NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.785
LogD:	1.856
LogS:	-3.456
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.65
Fsp3:	0.667
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:	-4.629
MDCK Permeability:	2.238624801975675e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	66.94291687011719%
Volume Distribution (VD):	1.016
Pgp-substrate:	32.44329071044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.28
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.432
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	6.974
Half-life (T1/2):	0.242

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.255
Drug-inuced Liver Injury (DILI):	0.206
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.767
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.699
Carcinogencity:	0.882
Eye Corrosion:	0.441
Eye Irritation:	0.885
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC90014

Natural Product ID:	NPC90014
*Common Name:**	Telekin
IUPAC Name:	(3aR,4aR,8aR,9aR)-4a-hydroxy-8a-methyl-3,5-dimethylidene-4,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
Synonyms:	Eudesmanolide; Telekin
Standard InCHIKey:	LIDPBIULZNRIJE-QHSBEEBCSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-9-5-4-6-14(3)8-12-11(7-15(9,14)17)10(2)13(16)18-12/h11-12,17H,1-2,4-8H2,3H3/t11-,12-,14-,15-/m1/s1
SMILES:	O=C1O[C@H]2[C@@H](C1=C)C[C@@]1([C@](C2)(C)CCCC1=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL406233
PubChem CID:	12443309
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
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[10364842]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[12392098]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23451797]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24996657]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	root	n.a.	PMID[25767328]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26316467]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32842729]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25152	Telekia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25152	Telekia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24797	Chuquiraga ulicina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25058	Mayetiola destructor	Species	Cecidomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24524	Gutierrezia gymnospermoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25152	Telekia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26335	Carpesium abrotanoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8815	Artemisia myriantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23330	Guatteria dumetorum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25374	Crotalaria sericea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24701	Schizonepeta annua	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	10

Activity Type	# Activity
Cell Line	7
CELL-LINE	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[485534]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8.14	ug.mL-1	PMID[485535]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4.27	ug.mL-1	PMID[485535]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	3.5	ug.mL-1	PMID[485535]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[485537]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	>	10000.0	nM	PMID[485537]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[485537]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	563800.0	nM	PMID[485533]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	36.0	ug.mL-1	PMID[485536]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[485536]

☑ 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 NPC90014 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	203
0.1-0.2	1439
0.2-0.3	4882
0.3-0.4	8512
0.4-0.5	12870
0.5-0.6	6377
0.6-0.7	6483
0.7-0.8	1784
0.8-0.85	90
0.85-0.9	40
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC147272
0.9255	High Similarity	NPC475958
0.9239	High Similarity	NPC93245
0.9239	High Similarity	NPC473964
0.9213	High Similarity	NPC116620
0.914	High Similarity	NPC473963
0.913	High Similarity	NPC56369
0.9022	High Similarity	NPC225474
0.9022	High Similarity	NPC24861
0.9022	High Similarity	NPC148000
0.9022	High Similarity	NPC469596
0.8989	High Similarity	NPC305029
0.8989	High Similarity	NPC181103
0.8936	High Similarity	NPC136781
0.8936	High Similarity	NPC474921
0.8925	High Similarity	NPC259042
0.8925	High Similarity	NPC157686
0.8876	High Similarity	NPC85698
0.8876	High Similarity	NPC9231
0.8842	High Similarity	NPC476806
0.8842	High Similarity	NPC476807
0.8778	High Similarity	NPC175293
0.8696	High Similarity	NPC475776
0.8673	High Similarity	NPC61442
0.8673	High Similarity	NPC72842
0.8673	High Similarity	NPC99510
0.8652	High Similarity	NPC97505
0.8636	High Similarity	NPC226988
0.8632	High Similarity	NPC228766
0.8632	High Similarity	NPC284518
0.8632	High Similarity	NPC165528
0.86	High Similarity	NPC78966
0.86	High Similarity	NPC284732
0.8587	High Similarity	NPC194642
0.8586	High Similarity	NPC283850
0.8571	High Similarity	NPC164551
0.8571	High Similarity	NPC162973
0.8557	High Similarity	NPC47024
0.8515	High Similarity	NPC37628
0.8469	Intermediate Similarity	NPC242666
0.8462	Intermediate Similarity	NPC477920
0.8462	Intermediate Similarity	NPC185638
0.8454	Intermediate Similarity	NPC216478
0.8431	Intermediate Similarity	NPC474243
0.8421	Intermediate Similarity	NPC474841
0.8421	Intermediate Similarity	NPC250075
0.8421	Intermediate Similarity	NPC473434
0.8421	Intermediate Similarity	NPC66581
0.8421	Intermediate Similarity	NPC471446
0.8416	Intermediate Similarity	NPC110496
0.8404	Intermediate Similarity	NPC233345
0.8404	Intermediate Similarity	NPC186363
0.837	Intermediate Similarity	NPC470012
0.8367	Intermediate Similarity	NPC471413
0.8333	Intermediate Similarity	NPC243347
0.8333	Intermediate Similarity	NPC275539
0.8333	Intermediate Similarity	NPC189075
0.8315	Intermediate Similarity	NPC223330
0.8315	Intermediate Similarity	NPC209318
0.8298	Intermediate Similarity	NPC153853
0.8298	Intermediate Similarity	NPC158488
0.8283	Intermediate Similarity	NPC308824
0.8283	Intermediate Similarity	NPC111292
0.8283	Intermediate Similarity	NPC471412
0.828	Intermediate Similarity	NPC277771
0.828	Intermediate Similarity	NPC50847
0.8265	Intermediate Similarity	NPC23364
0.8247	Intermediate Similarity	NPC256227
0.8247	Intermediate Similarity	NPC200054
0.8247	Intermediate Similarity	NPC29952
0.8247	Intermediate Similarity	NPC29410
0.819	Intermediate Similarity	NPC269530
0.8163	Intermediate Similarity	NPC474343
0.8163	Intermediate Similarity	NPC474395
0.8144	Intermediate Similarity	NPC98639
0.8137	Intermediate Similarity	NPC469607
0.8132	Intermediate Similarity	NPC194637
0.8119	Intermediate Similarity	NPC254202
0.8119	Intermediate Similarity	NPC156681
0.8119	Intermediate Similarity	NPC87927
0.8113	Intermediate Similarity	NPC25909
0.8111	Intermediate Similarity	NPC38642
0.8105	Intermediate Similarity	NPC152467
0.809	Intermediate Similarity	NPC263951
0.8081	Intermediate Similarity	NPC162459
0.8081	Intermediate Similarity	NPC38296
0.8081	Intermediate Similarity	NPC471038
0.8081	Intermediate Similarity	NPC38471
0.8081	Intermediate Similarity	NPC98837
0.8081	Intermediate Similarity	NPC28864
0.8081	Intermediate Similarity	NPC89099
0.8081	Intermediate Similarity	NPC20479
0.8043	Intermediate Similarity	NPC470011
0.8043	Intermediate Similarity	NPC219011
0.8041	Intermediate Similarity	NPC475118
0.8041	Intermediate Similarity	NPC57117
0.8039	Intermediate Similarity	NPC258532
0.802	Intermediate Similarity	NPC476081
0.802	Intermediate Similarity	NPC170615
0.8019	Intermediate Similarity	NPC194951
0.8019	Intermediate Similarity	NPC12046
0.8	Intermediate Similarity	NPC267921
0.8	Intermediate Similarity	NPC5103
0.8	Intermediate Similarity	NPC293866
0.798	Intermediate Similarity	NPC10864
0.798	Intermediate Similarity	NPC111348
0.7979	Intermediate Similarity	NPC476932
0.7961	Intermediate Similarity	NPC478208
0.7959	Intermediate Similarity	NPC316215
0.7959	Intermediate Similarity	NPC470232
0.7959	Intermediate Similarity	NPC183012
0.7959	Intermediate Similarity	NPC470229
0.7955	Intermediate Similarity	NPC92489
0.7944	Intermediate Similarity	NPC157441
0.7941	Intermediate Similarity	NPC36688
0.7938	Intermediate Similarity	NPC199543
0.7935	Intermediate Similarity	NPC107253
0.7925	Intermediate Similarity	NPC469655
0.7925	Intermediate Similarity	NPC304180
0.7925	Intermediate Similarity	NPC474846
0.7925	Intermediate Similarity	NPC469656
0.7925	Intermediate Similarity	NPC179798
0.7921	Intermediate Similarity	NPC52899
0.7921	Intermediate Similarity	NPC46848
0.7921	Intermediate Similarity	NPC121218
0.7921	Intermediate Similarity	NPC253886
0.7921	Intermediate Similarity	NPC289148
0.7921	Intermediate Similarity	NPC252614
0.7921	Intermediate Similarity	NPC39683
0.7921	Intermediate Similarity	NPC81530
0.7921	Intermediate Similarity	NPC163963
0.79	Intermediate Similarity	NPC474793
0.79	Intermediate Similarity	NPC473155
0.7885	Intermediate Similarity	NPC187435
0.7885	Intermediate Similarity	NPC67321
0.7885	Intermediate Similarity	NPC230541
0.7879	Intermediate Similarity	NPC219353
0.7879	Intermediate Similarity	NPC134072
0.7879	Intermediate Similarity	NPC329910
0.7879	Intermediate Similarity	NPC234993
0.7872	Intermediate Similarity	NPC250981
0.7872	Intermediate Similarity	NPC470242
0.7872	Intermediate Similarity	NPC6979
0.7864	Intermediate Similarity	NPC146731
0.7864	Intermediate Similarity	NPC296950
0.7864	Intermediate Similarity	NPC118911
0.7864	Intermediate Similarity	NPC13149
0.7857	Intermediate Similarity	NPC470385
0.7857	Intermediate Similarity	NPC470386
0.785	Intermediate Similarity	NPC472002
0.7849	Intermediate Similarity	NPC130966
0.7843	Intermediate Similarity	NPC31058
0.7843	Intermediate Similarity	NPC286519
0.7843	Intermediate Similarity	NPC273005
0.7843	Intermediate Similarity	NPC88203
0.7843	Intermediate Similarity	NPC469606
0.7843	Intermediate Similarity	NPC304832
0.7843	Intermediate Similarity	NPC275990
0.7843	Intermediate Similarity	NPC246736
0.7843	Intermediate Similarity	NPC214946
0.7843	Intermediate Similarity	NPC136289
0.7843	Intermediate Similarity	NPC58329
0.7843	Intermediate Similarity	NPC148628
0.7843	Intermediate Similarity	NPC76866
0.7843	Intermediate Similarity	NPC295791
0.7841	Intermediate Similarity	NPC39362
0.7835	Intermediate Similarity	NPC198054
0.7835	Intermediate Similarity	NPC165180
0.783	Intermediate Similarity	NPC478211
0.783	Intermediate Similarity	NPC253906
0.7822	Intermediate Similarity	NPC287676
0.7822	Intermediate Similarity	NPC470388
0.7822	Intermediate Similarity	NPC471041
0.7822	Intermediate Similarity	NPC476303
0.7812	Intermediate Similarity	NPC73995
0.7812	Intermediate Similarity	NPC474396
0.7812	Intermediate Similarity	NPC50488
0.781	Intermediate Similarity	NPC255082
0.781	Intermediate Similarity	NPC231278
0.781	Intermediate Similarity	NPC218123
0.781	Intermediate Similarity	NPC112895
0.78	Intermediate Similarity	NPC254496
0.7789	Intermediate Similarity	NPC118601
0.7788	Intermediate Similarity	NPC37600
0.7788	Intermediate Similarity	NPC102352
0.7788	Intermediate Similarity	NPC295366
0.7788	Intermediate Similarity	NPC127609
0.7788	Intermediate Similarity	NPC28791
0.7778	Intermediate Similarity	NPC477126
0.7778	Intermediate Similarity	NPC471624
0.7778	Intermediate Similarity	NPC56448
0.7778	Intermediate Similarity	NPC197158
0.7778	Intermediate Similarity	NPC469454
0.7778	Intermediate Similarity	NPC469496
0.7778	Intermediate Similarity	NPC469463
0.7767	Intermediate Similarity	NPC221421
0.7767	Intermediate Similarity	NPC159442
0.7767	Intermediate Similarity	NPC96217
0.7767	Intermediate Similarity	NPC209298
0.7767	Intermediate Similarity	NPC122811

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 NPC90014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1841
0.2-0.3	3836
0.3-0.4	2134
0.4-0.5	685
0.5-0.6	221
0.6-0.7	196
0.7-0.8	46
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
0.7477	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7639	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD6008	Approved
0.7379	Intermediate Similarity	NPD4225	Approved
0.7379	Intermediate Similarity	NPD7638	Approved
0.7339	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8034	Phase 2
0.73	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1694	Approved
0.7064	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5697	Approved
0.7059	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.6972	Remote Similarity	NPD6402	Approved
0.6972	Remote Similarity	NPD7128	Approved
0.6972	Remote Similarity	NPD5739	Approved
0.6972	Remote Similarity	NPD6675	Approved
0.6964	Remote Similarity	NPD6649	Approved
0.6964	Remote Similarity	NPD6650	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6952	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD6012	Approved
0.6937	Remote Similarity	NPD6014	Approved
0.6937	Remote Similarity	NPD6013	Approved
0.6937	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5701	Approved
0.6907	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD7290	Approved
0.6875	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD7102	Approved
0.6869	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5211	Phase 2
0.6847	Remote Similarity	NPD7320	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6842	Remote Similarity	NPD8133	Approved
0.6827	Remote Similarity	NPD7748	Approved
0.6814	Remote Similarity	NPD6847	Approved
0.6814	Remote Similarity	NPD6869	Approved
0.6814	Remote Similarity	NPD8130	Phase 1
0.6814	Remote Similarity	NPD6617	Approved
0.681	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD3618	Phase 1
0.6796	Remote Similarity	NPD6079	Approved
0.678	Remote Similarity	NPD6319	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6765	Remote Similarity	NPD1695	Approved
0.6765	Remote Similarity	NPD5328	Approved
0.6754	Remote Similarity	NPD8297	Approved
0.6754	Remote Similarity	NPD6882	Approved
0.6727	Remote Similarity	NPD5141	Approved
0.6723	Remote Similarity	NPD6921	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6635	Remote Similarity	NPD7515	Phase 2
0.6613	Remote Similarity	NPD7319	Approved
0.6612	Remote Similarity	NPD7604	Phase 2
0.6609	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD5344	Discontinued
0.6585	Remote Similarity	NPD7078	Approved
0.6583	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6581	Remote Similarity	NPD6274	Approved
0.6571	Remote Similarity	NPD5778	Approved
0.6571	Remote Similarity	NPD5779	Approved
0.6571	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD3667	Approved
0.6545	Remote Similarity	NPD5226	Approved
0.6545	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5224	Approved
0.6545	Remote Similarity	NPD4633	Approved
0.6542	Remote Similarity	NPD5222	Approved
0.6542	Remote Similarity	NPD4697	Phase 3
0.6542	Remote Similarity	NPD5221	Approved
0.6542	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7736	Approved
0.6529	Remote Similarity	NPD6370	Approved
0.6529	Remote Similarity	NPD5988	Approved
0.6526	Remote Similarity	NPD3703	Phase 2
0.6525	Remote Similarity	NPD6317	Approved
0.6514	Remote Similarity	NPD4700	Approved
0.6514	Remote Similarity	NPD6648	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.65	Remote Similarity	NPD4788	Approved
0.65	Remote Similarity	NPD6059	Approved
0.6495	Remote Similarity	NPD6115	Approved
0.6495	Remote Similarity	NPD6118	Approved
0.6495	Remote Similarity	NPD6114	Approved
0.6495	Remote Similarity	NPD6697	Approved
0.6486	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD6313	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD6335	Approved
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6471	Remote Similarity	NPD6314	Approved
0.6455	Remote Similarity	NPD1700	Approved
0.6452	Remote Similarity	NPD8293	Discontinued
0.6449	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8515	Approved
0.6446	Remote Similarity	NPD8516	Approved
0.6446	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD8513	Phase 3
0.6436	Remote Similarity	NPD4786	Approved
0.6435	Remote Similarity	NPD4634	Approved
0.6435	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD5696	Approved
0.6417	Remote Similarity	NPD7100	Approved
0.6417	Remote Similarity	NPD7101	Approved
0.6392	Remote Similarity	NPD6116	Phase 1
0.6387	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5282	Discontinued
0.6355	Remote Similarity	NPD6001	Approved
0.6354	Remote Similarity	NPD3702	Approved
0.6348	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6903	Approved
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8328	Phase 3
0.6339	Remote Similarity	NPD4754	Approved
0.6333	Remote Similarity	NPD7327	Approved
0.6333	Remote Similarity	NPD7328	Approved
0.633	Remote Similarity	NPD6083	Phase 2
0.633	Remote Similarity	NPD6084	Phase 2
0.6321	Remote Similarity	NPD6411	Approved
0.6321	Remote Similarity	NPD5693	Phase 1
0.6316	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6868	Approved
0.6296	Remote Similarity	NPD5695	Phase 3
0.6289	Remote Similarity	NPD6117	Approved
0.6281	Remote Similarity	NPD7516	Approved
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD3665	Phase 1
0.6261	Remote Similarity	NPD4730	Approved
0.6261	Remote Similarity	NPD5128	Approved
0.6261	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7260	Phase 2
0.6228	Remote Similarity	NPD4767	Approved
0.6228	Remote Similarity	NPD4768	Approved
0.6226	Remote Similarity	NPD6698	Approved
0.6226	Remote Similarity	NPD46	Approved
0.6226	Remote Similarity	NPD5785	Approved
0.6202	Remote Similarity	NPD6845	Suspended
0.619	Remote Similarity	NPD6672	Approved
0.619	Remote Similarity	NPD5737	Approved
0.619	Remote Similarity	NPD8074	Phase 3
0.6179	Remote Similarity	NPD6908	Approved
0.6179	Remote Similarity	NPD8033	Approved
0.6179	Remote Similarity	NPD6909	Approved
0.6174	Remote Similarity	NPD6412	Phase 2
0.6168	Remote Similarity	NPD5281	Approved
0.6168	Remote Similarity	NPD5284	Approved
0.6168	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD5169	Approved
0.6154	Remote Similarity	NPD4519	Discontinued
0.6154	Remote Similarity	NPD5135	Approved
0.6154	Remote Similarity	NPD5251	Approved
0.6154	Remote Similarity	NPD4623	Approved
0.6154	Remote Similarity	NPD5248	Approved
0.6154	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD5250	Approved
0.6154	Remote Similarity	NPD5249	Phase 3
0.6154	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6033	Approved
0.6132	Remote Similarity	NPD6101	Approved
0.6132	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3668	Phase 3
0.6117	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5217	Approved
0.6102	Remote Similarity	NPD5216	Approved
0.6102	Remote Similarity	NPD5127	Approved
0.6102	Remote Similarity	NPD5215	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