NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	1.289
LogD:	1.117
LogS:	-2.768
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	4.885
Fsp3:	0.8
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:	-5.025
MDCK Permeability:	4.785100827575661e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.45
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.659
Plasma Protein Binding (PPB):	45.08900451660156%
Volume Distribution (VD):	1.548
Pgp-substrate:	64.2159423828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.456
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.716

ADMET: Excretion

Clearance (CL):	6.135
Half-life (T1/2):	0.191

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.51
Drug-inuced Liver Injury (DILI):	0.411
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.094
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.169
Carcinogencity:	0.894
Eye Corrosion:	0.007
Eye Irritation:	0.137
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC147272

Natural Product ID:	NPC147272
*Common Name:**	2Alpha,5Alpha-Dihydroxy-11Alpha(H)-Eudesma-4(15)-En-8Beta,12-Olide
IUPAC Name:	(3S,3aR,4aR,7S,8aR,9aR)-4a,7-dihydroxy-3,8a-dimethyl-5-methylidene-3,3a,4,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	KGJUZQMPTQIFAB-IDMWBNCISA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-8-4-10(16)5-14(3)7-12-11(6-15(8,14)18)9(2)13(17)19-12/h9-12,16,18H,1,4-7H2,2-3H3/t9-,10-,11+,12+,14+,15+/m0/s1
SMILES:	O[C@H]1CC(=C)[C@]2([C@@](C1)(C)C[C@@H]1[C@H](C2)[C@@H](C(=O)O1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644109
PubChem CID:	53323206
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
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO23499	Carpesium faberi	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[448891]

☑ 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 NPC147272 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	190
0.1-0.2	1423
0.2-0.3	4932
0.3-0.4	9930
0.4-0.5	11479
0.5-0.6	6008
0.6-0.7	6356
0.7-0.8	2176
0.8-0.85	156
0.85-0.9	37
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC90014
0.9205	High Similarity	NPC194642
0.907	High Similarity	NPC97505
0.9043	High Similarity	NPC475958
0.9022	High Similarity	NPC93245
0.8925	High Similarity	NPC473963
0.8889	High Similarity	NPC153853
0.8817	High Similarity	NPC256227
0.8817	High Similarity	NPC473964
0.8804	High Similarity	NPC469596
0.8804	High Similarity	NPC24861
0.8804	High Similarity	NPC148000
0.8804	High Similarity	NPC225474
0.8778	High Similarity	NPC116620
0.8723	High Similarity	NPC136781
0.8721	High Similarity	NPC209318
0.8721	High Similarity	NPC223330
0.871	High Similarity	NPC259042
0.871	High Similarity	NPC157686
0.8632	High Similarity	NPC476806
0.8632	High Similarity	NPC476807
0.8556	High Similarity	NPC181103
0.8556	High Similarity	NPC305029
0.8526	High Similarity	NPC474921
0.8523	High Similarity	NPC243347
0.8511	High Similarity	NPC56369
0.8469	Intermediate Similarity	NPC61442
0.8469	Intermediate Similarity	NPC72842
0.8454	Intermediate Similarity	NPC121218
0.8454	Intermediate Similarity	NPC39683
0.8454	Intermediate Similarity	NPC253886
0.8444	Intermediate Similarity	NPC85698
0.8421	Intermediate Similarity	NPC200054
0.8421	Intermediate Similarity	NPC29410
0.8421	Intermediate Similarity	NPC165528
0.8421	Intermediate Similarity	NPC228766
0.8421	Intermediate Similarity	NPC284518
0.8404	Intermediate Similarity	NPC250075
0.84	Intermediate Similarity	NPC230541
0.84	Intermediate Similarity	NPC78966
0.84	Intermediate Similarity	NPC284732
0.8387	Intermediate Similarity	NPC198054
0.8367	Intermediate Similarity	NPC164551
0.8352	Intermediate Similarity	NPC175293
0.8351	Intermediate Similarity	NPC47024
0.8317	Intermediate Similarity	NPC37628
0.8316	Intermediate Similarity	NPC98639
0.83	Intermediate Similarity	NPC37600
0.8283	Intermediate Similarity	NPC99510
0.8283	Intermediate Similarity	NPC87927
0.828	Intermediate Similarity	NPC475776
0.8265	Intermediate Similarity	NPC295276
0.8265	Intermediate Similarity	NPC242666
0.8252	Intermediate Similarity	NPC157476
0.8247	Intermediate Similarity	NPC216478
0.8247	Intermediate Similarity	NPC89099
0.8247	Intermediate Similarity	NPC38296
0.8247	Intermediate Similarity	NPC162459
0.8247	Intermediate Similarity	NPC38471
0.8247	Intermediate Similarity	NPC471038
0.8247	Intermediate Similarity	NPC28864
0.8247	Intermediate Similarity	NPC98837
0.8247	Intermediate Similarity	NPC20479
0.8242	Intermediate Similarity	NPC185638
0.8242	Intermediate Similarity	NPC9231
0.8242	Intermediate Similarity	NPC6979
0.8235	Intermediate Similarity	NPC154906
0.8235	Intermediate Similarity	NPC474243
0.8235	Intermediate Similarity	NPC141350
0.82	Intermediate Similarity	NPC47281
0.82	Intermediate Similarity	NPC283850
0.82	Intermediate Similarity	NPC258532
0.8182	Intermediate Similarity	NPC170615
0.8182	Intermediate Similarity	NPC162973
0.8173	Intermediate Similarity	NPC472002
0.8163	Intermediate Similarity	NPC293866
0.8163	Intermediate Similarity	NPC267921
0.8155	Intermediate Similarity	NPC130302
0.8144	Intermediate Similarity	NPC10864
0.8144	Intermediate Similarity	NPC253586
0.8144	Intermediate Similarity	NPC111348
0.814	Intermediate Similarity	NPC92489
0.8137	Intermediate Similarity	NPC189075
0.8137	Intermediate Similarity	NPC275539
0.8125	Intermediate Similarity	NPC470232
0.8125	Intermediate Similarity	NPC134067
0.8119	Intermediate Similarity	NPC469607
0.8119	Intermediate Similarity	NPC285927
0.8119	Intermediate Similarity	NPC50535
0.8119	Intermediate Similarity	NPC102352
0.8113	Intermediate Similarity	NPC179626
0.8111	Intermediate Similarity	NPC15091
0.8105	Intermediate Similarity	NPC199543
0.81	Intermediate Similarity	NPC225238
0.81	Intermediate Similarity	NPC469985
0.8085	Intermediate Similarity	NPC100313
0.8085	Intermediate Similarity	NPC232202
0.8081	Intermediate Similarity	NPC52899
0.8081	Intermediate Similarity	NPC471412
0.8081	Intermediate Similarity	NPC111292
0.8081	Intermediate Similarity	NPC252614
0.8081	Intermediate Similarity	NPC75941
0.8081	Intermediate Similarity	NPC289148
0.8081	Intermediate Similarity	NPC81530
0.8081	Intermediate Similarity	NPC163963
0.8081	Intermediate Similarity	NPC308824
0.8081	Intermediate Similarity	NPC46848
0.8065	Intermediate Similarity	NPC92370
0.8061	Intermediate Similarity	NPC474724
0.8061	Intermediate Similarity	NPC23364
0.8061	Intermediate Similarity	NPC474793
0.8058	Intermediate Similarity	NPC472534
0.8058	Intermediate Similarity	NPC143706
0.8046	Intermediate Similarity	NPC307865
0.8043	Intermediate Similarity	NPC477920
0.8041	Intermediate Similarity	NPC329910
0.8041	Intermediate Similarity	NPC219353
0.8039	Intermediate Similarity	NPC144854
0.8039	Intermediate Similarity	NPC471246
0.8039	Intermediate Similarity	NPC3316
0.8039	Intermediate Similarity	NPC110496
0.8039	Intermediate Similarity	NPC59530
0.8037	Intermediate Similarity	NPC176513
0.8037	Intermediate Similarity	NPC470775
0.8022	Intermediate Similarity	NPC130966
0.8021	Intermediate Similarity	NPC475118
0.8021	Intermediate Similarity	NPC471446
0.8021	Intermediate Similarity	NPC473434
0.8021	Intermediate Similarity	NPC280804
0.8021	Intermediate Similarity	NPC470385
0.8021	Intermediate Similarity	NPC474841
0.8021	Intermediate Similarity	NPC470386
0.802	Intermediate Similarity	NPC13149
0.8019	Intermediate Similarity	NPC117712
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC136289
0.8	Intermediate Similarity	NPC471747
0.8	Intermediate Similarity	NPC88203
0.8	Intermediate Similarity	NPC226988
0.8	Intermediate Similarity	NPC286519
0.8	Intermediate Similarity	NPC304832
0.8	Intermediate Similarity	NPC76866
0.8	Intermediate Similarity	NPC275990
0.8	Intermediate Similarity	NPC214946
0.8	Intermediate Similarity	NPC186363
0.8	Intermediate Similarity	NPC148628
0.8	Intermediate Similarity	NPC233345
0.8	Intermediate Similarity	NPC246736
0.7981	Intermediate Similarity	NPC255655
0.7981	Intermediate Similarity	NPC98633
0.798	Intermediate Similarity	NPC477656
0.798	Intermediate Similarity	NPC471413
0.798	Intermediate Similarity	NPC287676
0.798	Intermediate Similarity	NPC180733
0.798	Intermediate Similarity	NPC41971
0.798	Intermediate Similarity	NPC37047
0.798	Intermediate Similarity	NPC477655
0.798	Intermediate Similarity	NPC108371
0.798	Intermediate Similarity	NPC470388
0.7979	Intermediate Similarity	NPC291875
0.7979	Intermediate Similarity	NPC253618
0.7979	Intermediate Similarity	NPC77001
0.7978	Intermediate Similarity	NPC134227
0.7978	Intermediate Similarity	NPC125366
0.7961	Intermediate Similarity	NPC112895
0.7961	Intermediate Similarity	NPC218123
0.7961	Intermediate Similarity	NPC154608
0.7961	Intermediate Similarity	NPC231278
0.7961	Intermediate Similarity	NPC277017
0.7961	Intermediate Similarity	NPC192813
0.7959	Intermediate Similarity	NPC254496
0.7959	Intermediate Similarity	NPC474343
0.7959	Intermediate Similarity	NPC474395
0.7959	Intermediate Similarity	NPC190080
0.7959	Intermediate Similarity	NPC189880
0.7959	Intermediate Similarity	NPC111187
0.7957	Intermediate Similarity	NPC470012
0.7944	Intermediate Similarity	NPC474734
0.7941	Intermediate Similarity	NPC478208
0.7941	Intermediate Similarity	NPC28791
0.7941	Intermediate Similarity	NPC295366
0.7941	Intermediate Similarity	NPC127609
0.7938	Intermediate Similarity	NPC266899
0.7938	Intermediate Similarity	NPC470229
0.7935	Intermediate Similarity	NPC164424
0.7935	Intermediate Similarity	NPC52628
0.7925	Intermediate Similarity	NPC285086
0.7925	Intermediate Similarity	NPC25909
0.7925	Intermediate Similarity	NPC474271
0.7921	Intermediate Similarity	NPC209298
0.7921	Intermediate Similarity	NPC139347
0.7921	Intermediate Similarity	NPC277074
0.7921	Intermediate Similarity	NPC159442
0.7921	Intermediate Similarity	NPC122811
0.7921	Intermediate Similarity	NPC96217
0.7921	Intermediate Similarity	NPC36688
0.7921	Intermediate Similarity	NPC156681
0.7921	Intermediate Similarity	NPC216114
0.7921	Intermediate Similarity	NPC140723
0.7917	Intermediate Similarity	NPC244356

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 NPC147272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1863
0.2-0.3	3877
0.3-0.4	2110
0.4-0.5	627
0.5-0.6	230
0.6-0.7	212
0.7-0.8	59
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
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7619	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6008	Approved
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7374	Intermediate Similarity	NPD6399	Phase 3
0.7368	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7638	Approved
0.7264	Intermediate Similarity	NPD7128	Approved
0.7264	Intermediate Similarity	NPD6675	Approved
0.7264	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD6373	Approved
0.7222	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5697	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7184	Intermediate Similarity	NPD4225	Approved
0.7156	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.713	Intermediate Similarity	NPD6011	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.7117	Intermediate Similarity	NPD4632	Approved
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7087	Intermediate Similarity	NPD7902	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD6014	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6981	Remote Similarity	NPD7632	Discontinued
0.6981	Remote Similarity	NPD5211	Phase 2
0.6964	Remote Similarity	NPD8133	Approved
0.6961	Remote Similarity	NPD7748	Approved
0.6939	Remote Similarity	NPD3618	Phase 1
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6931	Remote Similarity	NPD7515	Phase 2
0.693	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD4755	Approved
0.69	Remote Similarity	NPD5328	Approved
0.6897	Remote Similarity	NPD6319	Approved
0.6882	Remote Similarity	NPD6116	Phase 1
0.6881	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8297	Approved
0.6875	Remote Similarity	NPD6882	Approved
0.6875	Remote Similarity	NPD3667	Approved
0.6852	Remote Similarity	NPD5141	Approved
0.6848	Remote Similarity	NPD3703	Phase 2
0.6838	Remote Similarity	NPD6921	Approved
0.6838	Remote Similarity	NPD5983	Phase 2
0.6827	Remote Similarity	NPD4697	Phase 3
0.6807	Remote Similarity	NPD7492	Approved
0.6796	Remote Similarity	NPD7900	Approved
0.6796	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5286	Approved
0.6792	Remote Similarity	NPD5285	Approved
0.6792	Remote Similarity	NPD4700	Approved
0.6792	Remote Similarity	NPD4696	Approved
0.6783	Remote Similarity	NPD7115	Discovery
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6117	Approved
0.6765	Remote Similarity	NPD6411	Approved
0.6765	Remote Similarity	NPD6079	Approved
0.6757	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6735	Remote Similarity	NPD4786	Approved
0.6731	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD1700	Approved
0.6729	Remote Similarity	NPD5223	Approved
0.6723	Remote Similarity	NPD7604	Phase 2
0.67	Remote Similarity	NPD3573	Approved
0.6699	Remote Similarity	NPD4202	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6695	Remote Similarity	NPD6015	Approved
0.6695	Remote Similarity	NPD6016	Approved
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6317	Approved
0.6612	Remote Similarity	NPD6336	Discontinued
0.6606	Remote Similarity	NPD5175	Approved
0.6606	Remote Similarity	NPD5174	Approved
0.6606	Remote Similarity	NPD4754	Approved
0.6604	Remote Similarity	NPD5173	Approved
0.6604	Remote Similarity	NPD6083	Phase 2
0.6604	Remote Similarity	NPD6084	Phase 2
0.6602	Remote Similarity	NPD7637	Suspended
0.6585	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD8328	Phase 3
0.6581	Remote Similarity	NPD6314	Approved
0.6581	Remote Similarity	NPD6335	Approved
0.6581	Remote Similarity	NPD6313	Approved
0.6579	Remote Similarity	NPD6053	Discontinued
0.6571	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8517	Approved
0.6555	Remote Similarity	NPD8513	Phase 3
0.6555	Remote Similarity	NPD8516	Approved
0.6555	Remote Similarity	NPD8515	Approved
0.6549	Remote Similarity	NPD4634	Approved
0.6542	Remote Similarity	NPD5696	Approved
0.6531	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD7100	Approved
0.6495	Remote Similarity	NPD7525	Registered
0.6489	Remote Similarity	NPD3702	Approved
0.6486	Remote Similarity	NPD4768	Approved
0.6486	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD5282	Discontinued
0.6465	Remote Similarity	NPD6695	Phase 3
0.6465	Remote Similarity	NPD4788	Approved
0.6442	Remote Similarity	NPD7983	Approved
0.6436	Remote Similarity	NPD7334	Approved
0.6436	Remote Similarity	NPD6409	Approved
0.6436	Remote Similarity	NPD7521	Approved
0.6436	Remote Similarity	NPD7146	Approved
0.6436	Remote Similarity	NPD5330	Approved
0.6436	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6412	Phase 2
0.6422	Remote Similarity	NPD5344	Discontinued
0.6417	Remote Similarity	NPD6909	Approved
0.6417	Remote Similarity	NPD6908	Approved
0.6415	Remote Similarity	NPD5695	Phase 3
0.641	Remote Similarity	NPD6868	Approved
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD3133	Approved
0.64	Remote Similarity	NPD3668	Phase 3
0.6372	Remote Similarity	NPD4730	Approved
0.6372	Remote Similarity	NPD4729	Approved
0.6372	Remote Similarity	NPD5128	Approved
0.6371	Remote Similarity	NPD6033	Approved
0.6337	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6001	Approved
0.6311	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD6903	Approved
0.6311	Remote Similarity	NPD6672	Approved
0.6304	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7328	Approved
0.6303	Remote Similarity	NPD7327	Approved
0.629	Remote Similarity	NPD8074	Phase 3
0.6286	Remote Similarity	NPD5281	Approved
0.6286	Remote Similarity	NPD5284	Approved
0.6275	Remote Similarity	NPD4249	Approved
0.6275	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD5786	Approved
0.6263	Remote Similarity	NPD1780	Approved
0.6263	Remote Similarity	NPD1779	Approved
0.6261	Remote Similarity	NPD5251	Approved
0.6261	Remote Similarity	NPD5250	Approved
0.6261	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5248	Approved
0.6261	Remote Similarity	NPD5249	Phase 3
0.6261	Remote Similarity	NPD5169	Approved
0.6261	Remote Similarity	NPD5247	Approved
0.6261	Remote Similarity	NPD5135	Approved
0.6261	Remote Similarity	NPD6371	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD1695	Approved
0.625	Remote Similarity	NPD7516	Approved
0.6214	Remote Similarity	NPD7524	Approved
0.6214	Remote Similarity	NPD4251	Approved
0.6214	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4250	Approved
0.6214	Remote Similarity	NPD7750	Discontinued
0.6207	Remote Similarity	NPD5127	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