NPASS Compound

Structure

NPC474339 OpenBabel07101718292D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.7536 4.9632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 3.1361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3545 2.5248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7591 4.8587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 3.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4410 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0287 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0287 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3578 3.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 2.1180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0287 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 4.6496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5455 3.1126 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 -0.9511 2.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8948 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 8 13 1 0 0 0 0 8 20 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 11 19 1 0 0 0 0 12 7 1 1 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 1 0 0 0 14 11 1 1 0 0 0 15 21 2 0 0 0 0 16 15 1 6 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 1 0 0 0 17 27 1 0 0 0 0 18 22 2 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	374.52
LogP:	1.285
LogD:	0.587
LogS:	-2.059
# Rotatable Bonds:	3
TPSA:	102.43
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.643
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	1.2673239325522445e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.186
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.718

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	79.66472625732422%
Volume Distribution (VD):	0.986
Pgp-substrate:	27.016220092773438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.65
CYP2C9-inhibitor:	0.414
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.442
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	6.845
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.933
Carcinogencity:	0.315
Eye Corrosion:	0.941
Eye Irritation:	0.722
Respiratory Toxicity:	0.882

Download Data

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

Natural Product: NPC474339

Natural Product ID:	NPC474339
*Common Name:**	Eupakirunsin E
IUPAC Name:	n.a.
Synonyms:	eupakirunsin E
Standard InCHIKey:	RFSYEWLTJLURJR-GPSFEMRQSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-6-9(2)18(22)26-13-8-20(5,24)17-16(27-17)15(21)10(3)7-12-14(13)11(4)19(23)25-12/h6-7,12-14,16-17,24H,4,8H2,1-3,5H3/b9-6+,10-7-/t12-,13+,14-,16-,17+,20+/m0/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1C[C@@](C)(O)[C@@H]2O[C@H]2C(=O)/C(=C[C@H]2[C@@H]1C(=C)C(=O)O2)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465406
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	Taiwan	n.a.	PMID[15921421]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921421]
NPO9285	Eupatorium kiirunense	Species	Asteraceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475248]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[475248]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[475248]

☑ 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 NPC474339 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	240
0.1-0.2	1419
0.2-0.3	5022
0.3-0.4	8915
0.4-0.5	14636
0.5-0.6	7553
0.6-0.7	3469
0.7-0.8	1165
0.8-0.85	181
0.85-0.9	82
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC164598
0.9479	High Similarity	NPC471148
0.9293	High Similarity	NPC477513
0.9278	High Similarity	NPC149371
0.9175	High Similarity	NPC47880
0.9175	High Similarity	NPC201718
0.9091	High Similarity	NPC474741
0.9072	High Similarity	NPC475949
0.9072	High Similarity	NPC288876
0.9062	High Similarity	NPC471140
0.9053	High Similarity	NPC475659
0.898	High Similarity	NPC264477
0.898	High Similarity	NPC477511
0.898	High Similarity	NPC476270
0.8969	High Similarity	NPC471144
0.8958	High Similarity	NPC473859
0.8958	High Similarity	NPC279621
0.8958	High Similarity	NPC230800
0.8958	High Similarity	NPC17585
0.8854	High Similarity	NPC471141
0.8842	High Similarity	NPC125674
0.8842	High Similarity	NPC475838
0.8842	High Similarity	NPC228451
0.8812	High Similarity	NPC9303
0.8812	High Similarity	NPC16313
0.88	High Similarity	NPC475871
0.88	High Similarity	NPC475945
0.8788	High Similarity	NPC474742
0.8776	High Similarity	NPC473326
0.875	High Similarity	NPC474247
0.875	High Similarity	NPC121825
0.8737	High Similarity	NPC20713
0.8725	High Similarity	NPC72813
0.8725	High Similarity	NPC474421
0.8725	High Similarity	NPC324327
0.8725	High Similarity	NPC326994
0.8725	High Similarity	NPC194620
0.8713	High Similarity	NPC471143
0.8713	High Similarity	NPC477510
0.871	High Similarity	NPC266957
0.87	High Similarity	NPC474747
0.8687	High Similarity	NPC477512
0.866	High Similarity	NPC270013
0.866	High Similarity	NPC14961
0.8646	High Similarity	NPC469692
0.8646	High Similarity	NPC165383
0.8646	High Similarity	NPC212486
0.8646	High Similarity	NPC469645
0.8641	High Similarity	NPC474664
0.8641	High Similarity	NPC55972
0.8641	High Similarity	NPC14862
0.8641	High Similarity	NPC169888
0.8641	High Similarity	NPC233379
0.8641	High Similarity	NPC327286
0.8632	High Similarity	NPC179394
0.8632	High Similarity	NPC144133
0.8627	High Similarity	NPC475802
0.8614	High Similarity	NPC472755
0.8602	High Similarity	NPC50637
0.86	High Similarity	NPC110443
0.86	High Similarity	NPC133907
0.86	High Similarity	NPC46998
0.86	High Similarity	NPC128733
0.86	High Similarity	NPC15993
0.86	High Similarity	NPC185141
0.86	High Similarity	NPC472753
0.8558	High Similarity	NPC475922
0.8558	High Similarity	NPC38154
0.8558	High Similarity	NPC15218
0.8557	High Similarity	NPC303942
0.8557	High Similarity	NPC473330
0.8557	High Similarity	NPC474035
0.8557	High Similarity	NPC81386
0.8557	High Similarity	NPC473316
0.8557	High Similarity	NPC57405
0.8557	High Similarity	NPC471147
0.8557	High Similarity	NPC140543
0.8529	High Similarity	NPC472756
0.8526	High Similarity	NPC166919
0.8526	High Similarity	NPC151770
0.8515	High Similarity	NPC472754
0.8515	High Similarity	NPC320019
0.8515	High Similarity	NPC324017
0.8476	Intermediate Similarity	NPC161816
0.8476	Intermediate Similarity	NPC115257
0.8469	Intermediate Similarity	NPC471142
0.8454	Intermediate Similarity	NPC475912
0.8454	Intermediate Similarity	NPC273579
0.8454	Intermediate Similarity	NPC295204
0.8454	Intermediate Similarity	NPC476300
0.8454	Intermediate Similarity	NPC162205
0.8454	Intermediate Similarity	NPC288240
0.8454	Intermediate Similarity	NPC475302
0.8438	Intermediate Similarity	NPC51004
0.8438	Intermediate Similarity	NPC473619
0.8438	Intermediate Similarity	NPC475855
0.8431	Intermediate Similarity	NPC4620
0.8431	Intermediate Similarity	NPC475873
0.8416	Intermediate Similarity	NPC473332
0.84	Intermediate Similarity	NPC474213
0.84	Intermediate Similarity	NPC208233
0.84	Intermediate Similarity	NPC161855
0.8384	Intermediate Similarity	NPC476275
0.8384	Intermediate Similarity	NPC473291
0.8384	Intermediate Similarity	NPC39859
0.8384	Intermediate Similarity	NPC470883
0.8384	Intermediate Similarity	NPC158416
0.8384	Intermediate Similarity	NPC477921
0.8384	Intermediate Similarity	NPC476315
0.8384	Intermediate Similarity	NPC35498
0.8384	Intermediate Similarity	NPC76862
0.8367	Intermediate Similarity	NPC476267
0.8367	Intermediate Similarity	NPC190294
0.8365	Intermediate Similarity	NPC26617
0.8351	Intermediate Similarity	NPC476705
0.8351	Intermediate Similarity	NPC184463
0.8351	Intermediate Similarity	NPC30515
0.8351	Intermediate Similarity	NPC473321
0.835	Intermediate Similarity	NPC100487
0.835	Intermediate Similarity	NPC220964
0.835	Intermediate Similarity	NPC475676
0.8349	Intermediate Similarity	NPC471146
0.8333	Intermediate Similarity	NPC475971
0.8333	Intermediate Similarity	NPC307411
0.8333	Intermediate Similarity	NPC39996
0.8318	Intermediate Similarity	NPC473877
0.8316	Intermediate Similarity	NPC231889
0.8283	Intermediate Similarity	NPC475900
0.8283	Intermediate Similarity	NPC477922
0.8283	Intermediate Similarity	NPC474947
0.8283	Intermediate Similarity	NPC36954
0.8265	Intermediate Similarity	NPC81419
0.8265	Intermediate Similarity	NPC179746
0.8252	Intermediate Similarity	NPC474166
0.8252	Intermediate Similarity	NPC19239
0.8247	Intermediate Similarity	NPC469718
0.8247	Intermediate Similarity	NPC251385
0.8247	Intermediate Similarity	NPC474232
0.8247	Intermediate Similarity	NPC329857
0.8247	Intermediate Similarity	NPC49342
0.8247	Intermediate Similarity	NPC475748
0.8229	Intermediate Similarity	NPC476706
0.8229	Intermediate Similarity	NPC475902
0.8229	Intermediate Similarity	NPC202672
0.8229	Intermediate Similarity	NPC476707
0.8229	Intermediate Similarity	NPC287089
0.8229	Intermediate Similarity	NPC476803
0.8224	Intermediate Similarity	NPC317107
0.8218	Intermediate Similarity	NPC187268
0.8211	Intermediate Similarity	NPC475461
0.8211	Intermediate Similarity	NPC469910
0.8211	Intermediate Similarity	NPC305475
0.82	Intermediate Similarity	NPC476009
0.82	Intermediate Similarity	NPC31645
0.819	Intermediate Similarity	NPC266514
0.8173	Intermediate Similarity	NPC203659
0.8163	Intermediate Similarity	NPC208886
0.8163	Intermediate Similarity	NPC158061
0.8163	Intermediate Similarity	NPC12172
0.8155	Intermediate Similarity	NPC140591
0.8155	Intermediate Similarity	NPC189609
0.8155	Intermediate Similarity	NPC303653
0.8155	Intermediate Similarity	NPC291500
0.8155	Intermediate Similarity	NPC183571
0.8155	Intermediate Similarity	NPC197835
0.8148	Intermediate Similarity	NPC317687
0.8144	Intermediate Similarity	NPC474032
0.8119	Intermediate Similarity	NPC323421
0.8119	Intermediate Similarity	NPC328562
0.8113	Intermediate Similarity	NPC94377
0.8108	Intermediate Similarity	NPC475401
0.8105	Intermediate Similarity	NPC470755
0.8105	Intermediate Similarity	NPC255307
0.8105	Intermediate Similarity	NPC319795
0.8105	Intermediate Similarity	NPC50362
0.8105	Intermediate Similarity	NPC38468
0.8095	Intermediate Similarity	NPC243998
0.8095	Intermediate Similarity	NPC223450
0.8091	Intermediate Similarity	NPC474333
0.8085	Intermediate Similarity	NPC474703
0.8085	Intermediate Similarity	NPC128429
0.8077	Intermediate Similarity	NPC110989
0.8077	Intermediate Similarity	NPC472747
0.8077	Intermediate Similarity	NPC69171
0.8077	Intermediate Similarity	NPC472750
0.8077	Intermediate Similarity	NPC474165
0.8065	Intermediate Similarity	NPC141810
0.8061	Intermediate Similarity	NPC476004
0.8061	Intermediate Similarity	NPC65359
0.8061	Intermediate Similarity	NPC312042
0.8061	Intermediate Similarity	NPC474761
0.8041	Intermediate Similarity	NPC476805
0.8041	Intermediate Similarity	NPC473715
0.8041	Intermediate Similarity	NPC475819
0.8039	Intermediate Similarity	NPC279561
0.8037	Intermediate Similarity	NPC42662
0.8037	Intermediate Similarity	NPC477102
0.8036	Intermediate Similarity	NPC477092
0.8021	Intermediate Similarity	NPC469483
0.8021	Intermediate Similarity	NPC261721

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 NPC474339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	2035
0.2-0.3	3676
0.3-0.4	2091
0.4-0.5	744
0.5-0.6	289
0.6-0.7	85
0.7-0.8	8
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8365	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6698	Approved
0.8061	Intermediate Similarity	NPD46	Approved
0.7963	Intermediate Similarity	NPD6371	Approved
0.77	Intermediate Similarity	NPD7838	Discovery
0.7476	Intermediate Similarity	NPD5282	Discontinued
0.7426	Intermediate Similarity	NPD1695	Approved
0.7404	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7983	Approved
0.7257	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4225	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7019	Intermediate Similarity	NPD5785	Approved
0.6991	Remote Similarity	NPD6686	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5363	Approved
0.6818	Remote Similarity	NPD6648	Approved
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6319	Approved
0.6748	Remote Similarity	NPD7642	Approved
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5369	Approved
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD8517	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6574	Remote Similarity	NPD5779	Approved
0.6569	Remote Similarity	NPD4270	Approved
0.6569	Remote Similarity	NPD5209	Approved
0.6569	Remote Similarity	NPD4269	Approved
0.656	Remote Similarity	NPD7492	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1694	Approved
0.6508	Remote Similarity	NPD6616	Approved
0.6505	Remote Similarity	NPD7154	Phase 3
0.6505	Remote Similarity	NPD6110	Phase 1
0.6504	Remote Similarity	NPD6054	Approved
0.648	Remote Similarity	NPD7829	Approved
0.648	Remote Similarity	NPD7830	Approved
0.6476	Remote Similarity	NPD5786	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD6053	Discontinued
0.6466	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7078	Approved
0.6455	Remote Similarity	NPD5695	Phase 3
0.6452	Remote Similarity	NPD6015	Approved
0.6452	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6016	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6417	Remote Similarity	NPD4632	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.6415	Remote Similarity	NPD4250	Approved
0.6408	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD6370	Approved
0.64	Remote Similarity	NPD4756	Discovery
0.64	Remote Similarity	NPD5988	Approved
0.6387	Remote Similarity	NPD2204	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6378	Remote Similarity	NPD8273	Phase 1
0.6373	Remote Similarity	NPD4252	Approved
0.6371	Remote Similarity	NPD6059	Approved
0.6349	Remote Similarity	NPD8328	Phase 3
0.6339	Remote Similarity	NPD6083	Phase 2
0.6339	Remote Similarity	NPD6084	Phase 2
0.6333	Remote Similarity	NPD8297	Approved
0.6328	Remote Similarity	NPD8074	Phase 3
0.6328	Remote Similarity	NPD8293	Discontinued
0.6325	Remote Similarity	NPD5697	Approved
0.6283	Remote Similarity	NPD7638	Approved
0.6271	Remote Similarity	NPD6881	Approved
0.6271	Remote Similarity	NPD6899	Approved
0.627	Remote Similarity	NPD8080	Discontinued
0.626	Remote Similarity	NPD7260	Phase 2
0.626	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD6650	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6231	Remote Similarity	NPD7319	Approved
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6226	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7604	Phase 2
0.6218	Remote Similarity	NPD6372	Approved
0.6218	Remote Similarity	NPD6013	Approved
0.6218	Remote Similarity	NPD6014	Approved
0.6218	Remote Similarity	NPD6012	Approved
0.6218	Remote Similarity	NPD6373	Approved
0.6214	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD4820	Approved
0.619	Remote Similarity	NPD5983	Phase 2
0.619	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD5701	Approved
0.6182	Remote Similarity	NPD5693	Phase 1
0.6167	Remote Similarity	NPD7290	Approved
0.6167	Remote Similarity	NPD4634	Approved
0.6167	Remote Similarity	NPD7102	Approved
0.6167	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6011	Approved
0.6134	Remote Similarity	NPD7320	Approved
0.6129	Remote Similarity	NPD7500	Approved
0.6126	Remote Similarity	NPD6399	Phase 3
0.6124	Remote Similarity	NPD8451	Approved
0.6124	Remote Similarity	NPD7507	Approved
0.6116	Remote Similarity	NPD6847	Approved
0.6116	Remote Similarity	NPD6617	Approved
0.6116	Remote Similarity	NPD6869	Approved
0.6116	Remote Similarity	NPD8130	Phase 1
0.609	Remote Similarity	NPD6845	Suspended
0.608	Remote Similarity	NPD7641	Discontinued
0.6077	Remote Similarity	NPD8448	Approved
0.6066	Remote Similarity	NPD6882	Approved
0.6063	Remote Similarity	NPD8444	Approved
0.6063	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5956	Approved
0.6058	Remote Similarity	NPD5368	Approved
0.6055	Remote Similarity	NPD6672	Approved
0.6055	Remote Similarity	NPD5737	Approved
0.6036	Remote Similarity	NPD7637	Suspended
0.6036	Remote Similarity	NPD6411	Approved
0.6033	Remote Similarity	NPD2067	Discontinued
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.594	Remote Similarity	NPD8390	Approved
0.594	Remote Similarity	NPD8392	Approved
0.594	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD6921	Approved
0.5923	Remote Similarity	NPD8342	Approved
0.5923	Remote Similarity	NPD8299	Approved
0.5923	Remote Similarity	NPD8340	Approved
0.5923	Remote Similarity	NPD8341	Approved
0.592	Remote Similarity	NPD6274	Approved
0.5913	Remote Similarity	NPD7902	Approved
0.5909	Remote Similarity	NPD6033	Approved
0.5905	Remote Similarity	NPD4695	Discontinued
0.5893	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8415	Approved
0.5877	Remote Similarity	NPD5210	Approved
0.5877	Remote Similarity	NPD4629	Approved
0.5856	Remote Similarity	NPD6080	Approved
0.5856	Remote Similarity	NPD6673	Approved
0.5856	Remote Similarity	NPD4753	Phase 2
0.5856	Remote Similarity	NPD6904	Approved
0.5854	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD3197	Phase 1
0.5833	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7327	Approved
0.5827	Remote Similarity	NPD7328	Approved
0.5826	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8033	Approved
0.5814	Remote Similarity	NPD7503	Approved
0.5812	Remote Similarity	NPD5285	Approved
0.5812	Remote Similarity	NPD5286	Approved
0.5812	Remote Similarity	NPD4696	Approved
0.5804	Remote Similarity	NPD5692	Phase 3
0.5789	Remote Similarity	NPD7748	Approved
0.5781	Remote Similarity	NPD7516	Approved
0.5781	Remote Similarity	NPD4522	Approved
0.5781	Remote Similarity	NPD7100	Approved
0.5781	Remote Similarity	NPD7101	Approved
0.5776	Remote Similarity	NPD4755	Approved
0.5763	Remote Similarity	NPD1700	Approved
0.576	Remote Similarity	NPD8133	Approved
0.5752	Remote Similarity	NPD5284	Approved
0.5752	Remote Similarity	NPD5694	Approved
0.5752	Remote Similarity	NPD6050	Approved
0.5752	Remote Similarity	NPD5281	Approved
0.575	Remote Similarity	NPD5141	Approved
0.5748	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6317	Approved
0.5741	Remote Similarity	NPD5331	Approved
0.5741	Remote Similarity	NPD5332	Approved
0.5739	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8294	Approved
0.5736	Remote Similarity	NPD8377	Approved
0.5736	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD2664	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