NPASS Compound

Structure

NPC215988 OpenBabel07101718222D 22 24 0 0 1 0 0 0 0 0999 V2000 4.6990 0.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6386 -4.2061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5486 2.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3087 1.5533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2217 1.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7860 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2217 -1.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3957 1.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0853 -3.0776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7860 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7616 -4.5966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3087 -1.5533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3087 -2.5133 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3957 -1.2567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3957 -2.8100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9850 -4.0323 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6613 -5.5513 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0990 -3.7230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -2.0333 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 1 10 1 0 0 0 0 2 11 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 11 18 2 3 0 0 0 11 19 1 0 0 0 0 12 7 1 1 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 9 1 6 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 17 1 6 0 0 0 15 22 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 3 1 1 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.18
Volume:	315.167
LogP:	1.947
LogD:	2.038
LogS:	-3.117
# Rotatable Bonds:	3
TPSA:	67.93
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	4.714
Fsp3:	0.765
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:	-4.644
MDCK Permeability:	2.4558727091061883e-05
Pgp-inhibitor:	0.453
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.095
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.882
Plasma Protein Binding (PPB):	51.24909591674805%
Volume Distribution (VD):	0.893
Pgp-substrate:	57.425689697265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.606
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.142
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	5.425
Half-life (T1/2):	0.469

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.066
Skin Sensitization:	0.487
Carcinogencity:	0.24
Eye Corrosion:	0.005
Eye Irritation:	0.071
Respiratory Toxicity:	0.402

Download Data

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

Natural Product: NPC215988

Natural Product ID:	NPC215988
*Common Name:**	AETACSMBICRTEP-SYYWLGBQSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-N-Acetylparthenolidine
Standard InCHIKey:	AETACSMBICRTEP-SYYWLGBQSA-N
Standard InCHI:	InChI=1S/C17H25NO4/c1-10-5-4-8-17(3)15(22-17)14-12(7-6-10)13(16(20)21-14)9-18-11(2)19/h5,12-15H,4,6-9H2,1-3H3,(H,18,19)/b10-5+/t12-,13-,14-,15-,17+/m0/s1
SMILES:	C/C/1=CCC[C@]2(C)[C@H]([C@@H]3[C@@H](CC1)[C@H](CN=C(C)O)C(=O)O3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519906
PubChem CID:	n.a.
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:0001771] Germacranolides 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
NPO5710	Michelia rajaniana	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3236012]
NPO5710	Michelia rajaniana	Species	Magnoliaceae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[520186]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[520186]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[520186]

☑ 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 NPC215988 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	87
0.1-0.2	688
0.2-0.3	4818
0.3-0.4	19550
0.4-0.5	11019
0.5-0.6	5794
0.6-0.7	695
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9596	High Similarity	NPC70235
0.7895	Intermediate Similarity	NPC207188
0.7451	Intermediate Similarity	NPC151770
0.7264	Intermediate Similarity	NPC475659
0.7238	Intermediate Similarity	NPC212486
0.7228	Intermediate Similarity	NPC319795
0.7228	Intermediate Similarity	NPC38468
0.7228	Intermediate Similarity	NPC50362
0.7196	Intermediate Similarity	NPC473859
0.717	Intermediate Similarity	NPC473316
0.717	Intermediate Similarity	NPC57405
0.717	Intermediate Similarity	NPC473330
0.717	Intermediate Similarity	NPC303942
0.7156	Intermediate Similarity	NPC288876
0.7115	Intermediate Similarity	NPC166919
0.7103	Intermediate Similarity	NPC270013
0.7103	Intermediate Similarity	NPC14961
0.7087	Intermediate Similarity	NPC231889
0.7064	Intermediate Similarity	NPC473326
0.7048	Intermediate Similarity	NPC49342
0.7048	Intermediate Similarity	NPC251385
0.7048	Intermediate Similarity	NPC312042
0.7048	Intermediate Similarity	NPC475748
0.7037	Intermediate Similarity	NPC476315
0.7037	Intermediate Similarity	NPC279621
0.7009	Intermediate Similarity	NPC81386
0.7009	Intermediate Similarity	NPC476267
0.7009	Intermediate Similarity	NPC474035
0.7009	Intermediate Similarity	NPC471147
0.7	Intermediate Similarity	NPC473224
0.6991	Remote Similarity	NPC473252
0.699	Remote Similarity	NPC50637
0.6981	Remote Similarity	NPC184463
0.6975	Remote Similarity	NPC147707
0.6972	Remote Similarity	NPC476344
0.6957	Remote Similarity	NPC474725
0.6952	Remote Similarity	NPC474032
0.6952	Remote Similarity	NPC307411
0.6944	Remote Similarity	NPC107476
0.6944	Remote Similarity	NPC150041
0.6923	Remote Similarity	NPC5130
0.6916	Remote Similarity	NPC475838
0.6916	Remote Similarity	NPC475912
0.6916	Remote Similarity	NPC228451
0.6916	Remote Similarity	NPC125674
0.6916	Remote Similarity	NPC476300
0.6909	Remote Similarity	NPC279561
0.6909	Remote Similarity	NPC208233
0.6909	Remote Similarity	NPC234542
0.6907	Remote Similarity	NPC93213
0.6903	Remote Similarity	NPC14537
0.6899	Remote Similarity	NPC472428
0.6887	Remote Similarity	NPC51004
0.6885	Remote Similarity	NPC23963
0.6863	Remote Similarity	NPC272814
0.6857	Remote Similarity	NPC476704
0.6857	Remote Similarity	NPC202672
0.6857	Remote Similarity	NPC281516
0.6852	Remote Similarity	NPC474247
0.6852	Remote Similarity	NPC140543
0.6846	Remote Similarity	NPC472430
0.6822	Remote Similarity	NPC12172
0.6822	Remote Similarity	NPC30515
0.6822	Remote Similarity	NPC208886
0.6792	Remote Similarity	NPC39290
0.6792	Remote Similarity	NPC473564
0.6792	Remote Similarity	NPC159369
0.6789	Remote Similarity	NPC471141
0.6789	Remote Similarity	NPC36954
0.6786	Remote Similarity	NPC164598
0.6786	Remote Similarity	NPC474339
0.6786	Remote Similarity	NPC476270
0.6786	Remote Similarity	NPC477511
0.6786	Remote Similarity	NPC264477
0.6786	Remote Similarity	NPC47880
0.6783	Remote Similarity	NPC475800
0.6783	Remote Similarity	NPC477513
0.6783	Remote Similarity	NPC271562
0.6777	Remote Similarity	NPC156336
0.6777	Remote Similarity	NPC120599
0.6777	Remote Similarity	NPC200412
0.6774	Remote Similarity	NPC280498
0.6762	Remote Similarity	NPC475703
0.6759	Remote Similarity	NPC477615
0.6759	Remote Similarity	NPC81419
0.6759	Remote Similarity	NPC179746
0.6757	Remote Similarity	NPC474213
0.6754	Remote Similarity	NPC474741
0.6754	Remote Similarity	NPC119329
0.6733	Remote Similarity	NPC103634
0.6731	Remote Similarity	NPC149725
0.6731	Remote Similarity	NPC47958
0.6731	Remote Similarity	NPC304509
0.6729	Remote Similarity	NPC476004
0.6729	Remote Similarity	NPC473619
0.6729	Remote Similarity	NPC65359
0.6729	Remote Similarity	NPC474761
0.6727	Remote Similarity	NPC230800
0.6727	Remote Similarity	NPC35498
0.6727	Remote Similarity	NPC17585
0.6726	Remote Similarity	NPC471148
0.6726	Remote Similarity	NPC149371
0.6699	Remote Similarity	NPC231601
0.6698	Remote Similarity	NPC476706
0.6698	Remote Similarity	NPC476707
0.6696	Remote Similarity	NPC9303
0.6696	Remote Similarity	NPC475949
0.6696	Remote Similarity	NPC475802
0.6696	Remote Similarity	NPC16313
0.6696	Remote Similarity	NPC243998
0.6696	Remote Similarity	NPC223450
0.6667	Remote Similarity	NPC70251
0.6667	Remote Similarity	NPC469627
0.6667	Remote Similarity	NPC473321
0.6667	Remote Similarity	NPC475881
0.6667	Remote Similarity	NPC475491
0.6667	Remote Similarity	NPC469626
0.6667	Remote Similarity	NPC471140
0.6641	Remote Similarity	NPC164476
0.6641	Remote Similarity	NPC471471
0.6639	Remote Similarity	NPC9714
0.6639	Remote Similarity	NPC235625
0.6638	Remote Similarity	NPC194620
0.6638	Remote Similarity	NPC474421
0.6638	Remote Similarity	NPC72813
0.6638	Remote Similarity	NPC326994
0.6638	Remote Similarity	NPC324327
0.6637	Remote Similarity	NPC473332
0.6637	Remote Similarity	NPC201718
0.6637	Remote Similarity	NPC474742
0.6636	Remote Similarity	NPC471142
0.6636	Remote Similarity	NPC475971
0.6635	Remote Similarity	NPC72464
0.6635	Remote Similarity	NPC472957
0.6635	Remote Similarity	NPC472958
0.6614	Remote Similarity	NPC204556
0.6609	Remote Similarity	NPC471143
0.6609	Remote Similarity	NPC477510
0.6607	Remote Similarity	NPC471144
0.6606	Remote Similarity	NPC288240
0.6606	Remote Similarity	NPC273579
0.6606	Remote Similarity	NPC162205
0.6606	Remote Similarity	NPC295204
0.6604	Remote Similarity	NPC474765
0.6604	Remote Similarity	NPC179659
0.6604	Remote Similarity	NPC248602
0.6581	Remote Similarity	NPC94377
0.6581	Remote Similarity	NPC55972
0.6581	Remote Similarity	NPC117604
0.6581	Remote Similarity	NPC233379
0.6581	Remote Similarity	NPC169888
0.6581	Remote Similarity	NPC474664
0.6581	Remote Similarity	NPC14862
0.6581	Remote Similarity	NPC327286
0.6579	Remote Similarity	NPC474747
0.6579	Remote Similarity	NPC183571
0.6577	Remote Similarity	NPC123141
0.6574	Remote Similarity	NPC179394
0.6574	Remote Similarity	NPC469718
0.6574	Remote Similarity	NPC475855
0.6574	Remote Similarity	NPC144133
0.6574	Remote Similarity	NPC329857
0.6574	Remote Similarity	NPC62815
0.6571	Remote Similarity	NPC474547
0.6571	Remote Similarity	NPC475206
0.6569	Remote Similarity	NPC474739
0.6566	Remote Similarity	NPC471491
0.6552	Remote Similarity	NPC154601
0.6552	Remote Similarity	NPC236644
0.6549	Remote Similarity	NPC477512
0.6545	Remote Similarity	NPC476716
0.6542	Remote Similarity	NPC227379
0.6542	Remote Similarity	NPC474471
0.6542	Remote Similarity	NPC473715
0.6542	Remote Similarity	NPC153805
0.6538	Remote Similarity	NPC257358
0.6538	Remote Similarity	NPC11620
0.6538	Remote Similarity	NPC475622
0.6538	Remote Similarity	NPC474472
0.6538	Remote Similarity	NPC108045
0.6529	Remote Similarity	NPC471645
0.6525	Remote Similarity	NPC15218
0.6525	Remote Similarity	NPC475922
0.6522	Remote Similarity	NPC475873
0.6522	Remote Similarity	NPC4620
0.6522	Remote Similarity	NPC474166
0.6522	Remote Similarity	NPC475871
0.6522	Remote Similarity	NPC69171
0.6522	Remote Similarity	NPC474165
0.6522	Remote Similarity	NPC475945
0.6522	Remote Similarity	NPC19239
0.6522	Remote Similarity	NPC475321
0.6514	Remote Similarity	NPC20713
0.6514	Remote Similarity	NPC470373
0.6514	Remote Similarity	NPC476705
0.6514	Remote Similarity	NPC470379
0.6514	Remote Similarity	NPC133698
0.6514	Remote Similarity	NPC314500
0.6512	Remote Similarity	NPC121601
0.6509	Remote Similarity	NPC122502

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 NPC215988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	88
0.1-0.2	692
0.2-0.3	3709
0.3-0.4	3511
0.4-0.5	860
0.5-0.6	277
0.6-0.7	12
0.7-0.8	1
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
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5781	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6421	Discontinued
0.6417	Remote Similarity	NPD1719	Phase 1
0.6333	Remote Similarity	NPD6420	Discontinued
0.633	Remote Similarity	NPD1695	Approved
0.6293	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6698	Approved
0.6273	Remote Similarity	NPD46	Approved
0.6273	Remote Similarity	NPD3168	Discontinued
0.624	Remote Similarity	NPD7641	Discontinued
0.6216	Remote Similarity	NPD7983	Approved
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD2204	Approved
0.614	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5357	Phase 1
0.6132	Remote Similarity	NPD6435	Approved
0.6124	Remote Similarity	NPD7642	Approved
0.6107	Remote Similarity	NPD8074	Phase 3
0.6083	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8340	Approved
0.6077	Remote Similarity	NPD8299	Approved
0.6077	Remote Similarity	NPD8341	Approved
0.6077	Remote Similarity	NPD8342	Approved
0.6038	Remote Similarity	NPD857	Phase 3
0.6032	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6935	Phase 3
0.6031	Remote Similarity	NPD8273	Phase 1
0.6031	Remote Similarity	NPD8451	Approved
0.6018	Remote Similarity	NPD5779	Approved
0.6018	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD7839	Suspended
0.5985	Remote Similarity	NPD8448	Approved
0.5984	Remote Similarity	NPD6918	Phase 1
0.5981	Remote Similarity	NPD7345	Approved
0.597	Remote Similarity	NPD8390	Approved
0.597	Remote Similarity	NPD8392	Approved
0.597	Remote Similarity	NPD8391	Approved
0.5969	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5282	Discontinued
0.5946	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5368	Approved
0.5935	Remote Similarity	NPD6371	Approved
0.5923	Remote Similarity	NPD8080	Discontinued
0.5913	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD6334	Approved
0.5899	Remote Similarity	NPD6333	Approved
0.5893	Remote Similarity	NPD6101	Approved
0.5893	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5369	Approved
0.5878	Remote Similarity	NPD7830	Approved
0.5878	Remote Similarity	NPD7829	Approved
0.5862	Remote Similarity	NPD4228	Discovery
0.5846	Remote Similarity	NPD6921	Approved
0.5846	Remote Similarity	NPD8268	Approved
0.5846	Remote Similarity	NPD8269	Approved
0.5846	Remote Similarity	NPD8266	Approved
0.5846	Remote Similarity	NPD8267	Approved
0.5841	Remote Similarity	NPD7838	Discovery
0.5833	Remote Similarity	NPD2258	Approved
0.5833	Remote Similarity	NPD2259	Approved
0.5789	Remote Similarity	NPD6411	Approved
0.578	Remote Similarity	NPD7154	Phase 3
0.5766	Remote Similarity	NPD5786	Approved
0.5766	Remote Similarity	NPD4249	Approved
0.576	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7604	Phase 2
0.5738	Remote Similarity	NPD4211	Phase 1
0.5736	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6914	Discontinued
0.5726	Remote Similarity	NPD6413	Approved
0.5725	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD4251	Approved
0.5714	Remote Similarity	NPD4250	Approved
0.5704	Remote Similarity	NPD8336	Approved
0.5704	Remote Similarity	NPD8337	Approved
0.5693	Remote Similarity	NPD7260	Phase 2
0.5691	Remote Similarity	NPD8140	Approved
0.5691	Remote Similarity	NPD8307	Discontinued
0.568	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7500	Approved
0.5652	Remote Similarity	NPD6845	Suspended
0.5645	Remote Similarity	NPD6686	Approved
0.5643	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD3614	Approved
0.5643	Remote Similarity	NPD3615	Approved
0.5643	Remote Similarity	NPD2571	Approved
0.5643	Remote Similarity	NPD3616	Approved
0.5643	Remote Similarity	NPD3087	Approved
0.5643	Remote Similarity	NPD3088	Approved
0.5643	Remote Similarity	NPD2570	Approved
0.5643	Remote Similarity	NPD3089	Approved
0.5643	Remote Similarity	NPD4745	Approved
0.5643	Remote Similarity	NPD4746	Phase 3
0.5643	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD3090	Approved
0.5643	Remote Similarity	NPD2566	Approved
0.5643	Remote Similarity	NPD2574	Discontinued
0.5643	Remote Similarity	NPD2573	Approved
0.5636	Remote Similarity	NPD5362	Discontinued
0.5635	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.562	Remote Similarity	NPD8084	Approved
0.562	Remote Similarity	NPD8138	Approved
0.562	Remote Similarity	NPD8085	Approved
0.562	Remote Similarity	NPD8139	Approved
0.562	Remote Similarity	NPD8086	Approved
0.562	Remote Similarity	NPD8082	Approved
0.562	Remote Similarity	NPD8083	Approved
0.5606	Remote Similarity	NPD6909	Approved
0.5606	Remote Similarity	NPD6908	Approved
0.5606	Remote Similarity	NPD8517	Approved
0.5606	Remote Similarity	NPD8513	Phase 3
0.5606	Remote Similarity	NPD8515	Approved
0.5606	Remote Similarity	NPD5981	Approved
0.5606	Remote Similarity	NPD8516	Approved
0.5603	Remote Similarity	NPD6399	Phase 3
0.56	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8306	Approved
0.56	Remote Similarity	NPD8305	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