NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.17
Volume:	292.561
LogP:	2.897
LogD:	2.679
LogS:	-3.338
# Rotatable Bonds:	7
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.52
Synthetic Accessibility Score:	4.269
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.513
MDCK Permeability:	2.689014218049124e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.831
30% Bioavailability (F30%):	0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	89.77163696289062%
Volume Distribution (VD):	0.548
Pgp-substrate:	5.466970443725586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.555
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.491
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.803
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	7.674
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.381
Drug-inuced Liver Injury (DILI):	0.72
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.854
Skin Sensitization:	0.88
Carcinogencity:	0.9
Eye Corrosion:	0.006
Eye Irritation:	0.168
Respiratory Toxicity:	0.322

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC470688

Natural Product ID:	NPC470688
*Common Name:**	(-)-Plakilactone C
IUPAC Name:	(5R)-3,5-diethyl-5-[(E,2R)-2-ethyl-5-oxohex-3-enyl]furan-2-one
Synonyms:	(-)-Plakilactone C
Standard InCHIKey:	YKBFZCLRVPKNRE-FTJFNGAWSA-N
Standard InCHI:	InChI=1S/C16H24O3/c1-5-13(9-8-12(4)17)10-16(7-3)11-14(6-2)15(18)19-16/h8-9,11,13H,5-7,10H2,1-4H3/b9-8+/t13-,16+/m0/s1
SMILES:	CCC1=CC(OC1=O)(CC)CC(CC)C=CC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2178586
PubChem CID:	71451878
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33167	plakinastrella mamillaris	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934537]

☑ 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	NP ID	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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	EC50	=	2000.0	nM	PMID[520161]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC470688 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1874
0.2-0.3	10699
0.3-0.4	16906
0.4-0.5	7545
0.5-0.6	4159
0.6-0.7	1191
0.7-0.8	144
0.8-0.85	10
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC265574
0.8788	High Similarity	NPC470693
0.8615	High Similarity	NPC191233
0.8462	Intermediate Similarity	NPC220766
0.8358	Intermediate Similarity	NPC470256
0.8286	Intermediate Similarity	NPC15499
0.8286	Intermediate Similarity	NPC259599
0.8286	Intermediate Similarity	NPC474758
0.8286	Intermediate Similarity	NPC117746
0.8286	Intermediate Similarity	NPC294434
0.8209	Intermediate Similarity	NPC21998
0.8169	Intermediate Similarity	NPC329852
0.8143	Intermediate Similarity	NPC287878
0.8116	Intermediate Similarity	NPC67183
0.8088	Intermediate Similarity	NPC276290
0.8	Intermediate Similarity	NPC151648
0.8	Intermediate Similarity	NPC151919
0.7971	Intermediate Similarity	NPC232812
0.7945	Intermediate Similarity	NPC57744
0.7941	Intermediate Similarity	NPC194871
0.7941	Intermediate Similarity	NPC472266
0.7879	Intermediate Similarity	NPC474658
0.7879	Intermediate Similarity	NPC155849
0.7857	Intermediate Similarity	NPC64234
0.7857	Intermediate Similarity	NPC37929
0.7838	Intermediate Similarity	NPC128276
0.7833	Intermediate Similarity	NPC148056
0.7826	Intermediate Similarity	NPC218477
0.7808	Intermediate Similarity	NPC123360
0.7808	Intermediate Similarity	NPC27205
0.7794	Intermediate Similarity	NPC248125
0.7778	Intermediate Similarity	NPC476355
0.7778	Intermediate Similarity	NPC470686
0.7763	Intermediate Similarity	NPC325031
0.7763	Intermediate Similarity	NPC42470
0.7761	Intermediate Similarity	NPC34883
0.7746	Intermediate Similarity	NPC163003
0.7746	Intermediate Similarity	NPC257618
0.7733	Intermediate Similarity	NPC178277
0.7714	Intermediate Similarity	NPC476591
0.7714	Intermediate Similarity	NPC88877
0.7703	Intermediate Similarity	NPC180290
0.7681	Intermediate Similarity	NPC203335
0.7667	Intermediate Similarity	NPC27264
0.7619	Intermediate Similarity	NPC478117
0.7612	Intermediate Similarity	NPC210303
0.7612	Intermediate Similarity	NPC44343
0.7612	Intermediate Similarity	NPC217940
0.7612	Intermediate Similarity	NPC179087
0.7612	Intermediate Similarity	NPC322457
0.76	Intermediate Similarity	NPC471220
0.76	Intermediate Similarity	NPC267231
0.76	Intermediate Similarity	NPC253749
0.7576	Intermediate Similarity	NPC79756
0.7536	Intermediate Similarity	NPC116013
0.7534	Intermediate Similarity	NPC140287
0.7532	Intermediate Similarity	NPC471325
0.75	Intermediate Similarity	NPC469617
0.75	Intermediate Similarity	NPC15912
0.75	Intermediate Similarity	NPC291712
0.75	Intermediate Similarity	NPC270126
0.7467	Intermediate Similarity	NPC471225
0.7465	Intermediate Similarity	NPC151481
0.7436	Intermediate Similarity	NPC85772
0.7436	Intermediate Similarity	NPC173609
0.7432	Intermediate Similarity	NPC244166
0.7424	Intermediate Similarity	NPC286189
0.7397	Intermediate Similarity	NPC12815
0.7397	Intermediate Similarity	NPC295633
0.7397	Intermediate Similarity	NPC238948
0.7397	Intermediate Similarity	NPC269206
0.7397	Intermediate Similarity	NPC276336
0.7397	Intermediate Similarity	NPC474705
0.7397	Intermediate Similarity	NPC58956
0.7397	Intermediate Similarity	NPC215745
0.7391	Intermediate Similarity	NPC182794
0.7391	Intermediate Similarity	NPC133904
0.7375	Intermediate Similarity	NPC215364
0.7368	Intermediate Similarity	NPC93763
0.7368	Intermediate Similarity	NPC108816
0.7368	Intermediate Similarity	NPC99182
0.7368	Intermediate Similarity	NPC299235
0.7361	Intermediate Similarity	NPC469660
0.7353	Intermediate Similarity	NPC68110
0.7333	Intermediate Similarity	NPC40353
0.7333	Intermediate Similarity	NPC473223
0.7313	Intermediate Similarity	NPC19241
0.7308	Intermediate Similarity	NPC59994
0.7308	Intermediate Similarity	NPC78677
0.7273	Intermediate Similarity	NPC472965
0.7273	Intermediate Similarity	NPC63649
0.7273	Intermediate Similarity	NPC264227
0.7273	Intermediate Similarity	NPC471299
0.726	Intermediate Similarity	NPC319163
0.726	Intermediate Similarity	NPC67076
0.726	Intermediate Similarity	NPC84038
0.726	Intermediate Similarity	NPC186531
0.725	Intermediate Similarity	NPC149869
0.725	Intermediate Similarity	NPC475100
0.7237	Intermediate Similarity	NPC141789
0.7237	Intermediate Similarity	NPC476028
0.7237	Intermediate Similarity	NPC65603
0.7237	Intermediate Similarity	NPC10572
0.7237	Intermediate Similarity	NPC171204
0.7237	Intermediate Similarity	NPC473825
0.7237	Intermediate Similarity	NPC41780
0.7237	Intermediate Similarity	NPC320630
0.7237	Intermediate Similarity	NPC116177
0.7237	Intermediate Similarity	NPC97516
0.7237	Intermediate Similarity	NPC7563
0.7237	Intermediate Similarity	NPC68156
0.7237	Intermediate Similarity	NPC187568
0.7231	Intermediate Similarity	NPC96663
0.7231	Intermediate Similarity	NPC245002
0.7222	Intermediate Similarity	NPC476059
0.7222	Intermediate Similarity	NPC473603
0.7215	Intermediate Similarity	NPC221231
0.7215	Intermediate Similarity	NPC94200
0.7215	Intermediate Similarity	NPC471326
0.7215	Intermediate Similarity	NPC26624
0.72	Intermediate Similarity	NPC68624
0.72	Intermediate Similarity	NPC226669
0.72	Intermediate Similarity	NPC138408
0.72	Intermediate Similarity	NPC155587
0.72	Intermediate Similarity	NPC193351
0.7195	Intermediate Similarity	NPC160138
0.7188	Intermediate Similarity	NPC474127
0.7183	Intermediate Similarity	NPC225272
0.7179	Intermediate Similarity	NPC47747
0.7179	Intermediate Similarity	NPC281132
0.7167	Intermediate Similarity	NPC8610
0.7167	Intermediate Similarity	NPC262558
0.7164	Intermediate Similarity	NPC133600
0.7162	Intermediate Similarity	NPC222244
0.7162	Intermediate Similarity	NPC16349
0.716	Intermediate Similarity	NPC189311
0.716	Intermediate Similarity	NPC261380
0.7143	Intermediate Similarity	NPC170167
0.7143	Intermediate Similarity	NPC184737
0.7125	Intermediate Similarity	NPC118423
0.7125	Intermediate Similarity	NPC193198
0.7125	Intermediate Similarity	NPC250315
0.7125	Intermediate Similarity	NPC16488
0.7125	Intermediate Similarity	NPC475947
0.7123	Intermediate Similarity	NPC316029
0.7123	Intermediate Similarity	NPC318766
0.7121	Intermediate Similarity	NPC165808
0.7108	Intermediate Similarity	NPC475902
0.7108	Intermediate Similarity	NPC475906
0.7108	Intermediate Similarity	NPC469631
0.7108	Intermediate Similarity	NPC469628
0.7108	Intermediate Similarity	NPC469653
0.7108	Intermediate Similarity	NPC471047
0.7105	Intermediate Similarity	NPC4509
0.7105	Intermediate Similarity	NPC4492
0.7105	Intermediate Similarity	NPC51391
0.7105	Intermediate Similarity	NPC235906
0.7097	Intermediate Similarity	NPC236338
0.7089	Intermediate Similarity	NPC301477
0.7089	Intermediate Similarity	NPC25684
0.7089	Intermediate Similarity	NPC281949
0.7089	Intermediate Similarity	NPC141810
0.7089	Intermediate Similarity	NPC275507
0.7089	Intermediate Similarity	NPC112868
0.7083	Intermediate Similarity	NPC474823
0.7083	Intermediate Similarity	NPC313444
0.7083	Intermediate Similarity	NPC476614
0.7073	Intermediate Similarity	NPC261721
0.7073	Intermediate Similarity	NPC38576
0.7073	Intermediate Similarity	NPC472863
0.7073	Intermediate Similarity	NPC234038
0.7073	Intermediate Similarity	NPC279859
0.7067	Intermediate Similarity	NPC476590
0.7067	Intermediate Similarity	NPC114727
0.7067	Intermediate Similarity	NPC20025
0.7051	Intermediate Similarity	NPC473981
0.7051	Intermediate Similarity	NPC617
0.7051	Intermediate Similarity	NPC473980
0.7051	Intermediate Similarity	NPC469690
0.7042	Intermediate Similarity	NPC315115
0.7037	Intermediate Similarity	NPC30486
0.7037	Intermediate Similarity	NPC196487
0.7037	Intermediate Similarity	NPC14575
0.7027	Intermediate Similarity	NPC316185
0.7027	Intermediate Similarity	NPC129665
0.7015	Intermediate Similarity	NPC474084
0.7013	Intermediate Similarity	NPC103987
0.7013	Intermediate Similarity	NPC122264
0.7013	Intermediate Similarity	NPC470240
0.7013	Intermediate Similarity	NPC53581
0.7013	Intermediate Similarity	NPC54996
0.7013	Intermediate Similarity	NPC316324
0.7013	Intermediate Similarity	NPC476794
0.7	Intermediate Similarity	NPC200513
0.7	Intermediate Similarity	NPC268122
0.7	Intermediate Similarity	NPC35556
0.7	Intermediate Similarity	NPC471296
0.7	Intermediate Similarity	NPC475690
0.7	Intermediate Similarity	NPC114464
0.7	Intermediate Similarity	NPC474291

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	2240
0.2-0.3	4511
0.3-0.4	1664
0.4-0.5	423
0.5-0.6	138
0.6-0.7	16
0.7-0.8	1
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
0.7647	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5209	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6927	Phase 3
0.6747	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD8039	Approved
0.6528	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5785	Approved
0.6353	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD4194	Approved
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD4191	Approved
0.625	Remote Similarity	NPD5343	Approved
0.625	Remote Similarity	NPD4192	Approved
0.6235	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3573	Approved
0.619	Remote Similarity	NPD3174	Discontinued
0.618	Remote Similarity	NPD7838	Discovery
0.6163	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD4220	Pre-registration
0.6145	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7331	Phase 2
0.6118	Remote Similarity	NPD7154	Phase 3
0.6098	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD1695	Approved
0.6064	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6097	Approved
0.6032	Remote Similarity	NPD6096	Approved
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD46	Approved
0.5976	Remote Similarity	NPD4756	Discovery
0.597	Remote Similarity	NPD29	Approved
0.597	Remote Similarity	NPD28	Approved
0.5955	Remote Similarity	NPD5208	Approved
0.5952	Remote Similarity	NPD4822	Approved
0.5952	Remote Similarity	NPD4820	Approved
0.5952	Remote Similarity	NPD4821	Approved
0.5952	Remote Similarity	NPD4819	Approved
0.5952	Remote Similarity	NPD4252	Approved
0.5938	Remote Similarity	NPD39	Approved
0.5938	Remote Similarity	NPD4222	Approved
0.5934	Remote Similarity	NPD5694	Approved
0.593	Remote Similarity	NPD5362	Discontinued
0.5921	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5330	Approved
0.5909	Remote Similarity	NPD7521	Approved
0.5909	Remote Similarity	NPD6409	Approved
0.5909	Remote Similarity	NPD7146	Approved
0.5909	Remote Similarity	NPD3173	Approved
0.5909	Remote Similarity	NPD7334	Approved
0.5909	Remote Similarity	NPD6684	Approved
0.5904	Remote Similarity	NPD4271	Approved
0.5904	Remote Similarity	NPD4268	Approved
0.5895	Remote Similarity	NPD4225	Approved
0.589	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD6673	Approved
0.5889	Remote Similarity	NPD6904	Approved
0.5889	Remote Similarity	NPD6080	Approved
0.5882	Remote Similarity	NPD5369	Approved
0.5824	Remote Similarity	NPD5692	Phase 3
0.5823	Remote Similarity	NPD4691	Approved
0.5814	Remote Similarity	NPD6435	Approved
0.5814	Remote Similarity	NPD4269	Approved
0.5814	Remote Similarity	NPD4270	Approved
0.5802	Remote Similarity	NPD4058	Approved
0.5797	Remote Similarity	NPD3172	Approved
0.5789	Remote Similarity	NPD7341	Phase 2
0.5778	Remote Similarity	NPD5737	Approved
0.5778	Remote Similarity	NPD6672	Approved
0.5778	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6903	Approved
0.5761	Remote Similarity	NPD6050	Approved
0.5747	Remote Similarity	NPD5331	Approved
0.5747	Remote Similarity	NPD5332	Approved
0.5738	Remote Similarity	NPD5783	Phase 3
0.5732	Remote Similarity	NPD1452	Discontinued
0.573	Remote Similarity	NPD4519	Discontinued
0.573	Remote Similarity	NPD5786	Approved
0.573	Remote Similarity	NPD6098	Approved
0.573	Remote Similarity	NPD4249	Approved
0.573	Remote Similarity	NPD4623	Approved
0.5729	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD3195	Phase 2
0.5714	Remote Similarity	NPD9298	Approved
0.5714	Remote Similarity	NPD4266	Approved
0.5714	Remote Similarity	NPD3194	Approved
0.5698	Remote Similarity	NPD4790	Discontinued
0.5696	Remote Similarity	NPD4137	Phase 3
0.5694	Remote Similarity	NPD8779	Phase 3
0.567	Remote Similarity	NPD7639	Approved
0.567	Remote Similarity	NPD7640	Approved
0.567	Remote Similarity	NPD6648	Approved
0.5667	Remote Similarity	NPD4250	Approved
0.5667	Remote Similarity	NPD4251	Approved
0.5657	Remote Similarity	NPD6647	Phase 2
0.5647	Remote Similarity	NPD4195	Approved
0.5644	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD6001	Approved
0.5631	Remote Similarity	NPD6371	Approved
0.5625	Remote Similarity	NPD5326	Phase 3
0.5625	Remote Similarity	NPD4747	Approved
0.5616	Remote Similarity	NPD287	Approved
0.5616	Remote Similarity	NPD6109	Phase 1
0.5612	Remote Similarity	NPD5344	Discontinued
0.561	Remote Similarity	NPD4687	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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