NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	348.23
Volume:	385.194
LogP:	1.78
LogD:	2.422
LogS:	-3.477
# Rotatable Bonds:	9
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	4.82
Fsp3:	0.571
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:	-5.056
MDCK Permeability:	0.00011452149192336947
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	94.67904663085938%
Volume Distribution (VD):	1.114
Pgp-substrate:	2.2861244678497314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.621
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	3.477
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.847
Carcinogencity:	0.815
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.682

Download Data

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

Natural Product: NPC478101

Natural Product ID:	NPC478101
*Common Name:**	Topsentolide C2
IUPAC Name:	(2S,4Z)-2-[(1E,4S,6Z,9Z)-4-hydroxy-3-methoxydodeca-1,6,9-trienyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
Synonyms:	Topsentolide C2
Standard InCHIKey:	QXHLHGKKWDCOOY-PUVVKPRFSA-N
Standard InCHI:	InChI=1S/C21H32O4/c1-3-4-5-6-7-11-14-19(22)20(24-2)17-16-18-13-10-8-9-12-15-21(23)25-18/h4-5,7-8,10-11,16-20,22H,3,6,9,12-15H2,1-2H3/b5-4-,10-8-,11-7-,17-16+/t18-,19-,20?/m0/s1
SMILES:	CC/C=C\C/C=C\C[C@@H](C(/C=C/[C@@H]1C/C=C\CCCC(=O)O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11681792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.8	ug/ml	PMID[16643027]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	5.1	ug/ml	PMID[16643027]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.3	ug/ml	PMID[16643027]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	7.6	ug/ml	PMID[16643027]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.4	ug/ml	PMID[16643027]

☑ 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 NPC478101 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	210
0.1-0.2	2764
0.2-0.3	11133
0.3-0.4	16917
0.4-0.5	7970
0.5-0.6	2683
0.6-0.7	860
0.7-0.8	146
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC478100
0.9524	High Similarity	NPC478097
0.9516	High Similarity	NPC478099
0.9516	High Similarity	NPC478098
0.8571	High Similarity	NPC81896
0.8571	High Similarity	NPC321919
0.8387	Intermediate Similarity	NPC323436
0.8382	Intermediate Similarity	NPC475982
0.8254	Intermediate Similarity	NPC478096
0.8125	Intermediate Similarity	NPC322186
0.8125	Intermediate Similarity	NPC478095
0.8088	Intermediate Similarity	NPC25298
0.806	Intermediate Similarity	NPC476655
0.806	Intermediate Similarity	NPC19769
0.806	Intermediate Similarity	NPC476657
0.806	Intermediate Similarity	NPC476654
0.7941	Intermediate Similarity	NPC201356
0.7941	Intermediate Similarity	NPC476659
0.7941	Intermediate Similarity	NPC476656
0.7879	Intermediate Similarity	NPC321838
0.7857	Intermediate Similarity	NPC130618
0.7846	Intermediate Similarity	NPC329249
0.7826	Intermediate Similarity	NPC104537
0.7826	Intermediate Similarity	NPC127091
0.7826	Intermediate Similarity	NPC26500
0.7826	Intermediate Similarity	NPC271921
0.7826	Intermediate Similarity	NPC99619
0.7826	Intermediate Similarity	NPC330426
0.7826	Intermediate Similarity	NPC148192
0.7826	Intermediate Similarity	NPC22101
0.7812	Intermediate Similarity	NPC323498
0.7812	Intermediate Similarity	NPC323597
0.7812	Intermediate Similarity	NPC211752
0.7808	Intermediate Similarity	NPC473948
0.7794	Intermediate Similarity	NPC96414
0.7746	Intermediate Similarity	NPC202011
0.7714	Intermediate Similarity	NPC324981
0.7714	Intermediate Similarity	NPC48218
0.7714	Intermediate Similarity	NPC473559
0.7714	Intermediate Similarity	NPC209327
0.7714	Intermediate Similarity	NPC141481
0.7714	Intermediate Similarity	NPC273508
0.7681	Intermediate Similarity	NPC276299
0.7681	Intermediate Similarity	NPC146811
0.7671	Intermediate Similarity	NPC107654
0.7671	Intermediate Similarity	NPC473489
0.7656	Intermediate Similarity	NPC327388
0.7647	Intermediate Similarity	NPC476658
0.7632	Intermediate Similarity	NPC99651
0.7612	Intermediate Similarity	NPC26810
0.7576	Intermediate Similarity	NPC322002
0.7571	Intermediate Similarity	NPC473829
0.7571	Intermediate Similarity	NPC475443
0.7568	Intermediate Similarity	NPC260396
0.7568	Intermediate Similarity	NPC473582
0.7536	Intermediate Similarity	NPC282760
0.7536	Intermediate Similarity	NPC273600
0.7534	Intermediate Similarity	NPC470435
0.7534	Intermediate Similarity	NPC284006
0.75	Intermediate Similarity	NPC473361
0.75	Intermediate Similarity	NPC476660
0.75	Intermediate Similarity	NPC329904
0.75	Intermediate Similarity	NPC42526
0.7467	Intermediate Similarity	NPC203277
0.7467	Intermediate Similarity	NPC49392
0.7467	Intermediate Similarity	NPC190400
0.7463	Intermediate Similarity	NPC328311
0.7463	Intermediate Similarity	NPC26223
0.7463	Intermediate Similarity	NPC327112
0.7432	Intermediate Similarity	NPC315843
0.7432	Intermediate Similarity	NPC326504
0.7397	Intermediate Similarity	NPC293114
0.7391	Intermediate Similarity	NPC475221
0.7361	Intermediate Similarity	NPC473772
0.7353	Intermediate Similarity	NPC201939
0.7353	Intermediate Similarity	NPC113293
0.7353	Intermediate Similarity	NPC320305
0.7353	Intermediate Similarity	NPC328776
0.7353	Intermediate Similarity	NPC55376
0.7333	Intermediate Similarity	NPC478196
0.7333	Intermediate Similarity	NPC161038
0.7333	Intermediate Similarity	NPC478195
0.7333	Intermediate Similarity	NPC478192
0.7333	Intermediate Similarity	NPC478193
0.7333	Intermediate Similarity	NPC478194
0.7333	Intermediate Similarity	NPC478191
0.7324	Intermediate Similarity	NPC49863
0.7324	Intermediate Similarity	NPC122627
0.7313	Intermediate Similarity	NPC302564
0.7313	Intermediate Similarity	NPC222852
0.7297	Intermediate Similarity	NPC325627
0.7286	Intermediate Similarity	NPC470123
0.7273	Intermediate Similarity	NPC318481
0.7273	Intermediate Similarity	NPC182292
0.7273	Intermediate Similarity	NPC279532
0.7273	Intermediate Similarity	NPC248775
0.7273	Intermediate Similarity	NPC473471
0.726	Intermediate Similarity	NPC476012
0.726	Intermediate Similarity	NPC476037
0.725	Intermediate Similarity	NPC229799
0.725	Intermediate Similarity	NPC253801
0.725	Intermediate Similarity	NPC284472
0.725	Intermediate Similarity	NPC286770
0.7246	Intermediate Similarity	NPC68110
0.7222	Intermediate Similarity	NPC63873
0.7215	Intermediate Similarity	NPC297440
0.7206	Intermediate Similarity	NPC243532
0.72	Intermediate Similarity	NPC474321
0.7195	Intermediate Similarity	NPC69082
0.7195	Intermediate Similarity	NPC279267
0.7188	Intermediate Similarity	NPC477780
0.7188	Intermediate Similarity	NPC477781
0.7183	Intermediate Similarity	NPC328653
0.7183	Intermediate Similarity	NPC475555
0.7183	Intermediate Similarity	NPC475675
0.7183	Intermediate Similarity	NPC83965
0.7179	Intermediate Similarity	NPC180725
0.7179	Intermediate Similarity	NPC1180
0.7179	Intermediate Similarity	NPC475210
0.7179	Intermediate Similarity	NPC470149
0.7179	Intermediate Similarity	NPC470148
0.7164	Intermediate Similarity	NPC254095
0.7164	Intermediate Similarity	NPC223679
0.7162	Intermediate Similarity	NPC316185
0.716	Intermediate Similarity	NPC474776
0.7143	Intermediate Similarity	NPC148233
0.7143	Intermediate Similarity	NPC328089
0.7143	Intermediate Similarity	NPC275530
0.7143	Intermediate Similarity	NPC475711
0.7143	Intermediate Similarity	NPC176329
0.7143	Intermediate Similarity	NPC474278
0.7143	Intermediate Similarity	NPC125365
0.7143	Intermediate Similarity	NPC51809
0.7143	Intermediate Similarity	NPC308457
0.7143	Intermediate Similarity	NPC25747
0.7143	Intermediate Similarity	NPC68343
0.7143	Intermediate Similarity	NPC49302
0.7143	Intermediate Similarity	NPC470808
0.7143	Intermediate Similarity	NPC474026
0.7143	Intermediate Similarity	NPC474818
0.7125	Intermediate Similarity	NPC65930
0.7125	Intermediate Similarity	NPC180363
0.7125	Intermediate Similarity	NPC11383
0.7125	Intermediate Similarity	NPC145914
0.7125	Intermediate Similarity	NPC473529
0.7125	Intermediate Similarity	NPC473780
0.7125	Intermediate Similarity	NPC475159
0.7125	Intermediate Similarity	NPC11332
0.7125	Intermediate Similarity	NPC310450
0.7125	Intermediate Similarity	NPC329829
0.7125	Intermediate Similarity	NPC73310
0.7125	Intermediate Similarity	NPC131002
0.7125	Intermediate Similarity	NPC474252
0.7125	Intermediate Similarity	NPC475046
0.7125	Intermediate Similarity	NPC474959
0.7125	Intermediate Similarity	NPC94875
0.7125	Intermediate Similarity	NPC473712
0.7123	Intermediate Similarity	NPC101622
0.7123	Intermediate Similarity	NPC470436
0.7108	Intermediate Similarity	NPC45409
0.7101	Intermediate Similarity	NPC151648
0.7089	Intermediate Similarity	NPC133226
0.7089	Intermediate Similarity	NPC470147
0.7083	Intermediate Similarity	NPC203335
0.7077	Intermediate Similarity	NPC137538
0.7073	Intermediate Similarity	NPC286338
0.7073	Intermediate Similarity	NPC132496
0.7073	Intermediate Similarity	NPC322529
0.7073	Intermediate Similarity	NPC82795
0.7073	Intermediate Similarity	NPC223871
0.7073	Intermediate Similarity	NPC66346
0.7073	Intermediate Similarity	NPC107986
0.7073	Intermediate Similarity	NPC283085
0.7073	Intermediate Similarity	NPC473669
0.7073	Intermediate Similarity	NPC473478
0.7073	Intermediate Similarity	NPC110710
0.7073	Intermediate Similarity	NPC231009
0.7073	Intermediate Similarity	NPC103284
0.7073	Intermediate Similarity	NPC1083
0.7073	Intermediate Similarity	NPC182383
0.7073	Intermediate Similarity	NPC473651
0.7067	Intermediate Similarity	NPC327383
0.7067	Intermediate Similarity	NPC185186
0.7067	Intermediate Similarity	NPC329890
0.7067	Intermediate Similarity	NPC329914
0.7059	Intermediate Similarity	NPC318306
0.7059	Intermediate Similarity	NPC97570
0.7051	Intermediate Similarity	NPC127526
0.7051	Intermediate Similarity	NPC133377
0.7051	Intermediate Similarity	NPC28049
0.7051	Intermediate Similarity	NPC221095
0.7051	Intermediate Similarity	NPC279214
0.7042	Intermediate Similarity	NPC136164
0.7042	Intermediate Similarity	NPC318420
0.7042	Intermediate Similarity	NPC176215
0.7042	Intermediate Similarity	NPC296436
0.7042	Intermediate Similarity	NPC320642
0.7042	Intermediate Similarity	NPC323045
0.7042	Intermediate Similarity	NPC323477
0.7042	Intermediate Similarity	NPC317881

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 NPC478101 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	3151
0.2-0.3	3808
0.3-0.4	1570
0.4-0.5	315
0.5-0.6	78
0.6-0.7	21
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
0.7969	Intermediate Similarity	NPD6109	Phase 1
0.7463	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5343	Approved
0.7164	Intermediate Similarity	NPD585	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3197	Phase 1
0.7143	Intermediate Similarity	NPD6927	Phase 3
0.6885	Remote Similarity	NPD4222	Approved
0.6721	Remote Similarity	NPD6097	Approved
0.6721	Remote Similarity	NPD6096	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6698	Approved
0.6613	Remote Similarity	NPD39	Approved
0.6562	Remote Similarity	NPD3173	Approved
0.6557	Remote Similarity	NPD5326	Phase 3
0.6477	Remote Similarity	NPD7838	Discovery
0.6429	Remote Similarity	NPD69	Approved
0.6429	Remote Similarity	NPD9119	Approved
0.6429	Remote Similarity	NPD7154	Phase 3
0.642	Remote Similarity	NPD4271	Approved
0.642	Remote Similarity	NPD4268	Approved
0.6404	Remote Similarity	NPD7983	Approved
0.6324	Remote Similarity	NPD4266	Approved
0.6324	Remote Similarity	NPD3196	Approved
0.6324	Remote Similarity	NPD3195	Phase 2
0.6324	Remote Similarity	NPD3194	Approved
0.6286	Remote Similarity	NPD9118	Approved
0.6265	Remote Similarity	NPD4822	Approved
0.6265	Remote Similarity	NPD4252	Approved
0.6265	Remote Similarity	NPD4819	Approved
0.6265	Remote Similarity	NPD4821	Approved
0.6265	Remote Similarity	NPD4820	Approved
0.6235	Remote Similarity	NPD5362	Discontinued
0.622	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3172	Approved
0.6136	Remote Similarity	NPD4251	Approved
0.6136	Remote Similarity	NPD4250	Approved
0.6118	Remote Similarity	NPD4270	Approved
0.6118	Remote Similarity	NPD4269	Approved
0.6111	Remote Similarity	NPD5785	Approved
0.6094	Remote Similarity	NPD3174	Discontinued
0.6094	Remote Similarity	NPD4265	Approved
0.6092	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3730	Approved
0.6087	Remote Similarity	NPD3728	Approved
0.6047	Remote Similarity	NPD5332	Approved
0.6047	Remote Similarity	NPD5331	Approved
0.6023	Remote Similarity	NPD5786	Approved
0.6023	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD4790	Discontinued
0.5977	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.593	Remote Similarity	NPD6435	Approved
0.5921	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5363	Approved
0.5882	Remote Similarity	NPD29	Approved
0.5882	Remote Similarity	NPD28	Approved
0.5862	Remote Similarity	NPD6110	Phase 1
0.5854	Remote Similarity	NPD8039	Approved
0.5833	Remote Similarity	NPD4225	Approved
0.5824	Remote Similarity	NPD5370	Suspended
0.5806	Remote Similarity	NPD5778	Approved
0.5806	Remote Similarity	NPD5779	Approved
0.5747	Remote Similarity	NPD5209	Approved
0.5714	Remote Similarity	NPD4756	Discovery
0.5714	Remote Similarity	NPD5344	Discontinued
0.5699	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7637	Suspended
0.5698	Remote Similarity	NPD5368	Approved
0.5673	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6101	Approved
0.5625	Remote Similarity	NPD4228	Discovery
0.5625	Remote Similarity	NPD7839	Suspended

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