NPASS Compound

Natural Product: NPC245122

Natural Product ID	NPC245122
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ascofuranone
IUPAC Name	5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde
Synonyms	Ascofuranone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL133046
PubChem CID	6434242
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 58 59 0 0 0 0 0 0 0 0999 V2000 1.2934 1.4756 -1.9678 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1226 0.8539 -0.6499 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0577 0.9961 0.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3191 1.7324 0.1320 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5015 0.8399 0.3665 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9162 -0.0392 -0.5776 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0138 -0.8808 -0.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4101 -1.8032 -1.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2344 -1.4430 -2.3073 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7248 -0.8407 0.8061 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8964 -1.7316 1.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3086 0.0505 1.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2191 0.8805 1.5657 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8096 1.7745 2.5449 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2012 0.1072 3.2728 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.2639 -0.1469 -1.7961 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1037 0.0574 -0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 0.9207 -0.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5736 0.1564 -0.1259 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5478 -0.0211 -1.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 0.5734 -2.3629 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7903 -0.7779 -0.7277 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9524 0.1697 -0.9242 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9298 -0.3918 0.0669 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1331 -0.3797 -0.0238 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0475 -0.9386 1.1354 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7641 0.2069 2.1013 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6891 -2.0946 1.8583 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8518 -1.2805 0.5391 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3072 1.6878 -2.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6034 2.3607 -2.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8942 0.7243 -2.7146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8859 0.5119 1.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3306 2.4668 0.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4392 2.3499 -0.7558 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0071 -2.8009 -1.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0779 -2.3111 0.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7707 -1.0747 1.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7261 -2.4326 1.8659 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1749 1.4670 3.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5972 -0.9121 -1.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1688 -0.7640 -1.0669 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0113 -0.3926 0.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3974 1.4238 -1.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2373 1.7232 0.3260 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7151 -0.2872 0.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3823 0.2747 -2.7860 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1373 0.1562 -3.0810 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5404 1.6612 -2.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8737 -1.5575 -1.5176 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3342 0.1731 -1.9486 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6763 1.1786 -0.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6756 0.3254 2.2782 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2739 0.0415 3.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1152 1.1840 1.6938 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5403 -2.9977 1.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7654 -1.8693 1.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1531 -2.2296 2.8040 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 2 0 6 7 1 0 7 8 1 0 8 9 2 0 7 10 2 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 12 15 1 0 6 16 1 0 2 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 26 28 1 0 26 29 1 0 13 5 1 0 29 22 1 0 1 30 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 8 36 1 0 11 37 1 0 11 38 1 0 11 39 1 0 14 40 1 0 16 41 1 0 17 42 1 0 17 43 1 0 18 44 1 0 18 45 1 0 19 46 1 0 21 47 1 0 21 48 1 0 21 49 1 0 22 50 1 6 23 51 1 0 23 52 1 0 27 53 1 0 27 54 1 0 27 55 1 0 28 56 1 0 28 57 1 0 28 58 1 0 M END

Standard InCHIKey	VGYPZLGWVQQOST-JUERRSSISA-N
Standard InCHI	InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
SMILES	C/C(=CCc1c(c(C=O)c(C)c(c1O)Cl)O)/CC/C=C(C)/[C@@H]1CC(=O)C(C)(C)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	420.17	Volume:	429.958 ? Van der Waals volume.
Dense:	0.977	LogP:	5.55 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.253 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	15.0
TPSA:	83.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.466	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.004	Fsp³:	0.478
MCE-18:	60.353 ? 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:	0.954	Fluc inhibitor:	0.02 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.332 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.63 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.575	Promiscuous compounds:	0.129

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.285	MDCK Permeability:	-4.834
Pgp-inhibitor:	0.997	Pgp-substrate:	0.0
PAMPA:	0.05 ? 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):	0.008
20% Bioavailability (F20%):	0.025	30% Bioavailability (F30%):	0.267
50% Bioavailability (F50%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.927
Plasma Protein Binding (PPB):	97.828%	Volume Distribution (VD):	0.035
Fu:	1.855% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.101
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.043	CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.885	CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.68	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.395	CYP3A4-substrate:	0.984
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.974
HLM stability:	0.998 ? 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):

3.524

Half-life (T1/2):

1.267

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.478
Human Hepatotoxicity (H-HT):	0.872	Drug-induced Liver Injury (DILI):	0.896
AMES Toxicity:	0.408	Rat Oral Acute Toxicity:	0.77
Maximum Recommended Daily Dose:	0.88	Skin Sensitization:	0.983
Carcinogencity:	0.287	Eye Corrosion:	0.0
Eye Irritation:	0.448	Respiratory Toxicity:	0.976
Drug-induced Neurotoxicity:	0.606	Ototoxicity:	0.532
Hematotoxicity:	0.412	Drug-induced Nephrotoxicity:	0.592
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.288
A549 Cytotoxicity:	0.794	Hek293 Cytotoxicity:	0.867
BCF:	1.769 ? 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:	5.013 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.344 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.998 ? 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
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]
NPO32557	aschochyta viciae	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9084049]
NPO32963	Acremonium sp.	Species	n.a.	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
MEC	1
IC50	10
Ki	1
IC100	1
MIC	22
Inhibition	1

Activity Type	# Activity
Individual protein	1
Cell line	7
Single protein	4
Organism	23
Unchecked	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT26630	Single protein	Alternative oxidase, mitochondrial	Trypanosoma brucei brucei	IC50	=	2.0	nM	PMID[30258542]
NPT26630	Single protein	Alternative oxidase, mitochondrial	Trypanosoma brucei brucei	Ki	=	0.13	nM	PMID[29107420]
NPT21852	Single protein	Dihydroorotate dehydrogenase	Homo sapiens	IC50	=	37.5	nM	PMID[32652407]
NPT21852	Single protein	Dihydroorotate dehydrogenase	Homo sapiens	IC50	=	5400.0	nM	PMID[34516133]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	MEC	=	3.0	uM	PMID[12954063]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4727	Cell line	C3H 10T1/2	Mus musculus	IC50	=	3200.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	IC50	=	900.0	nM	PMID[34781681]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	900.0	nM	PMID[34781681]
NPT784	Cell line	MDA-MB-468	Homo sapiens	IC50	=	7100.0	nM	PMID[34516133]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	5200.0	nM	PMID[34516133]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	=	100.0	%	PMID[35178188]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	16.0	ug.mL-1	PMID[34781681]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	32.0	ug.mL-1	PMID[34781681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[34781681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[34781681]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4.0	ug.mL-1	PMID[34781681]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	128.0	ug.mL-1	PMID[34781681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[34781681]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	128.0	ug.mL-1	PMID[34781681]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[34781681]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC100	=	0.03	uM	PMID[11844671]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	250000.0	nM	PMID[29544150]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	30.0	nM	PMID[30258542]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	=	30000.0	nM	PMID[29544150]

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 NPC245122 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	12185
0.1-0.2	36340
0.2-0.3	1237
0.3-0.4	83
0.4-0.5	9
0.5-0.6	1
0.6-0.7	1
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
0.7742	Intermediate Similarity	NPC603117
0.7018	Intermediate Similarity	NPC208891
0.6061	Remote Similarity	NPC602881
0.5286	Remote Similarity	NPC131390

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC245122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4521
0.1-0.2	4608
0.2-0.3	21
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