NPASS Compound

Natural Product: NPC39462

Natural Product ID	NPC39462
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KPHSEIXOJZXLJE-UCWKWJRUSA-N
IUPAC Name	n.a.
Synonyms	24-Methylenepollinastanone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL226241
PubChem CID	44423599
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 76 80 0 0 0 0 0 0 0 0999 V2000 5.6025 -1.5650 0.7246 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2942 -0.2523 0.9827 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5707 -0.2205 0.1899 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3420 0.8359 0.6014 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6990 1.6755 -0.3434 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0458 0.9135 1.2611 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9468 1.5955 0.5396 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3502 1.0517 -0.6703 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2237 0.7985 -1.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3234 0.0073 -0.6521 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5934 -1.3285 -0.0614 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1931 -1.9817 -0.0009 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7676 -0.9510 -0.5633 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7139 -1.0988 -2.0604 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1441 -1.0178 0.0061 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1138 -1.7864 -0.9075 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3309 -2.0632 -0.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0786 -0.7739 0.0522 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3547 -0.9304 0.8646 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0308 0.4141 0.8189 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2004 0.5261 0.5550 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1980 1.5956 1.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9426 1.6397 0.2291 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2214 0.3254 0.4883 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5213 0.2261 1.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7718 0.2487 0.3790 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0912 1.5168 0.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7428 1.4742 -0.5381 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0110 0.2951 -0.0655 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0553 0.2270 1.4371 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8521 -1.7247 1.5266 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3737 -2.3621 0.7078 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0898 -1.4884 -0.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5711 -0.1275 2.0583 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1372 0.7276 0.2860 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3368 -0.3420 -0.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2268 -1.0970 0.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6649 1.5562 -0.8188 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1226 2.5222 -0.7000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2472 1.5907 2.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7448 -0.0298 1.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2005 1.8843 1.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3906 2.6429 0.3438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7425 1.9794 -1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5547 0.3859 -2.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9627 0.0011 -1.7602 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6673 1.6764 -2.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1113 -0.2109 -1.7463 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0919 -1.3800 0.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1845 -1.9891 -0.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1290 -2.8770 -0.6287 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0533 -2.2872 1.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0848 -1.8240 -2.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7108 -0.1629 -2.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6498 -1.6251 -2.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0929 -1.7191 0.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7341 -2.7861 -1.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4969 -1.1834 -1.7239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9501 -2.7961 -0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0164 -2.4462 0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4318 -0.5603 -1.0003 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0112 -1.6219 0.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1597 -1.2510 1.8890 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7395 2.5420 1.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8024 1.4664 2.1576 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2842 1.7453 -0.8008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3602 2.5115 0.6095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3649 1.1320 2.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 -0.7197 2.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0642 2.1649 0.9740 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7479 2.1152 -0.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7963 1.6001 -1.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1661 2.3885 -0.1992 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7384 -0.5491 1.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9358 -0.0544 1.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4323 1.1849 1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 24 23 1 1 24 25 1 0 26 25 1 1 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 10 1 0 29 13 1 0 26 15 1 0 24 18 1 0 26 24 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 6 9 45 1 0 9 46 1 0 9 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 14 53 1 0 14 54 1 0 14 55 1 0 15 56 1 1 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 18 61 1 6 19 62 1 0 19 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 25 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 28 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 M END

Standard InCHIKey	KPHSEIXOJZXLJE-UCWKWJRUSA-N
Standard InCHI	InChI=1S/C29H46O/c1-19(2)20(3)7-8-21(4)24-12-13-27(6)25-10-9-22-17-23(30)11-14-28(22)18-29(25,28)16-15-26(24,27)5/h19,21-22,24-25H,3,7-18H2,1-2,4-6H3/t21-,22+,24-,25+,26-,27+,28-,29+/m1/s1
SMILES	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4CC(=O)CC[C@]54C[C@@]35CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	410.35	Volume:	470.875 ? Van der Waals volume.
Dense:	0.871	LogP:	4.977 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.821 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.196 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	17.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.42	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.44	Fsp³:	0.897
MCE-18:	123.018 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.952	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.85	Promiscuous compounds:	0.167

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753	MDCK Permeability:	-4.887
Pgp-inhibitor:	0.659	Pgp-substrate:	0.0
PAMPA:	0.003 ? 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%):	0.061	30% Bioavailability (F30%):	0.731
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.333	MRP1:	0.294
Plasma Protein Binding (PPB):	95.167%	Volume Distribution (VD):	0.366
Fu:	5.768% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.966
BSEP inhibitor:	0.879

ADMET: Metabolism

CYP1A2-inhibitor:	0.044	CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.9	CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.005	CYP2C8-inhibitor:	1.0
HLM stability:	0.925 ? 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):

10.499

Half-life (T1/2):

0.203

ADMET: Toxicity

hERG Blockers:	0.122	hERG Blockers (10um):	0.432
Human Hepatotoxicity (H-HT):	0.539	Drug-induced Liver Injury (DILI):	0.07
AMES Toxicity:	0.261	Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.508	Skin Sensitization:	0.669
Carcinogencity:	0.807	Eye Corrosion:	0.038
Eye Irritation:	0.527	Respiratory Toxicity:	0.828
Drug-induced Neurotoxicity:	0.215	Ototoxicity:	0.516
Hematotoxicity:	0.562	Drug-induced Nephrotoxicity:	0.412
Genotoxicity:	0.542	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.131	Hek293 Cytotoxicity:	0.153
BCF:	2.89 ? 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:	4.882 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.704 ? 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
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10846753]
NPO33305	musa sapientum	Species	Musaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17503850]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8971	Ammocharis coranica	Species	Amaryllidaceae	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	4
IC50	1
Activity	2

Activity Type	# Activity
Cell line	1
Organism	5
Others	1

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	33.2	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	73.8	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	95.6	%	PMID[17503850]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	10.2	nM	PMID[17503850]
NPT2	Others	Unspecified	n.a.	Activity	=	1.5	n.a.	PMID[17503850]

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 NPC39462 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	30308
0.1-0.2	17946
0.2-0.3	1363
0.3-0.4	158
0.4-0.5	66
0.5-0.6	12
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
0.7308	Intermediate Similarity	NPC107704
0.7037	Intermediate Similarity	NPC189917
0.7037	Intermediate Similarity	NPC96812
0.6316	Remote Similarity	NPC195489
0.5893	Remote Similarity	NPC254509
0.569	Remote Similarity	NPC49168
0.569	Remote Similarity	NPC5046
0.5645	Remote Similarity	NPC47808
0.5614	Remote Similarity	NPC477857
0.5424	Remote Similarity	NPC168824
0.5254	Remote Similarity	NPC214770
0.5254	Remote Similarity	NPC477856
0.5246	Remote Similarity	NPC477858
0.5085	Remote Similarity	NPC255650
0.5082	Remote Similarity	NPC76518
0.5075	Remote Similarity	NPC146937

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC39462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7912
0.1-0.2	1190
0.2-0.3	46
0.3-0.4	2
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