NPASS Compound

Structure

NPC472015 OpenBabel07101718332D 29 31 0 0 1 0 0 0 0 0999 V2000 5.5916 1.7999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7093 -2.0283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9088 1.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9339 1.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9339 -0.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5252 -0.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6906 1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2602 -1.1937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6906 0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9088 -0.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2592 -1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8827 -1.9307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 12 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 22 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 10 1 6 0 0 0 13 7 1 6 0 0 0 13 14 1 0 0 0 0 15 23 2 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.19
Volume:	405.879
LogP:	0.91
LogD:	0.494
LogS:	-2.322
# Rotatable Bonds:	5
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	4.842
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.291
MDCK Permeability:	6.976934673730284e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.925
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	85.99942779541016%
Volume Distribution (VD):	0.93
Pgp-substrate:	6.980922698974609%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.299
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	3.347
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.167
Skin Sensitization:	0.657
Carcinogencity:	0.459
Eye Corrosion:	0.005
Eye Irritation:	0.04
Respiratory Toxicity:	0.444

Download Data

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

Natural Product: NPC472015

Natural Product ID:	NPC472015
*Common Name:**	WGTPPFZNEIDERF-DLYIZJFUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WGTPPFZNEIDERF-DLYIZJFUSA-N
Standard InCHI:	InChI=1S/C21H30O8/c1-9-4-5-12(6-14-11(3)15(23)7-13(9)14)10(2)20(27)29-21-19(26)18(25)17(24)16(8-22)28-21/h9,12-13,16-19,21-22,24-26H,2,4-8H2,1,3H3/t9-,12+,13-,16+,17+,18-,19+,21-/m0/s1
SMILES:	CC1CCC(CC2=C(C(=O)CC12)C)C(=C)C(=O)OC3C(C(C(C(O3)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3325483
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4600.0	nM	PMID[531184]

☑ 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 NPC472015 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	207
0.1-0.2	1309
0.2-0.3	5076
0.3-0.4	9807
0.4-0.5	12852
0.5-0.6	7695
0.6-0.7	5090
0.7-0.8	634
0.8-0.85	24
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.866	High Similarity	NPC476613
0.866	High Similarity	NPC476612
0.8571	High Similarity	NPC49833
0.8571	High Similarity	NPC249171
0.8485	Intermediate Similarity	NPC473146
0.8469	Intermediate Similarity	NPC304445
0.8469	Intermediate Similarity	NPC236580
0.8416	Intermediate Similarity	NPC473148
0.84	Intermediate Similarity	NPC476611
0.8367	Intermediate Similarity	NPC54731
0.8367	Intermediate Similarity	NPC306041
0.8317	Intermediate Similarity	NPC80144
0.8317	Intermediate Similarity	NPC106668
0.8283	Intermediate Similarity	NPC472290
0.8269	Intermediate Similarity	NPC177524
0.8269	Intermediate Similarity	NPC219900
0.8269	Intermediate Similarity	NPC392
0.8247	Intermediate Similarity	NPC472195
0.8247	Intermediate Similarity	NPC472196
0.8247	Intermediate Similarity	NPC238090
0.8247	Intermediate Similarity	NPC320089
0.8235	Intermediate Similarity	NPC27687
0.8218	Intermediate Similarity	NPC67296
0.8182	Intermediate Similarity	NPC474297
0.8163	Intermediate Similarity	NPC159698
0.8137	Intermediate Similarity	NPC177013
0.8137	Intermediate Similarity	NPC4899
0.8137	Intermediate Similarity	NPC474730
0.8137	Intermediate Similarity	NPC35185
0.8119	Intermediate Similarity	NPC306344
0.8119	Intermediate Similarity	NPC22149
0.8119	Intermediate Similarity	NPC255677
0.8091	Intermediate Similarity	NPC475309
0.8081	Intermediate Similarity	NPC167893
0.8058	Intermediate Similarity	NPC37240
0.8058	Intermediate Similarity	NPC475928
0.8039	Intermediate Similarity	NPC28304
0.8039	Intermediate Similarity	NPC298255
0.8	Intermediate Similarity	NPC143446
0.7981	Intermediate Similarity	NPC474917
0.7961	Intermediate Similarity	NPC261117
0.7961	Intermediate Similarity	NPC222062
0.7961	Intermediate Similarity	NPC310804
0.7961	Intermediate Similarity	NPC86077
0.7961	Intermediate Similarity	NPC225353
0.7959	Intermediate Similarity	NPC472197
0.7959	Intermediate Similarity	NPC477749
0.7941	Intermediate Similarity	NPC130792
0.7928	Intermediate Similarity	NPC13710
0.7925	Intermediate Similarity	NPC475960
0.7921	Intermediate Similarity	NPC278506
0.7921	Intermediate Similarity	NPC261372
0.7921	Intermediate Similarity	NPC58267
0.7921	Intermediate Similarity	NPC263674
0.7905	Intermediate Similarity	NPC170432
0.79	Intermediate Similarity	NPC108141
0.7885	Intermediate Similarity	NPC110989
0.7885	Intermediate Similarity	NPC267869
0.7885	Intermediate Similarity	NPC197541
0.7885	Intermediate Similarity	NPC284929
0.7885	Intermediate Similarity	NPC234304
0.7885	Intermediate Similarity	NPC118761
0.7879	Intermediate Similarity	NPC61201
0.7864	Intermediate Similarity	NPC287539
0.7864	Intermediate Similarity	NPC198992
0.7864	Intermediate Similarity	NPC3488
0.7857	Intermediate Similarity	NPC202886
0.7843	Intermediate Similarity	NPC56071
0.7843	Intermediate Similarity	NPC70733
0.783	Intermediate Similarity	NPC148270
0.783	Intermediate Similarity	NPC80338
0.783	Intermediate Similarity	NPC197813
0.7822	Intermediate Similarity	NPC161293
0.7822	Intermediate Similarity	NPC241911
0.781	Intermediate Similarity	NPC203659
0.781	Intermediate Similarity	NPC86095
0.78	Intermediate Similarity	NPC63897
0.78	Intermediate Similarity	NPC477131
0.78	Intermediate Similarity	NPC2003
0.78	Intermediate Similarity	NPC71589
0.78	Intermediate Similarity	NPC25701
0.7789	Intermediate Similarity	NPC288471
0.7789	Intermediate Similarity	NPC266718
0.7788	Intermediate Similarity	NPC195510
0.7788	Intermediate Similarity	NPC471599
0.7788	Intermediate Similarity	NPC474747
0.7788	Intermediate Similarity	NPC121423
0.7788	Intermediate Similarity	NPC250545
0.7788	Intermediate Similarity	NPC13171
0.7778	Intermediate Similarity	NPC472199
0.7778	Intermediate Similarity	NPC131209
0.7778	Intermediate Similarity	NPC133698
0.7755	Intermediate Similarity	NPC477748
0.7745	Intermediate Similarity	NPC474182
0.7736	Intermediate Similarity	NPC85670
0.7736	Intermediate Similarity	NPC243998
0.7736	Intermediate Similarity	NPC223450
0.7723	Intermediate Similarity	NPC304886
0.7723	Intermediate Similarity	NPC471141
0.7719	Intermediate Similarity	NPC470829
0.7719	Intermediate Similarity	NPC473228
0.7714	Intermediate Similarity	NPC475871
0.7714	Intermediate Similarity	NPC151516
0.7714	Intermediate Similarity	NPC475945
0.77	Intermediate Similarity	NPC135776
0.7692	Intermediate Similarity	NPC473332
0.7692	Intermediate Similarity	NPC219038
0.7685	Intermediate Similarity	NPC273433
0.7679	Intermediate Similarity	NPC474483
0.7677	Intermediate Similarity	NPC473448
0.7677	Intermediate Similarity	NPC470573
0.7677	Intermediate Similarity	NPC270908
0.7677	Intermediate Similarity	NPC231710
0.7677	Intermediate Similarity	NPC303451
0.7677	Intermediate Similarity	NPC120021
0.7677	Intermediate Similarity	NPC216826
0.7677	Intermediate Similarity	NPC6414
0.7677	Intermediate Similarity	NPC65665
0.767	Intermediate Similarity	NPC198422
0.767	Intermediate Similarity	NPC187268
0.767	Intermediate Similarity	NPC40182
0.7664	Intermediate Similarity	NPC254538
0.7664	Intermediate Similarity	NPC26617
0.7664	Intermediate Similarity	NPC474285
0.766	Intermediate Similarity	NPC280367
0.7647	Intermediate Similarity	NPC476009
0.7642	Intermediate Similarity	NPC472748
0.7642	Intermediate Similarity	NPC100487
0.7642	Intermediate Similarity	NPC264584
0.7632	Intermediate Similarity	NPC470312
0.7624	Intermediate Similarity	NPC472198
0.7624	Intermediate Similarity	NPC256368
0.7624	Intermediate Similarity	NPC198853
0.7619	Intermediate Similarity	NPC313569
0.7619	Intermediate Similarity	NPC201191
0.7619	Intermediate Similarity	NPC223834
0.7615	Intermediate Similarity	NPC83005
0.7615	Intermediate Similarity	NPC193741
0.7611	Intermediate Similarity	NPC473617
0.7611	Intermediate Similarity	NPC473828
0.7607	Intermediate Similarity	NPC222307
0.7604	Intermediate Similarity	NPC475035
0.76	Intermediate Similarity	NPC184463
0.76	Intermediate Similarity	NPC9447
0.76	Intermediate Similarity	NPC235051
0.76	Intermediate Similarity	NPC470373
0.76	Intermediate Similarity	NPC470379
0.7596	Intermediate Similarity	NPC244878
0.7593	Intermediate Similarity	NPC110701
0.7573	Intermediate Similarity	NPC266842
0.7573	Intermediate Similarity	NPC40812
0.757	Intermediate Similarity	NPC472749
0.757	Intermediate Similarity	NPC41681
0.757	Intermediate Similarity	NPC472751
0.757	Intermediate Similarity	NPC127235
0.757	Intermediate Similarity	NPC239961
0.757	Intermediate Similarity	NPC82251
0.7551	Intermediate Similarity	NPC475037
0.7551	Intermediate Similarity	NPC248602
0.7549	Intermediate Similarity	NPC36954
0.7549	Intermediate Similarity	NPC93869
0.7549	Intermediate Similarity	NPC6765
0.7547	Intermediate Similarity	NPC472747
0.7547	Intermediate Similarity	NPC472750
0.7526	Intermediate Similarity	NPC477746
0.7526	Intermediate Similarity	NPC477747
0.7525	Intermediate Similarity	NPC273579
0.7525	Intermediate Similarity	NPC475912
0.7525	Intermediate Similarity	NPC473723
0.7525	Intermediate Similarity	NPC473663
0.7525	Intermediate Similarity	NPC473520
0.7525	Intermediate Similarity	NPC475173
0.7525	Intermediate Similarity	NPC288240
0.7525	Intermediate Similarity	NPC473561
0.7525	Intermediate Similarity	NPC471483
0.7525	Intermediate Similarity	NPC212486
0.7525	Intermediate Similarity	NPC162205
0.7525	Intermediate Similarity	NPC295204
0.7525	Intermediate Similarity	NPC476300
0.7524	Intermediate Similarity	NPC154127
0.7524	Intermediate Similarity	NPC474742
0.7524	Intermediate Similarity	NPC150923
0.7524	Intermediate Similarity	NPC20673
0.7523	Intermediate Similarity	NPC477102
0.7523	Intermediate Similarity	NPC257853
0.7523	Intermediate Similarity	NPC118225
0.75	Intermediate Similarity	NPC81483
0.75	Intermediate Similarity	NPC169468
0.75	Intermediate Similarity	NPC473619
0.75	Intermediate Similarity	NPC307517
0.75	Intermediate Similarity	NPC473311
0.75	Intermediate Similarity	NPC203627
0.75	Intermediate Similarity	NPC117596
0.75	Intermediate Similarity	NPC61630
0.75	Intermediate Similarity	NPC37866
0.75	Intermediate Similarity	NPC206614
0.75	Intermediate Similarity	NPC474323
0.75	Intermediate Similarity	NPC151093
0.75	Intermediate Similarity	NPC165439
0.75	Intermediate Similarity	NPC222303

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 NPC472015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1840
0.2-0.3	3869
0.3-0.4	2151
0.4-0.5	706
0.5-0.6	313
0.6-0.7	82
0.7-0.8	6
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
0.8269	Intermediate Similarity	NPD6686	Approved
0.8041	Intermediate Similarity	NPD46	Approved
0.8041	Intermediate Similarity	NPD6698	Approved
0.7664	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7455	Intermediate Similarity	NPD6371	Approved
0.7333	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7507	Approved
0.7157	Intermediate Similarity	NPD7838	Discovery
0.708	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1695	Approved
0.7009	Intermediate Similarity	NPD7641	Discontinued
0.6992	Remote Similarity	NPD7319	Approved
0.6975	Remote Similarity	NPD8516	Approved
0.6975	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD8517	Approved
0.6975	Remote Similarity	NPD8515	Approved
0.6957	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD7983	Approved
0.6903	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7328	Approved
0.6864	Remote Similarity	NPD7327	Approved
0.686	Remote Similarity	NPD7830	Approved
0.686	Remote Similarity	NPD7829	Approved
0.686	Remote Similarity	NPD7642	Approved
0.6833	Remote Similarity	NPD7503	Approved
0.6807	Remote Similarity	NPD7516	Approved
0.675	Remote Similarity	NPD8294	Approved
0.675	Remote Similarity	NPD8377	Approved
0.6721	Remote Similarity	NPD8328	Phase 3
0.67	Remote Similarity	NPD6435	Approved
0.6694	Remote Similarity	NPD8444	Approved
0.6694	Remote Similarity	NPD8379	Approved
0.6694	Remote Similarity	NPD8380	Approved
0.6694	Remote Similarity	NPD8296	Approved
0.6694	Remote Similarity	NPD8335	Approved
0.6694	Remote Similarity	NPD8378	Approved
0.6694	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5785	Approved
0.6636	Remote Similarity	NPD5282	Discontinued
0.6634	Remote Similarity	NPD7154	Phase 3
0.6609	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6053	Discontinued
0.6577	Remote Similarity	NPD5344	Discontinued
0.6545	Remote Similarity	NPD4225	Approved
0.6545	Remote Similarity	NPD7638	Approved
0.6514	Remote Similarity	NPD7839	Suspended
0.6508	Remote Similarity	NPD7736	Approved
0.6505	Remote Similarity	NPD5363	Approved
0.6504	Remote Similarity	NPD6370	Approved
0.6504	Remote Similarity	NPD8080	Discontinued
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD5368	Approved
0.6486	Remote Similarity	NPD7640	Approved
0.6486	Remote Similarity	NPD7639	Approved
0.6475	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD4249	Approved
0.6441	Remote Similarity	NPD6882	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6429	Remote Similarity	NPD8074	Phase 3
0.641	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7492	Approved
0.6387	Remote Similarity	NPD4632	Approved
0.6381	Remote Similarity	NPD4250	Approved
0.6381	Remote Similarity	NPD4251	Approved
0.6378	Remote Similarity	NPD8337	Approved
0.6378	Remote Similarity	NPD8336	Approved
0.6373	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7115	Discovery
0.6349	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD8451	Approved
0.6346	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6054	Approved
0.6337	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8297	Approved
0.63	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7078	Approved
0.6299	Remote Similarity	NPD8448	Approved
0.629	Remote Similarity	NPD6016	Approved
0.629	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6015	Approved
0.6275	Remote Similarity	NPD5369	Approved
0.624	Remote Similarity	NPD5988	Approved
0.6239	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD5778	Approved
0.6214	Remote Similarity	NPD4270	Approved
0.6214	Remote Similarity	NPD4269	Approved
0.6214	Remote Similarity	NPD5209	Approved
0.621	Remote Similarity	NPD6059	Approved
0.6195	Remote Similarity	NPD6648	Approved
0.619	Remote Similarity	NPD1694	Approved
0.619	Remote Similarity	NPD6067	Discontinued
0.6183	Remote Similarity	NPD8338	Approved
0.6176	Remote Similarity	NPD4819	Approved
0.6176	Remote Similarity	NPD4821	Approved
0.6176	Remote Similarity	NPD4822	Approved
0.6176	Remote Similarity	NPD4820	Approved
0.6161	Remote Similarity	NPD6084	Phase 2
0.6161	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD8391	Approved
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6110	Phase 1
0.6154	Remote Similarity	NPD8390	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6154	Remote Similarity	NPD8392	Approved
0.6142	Remote Similarity	NPD8340	Approved
0.6142	Remote Similarity	NPD8342	Approved
0.6142	Remote Similarity	NPD8341	Approved
0.6142	Remote Similarity	NPD8299	Approved
0.6139	Remote Similarity	NPD4271	Approved
0.6139	Remote Similarity	NPD4268	Approved
0.6132	Remote Similarity	NPD5786	Approved
0.6126	Remote Similarity	NPD5695	Phase 3
0.6111	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6101	Approved
0.6107	Remote Similarity	NPD7260	Phase 2
0.6102	Remote Similarity	NPD6899	Approved
0.6102	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6881	Approved
0.6098	Remote Similarity	NPD7500	Approved
0.6094	Remote Similarity	NPD8273	Phase 1
0.6091	Remote Similarity	NPD6399	Phase 3
0.6087	Remote Similarity	NPD7632	Discontinued
0.6083	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6649	Approved
0.6083	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD5739	Approved
0.6068	Remote Similarity	NPD6675	Approved
0.6068	Remote Similarity	NPD6402	Approved
0.6068	Remote Similarity	NPD7128	Approved
0.605	Remote Similarity	NPD6373	Approved
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6372	Approved
0.605	Remote Similarity	NPD6013	Approved
0.6032	Remote Similarity	NPD8268	Approved
0.6032	Remote Similarity	NPD5983	Phase 2
0.6032	Remote Similarity	NPD8269	Approved
0.6032	Remote Similarity	NPD8266	Approved
0.6032	Remote Similarity	NPD8267	Approved
0.6019	Remote Similarity	NPD4252	Approved
0.6017	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6411	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5981	Remote Similarity	NPD5330	Approved
0.5981	Remote Similarity	NPD7521	Approved
0.5981	Remote Similarity	NPD6684	Approved
0.5981	Remote Similarity	NPD6409	Approved
0.5981	Remote Similarity	NPD7146	Approved
0.5981	Remote Similarity	NPD7334	Approved
0.5966	Remote Similarity	NPD7320	Approved
0.5966	Remote Similarity	NPD6011	Approved
0.5965	Remote Similarity	NPD5696	Approved
0.595	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD6869	Approved
0.595	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD6847	Approved
0.5943	Remote Similarity	NPD3133	Approved
0.5943	Remote Similarity	NPD3665	Phase 1
0.5943	Remote Similarity	NPD3666	Approved
0.594	Remote Similarity	NPD6845	Suspended
0.5938	Remote Similarity	NPD7604	Phase 2
0.5909	Remote Similarity	NPD5956	Approved
0.5893	Remote Similarity	NPD7748	Approved
0.5877	Remote Similarity	NPD7902	Approved
0.5872	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6903	Approved
0.5872	Remote Similarity	NPD6672	Approved
0.5872	Remote Similarity	NPD5737	Approved
0.5868	Remote Similarity	NPD4634	Approved
0.5868	Remote Similarity	NPD6421	Discontinued
0.5856	Remote Similarity	NPD7515	Phase 2
0.5856	Remote Similarity	NPD5693	Phase 1
0.5849	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3669	Approved
0.5849	Remote Similarity	NPD5331	Approved
0.5849	Remote Similarity	NPD5332	Approved
0.5847	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD3618	Phase 1
0.5825	Remote Similarity	NPD4802	Phase 2
0.5825	Remote Similarity	NPD4238	Approved
0.5818	Remote Similarity	NPD4753	Phase 2
0.5812	Remote Similarity	NPD5211	Phase 2
0.5812	Remote Similarity	NPD8086	Approved
0.5812	Remote Similarity	NPD8139	Approved
0.5812	Remote Similarity	NPD8085	Approved
0.5812	Remote Similarity	NPD8082	Approved
0.5812	Remote Similarity	NPD8084	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