NPASS Compound

Natural Product: NPC236004

Natural Product ID	NPC236004
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Moluccensin I
IUPAC Name	n.a.
Synonyms	Moluccensin I
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076925
PubChem CID	46184328
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 76 81 0 0 0 0 0 0 0 0999 V2000 -0.4635 -11.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2865 -10.5199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4635 -9.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9635 -9.2208 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2865 -7.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0365 -6.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -7.5044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -9.0044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4635 -6.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0082 -5.3529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0982 -5.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5128 -4.8574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6521 -5.8331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3767 -7.3076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0667 -5.3344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5444 -2.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9352 -3.0224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8994 -1.8734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1045 -0.6013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8853 -6.1998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2135 -13.1179 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8355 -12.5689 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7626 -11.0689 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2304 -9.0876 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0126 -7.1718 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4599 -6.7275 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -10.5044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -9.0044 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7612 -9.1873 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8980 -6.1842 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2135 -7.9218 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4836 -5.5097 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5049 -3.9434 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1650 -6.8447 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -4.4101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0363 -5.3695 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9673 -2.2864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5230 -3.6951 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9024 -6.6223 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4814 -4.8356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5655 -6.7490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7441 -3.8695 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3808 -3.1841 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7010 -1.8481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5230 1.0971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5025 -3.5396 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2981 -4.4779 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6664 0.7895 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7054 -1.6620 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7877 0.1013 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4328 -2.7879 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4128 -5.9137 0.0000 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 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 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 21 27 1 6 27 28 1 0 17 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 16 39 1 6 10 40 1 6 11 6 1 0 18 13 1 0 38 34 2 0 22 7 1 0 21 10 1 0 33 16 1 0 1 41 1 0 1 42 1 0 1 43 1 0 5 44 1 0 5 45 1 0 6 46 1 1 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 9 51 1 0 12 52 1 0 12 53 1 0 12 54 1 0 13 55 1 6 14 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 22 60 1 6 26 61 1 0 26 62 1 0 26 63 1 0 28 64 1 0 28 65 1 0 28 66 1 0 29 67 1 0 29 68 1 0 33 69 1 1 35 70 1 0 36 71 1 0 38 72 1 0 39 73 1 0 39 74 1 0 39 75 1 0 40 76 1 0 M END

Standard InCHIKey	DXAWUJPEJQPCGT-IQXSIFHKSA-N
Standard InCHI	InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3/t17-,19-,24-,25-,26+,27-,28+,29+,30+/m0/s1
SMILES	COC(=O)C[C@H]1[C@]2(C)C[C@]3([C@]1(C)[C@H]1CC[C@@]4(C(=C1C(=O)[C@]3([C@H]2OC(=O)C)OC)CC(=O)O[C@H]4c1ccoc1)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	556.23	Volume:	545.544 ? Van der Waals volume.
Dense:	1.02	LogP:	1.732 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.978 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.662 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	138.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.425	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.199	Fsp³:	0.667
MCE-18:	154.88 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.102	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.056	Promiscuous compounds:	0.346

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.444	MDCK Permeability:	-4.923
Pgp-inhibitor:	0.554	Pgp-substrate:	0.091
PAMPA:	0.441 ? 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):	0.016
20% Bioavailability (F20%):	0.072	30% Bioavailability (F30%):	0.553
50% Bioavailability (F50%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128	MRP1:	0.903
Plasma Protein Binding (PPB):	63.902%	Volume Distribution (VD):	-0.196
Fu:	35.212% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.987
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.318
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.105	CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.032	CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.237	CYP3A4-substrate:	0.977
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.923
HLM stability:	0.941 ? 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):

7.634

Half-life (T1/2):

1.335

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.234
Human Hepatotoxicity (H-HT):	0.431	Drug-induced Liver Injury (DILI):	0.577
AMES Toxicity:	0.275	Rat Oral Acute Toxicity:	0.613
Maximum Recommended Daily Dose:	0.908	Skin Sensitization:	0.632
Carcinogencity:	0.78	Eye Corrosion:	0.0
Eye Irritation:	0.347	Respiratory Toxicity:	0.338
Drug-induced Neurotoxicity:	0.188	Ototoxicity:	0.499
Hematotoxicity:	0.16	Drug-induced Nephrotoxicity:	0.712
Genotoxicity:	0.955	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.005	Hek293 Cytotoxicity:	0.085
BCF:	0.703 ? 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:	3.651 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.921 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.254 ? 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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	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
IC50	6
MIC	2
Activity	2

Activity Type	# Activity
Cell line	3
Organism	4
Non-molecular	2
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
NPT845	Cell line	BT-474	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[16202584]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[12825955]
NPT323	Cell line	SW-620	Homo sapiens	IC50	>	10.0	ug.mL-1	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[20112995]
NPT4025	Organism	Staphylococcus hominis	Staphylococcus hominis	MIC	=	256.0	ug.mL-1	PMID[12398543]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	223.0	ug.mL-1	PMID[12398543]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	10.7	%	DOI[10.1007/s00044-013-0798-7]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	28.7	%	DOI[10.1039/C2MD20272G]
NPT2	Others	Unspecified	n.a.	IC50	>	27000.0	nM	PubChem BioAssay data set

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 NPC236004 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	10280
0.1-0.2	37923
0.2-0.3	1431
0.3-0.4	177
0.4-0.5	34
0.5-0.6	8
0.6-0.7	4
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
0.6977	Remote Similarity	NPC165218
0.6404	Remote Similarity	NPC478178
0.6154	Remote Similarity	NPC478177
0.6	Remote Similarity	NPC94763
0.5955	Remote Similarity	NPC292389
0.573	Remote Similarity	NPC469503
0.5652	Remote Similarity	NPC469338
0.5532	Remote Similarity	NPC469849
0.5444	Remote Similarity	NPC178932
0.5341	Remote Similarity	NPC142113
0.5104	Remote Similarity	NPC69028
0.5102	Remote Similarity	NPC329180

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC236004 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3852
0.1-0.2	5270
0.2-0.3	28
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