678 -0.4115 -2.7730 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1573 -0.7629 -4.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2582 -2.2010 -3.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6400 -0.4199 -6.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8569 0.3339 4.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3099 -2.0953 0.6030 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7383 -1.6417 2.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8780 1.7841 4.2288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1441 3.4342 -0.4679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8311 2.3635 -1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4103 3.1012 -0.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3337 1.7310 -0.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 0.5785 1.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4840 1.2588 1.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7587 0.8759 1.1623 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5235 -0.9312 1.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3340 -0.0222 -0.3238 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 13 16 1 0 10 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 24 28 1 0 22 29 1 0 18 30 1 0 30 31 1 0 6 32 1 0 2 33 1 0 14 9 1 0 27 17 1 0 26 21 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 0 4 39 1 0 5 40 1 0 5 41 1 0 7 42 1 0 8 43 1 0 8 44 1 0 11 45 1 0 12 46 1 0 15 47 1 0 16 48 1 0 23 49 1 0 25 50 1 0 28 51 1 0 29 52 1 0 31 53 1 0 31 54 1 0 31 55 1 0 32 56 1 0 32 57 1 0 32 58 1 0 33 59 1 0 33 60 1 0 33 61 1 0 M END

Standard InCHIKey	AGJPGVFVAYNHMZ-OVCLIPMQSA-N
Standard InCHI	InChI=1S/C26H28O7/c1-14(2)6-5-7-15(3)8-9-17-18(10-11-19(28)23(17)30)25-26(32-4)24(31)22-20(29)12-16(27)13-21(22)33-25/h6,8,10-13,27-30H,5,7,9H2,1-4H3/b15-8+
SMILES	CC(=CCC/C(=C/Cc1c(ccc(c1O)O)c1c(c(=O)c2c(cc(cc2o1)O)O)OC)/C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	452.18	Volume:	467.75 ? Van der Waals volume.
Dense:	0.967	LogP:	5.893 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.164 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.631 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	20.0
TPSA:	120.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.275	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.136	Fsp³:	0.269
MCE-18:	22.0 ? 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:	1
Colloidal aggregators:	0.957	Fluc inhibitor:	0.42 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.899 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.765 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.21	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149	MDCK Permeability:	-4.834
Pgp-inhibitor:	0.927	Pgp-substrate:	0.038
PAMPA:	0.044 ? 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):	0.017
20% Bioavailability (F20%):	0.866	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.847
Plasma Protein Binding (PPB):	97.564%	Volume Distribution (VD):	-0.009
Fu:	2.128% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.968
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.987
BSEP inhibitor:	0.971

ADMET: Metabolism

CYP1A2-inhibitor:	0.112	CYP1A2-substrate:	0.279
CYP2C19-inhibitor:	0.062	CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.268	CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.998	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.992
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

6.333

Half-life (T1/2):

1.269

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.601
Human Hepatotoxicity (H-HT):	0.598	Drug-induced Liver Injury (DILI):	0.81
AMES Toxicity:	0.246	Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.788	Skin Sensitization:	0.95
Carcinogencity:	0.516	Eye Corrosion:	0.002
Eye Irritation:	0.936	Respiratory Toxicity:	0.938
Drug-induced Neurotoxicity:	0.056	Ototoxicity:	0.309
Hematotoxicity:	0.11	Drug-induced Nephrotoxicity:	0.088
Genotoxicity:	0.982	RPMI-8226 Immunitoxicity:	0.083
A549 Cytotoxicity:	0.573	Hek293 Cytotoxicity:	0.723
BCF:	2.107 ? 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:	5.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.695 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.271 ? 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
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15165133]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO27089	Nectandra glabrescens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28584	Euphorbia indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27589	Artemisia lehmanniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29149	Zexmenia phyllocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27280	Stachys spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27478	Geodia japonica	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27071	Spirastrella coccinea	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27147	Habenaria repens	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27368	Sinularia mayi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27478	Geodia japonica	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29149	Zexmenia phyllocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27147	Habenaria repens	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27280	Stachys spectabilis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27589	Artemisia lehmanniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27368	Sinularia mayi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28803	Artocarpus chama	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28584	Euphorbia indica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27089	Nectandra glabrescens	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27071	Spirastrella coccinea	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27320	Morus notabilis	Species	Moraceae	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

Activity Type	# Activity
Cell line	2

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
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	513.55	%	PMID[21737271]
NPT520	Cell line	3T3-L1	Mus musculus	Activity	=	305.32	%	PMID[21737271]

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 NPC80534 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	18807
0.1-0.2	27079
0.2-0.3	3099
0.3-0.4	774
0.4-0.5	79
0.5-0.6	14
0.6-0.7	3
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
0.8382	Intermediate Similarity	NPC56786
0.6104	Remote Similarity	NPC259632
0.6098	Remote Similarity	NPC133392
0.6098	Remote Similarity	NPC273843
0.5897	Remote Similarity	NPC97255
0.5789	Remote Similarity	NPC158874
0.575	Remote Similarity	NPC269285
0.5732	Remote Similarity	NPC300727
0.5714	Remote Similarity	NPC153512
0.5542	Remote Similarity	NPC13408
0.5529	Remote Similarity	NPC470460
0.5488	Remote Similarity	NPC488731
0.5479	Remote Similarity	NPC286342
0.5366	Remote Similarity	NPC470458
0.5342	Remote Similarity	NPC103342
0.5233	Remote Similarity	NPC470461
0.5135	Remote Similarity	NPC184536
0.5067	Remote Similarity	NPC59951

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC80534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4222
0.1-0.2	4875
0.2-0.3	48
0.3-0.4	5
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