NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.09
Volume:	194.291
LogP:	0.095
LogD:	-0.107
LogS:	-1.36
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	4.338
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	5.413647522800602e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.169
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	12.65914535522461%
Volume Distribution (VD):	1.182
Pgp-substrate:	87.08940887451172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.721
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.274

ADMET: Excretion

Clearance (CL):	2.966
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.208
AMES Toxicity:	0.545
Rat Oral Acute Toxicity:	0.582
Maximum Recommended Daily Dose:	0.564
Skin Sensitization:	0.693
Carcinogencity:	0.315
Eye Corrosion:	0.008
Eye Irritation:	0.288
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC474280

Natural Product ID:	NPC474280
*Common Name:**	(3Ar,7Ar)-6-Hydroxy-2,3,3A,6,7,7A-Hexahydrobenzofuran-3A-Yl Acetate
IUPAC Name:	[(3aR,7aR)-6-hydroxy-3,6,7,7a-tetrahydro-2H-1-benzofuran-3a-yl] acetate
Synonyms:
Standard InCHIKey:	WICIHLJNNQJETR-XVBQNVSMSA-N
Standard InCHI:	InChI=1S/C10H14O4/c1-7(11)14-10-3-2-8(12)6-9(10)13-5-4-10/h2-3,8-9,12H,4-6H2,1H3/t8?,9-,10+/m1/s1
SMILES:	CC(=O)OC12CCOC1CC(C=C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464676
PubChem CID:	44567079
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO33459	cornus controversa	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236014]

☑ 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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	100.0	ug.mL-1	PMID[511833]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[511833]

☑ 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 NPC474280 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	134
0.1-0.2	1197
0.2-0.3	5234
0.3-0.4	15666
0.4-0.5	10980
0.5-0.6	6553
0.6-0.7	2590
0.7-0.8	338
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC474278
0.9315	High Similarity	NPC475210
0.8947	High Similarity	NPC474252
0.8551	High Similarity	NPC473722
0.7901	Intermediate Similarity	NPC44261
0.7901	Intermediate Similarity	NPC474809
0.7848	Intermediate Similarity	NPC471537
0.7831	Intermediate Similarity	NPC478112
0.7733	Intermediate Similarity	NPC4299
0.7722	Intermediate Similarity	NPC475699
0.7671	Intermediate Similarity	NPC276299
0.7654	Intermediate Similarity	NPC474894
0.7654	Intermediate Similarity	NPC52861
0.7654	Intermediate Similarity	NPC24417
0.7654	Intermediate Similarity	NPC475944
0.7632	Intermediate Similarity	NPC477087
0.7632	Intermediate Similarity	NPC477086
0.7625	Intermediate Similarity	NPC473981
0.7625	Intermediate Similarity	NPC473980
0.7619	Intermediate Similarity	NPC311163
0.7606	Intermediate Similarity	NPC55376
0.76	Intermediate Similarity	NPC101622
0.7595	Intermediate Similarity	NPC40049
0.759	Intermediate Similarity	NPC160517
0.759	Intermediate Similarity	NPC32676
0.759	Intermediate Similarity	NPC78673
0.759	Intermediate Similarity	NPC186155
0.7561	Intermediate Similarity	NPC229825
0.7558	Intermediate Similarity	NPC133450
0.7534	Intermediate Similarity	NPC96414
0.7534	Intermediate Similarity	NPC470123
0.7534	Intermediate Similarity	NPC19769
0.7532	Intermediate Similarity	NPC477085
0.75	Intermediate Similarity	NPC248775
0.75	Intermediate Similarity	NPC471494
0.75	Intermediate Similarity	NPC474816
0.75	Intermediate Similarity	NPC473361
0.75	Intermediate Similarity	NPC209135
0.75	Intermediate Similarity	NPC329904
0.75	Intermediate Similarity	NPC267231
0.75	Intermediate Similarity	NPC326753
0.75	Intermediate Similarity	NPC129630
0.7471	Intermediate Similarity	NPC177668
0.747	Intermediate Similarity	NPC169575
0.747	Intermediate Similarity	NPC40746
0.747	Intermediate Similarity	NPC131669
0.747	Intermediate Similarity	NPC473390
0.747	Intermediate Similarity	NPC52923
0.7468	Intermediate Similarity	NPC68819
0.7439	Intermediate Similarity	NPC112868
0.7432	Intermediate Similarity	NPC201356
0.7432	Intermediate Similarity	NPC37382
0.7412	Intermediate Similarity	NPC61527
0.7412	Intermediate Similarity	NPC469910
0.7412	Intermediate Similarity	NPC278283
0.7407	Intermediate Similarity	NPC180725
0.7407	Intermediate Similarity	NPC86971
0.7407	Intermediate Similarity	NPC98557
0.7407	Intermediate Similarity	NPC226226
0.7407	Intermediate Similarity	NPC470149
0.7407	Intermediate Similarity	NPC55304
0.7407	Intermediate Similarity	NPC139712
0.7407	Intermediate Similarity	NPC167881
0.7407	Intermediate Similarity	NPC470148
0.7381	Intermediate Similarity	NPC141193
0.7381	Intermediate Similarity	NPC158756
0.7381	Intermediate Similarity	NPC191476
0.7381	Intermediate Similarity	NPC114979
0.7381	Intermediate Similarity	NPC96259
0.7381	Intermediate Similarity	NPC476804
0.7375	Intermediate Similarity	NPC474026
0.7375	Intermediate Similarity	NPC7563
0.7375	Intermediate Similarity	NPC476439
0.7375	Intermediate Similarity	NPC475711
0.7375	Intermediate Similarity	NPC84360
0.7375	Intermediate Similarity	NPC262747
0.7375	Intermediate Similarity	NPC320630
0.7375	Intermediate Similarity	NPC116177
0.7356	Intermediate Similarity	NPC478110
0.7349	Intermediate Similarity	NPC89555
0.7349	Intermediate Similarity	NPC475690
0.7333	Intermediate Similarity	NPC193029
0.7333	Intermediate Similarity	NPC473357
0.7333	Intermediate Similarity	NPC25298
0.7326	Intermediate Similarity	NPC471056
0.7326	Intermediate Similarity	NPC471055
0.7317	Intermediate Similarity	NPC133226
0.7317	Intermediate Similarity	NPC470147
0.7303	Intermediate Similarity	NPC475912
0.7294	Intermediate Similarity	NPC470755
0.7294	Intermediate Similarity	NPC11804
0.7294	Intermediate Similarity	NPC165162
0.7294	Intermediate Similarity	NPC21469
0.7294	Intermediate Similarity	NPC255307
0.7284	Intermediate Similarity	NPC93763
0.7284	Intermediate Similarity	NPC127526
0.7284	Intermediate Similarity	NPC196653
0.7284	Intermediate Similarity	NPC108816
0.7284	Intermediate Similarity	NPC471465
0.7273	Intermediate Similarity	NPC3952
0.7273	Intermediate Similarity	NPC475855
0.7273	Intermediate Similarity	NPC474232
0.7262	Intermediate Similarity	NPC23748
0.7262	Intermediate Similarity	NPC116543
0.7262	Intermediate Similarity	NPC161045
0.7262	Intermediate Similarity	NPC472377
0.7262	Intermediate Similarity	NPC49208
0.7262	Intermediate Similarity	NPC315559
0.7262	Intermediate Similarity	NPC59097
0.7262	Intermediate Similarity	NPC231601
0.7253	Intermediate Similarity	NPC57664
0.725	Intermediate Similarity	NPC474197
0.725	Intermediate Similarity	NPC190400
0.725	Intermediate Similarity	NPC301525
0.725	Intermediate Similarity	NPC49392
0.7241	Intermediate Similarity	NPC476803
0.7241	Intermediate Similarity	NPC473715
0.7241	Intermediate Similarity	NPC136879
0.7237	Intermediate Similarity	NPC475760
0.7237	Intermediate Similarity	NPC63873
0.7237	Intermediate Similarity	NPC310210
0.7229	Intermediate Similarity	NPC246621
0.7229	Intermediate Similarity	NPC315731
0.7222	Intermediate Similarity	NPC258788
0.7222	Intermediate Similarity	NPC57405
0.7222	Intermediate Similarity	NPC256368
0.7222	Intermediate Similarity	NPC303942
0.7215	Intermediate Similarity	NPC470686
0.7215	Intermediate Similarity	NPC476590
0.7215	Intermediate Similarity	NPC107654
0.7215	Intermediate Similarity	NPC114727
0.7215	Intermediate Similarity	NPC315843
0.7209	Intermediate Similarity	NPC475461
0.7209	Intermediate Similarity	NPC305475
0.7195	Intermediate Similarity	NPC321728
0.7195	Intermediate Similarity	NPC1180
0.7195	Intermediate Similarity	NPC476701
0.7195	Intermediate Similarity	NPC291260
0.7191	Intermediate Similarity	NPC473321
0.7179	Intermediate Similarity	NPC316185
0.7179	Intermediate Similarity	NPC472254
0.7176	Intermediate Similarity	NPC243618
0.7176	Intermediate Similarity	NPC471301
0.7176	Intermediate Similarity	NPC70424
0.7176	Intermediate Similarity	NPC475035
0.7176	Intermediate Similarity	NPC295799
0.7174	Intermediate Similarity	NPC205143
0.716	Intermediate Similarity	NPC315394
0.7159	Intermediate Similarity	NPC218927
0.7159	Intermediate Similarity	NPC206001
0.7159	Intermediate Similarity	NPC20946
0.7143	Intermediate Similarity	NPC313677
0.7143	Intermediate Similarity	NPC36954
0.7143	Intermediate Similarity	NPC151481
0.7143	Intermediate Similarity	NPC471298
0.7143	Intermediate Similarity	NPC472947
0.7143	Intermediate Similarity	NPC270013
0.7143	Intermediate Similarity	NPC476720
0.7143	Intermediate Similarity	NPC130618
0.7143	Intermediate Similarity	NPC475004
0.7143	Intermediate Similarity	NPC323251
0.7143	Intermediate Similarity	NPC14961
0.7126	Intermediate Similarity	NPC131329
0.7125	Intermediate Similarity	NPC473948
0.7123	Intermediate Similarity	NPC26810
0.7111	Intermediate Similarity	NPC295204
0.7111	Intermediate Similarity	NPC288240
0.7111	Intermediate Similarity	NPC162205
0.7111	Intermediate Similarity	NPC273579
0.7111	Intermediate Similarity	NPC156553
0.7097	Intermediate Similarity	NPC203627
0.7093	Intermediate Similarity	NPC35933
0.7093	Intermediate Similarity	NPC475034
0.7093	Intermediate Similarity	NPC471156
0.7089	Intermediate Similarity	NPC470435
0.7089	Intermediate Similarity	NPC329890
0.7089	Intermediate Similarity	NPC327383
0.7089	Intermediate Similarity	NPC185186
0.7083	Intermediate Similarity	NPC220964
0.7083	Intermediate Similarity	NPC475676
0.7079	Intermediate Similarity	NPC474761
0.7079	Intermediate Similarity	NPC144133
0.7079	Intermediate Similarity	NPC473448
0.7079	Intermediate Similarity	NPC473619
0.7079	Intermediate Similarity	NPC476004
0.7079	Intermediate Similarity	NPC179394
0.7073	Intermediate Similarity	NPC323249
0.7073	Intermediate Similarity	NPC27949
0.7073	Intermediate Similarity	NPC68119
0.7073	Intermediate Similarity	NPC279532
0.7073	Intermediate Similarity	NPC13823
0.7073	Intermediate Similarity	NPC39547
0.7073	Intermediate Similarity	NPC260814
0.7073	Intermediate Similarity	NPC3852
0.7067	Intermediate Similarity	NPC282760
0.7065	Intermediate Similarity	NPC279621
0.7065	Intermediate Similarity	NPC476315
0.7059	Intermediate Similarity	NPC31019
0.7059	Intermediate Similarity	NPC263087
0.7059	Intermediate Similarity	NPC27314

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 NPC474280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	1567
0.2-0.3	3986
0.3-0.4	2535
0.4-0.5	665
0.5-0.6	223
0.6-0.7	50
0.7-0.8	5
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
0.7317	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4820	Approved
0.7108	Intermediate Similarity	NPD4819	Approved
0.7108	Intermediate Similarity	NPD4822	Approved
0.7108	Intermediate Similarity	NPD4821	Approved
0.7073	Intermediate Similarity	NPD4271	Approved
0.7073	Intermediate Similarity	NPD4268	Approved
0.7011	Intermediate Similarity	NPD4249	Approved
0.6977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4251	Approved
0.6932	Remote Similarity	NPD4250	Approved
0.6889	Remote Similarity	NPD7838	Discovery
0.6889	Remote Similarity	NPD46	Approved
0.6889	Remote Similarity	NPD6698	Approved
0.686	Remote Similarity	NPD7154	Phase 3
0.6771	Remote Similarity	NPD5344	Discontinued
0.6737	Remote Similarity	NPD4225	Approved
0.6737	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD368	Approved
0.663	Remote Similarity	NPD7983	Approved
0.6623	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6648	Approved
0.6486	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5362	Discontinued
0.6421	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5779	Approved
0.6383	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD4269	Approved
0.6364	Remote Similarity	NPD4270	Approved
0.6344	Remote Similarity	NPD5785	Approved
0.6333	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4252	Approved
0.6316	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD342	Phase 1
0.6292	Remote Similarity	NPD5332	Approved
0.6292	Remote Similarity	NPD5331	Approved
0.6279	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7637	Suspended
0.6267	Remote Similarity	NPD9119	Approved
0.6267	Remote Similarity	NPD69	Approved
0.6264	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD5363	Approved
0.6136	Remote Similarity	NPD5368	Approved
0.6133	Remote Similarity	NPD9118	Approved
0.6126	Remote Similarity	NPD8516	Approved
0.6126	Remote Similarity	NPD8517	Approved
0.6126	Remote Similarity	NPD8515	Approved
0.6126	Remote Similarity	NPD8513	Phase 3
0.6118	Remote Similarity	NPD8039	Approved
0.6117	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6371	Approved
0.6076	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4732	Discontinued
0.6064	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5370	Suspended
0.6064	Remote Similarity	NPD6101	Approved
0.6055	Remote Similarity	NPD7115	Discovery
0.6049	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7524	Approved
0.602	Remote Similarity	NPD7839	Suspended
0.5978	Remote Similarity	NPD1694	Approved
0.5938	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD6695	Phase 3
0.5909	Remote Similarity	NPD7505	Discontinued
0.5905	Remote Similarity	NPD6686	Approved
0.5895	Remote Similarity	NPD6051	Approved
0.5895	Remote Similarity	NPD1695	Approved
0.5875	Remote Similarity	NPD3197	Phase 1
0.5862	Remote Similarity	NPD8074	Phase 3
0.5844	Remote Similarity	NPD6109	Phase 1
0.5842	Remote Similarity	NPD7639	Approved
0.5842	Remote Similarity	NPD7640	Approved
0.5833	Remote Similarity	NPD6053	Discontinued
0.5833	Remote Similarity	NPD969	Suspended
0.5824	Remote Similarity	NPD5209	Approved
0.5795	Remote Similarity	NPD4756	Discovery
0.5794	Remote Similarity	NPD6421	Discontinued
0.5778	Remote Similarity	NPD7332	Phase 2
0.5778	Remote Similarity	NPD7514	Phase 3
0.5761	Remote Similarity	NPD6110	Phase 1
0.5747	Remote Similarity	NPD8264	Approved
0.5743	Remote Similarity	NPD7638	Approved
0.573	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD694	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6399	Phase 3
0.5702	Remote Similarity	NPD7503	Approved
0.5701	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7750	Discontinued
0.5657	Remote Similarity	NPD5282	Discontinued
0.5652	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4193	Approved
0.5625	Remote Similarity	NPD4192	Approved
0.5625	Remote Similarity	NPD4194	Approved
0.5625	Remote Similarity	NPD4191	Approved
0.5604	Remote Similarity	NPD6931	Approved
0.5604	Remote Similarity	NPD6930	Phase 2

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