NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.13
Volume:	275.549
LogP:	2.379
LogD:	2.403
LogS:	-2.121
# Rotatable Bonds:	8
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	3.218
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:	-4.654
MDCK Permeability:	5.683230483555235e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	89.31450653076172%
Volume Distribution (VD):	0.482
Pgp-substrate:	22.17066192626953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.297
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.118
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.32
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.189
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	8.579
Half-life (T1/2):	0.786

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.867
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.578
Skin Sensitization:	0.523
Carcinogencity:	0.82
Eye Corrosion:	0.876
Eye Irritation:	0.528
Respiratory Toxicity:	0.269

Download Data

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

Natural Product: NPC201356

Natural Product ID:	NPC201356
*Common Name:**	Pectinolide C
IUPAC Name:	[(Z,3S)-1-[(2S,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]hept-1-en-3-yl] acetate
Synonyms:	Pectinolide C
Standard InCHIKey:	DYWKRIWLCNEWRY-SHYGTOARSA-N
Standard InCHI:	InChI=1S/C14H20O5/c1-3-4-5-11(18-10(2)15)6-8-13-12(16)7-9-14(17)19-13/h6-9,11-13,16H,3-5H2,1-2H3/b8-6-/t11-,12-,13-/m0/s1
SMILES:	CCCC[C@@H](/C=C[C@H]1[C@H](C=CC(=O)O1)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458475
PubChem CID:	10038670
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO40549	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30601004]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496706]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO28865	Hyptis pectinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	11
IC50	3
MIC	5
Others	2

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	4
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[448080]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[448080]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[448080]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.2	ug ml-1	PMID[448080]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[448080]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[448080]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	1.9	ug ml-1	PMID[448080]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	2300.0	nM	PMID[448081]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	300.0	nM	PMID[448081]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1000.0	nM	PMID[448081]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	8.0	mm	PMID[448080]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	4.0	mm	PMID[448080]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[448080]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[448080]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[448080]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[448080]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	500.0	ug.mL-1	PMID[448080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.0	ug ml-1	PMID[448080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.3	ug ml-1	PMID[448080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.6	ug ml-1	PMID[448080]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.2	ug ml-1	PMID[448080]

☑ 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 NPC201356 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	162
0.1-0.2	2397
0.2-0.3	8828
0.3-0.4	19075
0.4-0.5	7931
0.5-0.6	3115
0.6-0.7	958
0.7-0.8	169
0.8-0.85	37
0.85-0.9	19
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9836	High Similarity	NPC96414
0.9516	High Similarity	NPC19769
0.9016	High Similarity	NPC302564
0.8939	High Similarity	NPC475982
0.8906	High Similarity	NPC273600
0.8871	High Similarity	NPC26223
0.8769	High Similarity	NPC276299
0.873	High Similarity	NPC26810
0.8529	High Similarity	NPC202011
0.8507	High Similarity	NPC63873
0.8485	Intermediate Similarity	NPC146811
0.8472	Intermediate Similarity	NPC248775
0.8462	Intermediate Similarity	NPC25747
0.8462	Intermediate Similarity	NPC308457
0.8462	Intermediate Similarity	NPC148233
0.8358	Intermediate Similarity	NPC122627
0.8356	Intermediate Similarity	NPC180725
0.8356	Intermediate Similarity	NPC470148
0.8356	Intermediate Similarity	NPC470149
0.8333	Intermediate Similarity	NPC474026
0.8333	Intermediate Similarity	NPC475711
0.8243	Intermediate Similarity	NPC470147
0.8243	Intermediate Similarity	NPC133226
0.8209	Intermediate Similarity	NPC124586
0.8209	Intermediate Similarity	NPC475675
0.8209	Intermediate Similarity	NPC475555
0.8182	Intermediate Similarity	NPC470808
0.8169	Intermediate Similarity	NPC107654
0.8169	Intermediate Similarity	NPC315843
0.8125	Intermediate Similarity	NPC22897
0.8125	Intermediate Similarity	NPC97570
0.8125	Intermediate Similarity	NPC159650
0.8116	Intermediate Similarity	NPC151481
0.8088	Intermediate Similarity	NPC478097
0.8088	Intermediate Similarity	NPC478100
0.806	Intermediate Similarity	NPC478099
0.806	Intermediate Similarity	NPC478098
0.806	Intermediate Similarity	NPC470123
0.8028	Intermediate Similarity	NPC327383
0.8028	Intermediate Similarity	NPC185186
0.8	Intermediate Similarity	NPC476037
0.7973	Intermediate Similarity	NPC318481
0.7971	Intermediate Similarity	NPC475760
0.7971	Intermediate Similarity	NPC238223
0.7941	Intermediate Similarity	NPC478101
0.7937	Intermediate Similarity	NPC472808
0.7937	Intermediate Similarity	NPC324224
0.7922	Intermediate Similarity	NPC315559
0.7895	Intermediate Similarity	NPC297440
0.7887	Intermediate Similarity	NPC316185
0.7887	Intermediate Similarity	NPC293114
0.7867	Intermediate Similarity	NPC1180
0.7826	Intermediate Similarity	NPC25298
0.7826	Intermediate Similarity	NPC132286
0.7808	Intermediate Similarity	NPC327041
0.7808	Intermediate Similarity	NPC285840
0.7794	Intermediate Similarity	NPC282760
0.7792	Intermediate Similarity	NPC313677
0.7778	Intermediate Similarity	NPC284006
0.7778	Intermediate Similarity	NPC329890
0.7746	Intermediate Similarity	NPC476012
0.7733	Intermediate Similarity	NPC28049
0.7733	Intermediate Similarity	NPC279532
0.7703	Intermediate Similarity	NPC326661
0.7703	Intermediate Similarity	NPC203277
0.7692	Intermediate Similarity	NPC473315
0.7692	Intermediate Similarity	NPC44261
0.7692	Intermediate Similarity	NPC142111
0.7692	Intermediate Similarity	NPC223679
0.7681	Intermediate Similarity	NPC37382
0.7639	Intermediate Similarity	NPC475762
0.7606	Intermediate Similarity	NPC130618
0.7595	Intermediate Similarity	NPC473308
0.7568	Intermediate Similarity	NPC161038
0.7568	Intermediate Similarity	NPC478194
0.7568	Intermediate Similarity	NPC478193
0.7568	Intermediate Similarity	NPC473582
0.7568	Intermediate Similarity	NPC478191
0.7568	Intermediate Similarity	NPC473948
0.7568	Intermediate Similarity	NPC478195
0.7568	Intermediate Similarity	NPC478192
0.7568	Intermediate Similarity	NPC260396
0.7568	Intermediate Similarity	NPC478196
0.7564	Intermediate Similarity	NPC251026
0.7541	Intermediate Similarity	NPC275316
0.7538	Intermediate Similarity	NPC129150
0.7538	Intermediate Similarity	NPC135863
0.7534	Intermediate Similarity	NPC329914
0.7532	Intermediate Similarity	NPC121374
0.75	Intermediate Similarity	NPC59558
0.75	Intermediate Similarity	NPC473361
0.75	Intermediate Similarity	NPC473471
0.75	Intermediate Similarity	NPC473737
0.75	Intermediate Similarity	NPC329904
0.7468	Intermediate Similarity	NPC161045
0.7467	Intermediate Similarity	NPC301207
0.7467	Intermediate Similarity	NPC127118
0.7467	Intermediate Similarity	NPC188860
0.7467	Intermediate Similarity	NPC209113
0.7467	Intermediate Similarity	NPC470705
0.7465	Intermediate Similarity	NPC474823
0.7465	Intermediate Similarity	NPC310210
0.7463	Intermediate Similarity	NPC81896
0.7463	Intermediate Similarity	NPC321919
0.7436	Intermediate Similarity	NPC469469
0.7432	Intermediate Similarity	NPC473489
0.7432	Intermediate Similarity	NPC474280
0.7432	Intermediate Similarity	NPC326504
0.7424	Intermediate Similarity	NPC474084
0.7424	Intermediate Similarity	NPC254095
0.7407	Intermediate Similarity	NPC208473
0.7403	Intermediate Similarity	NPC139712
0.7391	Intermediate Similarity	NPC475221
0.7385	Intermediate Similarity	NPC230296
0.7375	Intermediate Similarity	NPC475035
0.7375	Intermediate Similarity	NPC161670
0.7375	Intermediate Similarity	NPC474251
0.7368	Intermediate Similarity	NPC49302
0.7368	Intermediate Similarity	NPC233071
0.7368	Intermediate Similarity	NPC275530
0.7368	Intermediate Similarity	NPC474278
0.7368	Intermediate Similarity	NPC51809
0.7368	Intermediate Similarity	NPC474818
0.7368	Intermediate Similarity	NPC176329
0.7368	Intermediate Similarity	NPC125365
0.7361	Intermediate Similarity	NPC475004
0.7353	Intermediate Similarity	NPC55376
0.7342	Intermediate Similarity	NPC310450
0.7342	Intermediate Similarity	NPC11383
0.7342	Intermediate Similarity	NPC474959
0.7342	Intermediate Similarity	NPC475046
0.7313	Intermediate Similarity	NPC322186
0.7313	Intermediate Similarity	NPC222852
0.7286	Intermediate Similarity	NPC471566
0.7286	Intermediate Similarity	NPC471565
0.7286	Intermediate Similarity	NPC471556
0.7284	Intermediate Similarity	NPC11804
0.7284	Intermediate Similarity	NPC475034
0.7284	Intermediate Similarity	NPC471494
0.7284	Intermediate Similarity	NPC470124
0.7273	Intermediate Similarity	NPC212730
0.7273	Intermediate Similarity	NPC249850
0.7273	Intermediate Similarity	NPC265551
0.7273	Intermediate Similarity	NPC477314
0.7273	Intermediate Similarity	NPC323436
0.7273	Intermediate Similarity	NPC293437
0.7273	Intermediate Similarity	NPC279214
0.7273	Intermediate Similarity	NPC221095
0.7273	Intermediate Similarity	NPC294938
0.7262	Intermediate Similarity	NPC3952
0.725	Intermediate Similarity	NPC229799
0.725	Intermediate Similarity	NPC284472
0.725	Intermediate Similarity	NPC286770
0.7246	Intermediate Similarity	NPC475073
0.7246	Intermediate Similarity	NPC2328
0.7246	Intermediate Similarity	NPC474774
0.7246	Intermediate Similarity	NPC68110
0.7246	Intermediate Similarity	NPC29697
0.7237	Intermediate Similarity	NPC190400
0.7237	Intermediate Similarity	NPC49392
0.7231	Intermediate Similarity	NPC317899
0.7229	Intermediate Similarity	NPC470137
0.7215	Intermediate Similarity	NPC150502
0.72	Intermediate Similarity	NPC476590
0.72	Intermediate Similarity	NPC114727
0.72	Intermediate Similarity	NPC474545
0.7195	Intermediate Similarity	NPC311163
0.7179	Intermediate Similarity	NPC99651
0.7179	Intermediate Similarity	NPC475210
0.716	Intermediate Similarity	NPC266718
0.7143	Intermediate Similarity	NPC315394
0.7143	Intermediate Similarity	NPC133450
0.7121	Intermediate Similarity	NPC86948
0.7108	Intermediate Similarity	NPC475037
0.7101	Intermediate Similarity	NPC325929
0.7101	Intermediate Similarity	NPC66460
0.7101	Intermediate Similarity	NPC113293
0.7101	Intermediate Similarity	NPC271282
0.7083	Intermediate Similarity	NPC99619
0.7083	Intermediate Similarity	NPC203335
0.7083	Intermediate Similarity	NPC26500
0.7073	Intermediate Similarity	NPC182383
0.7067	Intermediate Similarity	NPC470435
0.7059	Intermediate Similarity	NPC177668
0.7059	Intermediate Similarity	NPC318306
0.7059	Intermediate Similarity	NPC82465
0.7051	Intermediate Similarity	NPC209135
0.7051	Intermediate Similarity	NPC474816
0.7051	Intermediate Similarity	NPC182292
0.7042	Intermediate Similarity	NPC182794
0.7042	Intermediate Similarity	NPC476657
0.7042	Intermediate Similarity	NPC476655
0.7042	Intermediate Similarity	NPC476654
0.7037	Intermediate Similarity	NPC253801
0.7037	Intermediate Similarity	NPC16488
0.7027	Intermediate Similarity	NPC4299
0.7015	Intermediate Similarity	NPC44542
0.7015	Intermediate Similarity	NPC472445
0.7013	Intermediate Similarity	NPC68819
0.7	Intermediate Similarity	NPC474980

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 NPC201356 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	2721
0.2-0.3	4093
0.3-0.4	1762
0.4-0.5	339
0.5-0.6	89
0.6-0.7	15
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
0.7424	Intermediate Similarity	NPD585	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD9119	Approved
0.6912	Remote Similarity	NPD6109	Phase 1
0.6912	Remote Similarity	NPD69	Approved
0.6765	Remote Similarity	NPD9118	Approved
0.6747	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7838	Discovery
0.6622	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6698	Approved
0.6477	Remote Similarity	NPD46	Approved
0.6383	Remote Similarity	NPD5344	Discontinued
0.6351	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4225	Approved
0.6344	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD3197	Phase 1
0.6129	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD6927	Phase 3
0.6111	Remote Similarity	NPD5785	Approved
0.6098	Remote Similarity	NPD4756	Discovery
0.6071	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4220	Pre-registration
0.5938	Remote Similarity	NPD6648	Approved
0.5909	Remote Similarity	NPD5343	Approved
0.5909	Remote Similarity	NPD5363	Approved
0.587	Remote Similarity	NPD7983	Approved
0.5862	Remote Similarity	NPD6110	Phase 1
0.5862	Remote Similarity	NPD7154	Phase 3
0.5846	Remote Similarity	NPD39	Approved
0.5846	Remote Similarity	NPD4222	Approved
0.5846	Remote Similarity	NPD4265	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5821	Remote Similarity	NPD3173	Approved
0.5758	Remote Similarity	NPD1407	Approved
0.5747	Remote Similarity	NPD5209	Approved
0.5701	Remote Similarity	NPD7115	Discovery
0.5698	Remote Similarity	NPD4821	Approved
0.5698	Remote Similarity	NPD4819	Approved
0.5698	Remote Similarity	NPD4252	Approved
0.5698	Remote Similarity	NPD4820	Approved
0.5698	Remote Similarity	NPD4822	Approved
0.5692	Remote Similarity	NPD6096	Approved
0.5692	Remote Similarity	NPD6097	Approved
0.5684	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5362	Discontinued
0.5667	Remote Similarity	NPD4249	Approved
0.5647	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD9090	Phase 3
0.5604	Remote Similarity	NPD4251	Approved
0.5604	Remote Similarity	NPD4250	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