NPASS Compound

Structure

NPC470693 OpenBabel07101718232D 23 23 0 0 1 0 0 0 0 0999 V2000 0.5307 2.9631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4612 -0.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5115 0.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9328 -3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2464 2.3337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9991 -0.0432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8007 1.0751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8672 0.7167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5779 0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0900 1.3461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4215 -0.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4190 -2.5472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -2.9074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 14 1 0 0 0 0 5 22 1 0 0 0 0 7 16 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 6 1 6 0 0 0 16 17 1 0 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 8 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.2
Volume:	350.602
LogP:	3.38
LogD:	2.955
LogS:	-3.725
# Rotatable Bonds:	9
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	4.294
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.502
MDCK Permeability:	2.611279887787532e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.42

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	89.93508911132812%
Volume Distribution (VD):	0.823
Pgp-substrate:	4.881093502044678%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.506
CYP2C19-inhibitor:	0.857
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.6
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	8.03
Half-life (T1/2):	0.646

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.892
Drug-inuced Liver Injury (DILI):	0.81
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.575
Carcinogencity:	0.818
Eye Corrosion:	0.004
Eye Irritation:	0.05
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC470693

Natural Product ID:	NPC470693
*Common Name:**	(-)-Gracilioether B
IUPAC Name:	methyl (2Z)-2-[(5R)-3,5-diethyl-5-[(E,2R)-2-ethyl-5-oxohex-3-enyl]furan-2-ylidene]acetate
Synonyms:	(-)-Gracilioether B
Standard InCHIKey:	DCHODBHTJLPAJL-WJNDYHRLSA-N
Standard InCHI:	InChI=1S/C19H28O4/c1-6-15(10-9-14(4)20)12-19(8-3)13-16(7-2)17(23-19)11-18(21)22-5/h9-11,13,15H,6-8,12H2,1-5H3/b10-9+,17-11-/t15-,19+/m0/s1
SMILES:	CCC1=CC(OC1=CC(=O)OC)(CC)CC(CC)C=CC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2178596
PubChem CID:	66575621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

*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	=	5000.0	nM	PMID[564921]

☑ 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 NPC470693 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	181
0.1-0.2	1499
0.2-0.3	7834
0.3-0.4	19313
0.4-0.5	8932
0.5-0.6	3885
0.6-0.7	910
0.7-0.8	132
0.8-0.85	3
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC191233
0.9375	High Similarity	NPC220766
0.8857	High Similarity	NPC470686
0.8824	High Similarity	NPC232812
0.8788	High Similarity	NPC470688
0.8696	High Similarity	NPC64234
0.8696	High Similarity	NPC37929
0.8194	Intermediate Similarity	NPC287878
0.8028	Intermediate Similarity	NPC265574
0.8	Intermediate Similarity	NPC291712
0.8	Intermediate Similarity	NPC473825
0.7838	Intermediate Similarity	NPC117746
0.7838	Intermediate Similarity	NPC15499
0.7838	Intermediate Similarity	NPC474758
0.7838	Intermediate Similarity	NPC294434
0.7838	Intermediate Similarity	NPC259599
0.7821	Intermediate Similarity	NPC42470
0.7763	Intermediate Similarity	NPC471225
0.7763	Intermediate Similarity	NPC68156
0.7746	Intermediate Similarity	NPC21998
0.7746	Intermediate Similarity	NPC472266
0.7681	Intermediate Similarity	NPC179087
0.7681	Intermediate Similarity	NPC210303
0.7681	Intermediate Similarity	NPC155849
0.7681	Intermediate Similarity	NPC44343
0.7671	Intermediate Similarity	NPC315285
0.7639	Intermediate Similarity	NPC470256
0.7639	Intermediate Similarity	NPC276290
0.7568	Intermediate Similarity	NPC316185
0.7534	Intermediate Similarity	NPC151481
0.7532	Intermediate Similarity	NPC57744
0.75	Intermediate Similarity	NPC329852
0.75	Intermediate Similarity	NPC194871
0.75	Intermediate Similarity	NPC133600
0.7467	Intermediate Similarity	NPC12815
0.7467	Intermediate Similarity	NPC238948
0.7467	Intermediate Similarity	NPC215745
0.7465	Intermediate Similarity	NPC182794
0.7439	Intermediate Similarity	NPC130030
0.7439	Intermediate Similarity	NPC281172
0.7436	Intermediate Similarity	NPC99182
0.7436	Intermediate Similarity	NPC128276
0.7432	Intermediate Similarity	NPC316029
0.7432	Intermediate Similarity	NPC315597
0.7432	Intermediate Similarity	NPC67183
0.7429	Intermediate Similarity	NPC217940
0.7424	Intermediate Similarity	NPC478117
0.7403	Intermediate Similarity	NPC123360
0.7397	Intermediate Similarity	NPC313444
0.7381	Intermediate Similarity	NPC260343
0.7368	Intermediate Similarity	NPC315843
0.7368	Intermediate Similarity	NPC476355
0.7368	Intermediate Similarity	NPC107654
0.7361	Intermediate Similarity	NPC248125
0.7361	Intermediate Similarity	NPC315115
0.7342	Intermediate Similarity	NPC271632
0.7342	Intermediate Similarity	NPC178277
0.7333	Intermediate Similarity	NPC181587
0.7326	Intermediate Similarity	NPC193396
0.7326	Intermediate Similarity	NPC32944
0.7313	Intermediate Similarity	NPC221763
0.7313	Intermediate Similarity	NPC150717
0.7313	Intermediate Similarity	NPC86948
0.7308	Intermediate Similarity	NPC54996
0.7308	Intermediate Similarity	NPC180290
0.7308	Intermediate Similarity	NPC316324
0.7308	Intermediate Similarity	NPC315394
0.7297	Intermediate Similarity	NPC473603
0.7297	Intermediate Similarity	NPC476059
0.7297	Intermediate Similarity	NPC476591
0.7297	Intermediate Similarity	NPC88877
0.7294	Intermediate Similarity	NPC64913
0.7294	Intermediate Similarity	NPC242877
0.7286	Intermediate Similarity	NPC151648
0.7284	Intermediate Similarity	NPC471326
0.7284	Intermediate Similarity	NPC221231
0.7284	Intermediate Similarity	NPC474028
0.7284	Intermediate Similarity	NPC474439
0.7273	Intermediate Similarity	NPC478120
0.7273	Intermediate Similarity	NPC12727
0.7273	Intermediate Similarity	NPC68624
0.726	Intermediate Similarity	NPC203335
0.726	Intermediate Similarity	NPC225272
0.7241	Intermediate Similarity	NPC282644
0.7241	Intermediate Similarity	NPC29798
0.7237	Intermediate Similarity	NPC16349
0.7237	Intermediate Similarity	NPC222244
0.7237	Intermediate Similarity	NPC276336
0.7229	Intermediate Similarity	NPC474424
0.7222	Intermediate Similarity	NPC471566
0.7222	Intermediate Similarity	NPC133904
0.7222	Intermediate Similarity	NPC471556
0.7215	Intermediate Similarity	NPC474005
0.7209	Intermediate Similarity	NPC224270
0.72	Intermediate Similarity	NPC469660
0.72	Intermediate Similarity	NPC59558
0.7195	Intermediate Similarity	NPC475714
0.7195	Intermediate Similarity	NPC288281
0.7195	Intermediate Similarity	NPC16488
0.7183	Intermediate Similarity	NPC322457
0.7183	Intermediate Similarity	NPC474658
0.7179	Intermediate Similarity	NPC4509
0.7179	Intermediate Similarity	NPC51391
0.7179	Intermediate Similarity	NPC4492
0.7179	Intermediate Similarity	NPC27205
0.7162	Intermediate Similarity	NPC474823
0.7162	Intermediate Similarity	NPC218477
0.716	Intermediate Similarity	NPC325031
0.716	Intermediate Similarity	NPC471325
0.7159	Intermediate Similarity	NPC143210
0.7143	Intermediate Similarity	NPC19241
0.7143	Intermediate Similarity	NPC79756
0.7143	Intermediate Similarity	NPC234038
0.7143	Intermediate Similarity	NPC140287
0.7143	Intermediate Similarity	NPC429928
0.7126	Intermediate Similarity	NPC32494
0.7126	Intermediate Similarity	NPC175842
0.7126	Intermediate Similarity	NPC166110
0.7125	Intermediate Similarity	NPC472965
0.7125	Intermediate Similarity	NPC63649
0.7125	Intermediate Similarity	NPC264227
0.7125	Intermediate Similarity	NPC270126
0.7123	Intermediate Similarity	NPC116013
0.7108	Intermediate Similarity	NPC475706
0.7105	Intermediate Similarity	NPC163003
0.7105	Intermediate Similarity	NPC257618
0.7101	Intermediate Similarity	NPC189700
0.7093	Intermediate Similarity	NPC142159
0.7093	Intermediate Similarity	NPC95364
0.7083	Intermediate Similarity	NPC34883
0.7077	Intermediate Similarity	NPC148056
0.7073	Intermediate Similarity	NPC85772
0.7073	Intermediate Similarity	NPC173609
0.7073	Intermediate Similarity	NPC94200
0.7067	Intermediate Similarity	NPC473277
0.7067	Intermediate Similarity	NPC475004
0.7059	Intermediate Similarity	NPC96663
0.7059	Intermediate Similarity	NPC245002
0.7059	Intermediate Similarity	NPC478145
0.7051	Intermediate Similarity	NPC329826
0.7051	Intermediate Similarity	NPC244166
0.7051	Intermediate Similarity	NPC469414
0.7045	Intermediate Similarity	NPC248193
0.7045	Intermediate Similarity	NPC59646
0.7037	Intermediate Similarity	NPC268827
0.7037	Intermediate Similarity	NPC160582
0.7031	Intermediate Similarity	NPC15912
0.7024	Intermediate Similarity	NPC215364
0.7024	Intermediate Similarity	NPC67081
0.7024	Intermediate Similarity	NPC471223
0.7013	Intermediate Similarity	NPC474705
0.7	Intermediate Similarity	NPC267231
0.7	Intermediate Similarity	NPC471220
0.7	Intermediate Similarity	NPC172998
0.7	Intermediate Similarity	NPC301596
0.7	Intermediate Similarity	NPC253749
0.7	Intermediate Similarity	NPC108816
0.7	Intermediate Similarity	NPC286189
0.7	Intermediate Similarity	NPC93763
0.7	Intermediate Similarity	NPC299396
0.6988	Remote Similarity	NPC170377
0.6988	Remote Similarity	NPC118423
0.6986	Remote Similarity	NPC471565
0.6977	Remote Similarity	NPC473658
0.6977	Remote Similarity	NPC472302
0.6977	Remote Similarity	NPC471956
0.6977	Remote Similarity	NPC26078
0.6977	Remote Similarity	NPC475739
0.6974	Remote Similarity	NPC329904
0.6974	Remote Similarity	NPC473361
0.697	Remote Similarity	NPC151919
0.6966	Remote Similarity	NPC470521
0.6962	Remote Similarity	NPC301525
0.6957	Remote Similarity	NPC474825
0.6951	Remote Similarity	NPC184208
0.6951	Remote Similarity	NPC315731
0.6951	Remote Similarity	NPC112868
0.6951	Remote Similarity	NPC8538
0.6944	Remote Similarity	NPC68110
0.6944	Remote Similarity	NPC473737
0.6944	Remote Similarity	NPC132243
0.6941	Remote Similarity	NPC316426
0.6941	Remote Similarity	NPC315395
0.6941	Remote Similarity	NPC168248
0.6933	Remote Similarity	NPC287705
0.6932	Remote Similarity	NPC32552
0.6923	Remote Similarity	NPC27264
0.6914	Remote Similarity	NPC471299
0.6914	Remote Similarity	NPC226226
0.6914	Remote Similarity	NPC265980
0.6914	Remote Similarity	NPC471537
0.6914	Remote Similarity	NPC63326
0.6914	Remote Similarity	NPC55304
0.6912	Remote Similarity	NPC173157
0.6905	Remote Similarity	NPC196487
0.6905	Remote Similarity	NPC14575
0.6905	Remote Similarity	NPC149869
0.6901	Remote Similarity	NPC130953
0.6901	Remote Similarity	NPC98519
0.6901	Remote Similarity	NPC26223

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 NPC470693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1787
0.2-0.3	4419
0.3-0.4	2175
0.4-0.5	493
0.5-0.6	108
0.6-0.7	14
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
0.75	Intermediate Similarity	NPD5209	Approved
0.7465	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4756	Discovery
0.6444	Remote Similarity	NPD7838	Discovery
0.642	Remote Similarity	NPD8039	Approved
0.6351	Remote Similarity	NPD4192	Approved
0.6351	Remote Similarity	NPD4194	Approved
0.6351	Remote Similarity	NPD4191	Approved
0.6351	Remote Similarity	NPD4193	Approved
0.6324	Remote Similarity	NPD6927	Phase 3
0.6322	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4220	Pre-registration
0.625	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD7154	Phase 3
0.6146	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5785	Approved
0.6082	Remote Similarity	NPD6648	Approved
0.5934	Remote Similarity	NPD1282	Approved
0.5889	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD5363	Approved
0.5862	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5694	Approved
0.5851	Remote Similarity	NPD5693	Phase 1
0.5833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4249	Approved
0.5823	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD8779	Phase 3
0.5806	Remote Similarity	NPD6051	Approved
0.5789	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4251	Approved
0.5761	Remote Similarity	NPD4250	Approved
0.5745	Remote Similarity	NPD5692	Phase 3
0.5745	Remote Similarity	NPD6698	Approved
0.5745	Remote Similarity	NPD46	Approved
0.5745	Remote Similarity	NPD5207	Approved
0.5743	Remote Similarity	NPD6647	Phase 2
0.5728	Remote Similarity	NPD3134	Approved
0.5714	Remote Similarity	NPD2067	Discontinued
0.57	Remote Similarity	NPD5344	Discontinued
0.5684	Remote Similarity	NPD6050	Approved
0.5684	Remote Similarity	NPD7637	Suspended
0.5682	Remote Similarity	NPD4820	Approved
0.5682	Remote Similarity	NPD4821	Approved
0.5682	Remote Similarity	NPD4819	Approved
0.5682	Remote Similarity	NPD4822	Approved
0.5682	Remote Similarity	NPD4252	Approved
0.5667	Remote Similarity	NPD5362	Discontinued
0.5657	Remote Similarity	NPD4225	Approved
0.5652	Remote Similarity	NPD5343	Approved
0.5638	Remote Similarity	NPD1695	Approved
0.5632	Remote Similarity	NPD4268	Approved
0.5632	Remote Similarity	NPD4271	Approved
0.5618	Remote Similarity	NPD5369	Approved
0.5616	Remote Similarity	NPD539	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