NPASS Compound

Structure

NPC168733 OpenBabel07101718272D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 1.2976 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 10 1 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 11 21 1 6 0 0 0 12 14 1 6 0 0 0 12 18 1 0 0 0 0 13 20 1 1 0 0 0 14 23 1 1 0 0 0 15 17 1 0 0 0 0 15 24 1 1 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.19
Volume:	382.266
LogP:	3.298
LogD:	3.332
LogS:	-3.551
# Rotatable Bonds:	3
TPSA:	96.71
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	5.238
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	1.2223038538650144e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.278
Plasma Protein Binding (PPB):	53.836219787597656%
Volume Distribution (VD):	2.615
Pgp-substrate:	46.443946838378906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.145
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.32
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.693
Half-life (T1/2):	0.575

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.561
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.11
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC168733

Natural Product ID:	NPC168733
*Common Name:**	Haterumaimide F
IUPAC Name:	(3R)-3-[(1S)-2-[(1S,4R,4aS,7S,8aR)-7-chloro-4-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione
Synonyms:	Haterumaimide F
Standard InCHIKey:	ILPIGMAGHRKRKI-WMRABNJFSA-N
Standard InCHI:	InChI=1S/C20H30ClNO4/c1-10-5-15(24)17-19(2,3)8-11(21)9-20(17,4)13(10)7-14(23)12-6-16(25)22-18(12)26/h11-15,17,23-24H,1,5-9H2,2-4H3,(H,22,25,26)/t11-,12+,13-,14-,15+,17-,20+/m0/s1
SMILES:	Cl[C@H]1CC(C)(C)[C@H]2[C@@](C1)(C)[C@@H](C[C@@H]([C@H]1CC(=NC1=O)O)O)C(=C)C[C@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465665
PubChem CID:	10475085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines [CHEMONTID:0001158] Pyrrolidones [CHEMONTID:0003031] Pyrrolidine-2-ones

*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
NPO33282	lissoclinum sp.	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575950]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.0055	ug.mL-1	PMID[493447]

☑ 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 NPC168733 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	102
0.1-0.2	1010
0.2-0.3	7259
0.3-0.4	19805
0.4-0.5	9166
0.5-0.6	5145
0.6-0.7	202
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC259476
0.9417	High Similarity	NPC92829
0.9333	High Similarity	NPC122404
0.9065	High Similarity	NPC24462
0.8704	High Similarity	NPC7797
0.8393	Intermediate Similarity	NPC216335
0.8241	Intermediate Similarity	NPC42590
0.6949	Remote Similarity	NPC46764
0.6917	Remote Similarity	NPC106479
0.6807	Remote Similarity	NPC328052
0.664	Remote Similarity	NPC323532
0.6555	Remote Similarity	NPC475800
0.6545	Remote Similarity	NPC77001
0.6545	Remote Similarity	NPC253618
0.6518	Remote Similarity	NPC59170
0.6514	Remote Similarity	NPC165895
0.6509	Remote Similarity	NPC110780
0.6505	Remote Similarity	NPC474433
0.6486	Remote Similarity	NPC80401
0.6486	Remote Similarity	NPC261994
0.6486	Remote Similarity	NPC149761
0.6486	Remote Similarity	NPC470378
0.6486	Remote Similarity	NPC180849
0.6481	Remote Similarity	NPC102292
0.6475	Remote Similarity	NPC12270
0.646	Remote Similarity	NPC302008
0.646	Remote Similarity	NPC191094
0.6452	Remote Similarity	NPC470540
0.6449	Remote Similarity	NPC291320
0.6449	Remote Similarity	NPC471036
0.6446	Remote Similarity	NPC474725
0.6429	Remote Similarity	NPC299185
0.6429	Remote Similarity	NPC278106
0.6429	Remote Similarity	NPC476168
0.6415	Remote Similarity	NPC209318
0.6415	Remote Similarity	NPC223330
0.6404	Remote Similarity	NPC29112
0.6404	Remote Similarity	NPC84018
0.6404	Remote Similarity	NPC231060
0.6404	Remote Similarity	NPC138245
0.6372	Remote Similarity	NPC181594
0.6372	Remote Similarity	NPC59350
0.6372	Remote Similarity	NPC144739
0.6364	Remote Similarity	NPC174619
0.6364	Remote Similarity	NPC477352
0.6364	Remote Similarity	NPC307903
0.6364	Remote Similarity	NPC259009
0.6364	Remote Similarity	NPC140251
0.6364	Remote Similarity	NPC128210
0.633	Remote Similarity	NPC471034
0.633	Remote Similarity	NPC190704
0.6316	Remote Similarity	NPC101233
0.6316	Remote Similarity	NPC104371
0.6316	Remote Similarity	NPC473314
0.6316	Remote Similarity	NPC292374
0.6316	Remote Similarity	NPC129004
0.6316	Remote Similarity	NPC64006
0.6316	Remote Similarity	NPC261333
0.6316	Remote Similarity	NPC91772
0.6316	Remote Similarity	NPC153775
0.6316	Remote Similarity	NPC29247
0.6316	Remote Similarity	NPC215271
0.6316	Remote Similarity	NPC111524
0.6316	Remote Similarity	NPC289539
0.6303	Remote Similarity	NPC474563
0.6299	Remote Similarity	NPC476956
0.6273	Remote Similarity	NPC185638
0.6262	Remote Similarity	NPC328264
0.6262	Remote Similarity	NPC14151
0.6262	Remote Similarity	NPC475951
0.6261	Remote Similarity	NPC142352
0.6261	Remote Similarity	NPC210214
0.6261	Remote Similarity	NPC41070
0.6261	Remote Similarity	NPC472485
0.626	Remote Similarity	NPC140409
0.626	Remote Similarity	NPC476290
0.626	Remote Similarity	NPC11491
0.626	Remote Similarity	NPC156248
0.625	Remote Similarity	NPC194642
0.625	Remote Similarity	NPC213832
0.625	Remote Similarity	NPC57954
0.6239	Remote Similarity	NPC475745
0.6239	Remote Similarity	NPC146683
0.6239	Remote Similarity	NPC97505
0.6239	Remote Similarity	NPC474482
0.6239	Remote Similarity	NPC234542
0.6228	Remote Similarity	NPC82138
0.6216	Remote Similarity	NPC298904
0.6216	Remote Similarity	NPC472495
0.6216	Remote Similarity	NPC57469
0.6216	Remote Similarity	NPC305029
0.6216	Remote Similarity	NPC153604
0.6216	Remote Similarity	NPC477926
0.6214	Remote Similarity	NPC102313
0.6214	Remote Similarity	NPC199316
0.621	Remote Similarity	NPC170294
0.6207	Remote Similarity	NPC13949
0.6207	Remote Similarity	NPC135548
0.6207	Remote Similarity	NPC264979
0.6207	Remote Similarity	NPC132824
0.6207	Remote Similarity	NPC140242
0.6195	Remote Similarity	NPC169933
0.6195	Remote Similarity	NPC100313
0.6186	Remote Similarity	NPC127408
0.6186	Remote Similarity	NPC473224
0.6186	Remote Similarity	NPC291785
0.6182	Remote Similarity	NPC197823
0.6174	Remote Similarity	NPC280804
0.6172	Remote Similarity	NPC470276
0.6168	Remote Similarity	NPC164999
0.6161	Remote Similarity	NPC471900
0.6161	Remote Similarity	NPC146937
0.6161	Remote Similarity	NPC474719
0.616	Remote Similarity	NPC476269
0.6154	Remote Similarity	NPC190080
0.6154	Remote Similarity	NPC111187
0.6154	Remote Similarity	NPC170978
0.6154	Remote Similarity	NPC167380
0.6154	Remote Similarity	NPC187933
0.6147	Remote Similarity	NPC118800
0.6147	Remote Similarity	NPC475726
0.6147	Remote Similarity	NPC312480
0.6147	Remote Similarity	NPC243347
0.6147	Remote Similarity	NPC472743
0.614	Remote Similarity	NPC211403
0.614	Remote Similarity	NPC250753
0.614	Remote Similarity	NPC314500
0.614	Remote Similarity	NPC155304
0.614	Remote Similarity	NPC198242
0.614	Remote Similarity	NPC187722
0.6134	Remote Similarity	NPC60947
0.6126	Remote Similarity	NPC2783
0.6126	Remote Similarity	NPC473226
0.6126	Remote Similarity	NPC472738
0.6126	Remote Similarity	NPC153699
0.6126	Remote Similarity	NPC6979
0.6126	Remote Similarity	NPC76164
0.6126	Remote Similarity	NPC470955
0.6126	Remote Similarity	NPC34190
0.6126	Remote Similarity	NPC85698
0.6121	Remote Similarity	NPC157686
0.6121	Remote Similarity	NPC205173
0.6121	Remote Similarity	NPC259042
0.6111	Remote Similarity	NPC473420
0.6111	Remote Similarity	NPC89018
0.6106	Remote Similarity	NPC229871
0.6106	Remote Similarity	NPC469319
0.6106	Remote Similarity	NPC119416
0.6103	Remote Similarity	NPC96425
0.6102	Remote Similarity	NPC174663
0.6102	Remote Similarity	NPC29765
0.6102	Remote Similarity	NPC111214
0.6102	Remote Similarity	NPC109059
0.6102	Remote Similarity	NPC471038
0.6102	Remote Similarity	NPC78427
0.6102	Remote Similarity	NPC164349
0.6102	Remote Similarity	NPC16911
0.6102	Remote Similarity	NPC271614
0.6102	Remote Similarity	NPC288
0.6094	Remote Similarity	NPC470275
0.6091	Remote Similarity	NPC264665
0.6091	Remote Similarity	NPC74595
0.6087	Remote Similarity	NPC158059
0.6087	Remote Similarity	NPC229281
0.6087	Remote Similarity	NPC470375
0.6087	Remote Similarity	NPC471902
0.6087	Remote Similarity	NPC118519
0.6087	Remote Similarity	NPC472496
0.6087	Remote Similarity	NPC287118
0.6087	Remote Similarity	NPC199543
0.6087	Remote Similarity	NPC473690
0.6087	Remote Similarity	NPC147272
0.6087	Remote Similarity	NPC202728
0.6087	Remote Similarity	NPC470376
0.6083	Remote Similarity	NPC272472
0.6071	Remote Similarity	NPC33768
0.6071	Remote Similarity	NPC264005
0.6071	Remote Similarity	NPC472497
0.6071	Remote Similarity	NPC181103
0.6071	Remote Similarity	NPC269360
0.6071	Remote Similarity	NPC73064
0.6068	Remote Similarity	NPC242848
0.6068	Remote Similarity	NPC165616
0.6068	Remote Similarity	NPC121857
0.6068	Remote Similarity	NPC223169
0.6068	Remote Similarity	NPC256227
0.6063	Remote Similarity	NPC226608
0.6063	Remote Similarity	NPC88867
0.6055	Remote Similarity	NPC46881
0.6055	Remote Similarity	NPC474605
0.6055	Remote Similarity	NPC48362
0.6055	Remote Similarity	NPC476292
0.6055	Remote Similarity	NPC212083
0.6055	Remote Similarity	NPC151519
0.6053	Remote Similarity	NPC227467
0.6053	Remote Similarity	NPC210037
0.6053	Remote Similarity	NPC290614
0.6053	Remote Similarity	NPC7260
0.6053	Remote Similarity	NPC46758
0.6053	Remote Similarity	NPC477872

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 NPC168733 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	842
0.2-0.3	4160
0.3-0.4	3238
0.4-0.5	597
0.5-0.6	212
0.6-0.7	11
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
0.6475	Remote Similarity	NPD1719	Phase 1
0.6341	Remote Similarity	NPD5215	Approved
0.619	Remote Similarity	NPD5167	Approved
0.6129	Remote Similarity	NPD5169	Approved
0.6126	Remote Similarity	NPD3618	Phase 1
0.6098	Remote Similarity	NPD5168	Approved
0.608	Remote Similarity	NPD5216	Approved
0.608	Remote Similarity	NPD5127	Approved
0.608	Remote Similarity	NPD5217	Approved
0.6071	Remote Similarity	NPD6333	Approved
0.6071	Remote Similarity	NPD6334	Approved
0.6055	Remote Similarity	NPD3667	Approved
0.6036	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD8034	Phase 2
0.5946	Remote Similarity	NPD4786	Approved
0.5917	Remote Similarity	NPD8418	Phase 2
0.5878	Remote Similarity	NPD4522	Approved
0.5873	Remote Similarity	NPD6420	Discontinued
0.584	Remote Similarity	NPD5128	Approved
0.5826	Remote Similarity	NPD5328	Approved
0.5812	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6399	Phase 3
0.5812	Remote Similarity	NPD4202	Approved
0.5802	Remote Similarity	NPD6313	Approved
0.5802	Remote Similarity	NPD6335	Approved
0.5802	Remote Similarity	NPD6314	Approved
0.5798	Remote Similarity	NPD4697	Phase 3
0.5769	Remote Similarity	NPD6868	Approved
0.5758	Remote Similarity	NPD7101	Approved
0.575	Remote Similarity	NPD4755	Approved
0.5726	Remote Similarity	NPD6079	Approved
0.5726	Remote Similarity	NPD7515	Phase 2
0.5702	Remote Similarity	NPD4225	Approved
0.5702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5222	Approved
0.5667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD5221	Approved
0.5664	Remote Similarity	NPD3668	Phase 3
0.5664	Remote Similarity	NPD3665	Phase 1
0.5664	Remote Similarity	NPD3666	Approved
0.5664	Remote Similarity	NPD3133	Approved
0.5656	Remote Similarity	NPD4696	Approved
0.5656	Remote Similarity	NPD4700	Approved
0.5656	Remote Similarity	NPD5286	Approved
0.5656	Remote Similarity	NPD5285	Approved
0.5652	Remote Similarity	NPD6033	Approved
0.562	Remote Similarity	NPD7902	Approved
0.562	Remote Similarity	NPD5173	Approved
0.561	Remote Similarity	NPD5223	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