NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.13
LogD:	2.608
LogS:	-3.768
# Rotatable Bonds:	0
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.139
Fsp3:	0.8
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:	-4.73
MDCK Permeability:	3.163868314004503e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	71.58533477783203%
Volume Distribution (VD):	1.431
Pgp-substrate:	28.080156326293945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.258
CYP1A2-substrate:	0.405
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.565
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.512
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	8.201
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.872
Carcinogencity:	0.483
Eye Corrosion:	0.904
Eye Irritation:	0.953
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC56369

Natural Product ID:	NPC56369
*Common Name:**	YIQKVCDNUFDAHB-HKKVUVRFSA-N
IUPAC Name:	n.a.
Synonyms:	5Alpha-Epoxyalantolactone
Standard InCHIKey:	YIQKVCDNUFDAHB-HKKVUVRFSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-5-4-6-14(3)7-10-11(9(2)13(16)17-10)12-15(8,14)18-12/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11+,12-,14+,15-/m0/s1
SMILES:	C[C@H]1CCC[C@]2(C)C[C@@H]3[C@@H](C(=C)C(=O)O3)[C@H]3[C@@]12O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332657
PubChem CID:	474521
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]
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]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO23861	Inula racemosa	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]
NPO23861	Inula racemosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17755	Inula helenium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17755	Inula helenium	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]

☑ 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	5
Others	1

Activity Type	# Activity
Cell Line	3
Organism	2
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	2.73	ug.mL-1	PMID[528572]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1.59	ug.mL-1	PMID[528572]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	1.32	ug.mL-1	PMID[528572]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	>	128.0	ug.mL-1	PMID[528573]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	118.4	ug.mL-1	PMID[528573]
NPT25209	PROTEIN-PROTEIN INTERACTION	Transforming growth factor beta-1 proprotein/Mothers against decapentaplegic homolog 3	Mus musculus	Inhibition	=	77.72	%	PMID[528574]

☑ 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 NPC56369 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	258
0.1-0.2	1877
0.2-0.3	5984
0.3-0.4	10564
0.4-0.5	10943
0.5-0.6	7202
0.6-0.7	4824
0.7-0.8	966
0.8-0.85	46
0.85-0.9	26
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC474921
0.9462	High Similarity	NPC475958
0.9231	High Similarity	NPC66581
0.914	High Similarity	NPC136781
0.913	High Similarity	NPC90014
0.9111	High Similarity	NPC475776
0.9032	High Similarity	NPC93245
0.9032	High Similarity	NPC473964
0.8936	High Similarity	NPC473963
0.8817	High Similarity	NPC474841
0.8817	High Similarity	NPC473434
0.8817	High Similarity	NPC225474
0.8817	High Similarity	NPC148000
0.8817	High Similarity	NPC471446
0.8817	High Similarity	NPC469596
0.8778	High Similarity	NPC175293
0.8723	High Similarity	NPC259042
0.8723	High Similarity	NPC157686
0.8646	High Similarity	NPC476807
0.8646	High Similarity	NPC476806
0.8636	High Similarity	NPC226988
0.8617	High Similarity	NPC24861
0.8587	High Similarity	NPC116620
0.8586	High Similarity	NPC283850
0.8529	High Similarity	NPC253906
0.8511	High Similarity	NPC147272
0.8485	Intermediate Similarity	NPC61442
0.8462	Intermediate Similarity	NPC9231
0.8438	Intermediate Similarity	NPC165528
0.8438	Intermediate Similarity	NPC228766
0.8416	Intermediate Similarity	NPC180744
0.84	Intermediate Similarity	NPC477127
0.837	Intermediate Similarity	NPC305029
0.8367	Intermediate Similarity	NPC47024
0.8333	Intermediate Similarity	NPC194637
0.83	Intermediate Similarity	NPC72842
0.83	Intermediate Similarity	NPC99510
0.8265	Intermediate Similarity	NPC216478
0.8261	Intermediate Similarity	NPC85698
0.8252	Intermediate Similarity	NPC469370
0.8247	Intermediate Similarity	NPC284518
0.8242	Intermediate Similarity	NPC219011
0.8242	Intermediate Similarity	NPC470011
0.8235	Intermediate Similarity	NPC78966
0.8235	Intermediate Similarity	NPC284732
0.82	Intermediate Similarity	NPC164551
0.8191	Intermediate Similarity	NPC194642
0.8172	Intermediate Similarity	NPC181103
0.8155	Intermediate Similarity	NPC37628
0.8131	Intermediate Similarity	NPC477509
0.8119	Intermediate Similarity	NPC254202
0.8111	Intermediate Similarity	NPC38642
0.8105	Intermediate Similarity	NPC152467
0.81	Intermediate Similarity	NPC242666
0.8095	Intermediate Similarity	NPC469656
0.8095	Intermediate Similarity	NPC474846
0.8095	Intermediate Similarity	NPC469655
0.8077	Intermediate Similarity	NPC474243
0.8068	Intermediate Similarity	NPC143250
0.8065	Intermediate Similarity	NPC477920
0.8043	Intermediate Similarity	NPC97505
0.8021	Intermediate Similarity	NPC49420
0.8021	Intermediate Similarity	NPC165180
0.802	Intermediate Similarity	NPC162973
0.8019	Intermediate Similarity	NPC222834
0.7979	Intermediate Similarity	NPC470012
0.7959	Intermediate Similarity	NPC217329
0.7955	Intermediate Similarity	NPC92489
0.7944	Intermediate Similarity	NPC477126
0.7921	Intermediate Similarity	NPC111292
0.7921	Intermediate Similarity	NPC308824
0.7917	Intermediate Similarity	NPC153853
0.7912	Intermediate Similarity	NPC475951
0.79	Intermediate Similarity	NPC98837
0.79	Intermediate Similarity	NPC162459
0.79	Intermediate Similarity	NPC89099
0.79	Intermediate Similarity	NPC72647
0.79	Intermediate Similarity	NPC28864
0.79	Intermediate Similarity	NPC20479
0.79	Intermediate Similarity	NPC38471
0.79	Intermediate Similarity	NPC107806
0.79	Intermediate Similarity	NPC38296
0.7885	Intermediate Similarity	NPC110496
0.7879	Intermediate Similarity	NPC475380
0.7879	Intermediate Similarity	NPC209297
0.7872	Intermediate Similarity	NPC185638
0.7857	Intermediate Similarity	NPC476722
0.7857	Intermediate Similarity	NPC250075
0.785	Intermediate Similarity	NPC476964
0.7849	Intermediate Similarity	NPC470238
0.7849	Intermediate Similarity	NPC138647
0.7843	Intermediate Similarity	NPC170615
0.7843	Intermediate Similarity	NPC476081
0.7835	Intermediate Similarity	NPC476934
0.7835	Intermediate Similarity	NPC186363
0.7835	Intermediate Similarity	NPC233345
0.7822	Intermediate Similarity	NPC293866
0.7822	Intermediate Similarity	NPC471413
0.7812	Intermediate Similarity	NPC73995
0.781	Intermediate Similarity	NPC275539
0.781	Intermediate Similarity	NPC189075
0.78	Intermediate Similarity	NPC10864
0.78	Intermediate Similarity	NPC111348
0.78	Intermediate Similarity	NPC475446
0.78	Intermediate Similarity	NPC474395
0.78	Intermediate Similarity	NPC100912
0.78	Intermediate Similarity	NPC311241
0.7798	Intermediate Similarity	NPC270478
0.7767	Intermediate Similarity	NPC87927
0.7767	Intermediate Similarity	NPC156681
0.7766	Intermediate Similarity	NPC110405
0.7745	Intermediate Similarity	NPC46848
0.7745	Intermediate Similarity	NPC471412
0.7742	Intermediate Similarity	NPC272814
0.7736	Intermediate Similarity	NPC112457
0.7736	Intermediate Similarity	NPC154906
0.7732	Intermediate Similarity	NPC158488
0.7727	Intermediate Similarity	NPC58662
0.7727	Intermediate Similarity	NPC469684
0.7727	Intermediate Similarity	NPC13713
0.7717	Intermediate Similarity	NPC223330
0.7717	Intermediate Similarity	NPC47635
0.7717	Intermediate Similarity	NPC209318
0.7708	Intermediate Similarity	NPC277771
0.7708	Intermediate Similarity	NPC215831
0.7708	Intermediate Similarity	NPC50847
0.77	Intermediate Similarity	NPC29410
0.77	Intermediate Similarity	NPC29952
0.77	Intermediate Similarity	NPC200054
0.77	Intermediate Similarity	NPC256227
0.77	Intermediate Similarity	NPC307164
0.7685	Intermediate Similarity	NPC269530
0.7684	Intermediate Similarity	NPC470242
0.7679	Intermediate Similarity	NPC4548
0.7679	Intermediate Similarity	NPC143755
0.7677	Intermediate Similarity	NPC100257
0.7677	Intermediate Similarity	NPC224410
0.7677	Intermediate Similarity	NPC140277
0.767	Intermediate Similarity	NPC275990
0.767	Intermediate Similarity	NPC88203
0.767	Intermediate Similarity	NPC246736
0.767	Intermediate Similarity	NPC304832
0.767	Intermediate Similarity	NPC76866
0.767	Intermediate Similarity	NPC148628
0.767	Intermediate Similarity	NPC286519
0.767	Intermediate Similarity	NPC214946
0.7653	Intermediate Similarity	NPC470230
0.7647	Intermediate Similarity	NPC469551
0.7647	Intermediate Similarity	NPC470761
0.7647	Intermediate Similarity	NPC473219
0.7642	Intermediate Similarity	NPC112895
0.7642	Intermediate Similarity	NPC218123
0.7642	Intermediate Similarity	NPC231278
0.7634	Intermediate Similarity	NPC178676
0.7624	Intermediate Similarity	NPC38530
0.7624	Intermediate Similarity	NPC469810
0.7624	Intermediate Similarity	NPC96839
0.7624	Intermediate Similarity	NPC190080
0.7624	Intermediate Similarity	NPC84335
0.7624	Intermediate Similarity	NPC111187
0.7619	Intermediate Similarity	NPC295366
0.7619	Intermediate Similarity	NPC28791
0.7619	Intermediate Similarity	NPC469607
0.7615	Intermediate Similarity	NPC470120
0.7615	Intermediate Similarity	NPC25909
0.7615	Intermediate Similarity	NPC33360
0.7611	Intermediate Similarity	NPC310511
0.7609	Intermediate Similarity	NPC134227
0.7609	Intermediate Similarity	NPC125366
0.7604	Intermediate Similarity	NPC270270
0.7604	Intermediate Similarity	NPC5130
0.76	Intermediate Similarity	NPC316215
0.76	Intermediate Similarity	NPC98639
0.7596	Intermediate Similarity	NPC120321
0.7593	Intermediate Similarity	NPC470467
0.7593	Intermediate Similarity	NPC94650
0.7589	Intermediate Similarity	NPC472667
0.7589	Intermediate Similarity	NPC475520
0.7576	Intermediate Similarity	NPC475657
0.7573	Intermediate Similarity	NPC253886
0.7573	Intermediate Similarity	NPC98225
0.7573	Intermediate Similarity	NPC289148
0.7573	Intermediate Similarity	NPC52899
0.7573	Intermediate Similarity	NPC163963
0.7573	Intermediate Similarity	NPC121218
0.757	Intermediate Similarity	NPC475191
0.7568	Intermediate Similarity	NPC53396
0.7568	Intermediate Similarity	NPC98249
0.7553	Intermediate Similarity	NPC243347
0.7549	Intermediate Similarity	NPC471038
0.7549	Intermediate Similarity	NPC469986
0.7549	Intermediate Similarity	NPC264378
0.7549	Intermediate Similarity	NPC252295
0.7549	Intermediate Similarity	NPC474793
0.7549	Intermediate Similarity	NPC473155
0.7549	Intermediate Similarity	NPC23364
0.7547	Intermediate Similarity	NPC302788
0.7547	Intermediate Similarity	NPC187435
0.7547	Intermediate Similarity	NPC67321
0.7547	Intermediate Similarity	NPC475510

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 NPC56369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2253
0.2-0.3	3970
0.3-0.4	1773
0.4-0.5	527
0.5-0.6	225
0.6-0.7	153
0.7-0.8	8
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
0.7788	Intermediate Similarity	NPD6008	Approved
0.7714	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1695	Approved
0.7216	Intermediate Similarity	NPD1694	Approved
0.6907	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3573	Approved
0.6887	Remote Similarity	NPD7638	Approved
0.6887	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD7640	Approved
0.6822	Remote Similarity	NPD7639	Approved
0.681	Remote Similarity	NPD7115	Discovery
0.6796	Remote Similarity	NPD8034	Phase 2
0.6796	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6372	Approved
0.6637	Remote Similarity	NPD6013	Approved
0.6637	Remote Similarity	NPD6014	Approved
0.6637	Remote Similarity	NPD6373	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD1700	Approved
0.6606	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6921	Approved
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD4632	Approved
0.6552	Remote Similarity	NPD8133	Approved
0.6549	Remote Similarity	NPD6011	Approved
0.6549	Remote Similarity	NPD7320	Approved
0.6549	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6001	Approved
0.6504	Remote Similarity	NPD7507	Approved
0.65	Remote Similarity	NPD6319	Approved
0.6481	Remote Similarity	NPD7902	Approved
0.648	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD7146	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	NPD6409	Approved
0.6466	Remote Similarity	NPD8297	Approved
0.6466	Remote Similarity	NPD6882	Approved
0.6423	Remote Similarity	NPD7492	Approved
0.6396	Remote Similarity	NPD7632	Discontinued
0.6396	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD6009	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD5286	Approved
0.6364	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD5285	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6355	Remote Similarity	NPD7748	Approved
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6903	Approved
0.6341	Remote Similarity	NPD7604	Phase 2
0.633	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6321	Remote Similarity	NPD6079	Approved
0.6321	Remote Similarity	NPD5693	Phase 1
0.632	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD5983	Phase 2
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD3618	Phase 1
0.6303	Remote Similarity	NPD6274	Approved
0.6286	Remote Similarity	NPD5328	Approved
0.6283	Remote Similarity	NPD5141	Approved
0.627	Remote Similarity	NPD7736	Approved
0.626	Remote Similarity	NPD5988	Approved
0.626	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5225	Approved
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6059	Approved
0.6226	Remote Similarity	NPD6698	Approved
0.6226	Remote Similarity	NPD46	Approved
0.6216	Remote Similarity	NPD4700	Approved
0.6198	Remote Similarity	NPD7328	Approved
0.6198	Remote Similarity	NPD7327	Approved
0.6195	Remote Similarity	NPD5174	Approved
0.6195	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD6672	Approved
0.619	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD5737	Approved
0.6179	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7515	Phase 2
0.6161	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD7516	Approved
0.6126	Remote Similarity	NPD5696	Approved
0.6116	Remote Similarity	NPD6317	Approved
0.6116	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6111	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD4202	Approved
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.608	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD3667	Approved
0.6075	Remote Similarity	NPD5207	Approved
0.6068	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6314	Approved
0.6066	Remote Similarity	NPD6335	Approved
0.6066	Remote Similarity	NPD6313	Approved
0.6055	Remote Similarity	NPD5282	Discontinued
0.6048	Remote Similarity	NPD8516	Approved
0.6048	Remote Similarity	NPD8517	Approved
0.6048	Remote Similarity	NPD8515	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.6038	Remote Similarity	NPD5208	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.6034	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3703	Phase 2
0.6019	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6115	Approved
0.6	Remote Similarity	NPD6114	Approved
0.6	Remote Similarity	NPD6118	Approved
0.6	Remote Similarity	NPD6697	Approved
0.5983	Remote Similarity	NPD5128	Approved
0.5983	Remote Similarity	NPD4730	Approved
0.5983	Remote Similarity	NPD4729	Approved
0.5981	Remote Similarity	NPD6051	Approved
0.5981	Remote Similarity	NPD6080	Approved
0.5981	Remote Similarity	NPD6904	Approved
0.5981	Remote Similarity	NPD6673	Approved
0.598	Remote Similarity	NPD1779	Approved
0.598	Remote Similarity	NPD1780	Approved
0.5962	Remote Similarity	NPD4786	Approved
0.5962	Remote Similarity	NPD3668	Phase 3
0.5948	Remote Similarity	NPD4768	Approved
0.5948	Remote Similarity	NPD4767	Approved
0.592	Remote Similarity	NPD8335	Approved
0.592	Remote Similarity	NPD8033	Approved
0.592	Remote Similarity	NPD8378	Approved
0.592	Remote Similarity	NPD8379	Approved
0.592	Remote Similarity	NPD6909	Approved
0.592	Remote Similarity	NPD8296	Approved
0.592	Remote Similarity	NPD6908	Approved
0.592	Remote Similarity	NPD8380	Approved
0.5913	Remote Similarity	NPD4754	Approved
0.5902	Remote Similarity	NPD6868	Approved
0.59	Remote Similarity	NPD6116	Phase 1
0.5897	Remote Similarity	NPD6412	Phase 2
0.5882	Remote Similarity	NPD5248	Approved
0.5882	Remote Similarity	NPD5250	Approved
0.5882	Remote Similarity	NPD5249	Phase 3
0.5882	Remote Similarity	NPD5247	Approved
0.5882	Remote Similarity	NPD5251	Approved
0.5878	Remote Similarity	NPD7260	Phase 2
0.5876	Remote Similarity	NPD5777	Approved
0.5872	Remote Similarity	NPD7637	Suspended
0.5859	Remote Similarity	NPD3702	Approved
0.5849	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8294	Approved
0.584	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.5833	Remote Similarity	NPD5215	Approved
0.5833	Remote Similarity	NPD5217	Approved
0.5833	Remote Similarity	NPD5216	Approved
0.5833	Remote Similarity	NPD6845	Suspended
0.5814	Remote Similarity	NPD8074	Phase 3

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