NPASS Compound

Structure

NPC469373 OpenBabel07101718182D 23 22 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 20 1 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 3 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 2 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.36
Volume:	657.955
LogP:	8.849
LogD:	5.702
LogS:	-4.29
# Rotatable Bonds:	8
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.102
Synthetic Accessibility Score:	6.122
Fsp3:	0.553
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	1.3001762454223353e-05
Pgp-inhibitor:	0.068
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	98.27002716064453%
Volume Distribution (VD):	1.218
Pgp-substrate:	6.581101417541504%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.186
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.723

ADMET: Excretion

Clearance (CL):	17.082
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.099
Carcinogencity:	0.28
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC469373

Natural Product ID:	NPC469373
*Common Name:**	(2E,4E,9Z)-1-Hydroxyoctadecatrien-6-Yn-18-Yl Acetate
IUPAC Name:	[(10Z,15E,17E)-18-hydroxyoctadeca-10,15,17-trien-12-ynyl] acetate
Synonyms:
Standard InCHIKey:	IVLWOEUKUICFOI-CQPDHRHYSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-20(22)23-19-17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-21/h2,4,12,14,16,18,21H,3,5,7,9-11,13,15,17,19H2,1H3/b4-2-,14-12+,18-16+
SMILES:	O/C=C/C=C/CC#C/C=CCCCCCCCCCOC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077018
PubChem CID:	46881222
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001722] Fatty alcohol esters

*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
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19994846]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16425	Bupleurum longiradiatum	Species	Apiaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[482534]

☑ 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 NPC469373 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	144
0.1-0.2	2577
0.2-0.3	15783
0.3-0.4	15354
0.4-0.5	6659
0.5-0.6	1684
0.6-0.7	372
0.7-0.8	114
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.85	High Similarity	NPC271282
0.85	High Similarity	NPC66460
0.85	High Similarity	NPC325929
0.8361	Intermediate Similarity	NPC29697
0.8333	Intermediate Similarity	NPC207815
0.8333	Intermediate Similarity	NPC299730
0.8136	Intermediate Similarity	NPC44542
0.7931	Intermediate Similarity	NPC269615
0.7869	Intermediate Similarity	NPC474267
0.7869	Intermediate Similarity	NPC222852
0.7833	Intermediate Similarity	NPC472445
0.7833	Intermediate Similarity	NPC225929
0.7759	Intermediate Similarity	NPC34577
0.7667	Intermediate Similarity	NPC179764
0.7667	Intermediate Similarity	NPC187777
0.7619	Intermediate Similarity	NPC475984
0.7586	Intermediate Similarity	NPC106531
0.7541	Intermediate Similarity	NPC212730
0.7541	Intermediate Similarity	NPC265551
0.75	Intermediate Similarity	NPC200845
0.75	Intermediate Similarity	NPC10316
0.75	Intermediate Similarity	NPC223677
0.75	Intermediate Similarity	NPC274290
0.75	Intermediate Similarity	NPC473863
0.75	Intermediate Similarity	NPC228473
0.75	Intermediate Similarity	NPC28779
0.75	Intermediate Similarity	NPC470965
0.75	Intermediate Similarity	NPC128061
0.75	Intermediate Similarity	NPC52264
0.75	Intermediate Similarity	NPC54766
0.746	Intermediate Similarity	NPC471278
0.7458	Intermediate Similarity	NPC284224
0.7458	Intermediate Similarity	NPC71761
0.7455	Intermediate Similarity	NPC276825
0.7414	Intermediate Similarity	NPC129263
0.7385	Intermediate Similarity	NPC470320
0.7385	Intermediate Similarity	NPC226592
0.7377	Intermediate Similarity	NPC18951
0.7368	Intermediate Similarity	NPC302310
0.7353	Intermediate Similarity	NPC473772
0.7344	Intermediate Similarity	NPC320305
0.7344	Intermediate Similarity	NPC328776
0.7344	Intermediate Similarity	NPC201939
0.7333	Intermediate Similarity	NPC137538
0.7333	Intermediate Similarity	NPC49059
0.7333	Intermediate Similarity	NPC110732
0.7333	Intermediate Similarity	NPC256209
0.7288	Intermediate Similarity	NPC161366
0.7273	Intermediate Similarity	NPC476657
0.7273	Intermediate Similarity	NPC476654
0.7273	Intermediate Similarity	NPC245947
0.7273	Intermediate Similarity	NPC255863
0.7273	Intermediate Similarity	NPC108195
0.7273	Intermediate Similarity	NPC136164
0.7273	Intermediate Similarity	NPC476655
0.7246	Intermediate Similarity	NPC476660
0.7213	Intermediate Similarity	NPC474672
0.7213	Intermediate Similarity	NPC474913
0.7213	Intermediate Similarity	NPC146551
0.7213	Intermediate Similarity	NPC470963
0.7213	Intermediate Similarity	NPC474513
0.7188	Intermediate Similarity	NPC243532
0.7188	Intermediate Similarity	NPC327112
0.7167	Intermediate Similarity	NPC36061
0.7167	Intermediate Similarity	NPC477724
0.7167	Intermediate Similarity	NPC39633
0.7167	Intermediate Similarity	NPC139545
0.7167	Intermediate Similarity	NPC1813
0.7167	Intermediate Similarity	NPC26102
0.7167	Intermediate Similarity	NPC294548
0.7167	Intermediate Similarity	NPC309606
0.7167	Intermediate Similarity	NPC187361
0.7167	Intermediate Similarity	NPC139029
0.7164	Intermediate Similarity	NPC476659
0.7164	Intermediate Similarity	NPC476656
0.7143	Intermediate Similarity	NPC76976
0.7121	Intermediate Similarity	NPC68343
0.7121	Intermediate Similarity	NPC476658
0.7121	Intermediate Similarity	NPC328089
0.7119	Intermediate Similarity	NPC284212
0.7119	Intermediate Similarity	NPC28205
0.7101	Intermediate Similarity	NPC475004
0.7097	Intermediate Similarity	NPC470964
0.7097	Intermediate Similarity	NPC311648
0.7091	Intermediate Similarity	NPC252978
0.7077	Intermediate Similarity	NPC321838
0.7059	Intermediate Similarity	NPC104537
0.7059	Intermediate Similarity	NPC473752
0.7059	Intermediate Similarity	NPC475443
0.7059	Intermediate Similarity	NPC127091
0.7059	Intermediate Similarity	NPC330426
0.7059	Intermediate Similarity	NPC271921
0.7059	Intermediate Similarity	NPC473829
0.7059	Intermediate Similarity	NPC148192
0.7059	Intermediate Similarity	NPC22101
0.7049	Intermediate Similarity	NPC281972
0.7049	Intermediate Similarity	NPC6095
0.7049	Intermediate Similarity	NPC87564
0.7049	Intermediate Similarity	NPC154245
0.7049	Intermediate Similarity	NPC32467
0.7049	Intermediate Similarity	NPC290563
0.7049	Intermediate Similarity	NPC25417
0.7049	Intermediate Similarity	NPC85813
0.7049	Intermediate Similarity	NPC424
0.7049	Intermediate Similarity	NPC261831
0.7049	Intermediate Similarity	NPC88966
0.7042	Intermediate Similarity	NPC329890
0.7042	Intermediate Similarity	NPC329914
0.7018	Intermediate Similarity	NPC180575
0.7015	Intermediate Similarity	NPC318420
0.7015	Intermediate Similarity	NPC326268
0.7	Intermediate Similarity	NPC92114
0.7	Intermediate Similarity	NPC281245
0.7	Intermediate Similarity	NPC236872
0.7	Intermediate Similarity	NPC18357
0.6984	Remote Similarity	NPC193975
0.6984	Remote Similarity	NPC48968
0.6984	Remote Similarity	NPC594
0.6984	Remote Similarity	NPC471277
0.6984	Remote Similarity	NPC471279
0.6957	Remote Similarity	NPC141481
0.6957	Remote Similarity	NPC473559
0.6957	Remote Similarity	NPC324981
0.6957	Remote Similarity	NPC474823
0.6957	Remote Similarity	NPC48218
0.6949	Remote Similarity	NPC224227
0.6949	Remote Similarity	NPC59051
0.6949	Remote Similarity	NPC301482
0.6944	Remote Similarity	NPC474321
0.6935	Remote Similarity	NPC477725
0.6935	Remote Similarity	NPC477726
0.6935	Remote Similarity	NPC45626
0.6935	Remote Similarity	NPC152668
0.6923	Remote Similarity	NPC251042
0.6923	Remote Similarity	NPC122521
0.6923	Remote Similarity	NPC328311
0.6923	Remote Similarity	NPC229252
0.6923	Remote Similarity	NPC235242
0.6923	Remote Similarity	NPC174447
0.6923	Remote Similarity	NPC143857
0.6909	Remote Similarity	NPC149668
0.6901	Remote Similarity	NPC320119
0.6885	Remote Similarity	NPC321062
0.6885	Remote Similarity	NPC61177
0.6885	Remote Similarity	NPC70387
0.6875	Remote Similarity	NPC267817
0.6875	Remote Similarity	NPC329819
0.6857	Remote Similarity	NPC470436
0.6857	Remote Similarity	NPC143396
0.6842	Remote Similarity	NPC269074
0.6833	Remote Similarity	NPC470410
0.6833	Remote Similarity	NPC262968
0.6833	Remote Similarity	NPC151782
0.6833	Remote Similarity	NPC71053
0.6833	Remote Similarity	NPC470412
0.6833	Remote Similarity	NPC59408
0.6825	Remote Similarity	NPC477201
0.6825	Remote Similarity	NPC473847
0.6825	Remote Similarity	NPC477661
0.6825	Remote Similarity	NPC475384
0.6825	Remote Similarity	NPC161838
0.6825	Remote Similarity	NPC470966
0.6825	Remote Similarity	NPC472808
0.6825	Remote Similarity	NPC470967
0.6825	Remote Similarity	NPC327388
0.6825	Remote Similarity	NPC324224
0.6825	Remote Similarity	NPC470968
0.6825	Remote Similarity	NPC471960
0.6825	Remote Similarity	NPC470969
0.6818	Remote Similarity	NPC40082
0.6818	Remote Similarity	NPC113293
0.6818	Remote Similarity	NPC477829
0.678	Remote Similarity	NPC85079
0.678	Remote Similarity	NPC31194
0.678	Remote Similarity	NPC149821
0.678	Remote Similarity	NPC163345
0.678	Remote Similarity	NPC248884
0.678	Remote Similarity	NPC98284
0.678	Remote Similarity	NPC473551
0.678	Remote Similarity	NPC5413
0.6774	Remote Similarity	NPC300121
0.6761	Remote Similarity	NPC476012
0.6761	Remote Similarity	NPC476037
0.6761	Remote Similarity	NPC42526
0.6757	Remote Similarity	NPC188860
0.6724	Remote Similarity	NPC19834
0.6724	Remote Similarity	NPC42304
0.6724	Remote Similarity	NPC55063
0.6721	Remote Similarity	NPC129458
0.6721	Remote Similarity	NPC142092
0.6719	Remote Similarity	NPC211752
0.6719	Remote Similarity	NPC323498
0.6719	Remote Similarity	NPC323597
0.6719	Remote Similarity	NPC470970
0.6716	Remote Similarity	NPC54925
0.6667	Remote Similarity	NPC473735
0.6667	Remote Similarity	NPC473910
0.6667	Remote Similarity	NPC289388
0.6667	Remote Similarity	NPC477984
0.6667	Remote Similarity	NPC146811

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 NPC469373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	115
0.1-0.2	2929
0.2-0.3	4163
0.3-0.4	1569
0.4-0.5	296
0.5-0.6	54
0.6-0.7	19
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
0.7188	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3172	Approved
0.7049	Intermediate Similarity	NPD3195	Phase 2
0.7049	Intermediate Similarity	NPD3194	Approved
0.7049	Intermediate Similarity	NPD4266	Approved
0.7049	Intermediate Similarity	NPD3196	Approved
0.6897	Remote Similarity	NPD5343	Approved
0.6866	Remote Similarity	NPD3197	Phase 1
0.6833	Remote Similarity	NPD28	Approved
0.6833	Remote Similarity	NPD29	Approved
0.678	Remote Similarity	NPD3173	Approved
0.6667	Remote Similarity	NPD6096	Approved
0.6667	Remote Similarity	NPD6097	Approved
0.6552	Remote Similarity	NPD3174	Discontinued
0.6552	Remote Similarity	NPD4222	Approved
0.6552	Remote Similarity	NPD39	Approved
0.6364	Remote Similarity	NPD6109	Phase 1
0.6338	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD622	Approved
0.623	Remote Similarity	NPD4220	Pre-registration
0.6207	Remote Similarity	NPD5326	Phase 3
0.6184	Remote Similarity	NPD8039	Approved
0.6143	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6927	Phase 3
0.6026	Remote Similarity	NPD4756	Discovery
0.6024	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5331	Approved
0.5976	Remote Similarity	NPD5332	Approved
0.5976	Remote Similarity	NPD7154	Phase 3
0.5857	Remote Similarity	NPD4192	Approved
0.5857	Remote Similarity	NPD4194	Approved
0.5857	Remote Similarity	NPD4193	Approved
0.5857	Remote Similarity	NPD4191	Approved
0.5854	Remote Similarity	NPD6435	Approved
0.5765	Remote Similarity	NPD4249	Approved
0.575	Remote Similarity	NPD4268	Approved
0.575	Remote Similarity	NPD3732	Approved
0.575	Remote Similarity	NPD4271	Approved
0.5747	Remote Similarity	NPD6101	Approved
0.5747	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4265	Approved
0.5732	Remote Similarity	NPD5369	Approved
0.5698	Remote Similarity	NPD4250	Approved
0.5698	Remote Similarity	NPD4251	Approved
0.5682	Remote Similarity	NPD7838	Discovery
0.5672	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD6411	Approved
0.5618	Remote Similarity	NPD7983	Approved
0.561	Remote Similarity	NPD4822	Approved
0.561	Remote Similarity	NPD4820	Approved
0.561	Remote Similarity	NPD5368	Approved
0.561	Remote Similarity	NPD4821	Approved
0.561	Remote Similarity	NPD4819	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