NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	285.298
LogP:	3.008
LogD:	1.626
LogS:	-3.474
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	3.992
Fsp3:	0.312
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:	-5.267
MDCK Permeability:	0.0004444418882485479
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.21517181396484%
Volume Distribution (VD):	0.284
Pgp-substrate:	2.0199031829833984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.288
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.854
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.522
CYP3A4-substrate:	0.06

ADMET: Excretion

Clearance (CL):	3.923
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.858
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.864
Maximum Recommended Daily Dose:	0.113
Skin Sensitization:	0.952
Carcinogencity:	0.474
Eye Corrosion:	0.678
Eye Irritation:	0.941
Respiratory Toxicity:	0.611

Download Data

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

Natural Product: NPC477829

Natural Product ID:	NPC477829
*Common Name:**	(E)-6-hydroxyhexadec-7-en-9,11,13,15-tetraynoic acid
IUPAC Name:	(E)-6-hydroxyhexadec-7-en-9,11,13,15-tetraynoic acid
Synonyms:
Standard InCHIKey:	JZVMTJSCYGZJFS-FMIVXFBMSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-2-3-4-5-6-7-8-9-12-15(17)13-10-11-14-16(18)19/h1,9,12,15,17H,10-11,13-14H2,(H,18,19)/b12-9+
SMILES:	C#CC#CC#CC#C/C=C/C(CCCCC(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44364739
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002949] Long-chain fatty acids

*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
NPO33530	Pseudomonas caryophylli	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8544177]

☑ 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
MIC	20

Activity Type	# Activity
Organism	20

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.1	ug/ml	PMID[8544177]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.1	ug/ml	PMID[8544177]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.2	ug/ml	PMID[8544177]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.8	ug/ml	PMID[8544177]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	0.8	ug/ml	PMID[8544177]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	0.8	ug/ml	PMID[8544177]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	1.5	ug/ml	PMID[8544177]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	=	0.8	ug/ml	PMID[8544177]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	0.2	ug/ml	PMID[8544177]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	=	0.4	ug/ml	PMID[8544177]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	=	6.2	ug/ml	PMID[8544177]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	25	ug/ml	PMID[8544177]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.05	ug/ml	PMID[8544177]
NPT3173	Organism	Arthroderma benhamiae	Arthroderma benhamiae	MIC	=	0.05	ug/ml	PMID[8544177]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	=	0.02	ug/ml	PMID[8544177]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	0.02	ug/ml	PMID[8544177]

☑ 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 NPC477829 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	189
0.1-0.2	2456
0.2-0.3	12904
0.3-0.4	15437
0.4-0.5	7548
0.5-0.6	3184
0.6-0.7	757
0.7-0.8	199
0.8-0.85	13
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC470320
0.9016	High Similarity	NPC226592
0.8571	High Similarity	NPC245947
0.8571	High Similarity	NPC136164
0.8571	High Similarity	NPC255863
0.8387	Intermediate Similarity	NPC475984
0.8308	Intermediate Similarity	NPC26500
0.8308	Intermediate Similarity	NPC99619
0.8254	Intermediate Similarity	NPC470965
0.8226	Intermediate Similarity	NPC327112
0.8226	Intermediate Similarity	NPC243532
0.8095	Intermediate Similarity	NPC201939
0.806	Intermediate Similarity	NPC143396
0.8	Intermediate Similarity	NPC326268
0.8	Intermediate Similarity	NPC473863
0.8	Intermediate Similarity	NPC274290
0.8	Intermediate Similarity	NPC318420
0.8	Intermediate Similarity	NPC54766
0.7969	Intermediate Similarity	NPC29697
0.7869	Intermediate Similarity	NPC187777
0.7869	Intermediate Similarity	NPC179764
0.7812	Intermediate Similarity	NPC271282
0.7812	Intermediate Similarity	NPC113293
0.7812	Intermediate Similarity	NPC325929
0.7812	Intermediate Similarity	NPC66460
0.7778	Intermediate Similarity	NPC473652
0.7742	Intermediate Similarity	NPC225929
0.7727	Intermediate Similarity	NPC323045
0.7727	Intermediate Similarity	NPC323477
0.7727	Intermediate Similarity	NPC317881
0.7714	Intermediate Similarity	NPC325627
0.7705	Intermediate Similarity	NPC146551
0.7705	Intermediate Similarity	NPC477725
0.7705	Intermediate Similarity	NPC474513
0.7705	Intermediate Similarity	NPC152668
0.7705	Intermediate Similarity	NPC470963
0.7705	Intermediate Similarity	NPC477726
0.7667	Intermediate Similarity	NPC139029
0.7667	Intermediate Similarity	NPC36061
0.7667	Intermediate Similarity	NPC294548
0.7667	Intermediate Similarity	NPC70387
0.7667	Intermediate Similarity	NPC321062
0.7667	Intermediate Similarity	NPC1813
0.7656	Intermediate Similarity	NPC235242
0.7656	Intermediate Similarity	NPC328311
0.7619	Intermediate Similarity	NPC34416
0.7619	Intermediate Similarity	NPC267817
0.7612	Intermediate Similarity	NPC328653
0.7606	Intermediate Similarity	NPC227396
0.7581	Intermediate Similarity	NPC471960
0.7581	Intermediate Similarity	NPC475384
0.7581	Intermediate Similarity	NPC470969
0.7581	Intermediate Similarity	NPC470967
0.7581	Intermediate Similarity	NPC473847
0.7581	Intermediate Similarity	NPC470968
0.7581	Intermediate Similarity	NPC161838
0.7581	Intermediate Similarity	NPC470966
0.7581	Intermediate Similarity	NPC470964
0.7581	Intermediate Similarity	NPC311648
0.7581	Intermediate Similarity	NPC477661
0.7581	Intermediate Similarity	NPC477201
0.7576	Intermediate Similarity	NPC328089
0.7576	Intermediate Similarity	NPC68343
0.7541	Intermediate Similarity	NPC424
0.7541	Intermediate Similarity	NPC281972
0.7541	Intermediate Similarity	NPC154245
0.7541	Intermediate Similarity	NPC6095
0.7541	Intermediate Similarity	NPC290563
0.7541	Intermediate Similarity	NPC85813
0.7541	Intermediate Similarity	NPC87564
0.7541	Intermediate Similarity	NPC32467
0.7541	Intermediate Similarity	NPC261831
0.7541	Intermediate Similarity	NPC256209
0.7541	Intermediate Similarity	NPC49059
0.7541	Intermediate Similarity	NPC88966
0.7541	Intermediate Similarity	NPC25417
0.7538	Intermediate Similarity	NPC321838
0.75	Intermediate Similarity	NPC18357
0.75	Intermediate Similarity	NPC148192
0.75	Intermediate Similarity	NPC330426
0.75	Intermediate Similarity	NPC49863
0.75	Intermediate Similarity	NPC22101
0.75	Intermediate Similarity	NPC104537
0.75	Intermediate Similarity	NPC127091
0.75	Intermediate Similarity	NPC271921
0.75	Intermediate Similarity	NPC322002
0.75	Intermediate Similarity	NPC281245
0.746	Intermediate Similarity	NPC44542
0.746	Intermediate Similarity	NPC48968
0.746	Intermediate Similarity	NPC470970
0.746	Intermediate Similarity	NPC594
0.7419	Intermediate Similarity	NPC52264
0.7419	Intermediate Similarity	NPC473896
0.7419	Intermediate Similarity	NPC473735
0.7419	Intermediate Similarity	NPC473721
0.7419	Intermediate Similarity	NPC473910
0.7419	Intermediate Similarity	NPC473725
0.7419	Intermediate Similarity	NPC475353
0.7414	Intermediate Similarity	NPC207292
0.7397	Intermediate Similarity	NPC279537
0.7391	Intermediate Similarity	NPC324981
0.7391	Intermediate Similarity	NPC48218
0.7391	Intermediate Similarity	NPC473559
0.7391	Intermediate Similarity	NPC141481
0.7377	Intermediate Similarity	NPC71761
0.7333	Intermediate Similarity	NPC28205
0.7333	Intermediate Similarity	NPC129263
0.7333	Intermediate Similarity	NPC470411
0.7333	Intermediate Similarity	NPC284212
0.7302	Intermediate Similarity	NPC18951
0.7288	Intermediate Similarity	NPC5413
0.7288	Intermediate Similarity	NPC149821
0.7286	Intermediate Similarity	NPC236208
0.7286	Intermediate Similarity	NPC470436
0.7273	Intermediate Similarity	NPC168407
0.7273	Intermediate Similarity	NPC320305
0.7273	Intermediate Similarity	NPC328776
0.7258	Intermediate Similarity	NPC110732
0.7258	Intermediate Similarity	NPC473532
0.7258	Intermediate Similarity	NPC137538
0.7246	Intermediate Similarity	NPC475443
0.7246	Intermediate Similarity	NPC25298
0.7246	Intermediate Similarity	NPC473829
0.7231	Intermediate Similarity	NPC106851
0.7231	Intermediate Similarity	NPC329249
0.7231	Intermediate Similarity	NPC274927
0.7231	Intermediate Similarity	NPC222852
0.7231	Intermediate Similarity	NPC318306
0.7213	Intermediate Similarity	NPC92114
0.7206	Intermediate Similarity	NPC320642
0.72	Intermediate Similarity	NPC192006
0.7188	Intermediate Similarity	NPC472445
0.7188	Intermediate Similarity	NPC265551
0.7188	Intermediate Similarity	NPC323436
0.7188	Intermediate Similarity	NPC212730
0.7183	Intermediate Similarity	NPC476660
0.7183	Intermediate Similarity	NPC42526
0.7167	Intermediate Similarity	NPC224227
0.7143	Intermediate Similarity	NPC28779
0.7143	Intermediate Similarity	NPC223677
0.7143	Intermediate Similarity	NPC10316
0.7143	Intermediate Similarity	NPC128061
0.7143	Intermediate Similarity	NPC200845
0.7123	Intermediate Similarity	NPC92558
0.7121	Intermediate Similarity	NPC471278
0.7121	Intermediate Similarity	NPC174447
0.7121	Intermediate Similarity	NPC122521
0.7121	Intermediate Similarity	NPC251042
0.7119	Intermediate Similarity	NPC180534
0.7097	Intermediate Similarity	NPC61177
0.7097	Intermediate Similarity	NPC139545
0.7097	Intermediate Similarity	NPC26102
0.7097	Intermediate Similarity	NPC217188
0.7097	Intermediate Similarity	NPC309606
0.7097	Intermediate Similarity	NPC477724
0.7097	Intermediate Similarity	NPC34577
0.7097	Intermediate Similarity	NPC39633
0.7097	Intermediate Similarity	NPC187361
0.7083	Intermediate Similarity	NPC186531
0.7083	Intermediate Similarity	NPC67076
0.7083	Intermediate Similarity	NPC319163
0.7067	Intermediate Similarity	NPC320630
0.7067	Intermediate Similarity	NPC7563
0.7067	Intermediate Similarity	NPC116177
0.7049	Intermediate Similarity	NPC151782
0.7049	Intermediate Similarity	NPC470412
0.7049	Intermediate Similarity	NPC262968
0.7049	Intermediate Similarity	NPC71053
0.7049	Intermediate Similarity	NPC59408
0.7049	Intermediate Similarity	NPC470410
0.7042	Intermediate Similarity	NPC473772
0.7042	Intermediate Similarity	NPC130618
0.7042	Intermediate Similarity	NPC317583
0.7031	Intermediate Similarity	NPC327388
0.7031	Intermediate Similarity	NPC472808
0.7031	Intermediate Similarity	NPC324224
0.7015	Intermediate Similarity	NPC40082
0.7	Intermediate Similarity	NPC471275
0.7	Intermediate Similarity	NPC478097
0.7	Intermediate Similarity	NPC471280
0.7	Intermediate Similarity	NPC471276
0.7	Intermediate Similarity	NPC125122
0.7	Intermediate Similarity	NPC153538
0.6986	Remote Similarity	NPC470435
0.6984	Remote Similarity	NPC48058
0.6974	Remote Similarity	NPC267231
0.6974	Remote Similarity	NPC469495
0.697	Remote Similarity	NPC322186
0.697	Remote Similarity	NPC474267
0.6957	Remote Similarity	NPC478099
0.6957	Remote Similarity	NPC478098
0.6949	Remote Similarity	NPC35141
0.6949	Remote Similarity	NPC124183
0.6935	Remote Similarity	NPC129458
0.6935	Remote Similarity	NPC161366
0.6933	Remote Similarity	NPC190400
0.6933	Remote Similarity	NPC49392
0.6923	Remote Similarity	NPC88735
0.6923	Remote Similarity	NPC211752
0.6923	Remote Similarity	NPC323597

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 NPC477829 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	3080
0.2-0.3	3842
0.3-0.4	1500
0.4-0.5	459
0.5-0.6	75
0.6-0.7	34
0.7-0.8	10
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8226	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD3197	Phase 1
0.7667	Intermediate Similarity	NPD3172	Approved
0.7541	Intermediate Similarity	NPD3194	Approved
0.7541	Intermediate Similarity	NPD3196	Approved
0.7541	Intermediate Similarity	NPD3195	Phase 2
0.7541	Intermediate Similarity	NPD4266	Approved
0.75	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD3173	Approved
0.7119	Intermediate Similarity	NPD622	Approved
0.7049	Intermediate Similarity	NPD29	Approved
0.7049	Intermediate Similarity	NPD28	Approved
0.6974	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4269	Approved
0.6835	Remote Similarity	NPD4270	Approved
0.6795	Remote Similarity	NPD4252	Approved
0.678	Remote Similarity	NPD3174	Discontinued
0.678	Remote Similarity	NPD4222	Approved
0.6753	Remote Similarity	NPD4271	Approved
0.6753	Remote Similarity	NPD4268	Approved
0.675	Remote Similarity	NPD5332	Approved
0.675	Remote Similarity	NPD5362	Discontinued
0.675	Remote Similarity	NPD5331	Approved
0.675	Remote Similarity	NPD7154	Phase 3
0.6585	Remote Similarity	NPD5363	Approved
0.6582	Remote Similarity	NPD4820	Approved
0.6582	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4822	Approved
0.6582	Remote Similarity	NPD4819	Approved
0.6582	Remote Similarity	NPD4821	Approved
0.6506	Remote Similarity	NPD5786	Approved
0.65	Remote Similarity	NPD4790	Discontinued
0.65	Remote Similarity	NPD39	Approved
0.641	Remote Similarity	NPD4756	Discovery
0.6375	Remote Similarity	NPD5368	Approved
0.6324	Remote Similarity	NPD6109	Phase 1
0.6296	Remote Similarity	NPD5369	Approved
0.629	Remote Similarity	NPD5343	Approved
0.622	Remote Similarity	NPD6435	Approved
0.6207	Remote Similarity	NPD5785	Approved
0.6167	Remote Similarity	NPD5326	Phase 3
0.6136	Remote Similarity	NPD7983	Approved
0.6125	Remote Similarity	NPD3732	Approved
0.6118	Remote Similarity	NPD4249	Approved
0.6092	Remote Similarity	NPD5370	Suspended
0.6067	Remote Similarity	NPD5778	Approved
0.6067	Remote Similarity	NPD5779	Approved
0.6047	Remote Similarity	NPD4251	Approved
0.6047	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD4265	Approved
0.5955	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD8039	Approved
0.5882	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7839	Suspended
0.5843	Remote Similarity	NPD46	Approved
0.5843	Remote Similarity	NPD6698	Approved
0.5806	Remote Similarity	NPD6096	Approved
0.5806	Remote Similarity	NPD6097	Approved
0.5758	Remote Similarity	NPD6927	Phase 3
0.5753	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4623	Approved
0.5747	Remote Similarity	NPD4519	Discontinued
0.5735	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3728	Approved
0.5735	Remote Similarity	NPD3730	Approved
0.5733	Remote Similarity	NPD3704	Approved
0.5733	Remote Similarity	NPD7331	Phase 2
0.573	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.573	Remote Similarity	NPD6101	Approved
0.5692	Remote Similarity	NPD4220	Pre-registration
0.5652	Remote Similarity	NPD342	Phase 1
0.5616	Remote Similarity	NPD368	Approved
0.5604	Remote Similarity	NPD6411	Approved
0.56	Remote Similarity	NPD2685	Clinical (unspecified phase)

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