NPASS Compound

Natural Product: NPC107646

Natural Product ID	NPC107646
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dihydrogedunin
IUPAC Name	n.a.
Synonyms	1,2-Dihydrogedunin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL462902
PubChem CID	21596330
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 3D 71 76 0 0 0 0 0 0 0 0999 V2000 -0.3501 -5.2934 -0.6511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8019 -4.0306 0.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3855 -4.0755 1.1516 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6007 -2.7898 -0.5206 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9970 -1.5647 0.0645 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0541 -0.9339 -0.7537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3817 0.4826 -0.4358 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8230 0.8217 -0.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7486 -0.3635 -0.3070 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2737 1.6104 -1.6218 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0950 1.7239 0.7696 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0054 1.5007 1.5421 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2154 2.9092 0.9428 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7592 2.5371 0.7072 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5791 1.0146 0.7665 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1578 0.7347 0.4119 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1962 -0.7292 0.3778 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7202 -1.2127 1.7381 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3390 -0.8764 -0.5716 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8999 -2.2290 -0.3814 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5487 -1.6831 -1.6685 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7945 -1.3781 -2.4212 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9150 -1.5883 -3.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9419 -0.8310 -1.8049 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6999 -0.3657 -0.4751 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3205 0.2637 -0.4948 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2210 1.1643 0.6675 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8693 1.5752 1.1222 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2331 1.0957 -1.7783 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7475 0.5536 -0.0126 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3103 0.5312 1.2764 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2400 1.5399 1.2762 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2527 2.1278 0.1072 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3763 1.5732 -0.6998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0651 0.5482 2.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3967 -5.0313 -1.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2154 -5.7515 -1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0961 -5.9644 0.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4873 -1.8681 1.0399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9945 -1.5404 -0.6231 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7870 -1.0948 -1.8395 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9440 1.0866 -1.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5899 -1.0297 0.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7861 0.0650 -0.1739 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8110 -0.9003 -1.2947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0032 2.3853 -1.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3434 2.1566 -1.9511 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5559 0.9484 -2.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3994 3.3314 1.9391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4790 3.6790 0.1700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3593 2.9663 -0.2126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2118 2.9132 1.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0682 1.0894 -0.6642 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6274 -1.8661 1.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0188 -1.8640 2.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9970 -0.4216 2.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -2.2890 -2.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6649 -1.2314 0.2316 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7768 2.1105 0.3833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8669 0.7526 1.4991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7354 1.5871 2.2310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6398 2.6422 0.8190 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1427 1.0395 -2.3938 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4297 0.6740 -2.4565 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0516 2.1672 -1.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 -0.1369 2.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8994 1.8551 2.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2157 1.8994 -1.7203 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5104 1.3845 2.6901 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3160 0.0906 2.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8980 -0.1972 2.0120 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 8 11 1 0 11 12 2 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 1 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 6 25 30 1 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 15 35 1 1 17 5 1 0 21 19 1 0 34 30 2 0 15 7 1 0 28 16 1 0 26 19 1 0 1 36 1 0 1 37 1 0 1 38 1 0 5 39 1 1 6 40 1 0 6 41 1 0 7 42 1 6 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 16 53 1 6 18 54 1 0 18 55 1 0 18 56 1 0 21 57 1 6 25 58 1 1 27 59 1 0 27 60 1 0 28 61 1 0 28 62 1 0 29 63 1 0 29 64 1 0 29 65 1 0 31 66 1 0 32 67 1 0 34 68 1 0 35 69 1 0 35 70 1 0 35 71 1 0 M END

Standard InCHIKey	ROWFSYNHZPRCKO-BHAPSIHVSA-N
Standard InCHI	InChI=1S/C28H36O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h9,12,14,17-18,20-22H,7-8,10-11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
SMILES	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)CC[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)c1ccoc1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	484.25	Volume:	489.855 ? Van der Waals volume.
Dense:	0.989	LogP:	2.375 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.523 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.882 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	31.0
TPSA:	95.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.44	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.449	Fsp³:	0.75
MCE-18:	193.714 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.572	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.18	Promiscuous compounds:	0.135

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.064	MDCK Permeability:	-4.682
Pgp-inhibitor:	0.988	Pgp-substrate:	0.009
PAMPA:	0.775 ? 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):	0.002
20% Bioavailability (F20%):	0.149	30% Bioavailability (F30%):	0.107
50% Bioavailability (F50%):	0.787

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	0.973
Plasma Protein Binding (PPB):	85.367%	Volume Distribution (VD):	0.255
Fu:	15.999% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.411
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.889	CYP2C19-substrate:	0.025
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.327
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.966
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.99 ? 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):

7.888

Half-life (T1/2):

0.677

ADMET: Toxicity

hERG Blockers:	0.088	hERG Blockers (10um):	0.345
Human Hepatotoxicity (H-HT):	0.689	Drug-induced Liver Injury (DILI):	0.9
AMES Toxicity:	0.529	Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.949	Skin Sensitization:	0.804
Carcinogencity:	0.84	Eye Corrosion:	0.002
Eye Irritation:	0.668	Respiratory Toxicity:	0.809
Drug-induced Neurotoxicity:	0.427	Ototoxicity:	0.391
Hematotoxicity:	0.503	Drug-induced Nephrotoxicity:	0.683
Genotoxicity:	0.992	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.072	Hek293 Cytotoxicity:	0.271
BCF:	0.881 ? 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:	3.738 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.616 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.083 ? 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
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

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	2
IC50	3
Activity	3

Activity Type	# Activity
Cell line	1
Individual protein	2
Organism	5

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	62.45	%	PMID[23368996]
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	35.54	%	PMID[11374971]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell line	KB	Homo sapiens	Activity	=	71.0	%	PMID[22940450]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[21684166]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.84	ug.mL-1	PMID[21531558]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	<	0.39	%	PMID[19618898]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	2.38	%	PMID[24878195]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.63	ug.mL-1	PMID[8377014]

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 NPC107646 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	14227
0.1-0.2	33036
0.2-0.3	2328
0.3-0.4	206
0.4-0.5	23
0.5-0.6	26
0.6-0.7	6
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
0.7671	Intermediate Similarity	NPC335761
0.7606	Intermediate Similarity	NPC604270
0.7237	Intermediate Similarity	NPC209364
0.7237	Intermediate Similarity	NPC605015
0.7162	Intermediate Similarity	NPC602263
0.7143	Intermediate Similarity	NPC475381
0.6974	Remote Similarity	NPC134254
0.6883	Remote Similarity	NPC302369
0.642	Remote Similarity	NPC126723
0.6329	Remote Similarity	NPC470939
0.6125	Remote Similarity	NPC39986
0.6024	Remote Similarity	NPC237155
0.5976	Remote Similarity	NPC286722
0.5882	Remote Similarity	NPC473753
0.5875	Remote Similarity	NPC60973
0.5875	Remote Similarity	NPC605384
0.5862	Remote Similarity	NPC302392
0.5833	Remote Similarity	NPC96443
0.5833	Remote Similarity	NPC472653
0.5833	Remote Similarity	NPC473473
0.5833	Remote Similarity	NPC290400
0.5833	Remote Similarity	NPC475295
0.5663	Remote Similarity	NPC5079
0.5647	Remote Similarity	NPC473766
0.5465	Remote Similarity	NPC305016
0.5455	Remote Similarity	NPC271235
0.5444	Remote Similarity	NPC469846
0.5412	Remote Similarity	NPC263265
0.5393	Remote Similarity	NPC25255
0.5217	Remote Similarity	NPC472651
0.519	Remote Similarity	NPC474379
0.5172	Remote Similarity	NPC609366
0.5172	Remote Similarity	NPC611370
0.5169	Remote Similarity	NPC193798
0.5169	Remote Similarity	NPC117986
0.5158	Remote Similarity	NPC472652
0.5111	Remote Similarity	NPC604177
0.5056	Remote Similarity	NPC611267

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC107646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4031
0.1-0.2	5067
0.2-0.3	52
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