NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.12
Volume:	275.732
LogP:	1.395
LogD:	1.13
LogS:	-3.442
# Rotatable Bonds:	0
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.972
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.876
MDCK Permeability:	2.0373061488498934e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	67.22352600097656%
Volume Distribution (VD):	0.428
Pgp-substrate:	37.46729278564453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.834
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.572

ADMET: Excretion

Clearance (CL):	5.468
Half-life (T1/2):	0.196

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.317
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.402
Carcinogencity:	0.047
Eye Corrosion:	0.043
Eye Irritation:	0.095
Respiratory Toxicity:	0.475

Download Data

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

Natural Product: NPC472644

Natural Product ID:	NPC472644
*Common Name:**	JLKSXTRHPGICRR-FFFUXKDYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JLKSXTRHPGICRR-FFFUXKDYSA-N
Standard InCHI:	InChI=1S/C15H18O5/c1-7-4-11(16)12(17)14(3)6-15(19)10(5-9(7)14)8(2)13(18)20-15/h4,9,12,17,19H,5-6H2,1-3H3/t9-,12+,14+,15-/m0/s1
SMILES:	CC1=CC(=O)C(C2(C1CC3=C(C(=O)OC3(C2)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581368
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 [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23337296]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24484201]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25739048]
NPO1371	Teucrium viscidum	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
IC50	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[493228]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[493228]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[493228]
NPT2	Others	Unspecified		IC50	=	568300.0	nM	PMID[493228]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[493228]

☑ 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 NPC472644 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	192
0.1-0.2	1139
0.2-0.3	3886
0.3-0.4	7409
0.4-0.5	14362
0.5-0.6	7517
0.6-0.7	6219
0.7-0.8	1864
0.8-0.85	95
0.85-0.9	8
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9681	High Similarity	NPC472643
0.9091	High Similarity	NPC472645
0.8763	High Similarity	NPC474343
0.8763	High Similarity	NPC69385
0.8723	High Similarity	NPC281942
0.8723	High Similarity	NPC232426
0.8673	High Similarity	NPC222011
0.8632	High Similarity	NPC141831
0.8571	High Similarity	NPC254496
0.8571	High Similarity	NPC208094
0.8469	Intermediate Similarity	NPC165632
0.8431	Intermediate Similarity	NPC118911
0.8421	Intermediate Similarity	NPC5509
0.8404	Intermediate Similarity	NPC312561
0.84	Intermediate Similarity	NPC476767
0.84	Intermediate Similarity	NPC117685
0.84	Intermediate Similarity	NPC476274
0.8384	Intermediate Similarity	NPC285513
0.8367	Intermediate Similarity	NPC134067
0.8367	Intermediate Similarity	NPC295347
0.8367	Intermediate Similarity	NPC183012
0.8351	Intermediate Similarity	NPC472303
0.8351	Intermediate Similarity	NPC109414
0.8351	Intermediate Similarity	NPC139692
0.8333	Intermediate Similarity	NPC477782
0.8317	Intermediate Similarity	NPC81530
0.8317	Intermediate Similarity	NPC476240
0.8317	Intermediate Similarity	NPC224720
0.8317	Intermediate Similarity	NPC476223
0.83	Intermediate Similarity	NPC23364
0.8298	Intermediate Similarity	NPC202394
0.8283	Intermediate Similarity	NPC234993
0.8283	Intermediate Similarity	NPC242848
0.8283	Intermediate Similarity	NPC134072
0.8269	Intermediate Similarity	NPC475294
0.8265	Intermediate Similarity	NPC250075
0.8247	Intermediate Similarity	NPC186363
0.8247	Intermediate Similarity	NPC233345
0.8247	Intermediate Similarity	NPC472811
0.8247	Intermediate Similarity	NPC289479
0.8247	Intermediate Similarity	NPC477783
0.8235	Intermediate Similarity	NPC295791
0.8235	Intermediate Similarity	NPC58329
0.8235	Intermediate Similarity	NPC308726
0.8235	Intermediate Similarity	NPC119601
0.8235	Intermediate Similarity	NPC136289
0.8218	Intermediate Similarity	NPC474012
0.8218	Intermediate Similarity	NPC476299
0.82	Intermediate Similarity	NPC38530
0.82	Intermediate Similarity	NPC84335
0.82	Intermediate Similarity	NPC253826
0.82	Intermediate Similarity	NPC475709
0.819	Intermediate Similarity	NPC476479
0.8182	Intermediate Similarity	NPC316215
0.8173	Intermediate Similarity	NPC127609
0.8173	Intermediate Similarity	NPC1679
0.8173	Intermediate Similarity	NPC469607
0.8163	Intermediate Similarity	NPC477435
0.8163	Intermediate Similarity	NPC477436
0.8163	Intermediate Similarity	NPC115021
0.8163	Intermediate Similarity	NPC472812
0.8163	Intermediate Similarity	NPC166346
0.8155	Intermediate Similarity	NPC132395
0.8155	Intermediate Similarity	NPC471365
0.8155	Intermediate Similarity	NPC471208
0.8155	Intermediate Similarity	NPC471364
0.8148	Intermediate Similarity	NPC51978
0.8144	Intermediate Similarity	NPC152467
0.8144	Intermediate Similarity	NPC51486
0.8137	Intermediate Similarity	NPC302537
0.8137	Intermediate Similarity	NPC471412
0.8137	Intermediate Similarity	NPC163372
0.8137	Intermediate Similarity	NPC303559
0.8119	Intermediate Similarity	NPC316598
0.8108	Intermediate Similarity	NPC476529
0.8108	Intermediate Similarity	NPC475775
0.8105	Intermediate Similarity	NPC473226
0.8105	Intermediate Similarity	NPC474062
0.8105	Intermediate Similarity	NPC220478
0.81	Intermediate Similarity	NPC184065
0.81	Intermediate Similarity	NPC202833
0.8085	Intermediate Similarity	NPC30486
0.8081	Intermediate Similarity	NPC53685
0.8081	Intermediate Similarity	NPC475572
0.8081	Intermediate Similarity	NPC474555
0.8081	Intermediate Similarity	NPC470255
0.8081	Intermediate Similarity	NPC474554
0.8077	Intermediate Similarity	NPC258532
0.8061	Intermediate Similarity	NPC177037
0.8061	Intermediate Similarity	NPC472814
0.8058	Intermediate Similarity	NPC469606
0.8058	Intermediate Similarity	NPC476769
0.8058	Intermediate Similarity	NPC162973
0.8058	Intermediate Similarity	NPC31058
0.8058	Intermediate Similarity	NPC476081
0.8058	Intermediate Similarity	NPC273005
0.8058	Intermediate Similarity	NPC137430
0.8056	Intermediate Similarity	NPC194951
0.8056	Intermediate Similarity	NPC12046
0.8041	Intermediate Similarity	NPC251528
0.8041	Intermediate Similarity	NPC470734
0.8041	Intermediate Similarity	NPC50488
0.8041	Intermediate Similarity	NPC474396
0.8041	Intermediate Similarity	NPC168131
0.8039	Intermediate Similarity	NPC471413
0.8039	Intermediate Similarity	NPC174314
0.8039	Intermediate Similarity	NPC472972
0.8037	Intermediate Similarity	NPC206595
0.8037	Intermediate Similarity	NPC5103
0.8036	Intermediate Similarity	NPC107338
0.8036	Intermediate Similarity	NPC109607
0.802	Intermediate Similarity	NPC151681
0.802	Intermediate Similarity	NPC132753
0.802	Intermediate Similarity	NPC175351
0.802	Intermediate Similarity	NPC121402
0.802	Intermediate Similarity	NPC224356
0.802	Intermediate Similarity	NPC170131
0.8019	Intermediate Similarity	NPC189075
0.8019	Intermediate Similarity	NPC275539
0.8019	Intermediate Similarity	NPC322903
0.8	Intermediate Similarity	NPC52628
0.8	Intermediate Similarity	NPC65661
0.8	Intermediate Similarity	NPC470978
0.8	Intermediate Similarity	NPC470974
0.8	Intermediate Similarity	NPC209355
0.8	Intermediate Similarity	NPC477438
0.8	Intermediate Similarity	NPC106416
0.8	Intermediate Similarity	NPC110405
0.8	Intermediate Similarity	NPC189311
0.8	Intermediate Similarity	NPC477437
0.8	Intermediate Similarity	NPC86316
0.7982	Intermediate Similarity	NPC157441
0.7981	Intermediate Similarity	NPC8196
0.7981	Intermediate Similarity	NPC99266
0.798	Intermediate Similarity	NPC476597
0.798	Intermediate Similarity	NPC476598
0.798	Intermediate Similarity	NPC53555
0.798	Intermediate Similarity	NPC242069
0.7979	Intermediate Similarity	NPC193198
0.7979	Intermediate Similarity	NPC222358
0.7963	Intermediate Similarity	NPC201992
0.7961	Intermediate Similarity	NPC207885
0.7961	Intermediate Similarity	NPC473384
0.7961	Intermediate Similarity	NPC472637
0.7961	Intermediate Similarity	NPC115862
0.7959	Intermediate Similarity	NPC134321
0.7959	Intermediate Similarity	NPC182136
0.7959	Intermediate Similarity	NPC472642
0.7959	Intermediate Similarity	NPC221111
0.7959	Intermediate Similarity	NPC280149
0.7959	Intermediate Similarity	NPC78973
0.7959	Intermediate Similarity	NPC158488
0.7944	Intermediate Similarity	NPC141350
0.7941	Intermediate Similarity	NPC216478
0.7941	Intermediate Similarity	NPC473154
0.7941	Intermediate Similarity	NPC478056
0.7938	Intermediate Similarity	NPC277771
0.7938	Intermediate Similarity	NPC472378
0.7938	Intermediate Similarity	NPC472809
0.7938	Intermediate Similarity	NPC472810
0.7935	Intermediate Similarity	NPC308038
0.7928	Intermediate Similarity	NPC473968
0.7925	Intermediate Similarity	NPC110496
0.7925	Intermediate Similarity	NPC144854
0.7925	Intermediate Similarity	NPC472925
0.7925	Intermediate Similarity	NPC67321
0.7925	Intermediate Similarity	NPC187435
0.7925	Intermediate Similarity	NPC3316
0.7921	Intermediate Similarity	NPC328371
0.7921	Intermediate Similarity	NPC472363
0.7921	Intermediate Similarity	NPC328162
0.7921	Intermediate Similarity	NPC472362
0.7921	Intermediate Similarity	NPC305483
0.7921	Intermediate Similarity	NPC240673
0.7921	Intermediate Similarity	NPC17578
0.7921	Intermediate Similarity	NPC154526
0.7921	Intermediate Similarity	NPC96859
0.7917	Intermediate Similarity	NPC6979
0.7917	Intermediate Similarity	NPC329692
0.7917	Intermediate Similarity	NPC250981
0.7917	Intermediate Similarity	NPC131813
0.7913	Intermediate Similarity	NPC470922
0.79	Intermediate Similarity	NPC477439
0.79	Intermediate Similarity	NPC104925
0.79	Intermediate Similarity	NPC476415
0.79	Intermediate Similarity	NPC298973
0.79	Intermediate Similarity	NPC57117
0.79	Intermediate Similarity	NPC196227
0.79	Intermediate Similarity	NPC476596
0.7895	Intermediate Similarity	NPC40687
0.7895	Intermediate Similarity	NPC31086
0.789	Intermediate Similarity	NPC264634
0.789	Intermediate Similarity	NPC11252
0.789	Intermediate Similarity	NPC475524
0.789	Intermediate Similarity	NPC302146
0.789	Intermediate Similarity	NPC289312
0.789	Intermediate Similarity	NPC100267
0.7885	Intermediate Similarity	NPC155332
0.7885	Intermediate Similarity	NPC32577
0.7885	Intermediate Similarity	NPC114540

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 NPC472644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1489
0.2-0.3	3464
0.3-0.4	2529
0.4-0.5	995
0.5-0.6	277
0.6-0.7	180
0.7-0.8	51
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
0.783	Intermediate Similarity	NPD5739	Approved
0.783	Intermediate Similarity	NPD6675	Approved
0.783	Intermediate Similarity	NPD7128	Approved
0.783	Intermediate Similarity	NPD6402	Approved
0.7757	Intermediate Similarity	NPD5701	Approved
0.7757	Intermediate Similarity	NPD5697	Approved
0.7727	Intermediate Similarity	NPD6882	Approved
0.7685	Intermediate Similarity	NPD6899	Approved
0.7685	Intermediate Similarity	NPD7320	Approved
0.7685	Intermediate Similarity	NPD6011	Approved
0.7685	Intermediate Similarity	NPD6881	Approved
0.7684	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6372	Approved
0.7615	Intermediate Similarity	NPD6012	Approved
0.7615	Intermediate Similarity	NPD6013	Approved
0.7615	Intermediate Similarity	NPD6014	Approved
0.7615	Intermediate Similarity	NPD6373	Approved
0.7596	Intermediate Similarity	NPD4225	Approved
0.7547	Intermediate Similarity	NPD5211	Phase 2
0.7545	Intermediate Similarity	NPD7290	Approved
0.7545	Intermediate Similarity	NPD7102	Approved
0.7545	Intermediate Similarity	NPD6883	Approved
0.7524	Intermediate Similarity	NPD7640	Approved
0.7524	Intermediate Similarity	NPD7639	Approved
0.7523	Intermediate Similarity	NPD6686	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7477	Intermediate Similarity	NPD6847	Approved
0.7477	Intermediate Similarity	NPD6869	Approved
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7477	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.7449	Intermediate Similarity	NPD1694	Approved
0.7429	Intermediate Similarity	NPD7638	Approved
0.7411	Intermediate Similarity	NPD8297	Approved
0.7407	Intermediate Similarity	NPD5141	Approved
0.7404	Intermediate Similarity	NPD5221	Approved
0.7404	Intermediate Similarity	NPD4697	Phase 3
0.7404	Intermediate Similarity	NPD5222	Approved
0.7404	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7748	Approved
0.7358	Intermediate Similarity	NPD5286	Approved
0.7358	Intermediate Similarity	NPD5285	Approved
0.7358	Intermediate Similarity	NPD4700	Approved
0.7358	Intermediate Similarity	NPD4696	Approved
0.7353	Intermediate Similarity	NPD7515	Phase 2
0.7347	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5173	Approved
0.7333	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD6083	Phase 2
0.7333	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD5328	Approved
0.7308	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD7115	Discovery
0.7304	Intermediate Similarity	NPD6009	Approved
0.729	Intermediate Similarity	NPD5223	Approved
0.7282	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD5779	Approved
0.7228	Intermediate Similarity	NPD6672	Approved
0.7228	Intermediate Similarity	NPD5737	Approved
0.7222	Intermediate Similarity	NPD5226	Approved
0.7222	Intermediate Similarity	NPD5225	Approved
0.7222	Intermediate Similarity	NPD5224	Approved
0.7222	Intermediate Similarity	NPD4633	Approved
0.7217	Intermediate Similarity	NPD6274	Approved
0.72	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD5279	Phase 3
0.7193	Intermediate Similarity	NPD4632	Approved
0.7184	Intermediate Similarity	NPD5693	Phase 1
0.7184	Intermediate Similarity	NPD6411	Approved
0.7184	Intermediate Similarity	NPD6079	Approved
0.7156	Intermediate Similarity	NPD5174	Approved
0.7156	Intermediate Similarity	NPD5175	Approved
0.7156	Intermediate Similarity	NPD4754	Approved
0.7155	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4695	Discontinued
0.7107	Intermediate Similarity	NPD7507	Approved
0.7103	Intermediate Similarity	NPD5696	Approved
0.71	Intermediate Similarity	NPD1696	Phase 3
0.7094	Intermediate Similarity	NPD6335	Approved
0.7094	Intermediate Similarity	NPD6314	Approved
0.7094	Intermediate Similarity	NPD6313	Approved
0.7087	Intermediate Similarity	NPD5785	Approved
0.7069	Intermediate Similarity	NPD6868	Approved
0.7048	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7900	Approved
0.7034	Intermediate Similarity	NPD7100	Approved
0.7034	Intermediate Similarity	NPD7101	Approved
0.703	Intermediate Similarity	NPD7146	Approved
0.703	Intermediate Similarity	NPD7521	Approved
0.703	Intermediate Similarity	NPD7334	Approved
0.703	Intermediate Similarity	NPD5330	Approved
0.703	Intermediate Similarity	NPD6684	Approved
0.703	Intermediate Similarity	NPD6409	Approved
0.7027	Intermediate Similarity	NPD4768	Approved
0.7027	Intermediate Similarity	NPD4767	Approved
0.7027	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD7492	Approved
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3133	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.7	Intermediate Similarity	NPD3666	Approved
0.699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4753	Phase 2
0.699	Remote Similarity	NPD6101	Approved
0.6975	Remote Similarity	NPD6059	Approved
0.6975	Remote Similarity	NPD6319	Approved
0.6975	Remote Similarity	NPD6054	Approved
0.6967	Remote Similarity	NPD6616	Approved
0.6961	Remote Similarity	NPD3573	Approved
0.6957	Remote Similarity	NPD6053	Discontinued
0.6952	Remote Similarity	NPD4202	Approved
0.6942	Remote Similarity	NPD8328	Phase 3
0.6935	Remote Similarity	NPD7319	Approved
0.693	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD6908	Approved
0.6917	Remote Similarity	NPD5983	Phase 2
0.6917	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6016	Approved
0.6911	Remote Similarity	NPD7078	Approved
0.6911	Remote Similarity	NPD8293	Discontinued
0.6909	Remote Similarity	NPD7632	Discontinued
0.6903	Remote Similarity	NPD5128	Approved
0.6903	Remote Similarity	NPD4729	Approved
0.6903	Remote Similarity	NPD4730	Approved
0.6893	Remote Similarity	NPD6903	Approved
0.6893	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5988	Approved
0.686	Remote Similarity	NPD6370	Approved
0.6855	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD6080	Approved
0.6827	Remote Similarity	NPD6673	Approved
0.6827	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6904	Approved
0.6814	Remote Similarity	NPD6412	Phase 2
0.6803	Remote Similarity	NPD7604	Phase 2
0.6783	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5251	Approved
0.6783	Remote Similarity	NPD5169	Approved
0.6783	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD5248	Approved
0.6783	Remote Similarity	NPD5250	Approved
0.6783	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD5135	Approved
0.6783	Remote Similarity	NPD5249	Phase 3
0.6768	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5692	Phase 3
0.6762	Remote Similarity	NPD46	Approved
0.6762	Remote Similarity	NPD6698	Approved
0.6754	Remote Similarity	NPD5168	Approved
0.6754	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5215	Approved
0.6724	Remote Similarity	NPD5127	Approved
0.6724	Remote Similarity	NPD5217	Approved
0.6724	Remote Similarity	NPD5216	Approved
0.6699	Remote Similarity	NPD4519	Discontinued
0.6699	Remote Similarity	NPD5786	Approved
0.6699	Remote Similarity	NPD4623	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD6050	Approved
0.6698	Remote Similarity	NPD5284	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5210	Approved
0.6638	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD6435	Approved
0.6602	Remote Similarity	NPD5363	Approved
0.6602	Remote Similarity	NPD5329	Approved
0.6587	Remote Similarity	NPD6033	Approved
0.6583	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5282	Discontinued
0.6569	Remote Similarity	NPD5362	Discontinued
0.6569	Remote Similarity	NPD7154	Phase 3
0.6566	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD7260	Phase 2
0.6555	Remote Similarity	NPD5167	Approved
0.6542	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD8034	Phase 2
0.6542	Remote Similarity	NPD8035	Phase 2
0.6538	Remote Similarity	NPD6098	Approved
0.6538	Remote Similarity	NPD5690	Phase 2
0.6538	Remote Similarity	NPD5280	Approved
0.6538	Remote Similarity	NPD4694	Approved
0.6529	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD7328	Approved
0.6518	Remote Similarity	NPD5344	Discontinued
0.6514	Remote Similarity	NPD6356	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