NPASS Compound

Structure

NPC185256 OpenBabel07101719132D 22 23 0 0 1 0 0 0 0 0999 V2000 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -2.5981 1.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 3 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 6 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 17 1 0 0 0 0 13 20 1 6 0 0 0 14 11 1 1 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 6 0 0 0 16 17 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.19
Volume:	324.154
LogP:	1.887
LogD:	1.566
LogS:	-2.096
# Rotatable Bonds:	7
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	4.234
Fsp3:	0.882
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:	-4.62
MDCK Permeability:	2.5660439860075712e-05
Pgp-inhibitor:	0.914
Pgp-substrate:	0.37
Human Intestinal Absorption (HIA):	0.269
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.423
Plasma Protein Binding (PPB):	53.909019470214844%
Volume Distribution (VD):	1.088
Pgp-substrate:	32.90928268432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.727
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	14.173
Half-life (T1/2):	0.807

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.207
Carcinogencity:	0.537
Eye Corrosion:	0.008
Eye Irritation:	0.091
Respiratory Toxicity:	0.062

Download Data

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

Natural Product: NPC185256

Natural Product ID:	NPC185256
*Common Name:**	7-O-Methylkoninginin D
IUPAC Name:	(2S,4R,8R)-8-hydroxy-2-[(1S)-1-hydroxyheptyl]-4-methoxy-2,3,4,6,7,8-hexahydrochromen-5-one
Synonyms:	7-O-Methylkoninginin D
Standard InCHIKey:	KZJHCFVWRNCUKY-PMOUVXMZSA-N
Standard InCHI:	InChI=1S/C17H28O5/c1-3-4-5-6-7-11(18)14-10-15(21-2)16-12(19)8-9-13(20)17(16)22-14/h11,13-15,18,20H,3-10H2,1-2H3/t11-,13+,14-,15+/m0/s1
SMILES:	CCCCCC[C@@H]([C@@H]1C[C@H](C2=C([C@@H](CCC2=O)O)O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099203
PubChem CID:	46833400
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans

*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
NPO5589	Trichoderma koningii	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0038-0717(88)90050-8]
NPO5589	Trichoderma koningii	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384316]
NPO5589	Trichoderma koningii	Species	Hypocreaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[558534]

☑ 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 NPC185256 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	219
0.1-0.2	1976
0.2-0.3	5929
0.3-0.4	11937
0.4-0.5	15668
0.5-0.6	5505
0.6-0.7	1361
0.7-0.8	94
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9024	High Similarity	NPC307126
0.9024	High Similarity	NPC68303
0.8261	Intermediate Similarity	NPC306908
0.8065	Intermediate Similarity	NPC35717
0.7976	Intermediate Similarity	NPC91332
0.7976	Intermediate Similarity	NPC162741
0.7889	Intermediate Similarity	NPC265856
0.7765	Intermediate Similarity	NPC47653
0.7692	Intermediate Similarity	NPC469464
0.7667	Intermediate Similarity	NPC472008
0.7556	Intermediate Similarity	NPC472007
0.7531	Intermediate Similarity	NPC477455
0.75	Intermediate Similarity	NPC166554
0.7473	Intermediate Similarity	NPC143025
0.7444	Intermediate Similarity	NPC472009
0.7419	Intermediate Similarity	NPC6099
0.7419	Intermediate Similarity	NPC114345
0.7419	Intermediate Similarity	NPC327760
0.7419	Intermediate Similarity	NPC303230
0.7412	Intermediate Similarity	NPC473536
0.7396	Intermediate Similarity	NPC20066
0.7353	Intermediate Similarity	NPC101018
0.7349	Intermediate Similarity	NPC144419
0.7347	Intermediate Similarity	NPC471401
0.7294	Intermediate Similarity	NPC49392
0.7294	Intermediate Similarity	NPC190400
0.7283	Intermediate Similarity	NPC228415
0.7283	Intermediate Similarity	NPC87189
0.7282	Intermediate Similarity	NPC99760
0.7263	Intermediate Similarity	NPC477241
0.7234	Intermediate Similarity	NPC472010
0.7228	Intermediate Similarity	NPC469852
0.7216	Intermediate Similarity	NPC473574
0.7216	Intermediate Similarity	NPC239895
0.7216	Intermediate Similarity	NPC20078
0.7204	Intermediate Similarity	NPC280612
0.7172	Intermediate Similarity	NPC181645
0.7158	Intermediate Similarity	NPC273579
0.7158	Intermediate Similarity	NPC295204
0.7158	Intermediate Similarity	NPC162205
0.7158	Intermediate Similarity	NPC288240
0.7143	Intermediate Similarity	NPC83895
0.7143	Intermediate Similarity	NPC187761
0.7143	Intermediate Similarity	NPC77971
0.7128	Intermediate Similarity	NPC471399
0.7128	Intermediate Similarity	NPC274075
0.7113	Intermediate Similarity	NPC135576
0.7113	Intermediate Similarity	NPC93271
0.71	Intermediate Similarity	NPC313569
0.7073	Intermediate Similarity	NPC477452
0.7065	Intermediate Similarity	NPC112685
0.7053	Intermediate Similarity	NPC475441
0.7041	Intermediate Similarity	NPC40812
0.7041	Intermediate Similarity	NPC266842
0.7033	Intermediate Similarity	NPC70424
0.7033	Intermediate Similarity	NPC474251
0.7033	Intermediate Similarity	NPC469809
0.7033	Intermediate Similarity	NPC243618
0.7021	Intermediate Similarity	NPC130359
0.7021	Intermediate Similarity	NPC477016
0.7021	Intermediate Similarity	NPC477017
0.7021	Intermediate Similarity	NPC14901
0.7019	Intermediate Similarity	NPC471400
0.7	Intermediate Similarity	NPC133907
0.7	Intermediate Similarity	NPC110443
0.7	Intermediate Similarity	NPC475046
0.7	Intermediate Similarity	NPC11383
0.7	Intermediate Similarity	NPC9878
0.7	Intermediate Similarity	NPC128733
0.7	Intermediate Similarity	NPC474959
0.7	Intermediate Similarity	NPC310450
0.7	Intermediate Similarity	NPC185141
0.7	Intermediate Similarity	NPC46998
0.699	Remote Similarity	NPC469853
0.6979	Remote Similarity	NPC469692
0.6979	Remote Similarity	NPC469645
0.6979	Remote Similarity	NPC11456
0.6977	Remote Similarity	NPC473948
0.697	Remote Similarity	NPC255592
0.697	Remote Similarity	NPC308567
0.697	Remote Similarity	NPC261377
0.697	Remote Similarity	NPC300584
0.6957	Remote Similarity	NPC182383
0.6957	Remote Similarity	NPC307112
0.6947	Remote Similarity	NPC474232
0.6939	Remote Similarity	NPC477921
0.6932	Remote Similarity	NPC315765
0.6923	Remote Similarity	NPC477786
0.6923	Remote Similarity	NPC477785
0.6923	Remote Similarity	NPC284472
0.6923	Remote Similarity	NPC229799
0.6923	Remote Similarity	NPC473807
0.6923	Remote Similarity	NPC477784
0.6923	Remote Similarity	NPC286770
0.6915	Remote Similarity	NPC89001
0.6907	Remote Similarity	NPC121825
0.6897	Remote Similarity	NPC301207
0.6889	Remote Similarity	NPC297440
0.6882	Remote Similarity	NPC308412
0.6882	Remote Similarity	NPC477015
0.6882	Remote Similarity	NPC134885
0.6882	Remote Similarity	NPC469483
0.6882	Remote Similarity	NPC134807
0.6882	Remote Similarity	NPC477010
0.6882	Remote Similarity	NPC219498
0.6882	Remote Similarity	NPC473687
0.6882	Remote Similarity	NPC469910
0.6882	Remote Similarity	NPC210218
0.6882	Remote Similarity	NPC204686
0.6882	Remote Similarity	NPC47937
0.6875	Remote Similarity	NPC473321
0.6875	Remote Similarity	NPC476705
0.6875	Remote Similarity	NPC146852
0.6869	Remote Similarity	NPC17326
0.6869	Remote Similarity	NPC478233
0.6869	Remote Similarity	NPC134454
0.6863	Remote Similarity	NPC159533
0.6863	Remote Similarity	NPC473624
0.6854	Remote Similarity	NPC258231
0.6848	Remote Similarity	NPC163093
0.6842	Remote Similarity	NPC477011
0.6837	Remote Similarity	NPC227494
0.6837	Remote Similarity	NPC91408
0.6837	Remote Similarity	NPC477922
0.6837	Remote Similarity	NPC471142
0.6832	Remote Similarity	NPC469851
0.6832	Remote Similarity	NPC224172
0.6827	Remote Similarity	NPC112780
0.6822	Remote Similarity	NPC66108
0.6818	Remote Similarity	NPC478206
0.6818	Remote Similarity	NPC49302
0.6818	Remote Similarity	NPC125365
0.6818	Remote Similarity	NPC474818
0.6818	Remote Similarity	NPC478205
0.6818	Remote Similarity	NPC176329
0.6818	Remote Similarity	NPC51809
0.6818	Remote Similarity	NPC108581
0.6813	Remote Similarity	NPC253364
0.6813	Remote Similarity	NPC474252
0.6813	Remote Similarity	NPC475690
0.6809	Remote Similarity	NPC476079
0.6809	Remote Similarity	NPC103743
0.6809	Remote Similarity	NPC300779
0.6809	Remote Similarity	NPC23622
0.6809	Remote Similarity	NPC113370
0.6809	Remote Similarity	NPC241054
0.6809	Remote Similarity	NPC178215
0.6804	Remote Similarity	NPC141447
0.6804	Remote Similarity	NPC61275
0.6804	Remote Similarity	NPC475912
0.68	Remote Similarity	NPC475284
0.68	Remote Similarity	NPC281608
0.68	Remote Similarity	NPC212465
0.68	Remote Similarity	NPC177232
0.6796	Remote Similarity	NPC100487
0.6786	Remote Similarity	NPC94488
0.6778	Remote Similarity	NPC470945
0.6778	Remote Similarity	NPC470947
0.6778	Remote Similarity	NPC470946
0.6774	Remote Similarity	NPC283085
0.6774	Remote Similarity	NPC477014
0.6774	Remote Similarity	NPC82795
0.6774	Remote Similarity	NPC477013
0.6774	Remote Similarity	NPC103284
0.6774	Remote Similarity	NPC66346
0.6774	Remote Similarity	NPC110710
0.6774	Remote Similarity	NPC1083
0.6774	Remote Similarity	NPC477018
0.6774	Remote Similarity	NPC132496
0.6774	Remote Similarity	NPC473651
0.6774	Remote Similarity	NPC470755
0.6774	Remote Similarity	NPC100921
0.6774	Remote Similarity	NPC223871
0.6774	Remote Similarity	NPC21469
0.6774	Remote Similarity	NPC120398
0.6774	Remote Similarity	NPC471567
0.6774	Remote Similarity	NPC286338
0.6774	Remote Similarity	NPC473478
0.6774	Remote Similarity	NPC107986
0.6774	Remote Similarity	NPC231009
0.6774	Remote Similarity	NPC473669
0.6771	Remote Similarity	NPC477684
0.6771	Remote Similarity	NPC131864
0.6771	Remote Similarity	NPC473455
0.6771	Remote Similarity	NPC473619
0.6768	Remote Similarity	NPC11396
0.6768	Remote Similarity	NPC472734
0.6768	Remote Similarity	NPC21302
0.6768	Remote Similarity	NPC472733
0.6768	Remote Similarity	NPC476797
0.6765	Remote Similarity	NPC295791
0.6765	Remote Similarity	NPC80781
0.6765	Remote Similarity	NPC70369
0.6759	Remote Similarity	NPC478212
0.6742	Remote Similarity	NPC221095
0.6742	Remote Similarity	NPC279214
0.6742	Remote Similarity	NPC473471
0.6739	Remote Similarity	NPC144415
0.6739	Remote Similarity	NPC475083
0.6737	Remote Similarity	NPC476803

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 NPC185256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2630
0.2-0.3	3723
0.3-0.4	1851
0.4-0.5	523
0.5-0.6	166
0.6-0.7	15
0.7-0.8	1
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
0.7037	Intermediate Similarity	NPD3704	Approved
0.6739	Remote Similarity	NPD6110	Phase 1
0.6598	Remote Similarity	NPD6698	Approved
0.6598	Remote Similarity	NPD46	Approved
0.6531	Remote Similarity	NPD7983	Approved
0.6444	Remote Similarity	NPD4756	Discovery
0.6337	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4225	Approved
0.63	Remote Similarity	NPD5778	Approved
0.63	Remote Similarity	NPD5779	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.6277	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6371	Approved
0.6118	Remote Similarity	NPD7341	Phase 2
0.61	Remote Similarity	NPD5785	Approved
0.6091	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5282	Discontinued
0.6071	Remote Similarity	NPD6053	Discontinued
0.6068	Remote Similarity	NPD8513	Phase 3
0.6047	Remote Similarity	NPD7331	Phase 2
0.6042	Remote Similarity	NPD7154	Phase 3
0.602	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.5932	Remote Similarity	NPD8515	Approved
0.5932	Remote Similarity	NPD8516	Approved
0.5932	Remote Similarity	NPD8517	Approved
0.5918	Remote Similarity	NPD5363	Approved
0.5909	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6411	Approved
0.5862	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6686	Approved
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7839	Suspended
0.5784	Remote Similarity	NPD7838	Discovery
0.5773	Remote Similarity	NPD4270	Approved
0.5773	Remote Similarity	NPD4269	Approved
0.5773	Remote Similarity	NPD6435	Approved
0.5758	Remote Similarity	NPD1694	Approved
0.5729	Remote Similarity	NPD4252	Approved
0.5702	Remote Similarity	NPD7642	Approved
0.5691	Remote Similarity	NPD8074	Phase 3
0.5688	Remote Similarity	NPD5211	Phase 2
0.5679	Remote Similarity	NPD3728	Approved
0.5679	Remote Similarity	NPD3730	Approved
0.5632	Remote Similarity	NPD3197	Phase 1
0.5625	Remote Similarity	NPD6412	Phase 2
0.5625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8080	Discontinued
0.5614	Remote Similarity	NPD4634	Approved
0.5607	Remote Similarity	NPD4755	Approved
0.56	Remote Similarity	NPD1733	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