NPASS Compound

Natural Product: NPC320026

Natural Product ID	NPC320026
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Meliasenin J
IUPAC Name	(5R,9R,10R,13S,14S,16S,17S)-17-[(E,2R)-6-hydroperoxy-6-methylhept-4-en-2-yl]-16-hydroxy-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms	Meliasenin J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1641918
PubChem CID	50908888
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 82 85 0 0 0 0 0 0 0 0999 V2000 8.3482 -1.8562 1.7625 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1780 -1.5349 1.3067 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2247 -1.0384 0.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8587 -0.6790 -0.4783 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8080 -0.7034 0.3189 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4440 -0.3245 -0.2502 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9046 0.8594 0.4986 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6000 1.3385 0.0386 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1372 2.5846 0.8345 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9009 3.6871 0.4754 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3143 2.7438 0.4586 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6743 1.4909 -0.3113 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3808 0.5082 0.2237 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1510 0.2998 1.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2738 -0.7410 -0.5494 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1225 -1.1130 -0.9658 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1838 -0.5067 -0.1163 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9937 0.9700 0.0246 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0317 1.6550 0.4291 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3511 1.1214 0.7624 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4907 -0.3414 0.5124 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5762 -0.7816 -0.6339 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8966 -0.0216 -1.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7014 -2.2735 -0.8396 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0698 -2.6918 -1.2565 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0868 -1.7776 -0.7325 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2074 -1.8480 -1.2618 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8975 -0.7920 0.3569 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8657 0.3571 0.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3601 -1.4822 1.6472 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5518 1.7039 -1.7703 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9996 1.9170 0.4091 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7715 -2.1244 -0.8867 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0691 0.2098 -0.0896 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2778 -2.4747 2.5309 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6939 -0.3873 -1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8770 -0.9778 1.3450 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5829 0.0166 -1.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8775 -1.2423 -0.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8651 0.5018 1.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7210 1.7309 -0.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2088 2.4641 1.9043 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7325 4.3810 1.1600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9727 2.9244 1.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3895 3.5932 -0.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0252 0.5249 2.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0149 -0.8155 1.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6968 0.8761 2.1003 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6820 -1.5646 0.1157 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9270 -0.6955 -1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2975 -0.9188 -2.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2032 -2.2298 -0.8519 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1663 -0.9311 0.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8980 2.7468 0.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1623 1.7265 0.2957 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5001 1.2931 1.8698 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0364 -0.8555 1.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0472 1.0460 -1.7330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1127 -0.1370 -2.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8277 -0.4206 -2.3377 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3651 -2.7876 0.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0054 -2.5861 -1.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2435 -3.7590 -0.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1337 -2.7451 -2.3832 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8994 0.9634 1.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8786 -0.1200 0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6817 0.9041 -0.7879 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0063 -0.8201 2.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9173 -2.3974 1.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4812 -1.7457 2.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1776 2.7062 -2.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1171 0.9866 -2.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 1.6180 -2.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9072 2.6845 1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9764 2.3242 -0.6076 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9585 1.3777 0.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0970 -2.9771 -0.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9119 -1.6700 -1.8899 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7194 -2.4694 -0.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0197 0.5713 -1.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6571 0.9954 0.5603 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1234 -0.0438 0.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 12 31 1 6 7 32 1 0 3 33 1 0 3 34 1 0 13 8 1 0 22 17 1 0 18 12 1 0 28 21 1 0 1 35 1 0 4 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 7 40 1 1 8 41 1 6 9 42 1 1 10 43 1 0 11 44 1 0 11 45 1 0 14 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 16 51 1 0 16 52 1 0 17 53 1 1 19 54 1 0 20 55 1 0 20 56 1 0 21 57 1 1 23 58 1 0 23 59 1 0 23 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 25 64 1 0 29 65 1 0 29 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 33 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 M END

Standard InCHIKey	KXEPOJYGPBBQJS-LKJGIETFSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-19(10-9-15-26(2,3)34-33)25-22(31)18-30(8)21-11-12-23-27(4,5)24(32)14-16-28(23,6)20(21)13-17-29(25,30)7/h9,11,15,19-20,22-23,25,31,33H,10,12-14,16-18H2,1-8H3/b15-9+/t19-,20+,22+,23+,25-,28-,29+,30-/m1/s1
SMILES	OOC(/C=C/C[C@H]([C@@H]1[C@@H](O)C[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	520.462 ? Van der Waals volume.
Dense:	0.908	LogP:	4.332 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.913 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.329 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.257	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.176	Fsp³:	0.833
MCE-18:	85.309 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.912	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.335	Promiscuous compounds:	0.178

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.132	MDCK Permeability:	-4.936
Pgp-inhibitor:	0.998	Pgp-substrate:	0.0
PAMPA:	0.03 ? 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):	0.001
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.057
50% Bioavailability (F50%):	0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.645
Plasma Protein Binding (PPB):	93.3%	Volume Distribution (VD):	0.194
Fu:	5.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.287
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.7	CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.995
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.794 ? 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):

10.796

Half-life (T1/2):

0.481

ADMET: Toxicity

hERG Blockers:	0.097	hERG Blockers (10um):	0.204
Human Hepatotoxicity (H-HT):	0.688	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.41	Rat Oral Acute Toxicity:	0.404
Maximum Recommended Daily Dose:	0.778	Skin Sensitization:	0.979
Carcinogencity:	0.907	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.399
Drug-induced Neurotoxicity:	0.321	Ototoxicity:	0.784
Hematotoxicity:	0.754	Drug-induced Nephrotoxicity:	0.711
Genotoxicity:	0.978	RPMI-8226 Immunitoxicity:	0.145
A549 Cytotoxicity:	0.15	Hek293 Cytotoxicity:	0.793
BCF:	1.567 ? 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:	3.905 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.494 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.771 ? 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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

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	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
NPT1045	Cell line	U2OS	Homo sapiens	IC50	=	14.3	ug.mL-1	PMID[20961091]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[20961091]

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 NPC320026 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	22808
0.1-0.2	23758
0.2-0.3	2962
0.3-0.4	262
0.4-0.5	39
0.5-0.6	10
0.6-0.7	7
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
0.803	Intermediate Similarity	NPC57416
0.7903	Intermediate Similarity	NPC2983
0.7302	Intermediate Similarity	NPC82902
0.7273	Intermediate Similarity	NPC317590
0.7231	Intermediate Similarity	NPC318390
0.7077	Intermediate Similarity	NPC469994
0.6769	Remote Similarity	NPC474218
0.6567	Remote Similarity	NPC171441
0.6338	Remote Similarity	NPC107243
0.6301	Remote Similarity	NPC322063
0.6197	Remote Similarity	NPC154101
0.6027	Remote Similarity	NPC218383
0.6027	Remote Similarity	NPC474327
0.5942	Remote Similarity	NPC470052
0.5694	Remote Similarity	NPC486521
0.5694	Remote Similarity	NPC262870
0.5588	Remote Similarity	NPC470078
0.5493	Remote Similarity	NPC90652
0.5493	Remote Similarity	NPC155255
0.5493	Remote Similarity	NPC260992
0.5278	Remote Similarity	NPC470417
0.527	Remote Similarity	NPC471224
0.507	Remote Similarity	NPC247220

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7513
0.1-0.2	1562
0.2-0.3	74
0.3-0.4	1
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