NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	0.943
LogD:	1.35
LogS:	-2.033
# 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:	0.392
Synthetic Accessibility Score:	4.793
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:	-4.723
MDCK Permeability:	5.1095717935822904e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.208
30% Bioavailability (F30%):	0.154

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.452
Plasma Protein Binding (PPB):	43.194068908691406%
Volume Distribution (VD):	1.049
Pgp-substrate:	68.58888244628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	11.339
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.233
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.383
Carcinogencity:	0.905
Eye Corrosion:	0.205
Eye Irritation:	0.078
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC225474

Natural Product ID:	NPC225474
*Common Name:**	Elegalactone A
IUPAC Name:	(3aS,4R,4aS,8S,8aS,9aS)-4,8-dihydroxy-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	XUTVRCGEUDNRBV-JSXSYOHWSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-7-4-5-10(16)15(3)6-9-11(13(17)12(7)15)8(2)14(18)19-9/h9-13,16-17H,1-2,4-6H2,3H3/t9-,10-,11+,12+,13-,15+/m0/s1
SMILES:	O=C1O[C@@H]2[C@@H](C1=C)[C@H](O)[C@@H]1[C@@](C2)(C)[C@@H](O)CCC1=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510333
PubChem CID:	11108214
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
NPO26031	Acacia auriculiformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(80)80226-3]
NPO12306	Gonospermum canariense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880311]
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844964]
NPO8759	Anthemis melanolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112996]
NPO11310	Baorangia pseudocalopus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26268	Salvia aethiopis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26536	Garcinia humilis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26431	Aplophyllum sieversii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25745	Grindelia arenicola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12306	Gonospermum canariense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26454	Acacia oswaldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26136	Abuta racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26658	Commiphora dalzielii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26981	Thunbergia laurifolia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26783	Jurinea eriobasis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26379	Metrosideros umbellata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26031	Acacia auriculiformis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8746	Melaleuca triumphalis	Species	Myrtaceae	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
GI50	1
IC50	1
MIC	2

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	55100.0	nM	PMID[548494]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	76000.0	nM	PMID[548495]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	50.0	ug.mL-1	PMID[548495]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[548495]

☑ 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 NPC225474 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	199
0.1-0.2	1352
0.2-0.3	4602
0.3-0.4	7960
0.4-0.5	13248
0.5-0.6	5954
0.6-0.7	6735
0.7-0.8	2391
0.8-0.85	176
0.85-0.9	39
0.9-0.95	28
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469596
1.0	High Similarity	NPC148000
0.9886	High Similarity	NPC259042
0.9886	High Similarity	NPC157686
0.9775	High Similarity	NPC93245
0.9773	High Similarity	NPC24861
0.9667	High Similarity	NPC473963
0.9556	High Similarity	NPC473964
0.954	High Similarity	NPC116620
0.9457	High Similarity	NPC47024
0.9451	High Similarity	NPC136781
0.9432	High Similarity	NPC475776
0.9355	High Similarity	NPC475958
0.9348	High Similarity	NPC216478
0.9348	High Similarity	NPC476807
0.9348	High Similarity	NPC476806
0.9341	High Similarity	NPC165528
0.9341	High Similarity	NPC228766
0.9341	High Similarity	NPC284518
0.9318	High Similarity	NPC194642
0.931	High Similarity	NPC305029
0.9195	High Similarity	NPC85698
0.9158	High Similarity	NPC61442
0.9091	High Similarity	NPC175293
0.9091	High Similarity	NPC181103
0.9053	High Similarity	NPC164551
0.9022	High Similarity	NPC90014
0.9	High Similarity	NPC153853
0.8977	High Similarity	NPC9231
0.8977	High Similarity	NPC185638
0.8966	High Similarity	NPC97505
0.8958	High Similarity	NPC72842
0.8947	High Similarity	NPC242666
0.8947	High Similarity	NPC308824
0.8913	High Similarity	NPC473434
0.8913	High Similarity	NPC474841
0.8913	High Similarity	NPC471446
0.8878	High Similarity	NPC78966
0.8878	High Similarity	NPC284732
0.883	High Similarity	NPC474921
0.883	High Similarity	NPC474395
0.8817	High Similarity	NPC56369
0.8804	High Similarity	NPC147272
0.8788	High Similarity	NPC37628
0.8764	High Similarity	NPC477920
0.8763	High Similarity	NPC99510
0.8763	High Similarity	NPC156681
0.875	High Similarity	NPC111292
0.8736	High Similarity	NPC226988
0.87	High Similarity	NPC474243
0.8696	High Similarity	NPC186363
0.8696	High Similarity	NPC233345
0.8673	High Similarity	NPC283850
0.8667	High Similarity	NPC470012
0.866	High Similarity	NPC476081
0.8621	High Similarity	NPC223330
0.8621	High Similarity	NPC209318
0.8587	High Similarity	NPC158488
0.8571	High Similarity	NPC277771
0.8542	High Similarity	NPC98837
0.8542	High Similarity	NPC89099
0.8542	High Similarity	NPC38296
0.8542	High Similarity	NPC20479
0.8542	High Similarity	NPC162459
0.8542	High Similarity	NPC38471
0.8542	High Similarity	NPC28864
0.8469	Intermediate Similarity	NPC170615
0.8454	Intermediate Similarity	NPC293866
0.8438	Intermediate Similarity	NPC70145
0.8438	Intermediate Similarity	NPC10864
0.8438	Intermediate Similarity	NPC91695
0.8421	Intermediate Similarity	NPC183012
0.8416	Intermediate Similarity	NPC275539
0.8416	Intermediate Similarity	NPC189075
0.8404	Intermediate Similarity	NPC199543
0.8384	Intermediate Similarity	NPC120321
0.8367	Intermediate Similarity	NPC46848
0.8351	Intermediate Similarity	NPC78427
0.8351	Intermediate Similarity	NPC473155
0.8351	Intermediate Similarity	NPC16911
0.8333	Intermediate Similarity	NPC29410
0.8333	Intermediate Similarity	NPC134072
0.8333	Intermediate Similarity	NPC470011
0.8333	Intermediate Similarity	NPC256227
0.8333	Intermediate Similarity	NPC234993
0.8333	Intermediate Similarity	NPC200054
0.8317	Intermediate Similarity	NPC110496
0.8317	Intermediate Similarity	NPC67321
0.8317	Intermediate Similarity	NPC187435
0.8316	Intermediate Similarity	NPC250075
0.8316	Intermediate Similarity	NPC57117
0.8316	Intermediate Similarity	NPC66581
0.83	Intermediate Similarity	NPC477127
0.8298	Intermediate Similarity	NPC72845
0.8283	Intermediate Similarity	NPC76866
0.8283	Intermediate Similarity	NPC273005
0.8283	Intermediate Similarity	NPC286519
0.8283	Intermediate Similarity	NPC88203
0.8283	Intermediate Similarity	NPC246736
0.8283	Intermediate Similarity	NPC165250
0.8283	Intermediate Similarity	NPC469606
0.8283	Intermediate Similarity	NPC31058
0.8283	Intermediate Similarity	NPC304832
0.8283	Intermediate Similarity	NPC275990
0.8283	Intermediate Similarity	NPC214946
0.8283	Intermediate Similarity	NPC58329
0.8283	Intermediate Similarity	NPC148628
0.8265	Intermediate Similarity	NPC287676
0.8247	Intermediate Similarity	NPC111348
0.8229	Intermediate Similarity	NPC98639
0.8222	Intermediate Similarity	NPC243347
0.8222	Intermediate Similarity	NPC194637
0.8218	Intermediate Similarity	NPC469607
0.8218	Intermediate Similarity	NPC295366
0.8218	Intermediate Similarity	NPC28791
0.8218	Intermediate Similarity	NPC34768
0.8211	Intermediate Similarity	NPC139692
0.8202	Intermediate Similarity	NPC38642
0.8202	Intermediate Similarity	NPC475743
0.82	Intermediate Similarity	NPC87927
0.82	Intermediate Similarity	NPC221421
0.819	Intermediate Similarity	NPC477126
0.8182	Intermediate Similarity	NPC289148
0.8182	Intermediate Similarity	NPC52899
0.8182	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC163963
0.8182	Intermediate Similarity	NPC121218
0.8182	Intermediate Similarity	NPC253886
0.8173	Intermediate Similarity	NPC469655
0.8173	Intermediate Similarity	NPC469656
0.8173	Intermediate Similarity	NPC474846
0.8172	Intermediate Similarity	NPC136879
0.8172	Intermediate Similarity	NPC477302
0.8163	Intermediate Similarity	NPC471038
0.8163	Intermediate Similarity	NPC23364
0.8163	Intermediate Similarity	NPC474793
0.8152	Intermediate Similarity	NPC250981
0.8152	Intermediate Similarity	NPC6979
0.8144	Intermediate Similarity	NPC202833
0.8137	Intermediate Similarity	NPC302788
0.8137	Intermediate Similarity	NPC251824
0.8137	Intermediate Similarity	NPC86852
0.8137	Intermediate Similarity	NPC143609
0.8132	Intermediate Similarity	NPC219011
0.8125	Intermediate Similarity	NPC3359
0.8125	Intermediate Similarity	NPC47853
0.8119	Intermediate Similarity	NPC296950
0.8119	Intermediate Similarity	NPC84928
0.8119	Intermediate Similarity	NPC301787
0.8105	Intermediate Similarity	NPC130840
0.8105	Intermediate Similarity	NPC198054
0.81	Intermediate Similarity	NPC162973
0.8095	Intermediate Similarity	NPC194951
0.8095	Intermediate Similarity	NPC12046
0.8085	Intermediate Similarity	NPC77001
0.8085	Intermediate Similarity	NPC206001
0.8085	Intermediate Similarity	NPC253618
0.8085	Intermediate Similarity	NPC218927
0.8085	Intermediate Similarity	NPC155935
0.8081	Intermediate Similarity	NPC471413
0.8081	Intermediate Similarity	NPC477656
0.8081	Intermediate Similarity	NPC293890
0.8081	Intermediate Similarity	NPC267921
0.8081	Intermediate Similarity	NPC477655
0.8081	Intermediate Similarity	NPC476303
0.8077	Intermediate Similarity	NPC478209
0.8077	Intermediate Similarity	NPC124053
0.8061	Intermediate Similarity	NPC474343
0.8061	Intermediate Similarity	NPC253586
0.8058	Intermediate Similarity	NPC218123
0.8058	Intermediate Similarity	NPC255082
0.8058	Intermediate Similarity	NPC306265
0.8058	Intermediate Similarity	NPC112895
0.8058	Intermediate Similarity	NPC273155
0.8058	Intermediate Similarity	NPC231278
0.8046	Intermediate Similarity	NPC92489
0.8041	Intermediate Similarity	NPC210214
0.8041	Intermediate Similarity	NPC276110
0.8041	Intermediate Similarity	NPC470232
0.8039	Intermediate Similarity	NPC37600
0.8039	Intermediate Similarity	NPC478208
0.8039	Intermediate Similarity	NPC222833
0.8039	Intermediate Similarity	NPC138908
0.8039	Intermediate Similarity	NPC111952
0.8039	Intermediate Similarity	NPC200957
0.8022	Intermediate Similarity	NPC15091
0.8021	Intermediate Similarity	NPC294263
0.802	Intermediate Similarity	NPC216114
0.802	Intermediate Similarity	NPC96217
0.802	Intermediate Similarity	NPC36688
0.802	Intermediate Similarity	NPC159533
0.802	Intermediate Similarity	NPC139347
0.802	Intermediate Similarity	NPC254202
0.802	Intermediate Similarity	NPC476237
0.8019	Intermediate Similarity	NPC157441
0.8019	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC236585
0.8	Intermediate Similarity	NPC475951
0.8	Intermediate Similarity	NPC148279
0.8	Intermediate Similarity	NPC94650

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 NPC225474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1741
0.2-0.3	3775
0.3-0.4	2237
0.4-0.5	709
0.5-0.6	251
0.6-0.7	200
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
0.78	Intermediate Similarity	NPD7638	Approved
0.78	Intermediate Similarity	NPD4225	Approved
0.7723	Intermediate Similarity	NPD7639	Approved
0.7723	Intermediate Similarity	NPD7640	Approved
0.7642	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD8034	Phase 2
0.7547	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6686	Approved
0.73	Intermediate Similarity	NPD6399	Phase 3
0.7292	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1694	Approved
0.729	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7632	Discontinued
0.7207	Intermediate Similarity	NPD8133	Approved
0.7196	Intermediate Similarity	NPD6008	Approved
0.7184	Intermediate Similarity	NPD7902	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7158	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD6899	Approved
0.7064	Intermediate Similarity	NPD6881	Approved
0.7059	Intermediate Similarity	NPD7748	Approved
0.7041	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD5739	Approved
0.7037	Intermediate Similarity	NPD6402	Approved
0.7037	Intermediate Similarity	NPD7128	Approved
0.7037	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD7515	Phase 2
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6972	Remote Similarity	NPD5701	Approved
0.6937	Remote Similarity	NPD7290	Approved
0.6937	Remote Similarity	NPD6883	Approved
0.6937	Remote Similarity	NPD7102	Approved
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6909	Remote Similarity	NPD6011	Approved
0.6909	Remote Similarity	NPD7320	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6869	Approved
0.6875	Remote Similarity	NPD8130	Phase 1
0.6875	Remote Similarity	NPD6847	Approved
0.6875	Remote Similarity	NPD6617	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6319	Approved
0.6833	Remote Similarity	NPD7507	Approved
0.6832	Remote Similarity	NPD1695	Approved
0.6822	Remote Similarity	NPD5344	Discontinued
0.6814	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD6882	Approved
0.6809	Remote Similarity	NPD6116	Phase 1
0.6804	Remote Similarity	NPD3667	Approved
0.6803	Remote Similarity	NPD7319	Approved
0.678	Remote Similarity	NPD6921	Approved
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6759	Remote Similarity	NPD5211	Phase 2
0.675	Remote Similarity	NPD7492	Approved
0.6729	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD5285	Approved
0.6729	Remote Similarity	NPD5286	Approved
0.6724	Remote Similarity	NPD6009	Approved
0.6702	Remote Similarity	NPD6117	Approved
0.6699	Remote Similarity	NPD6079	Approved
0.6699	Remote Similarity	NPD7637	Suspended
0.6698	Remote Similarity	NPD6084	Phase 2
0.6698	Remote Similarity	NPD4755	Approved
0.6698	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6637	Remote Similarity	NPD6371	Approved
0.6636	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD4202	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.661	Remote Similarity	NPD7516	Approved
0.6606	Remote Similarity	NPD5225	Approved
0.6606	Remote Similarity	NPD5226	Approved
0.6606	Remote Similarity	NPD4633	Approved
0.6606	Remote Similarity	NPD5224	Approved
0.6604	Remote Similarity	NPD5221	Approved
0.6604	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5222	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.66	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7736	Approved
0.6583	Remote Similarity	NPD6370	Approved
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6648	Approved
0.6574	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD5282	Discontinued
0.6566	Remote Similarity	NPD4788	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6545	Remote Similarity	NPD5174	Approved
0.6545	Remote Similarity	NPD5175	Approved
0.6542	Remote Similarity	NPD5173	Approved
0.6538	Remote Similarity	NPD6411	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.6529	Remote Similarity	NPD8328	Phase 3
0.6529	Remote Similarity	NPD7604	Phase 2
0.6518	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5223	Approved
0.6509	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5695	Phase 3
0.6504	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD8296	Approved
0.65	Remote Similarity	NPD3133	Approved
0.65	Remote Similarity	NPD8380	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD8033	Approved
0.65	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD8335	Approved
0.65	Remote Similarity	NPD8378	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.6491	Remote Similarity	NPD4634	Approved
0.6489	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3573	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6442	Remote Similarity	NPD5785	Approved
0.6441	Remote Similarity	NPD6317	Approved
0.6423	Remote Similarity	NPD6336	Discontinued
0.6421	Remote Similarity	NPD3703	Phase 2
0.6417	Remote Similarity	NPD8294	Approved
0.6417	Remote Similarity	NPD8377	Approved
0.6408	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5737	Approved
0.6408	Remote Similarity	NPD6672	Approved
0.6408	Remote Similarity	NPD6903	Approved
0.64	Remote Similarity	NPD6695	Phase 3
0.6387	Remote Similarity	NPD6313	Approved
0.6387	Remote Similarity	NPD6314	Approved
0.6387	Remote Similarity	NPD6335	Approved
0.6381	Remote Similarity	NPD5693	Phase 1
0.6373	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8517	Approved
0.6364	Remote Similarity	NPD1700	Approved
0.6364	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD8516	Approved
0.6364	Remote Similarity	NPD7503	Approved
0.6364	Remote Similarity	NPD8515	Approved
0.6356	Remote Similarity	NPD6868	Approved
0.6355	Remote Similarity	NPD5210	Approved
0.6355	Remote Similarity	NPD4629	Approved
0.6346	Remote Similarity	NPD6101	Approved
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4753	Phase 2
0.6337	Remote Similarity	NPD3668	Phase 3
0.6316	Remote Similarity	NPD4729	Approved
0.6316	Remote Similarity	NPD5128	Approved
0.6316	Remote Similarity	NPD4730	Approved
0.6293	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7838	Discovery
0.6283	Remote Similarity	NPD4768	Approved
0.6283	Remote Similarity	NPD4767	Approved
0.6263	Remote Similarity	NPD4695	Discontinued
0.6263	Remote Similarity	NPD7525	Registered
0.6262	Remote Similarity	NPD6001	Approved
0.626	Remote Similarity	NPD6067	Discontinued
0.625	Remote Similarity	NPD4754	Approved
0.6237	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6908	Approved
0.623	Remote Similarity	NPD6909	Approved
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD4249	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