NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	1.816
LogD:	1.805
LogS:	-3.213
# Rotatable Bonds:	0
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	5.034
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:	-4.648
MDCK Permeability:	2.6749561584438197e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.607
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.748

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859
Plasma Protein Binding (PPB):	74.52111053466797%
Volume Distribution (VD):	0.996
Pgp-substrate:	25.8845157623291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	10.101
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.76
Carcinogencity:	0.769
Eye Corrosion:	0.928
Eye Irritation:	0.808
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC57405

Natural Product ID:	NPC57405
*Common Name:**	RZUCCKARTVHQBW-MPFAERRBSA-N
IUPAC Name:	n.a.
Synonyms:	9Beta-Hydroxyparthenolide
Standard InCHIKey:	RZUCCKARTVHQBW-MPFAERRBSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-5-4-6-15(3)13(19-15)12-10(7-11(8)16)9(2)14(17)18-12/h5,10-13,16H,2,4,6-7H2,1,3H3/b8-5+/t10-,11-,12-,13-,15+/m0/s1
SMILES:	C/C/1=CCC[C@]2(C)[C@H]([C@@H]3[C@@H](C[C@@H]1O)C(=C)C(=O)O3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462949
PubChem CID:	14466188
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
NPO24419	Anvillea garcinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087618]
NPO24419	Anvillea garcinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699183]
NPO24419	Anvillea garcinii	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
ED50	16
IC50	6
Others	1

Activity Type	# Activity
Cell Line	21
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[525210]
NPT112	Cell Line	MOLT-4	Homo sapiens	ED50	=	0.68	ug ml-1	PMID[525210]
NPT379	Cell Line	HOP-62	Homo sapiens	ED50	=	4.57	ug ml-1	PMID[525210]
NPT455	Cell Line	NCI-H522	Homo sapiens	ED50	=	0.45	ug ml-1	PMID[525210]
NPT393	Cell Line	HCT-116	Homo sapiens	ED50	=	3.83	ug ml-1	PMID[525210]
NPT323	Cell Line	SW-620	Homo sapiens	ED50	=	0.55	ug ml-1	PMID[525210]
NPT395	Cell Line	SF-268	Homo sapiens	ED50	=	7.76	ug ml-1	PMID[525210]
NPT392	Cell Line	SNB-75	Homo sapiens	ED50	=	8.53	ug ml-1	PMID[525210]
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	=	2.46	ug ml-1	PMID[525210]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	=	1.62	ug ml-1	PMID[525210]
NPT458	Cell Line	IGROV-1	Homo sapiens	ED50	=	3.91	ug ml-1	PMID[525210]
NPT381	Cell Line	OVCAR-8	Homo sapiens	ED50	=	4.75	ug ml-1	PMID[525210]
NPT369	Cell Line	ACHN	Homo sapiens	ED50	=	2.21	ug ml-1	PMID[525210]
NPT371	Cell Line	UO-31	Homo sapiens	ED50	=	3.88	ug ml-1	PMID[525210]
NPT90	Cell Line	DU-145	Homo sapiens	ED50	=	5.6	ug ml-1	PMID[525210]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	ED50	=	4.99	ug ml-1	PMID[525210]
NPT5027	Cell Line	Hs 683	Homo sapiens	IC50	=	25000.0	nM	PMID[525211]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	24000.0	nM	PMID[525211]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	23000.0	nM	PMID[525211]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	25000.0	nM	PMID[525211]
NPT1125	Cell Line	T98G	Homo sapiens	IC50	=	25000.0	nM	PMID[525211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15000.0	nM	PMID[525211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	>	90000.0	nM	PMID[525212]

☑ 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 NPC57405 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	210
0.1-0.2	1286
0.2-0.3	4950
0.3-0.4	9413
0.4-0.5	14895
0.5-0.6	7234
0.6-0.7	3435
0.7-0.8	1043
0.8-0.85	134
0.85-0.9	64
0.9-0.95	28
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303942
0.9556	High Similarity	NPC473859
0.9457	High Similarity	NPC288876
0.9444	High Similarity	NPC270013
0.9444	High Similarity	NPC475659
0.9444	High Similarity	NPC14961
0.9348	High Similarity	NPC473326
0.9341	High Similarity	NPC279621
0.9341	High Similarity	NPC476315
0.9333	High Similarity	NPC81386
0.9333	High Similarity	NPC474035
0.9318	High Similarity	NPC474032
0.9222	High Similarity	NPC475912
0.9222	High Similarity	NPC228451
0.9222	High Similarity	NPC212486
0.9222	High Similarity	NPC475838
0.9222	High Similarity	NPC125674
0.9205	High Similarity	NPC473715
0.9121	High Similarity	NPC474247
0.9111	High Similarity	NPC473321
0.9101	High Similarity	NPC151770
0.908	High Similarity	NPC38468
0.908	High Similarity	NPC319795
0.908	High Similarity	NPC50362
0.9022	High Similarity	NPC36954
0.9011	High Similarity	NPC288240
0.9011	High Similarity	NPC162205
0.9011	High Similarity	NPC273579
0.9011	High Similarity	NPC295204
0.9	High Similarity	NPC473619
0.8936	High Similarity	NPC474213
0.8925	High Similarity	NPC230800
0.8913	High Similarity	NPC473316
0.8913	High Similarity	NPC473330
0.8913	High Similarity	NPC471147
0.8901	High Similarity	NPC184463
0.8901	High Similarity	NPC30515
0.8889	High Similarity	NPC166919
0.8876	High Similarity	NPC231889
0.8842	High Similarity	NPC475949
0.8817	High Similarity	NPC477922
0.8817	High Similarity	NPC471142
0.8804	High Similarity	NPC81419
0.8804	High Similarity	NPC179746
0.8804	High Similarity	NPC476300
0.8791	High Similarity	NPC474761
0.8791	High Similarity	NPC251385
0.8791	High Similarity	NPC475855
0.8791	High Similarity	NPC51004
0.8791	High Similarity	NPC476004
0.8791	High Similarity	NPC49342
0.8791	High Similarity	NPC475748
0.8778	High Similarity	NPC202672
0.8764	High Similarity	NPC50637
0.875	High Similarity	NPC114979
0.875	High Similarity	NPC191476
0.875	High Similarity	NPC96259
0.875	High Similarity	NPC141193
0.8723	High Similarity	NPC477921
0.8696	High Similarity	NPC70251
0.8696	High Similarity	NPC12172
0.8696	High Similarity	NPC208886
0.8696	High Similarity	NPC475881
0.8687	High Similarity	NPC477513
0.8681	High Similarity	NPC307411
0.866	High Similarity	NPC471148
0.8652	High Similarity	NPC255307
0.8652	High Similarity	NPC21469
0.8621	High Similarity	NPC24417
0.8617	High Similarity	NPC471141
0.8587	High Similarity	NPC179394
0.8587	High Similarity	NPC312042
0.8587	High Similarity	NPC144133
0.8586	High Similarity	NPC243998
0.8557	High Similarity	NPC476270
0.8557	High Similarity	NPC201718
0.8557	High Similarity	NPC474339
0.8557	High Similarity	NPC473332
0.8557	High Similarity	NPC164598
0.8556	High Similarity	NPC475461
0.8556	High Similarity	NPC305475
0.8542	High Similarity	NPC471144
0.8542	High Similarity	NPC208233
0.8542	High Similarity	NPC279561
0.8539	High Similarity	NPC476804
0.8526	High Similarity	NPC35498
0.8523	High Similarity	NPC229825
0.8511	High Similarity	NPC140543
0.8478	Intermediate Similarity	NPC295312
0.8469	Intermediate Similarity	NPC149371
0.8462	Intermediate Similarity	NPC5130
0.8427	Intermediate Similarity	NPC131669
0.8427	Intermediate Similarity	NPC272814
0.8427	Intermediate Similarity	NPC473390
0.8427	Intermediate Similarity	NPC40746
0.8427	Intermediate Similarity	NPC169575
0.8409	Intermediate Similarity	NPC52861
0.84	Intermediate Similarity	NPC223450
0.8391	Intermediate Similarity	NPC98557
0.8391	Intermediate Similarity	NPC167881
0.8387	Intermediate Similarity	NPC469368
0.8387	Intermediate Similarity	NPC474232
0.837	Intermediate Similarity	NPC227379
0.837	Intermediate Similarity	NPC153805
0.837	Intermediate Similarity	NPC474471
0.837	Intermediate Similarity	NPC476803
0.837	Intermediate Similarity	NPC281516
0.8367	Intermediate Similarity	NPC264477
0.8367	Intermediate Similarity	NPC47880
0.8367	Intermediate Similarity	NPC477511
0.8352	Intermediate Similarity	NPC469910
0.8352	Intermediate Similarity	NPC470242
0.8352	Intermediate Similarity	NPC122502
0.8351	Intermediate Similarity	NPC187268
0.8333	Intermediate Similarity	NPC17585
0.8333	Intermediate Similarity	NPC158756
0.8316	Intermediate Similarity	NPC476267
0.83	Intermediate Similarity	NPC100487
0.83	Intermediate Similarity	NPC474741
0.8276	Intermediate Similarity	NPC471465
0.8276	Intermediate Similarity	NPC196653
0.8261	Intermediate Similarity	NPC186148
0.8261	Intermediate Similarity	NPC475703
0.8247	Intermediate Similarity	NPC471140
0.8242	Intermediate Similarity	NPC470755
0.8242	Intermediate Similarity	NPC47958
0.8242	Intermediate Similarity	NPC149725
0.8242	Intermediate Similarity	NPC304509
0.8242	Intermediate Similarity	NPC137033
0.8242	Intermediate Similarity	NPC165162
0.8229	Intermediate Similarity	NPC107476
0.8229	Intermediate Similarity	NPC304886
0.8222	Intermediate Similarity	NPC116543
0.8222	Intermediate Similarity	NPC59097
0.8222	Intermediate Similarity	NPC250315
0.8202	Intermediate Similarity	NPC207188
0.8202	Intermediate Similarity	NPC141810
0.82	Intermediate Similarity	NPC475871
0.82	Intermediate Similarity	NPC475945
0.8191	Intermediate Similarity	NPC71533
0.8191	Intermediate Similarity	NPC106510
0.8191	Intermediate Similarity	NPC62815
0.8172	Intermediate Similarity	NPC475819
0.8172	Intermediate Similarity	NPC177629
0.8172	Intermediate Similarity	NPC476805
0.8172	Intermediate Similarity	NPC58219
0.8163	Intermediate Similarity	NPC221615
0.8152	Intermediate Similarity	NPC150755
0.8144	Intermediate Similarity	NPC306041
0.8132	Intermediate Similarity	NPC138647
0.8132	Intermediate Similarity	NPC470238
0.8132	Intermediate Similarity	NPC70424
0.8132	Intermediate Similarity	NPC472958
0.8132	Intermediate Similarity	NPC474780
0.8132	Intermediate Similarity	NPC472957
0.8132	Intermediate Similarity	NPC243618
0.8125	Intermediate Similarity	NPC71589
0.8125	Intermediate Similarity	NPC474338
0.8125	Intermediate Similarity	NPC190294
0.8125	Intermediate Similarity	NPC262133
0.8125	Intermediate Similarity	NPC470010
0.8125	Intermediate Similarity	NPC323008
0.8125	Intermediate Similarity	NPC470013
0.8119	Intermediate Similarity	NPC471143
0.8119	Intermediate Similarity	NPC477510
0.8105	Intermediate Similarity	NPC131209
0.8105	Intermediate Similarity	NPC158061
0.8105	Intermediate Similarity	NPC470373
0.8105	Intermediate Similarity	NPC470379
0.8105	Intermediate Similarity	NPC20713
0.81	Intermediate Similarity	NPC474747
0.81	Intermediate Similarity	NPC320019
0.81	Intermediate Similarity	NPC324017
0.81	Intermediate Similarity	NPC86077
0.8085	Intermediate Similarity	NPC473564
0.8085	Intermediate Similarity	NPC92974
0.8081	Intermediate Similarity	NPC475053
0.8081	Intermediate Similarity	NPC477512
0.8065	Intermediate Similarity	NPC160138
0.8065	Intermediate Similarity	NPC266957
0.8065	Intermediate Similarity	NPC248602
0.8065	Intermediate Similarity	NPC179659
0.8061	Intermediate Similarity	NPC40812
0.8058	Intermediate Similarity	NPC474664
0.8058	Intermediate Similarity	NPC233379
0.8058	Intermediate Similarity	NPC14862
0.8046	Intermediate Similarity	NPC68819
0.8041	Intermediate Similarity	NPC52044
0.8041	Intermediate Similarity	NPC474947
0.8041	Intermediate Similarity	NPC170120
0.8039	Intermediate Similarity	NPC54737
0.8039	Intermediate Similarity	NPC475802
0.8022	Intermediate Similarity	NPC231601
0.8022	Intermediate Similarity	NPC11620
0.8022	Intermediate Similarity	NPC170286
0.8021	Intermediate Similarity	NPC135776
0.8021	Intermediate Similarity	NPC475302
0.802	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC329857
0.8	Intermediate Similarity	NPC473448

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 NPC57405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1872
0.2-0.3	3765
0.3-0.4	2228
0.4-0.5	731
0.5-0.6	285
0.6-0.7	63
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD1733	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD6698	Approved
0.8191	Intermediate Similarity	NPD46	Approved
0.7732	Intermediate Similarity	NPD7983	Approved
0.7708	Intermediate Similarity	NPD1695	Approved
0.7629	Intermediate Similarity	NPD7838	Discovery
0.757	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5344	Discontinued
0.7083	Intermediate Similarity	NPD7154	Phase 3
0.7041	Intermediate Similarity	NPD4249	Approved
0.697	Remote Similarity	NPD4250	Approved
0.697	Remote Similarity	NPD4251	Approved
0.6961	Remote Similarity	NPD5779	Approved
0.6961	Remote Similarity	NPD5778	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6931	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6923	Remote Similarity	NPD8513	Phase 3
0.6909	Remote Similarity	NPD6686	Approved
0.6887	Remote Similarity	NPD6648	Approved
0.6869	Remote Similarity	NPD5786	Approved
0.6814	Remote Similarity	NPD6053	Discontinued
0.6804	Remote Similarity	NPD6435	Approved
0.6771	Remote Similarity	NPD4819	Approved
0.6771	Remote Similarity	NPD4821	Approved
0.6771	Remote Similarity	NPD4820	Approved
0.6771	Remote Similarity	NPD4822	Approved
0.6771	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5363	Approved
0.6762	Remote Similarity	NPD7839	Suspended
0.6735	Remote Similarity	NPD5362	Discontinued
0.6724	Remote Similarity	NPD7115	Discovery
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7642	Approved
0.6639	Remote Similarity	NPD8074	Phase 3
0.6637	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4269	Approved
0.6633	Remote Similarity	NPD4270	Approved
0.66	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5368	Approved
0.6571	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD4271	Approved
0.6562	Remote Similarity	NPD4268	Approved
0.6531	Remote Similarity	NPD5369	Approved
0.6529	Remote Similarity	NPD7830	Approved
0.6529	Remote Similarity	NPD7829	Approved
0.6517	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD6008	Approved
0.6429	Remote Similarity	NPD4252	Approved
0.6422	Remote Similarity	NPD7640	Approved
0.6422	Remote Similarity	NPD7639	Approved
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD7638	Approved
0.63	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7507	Approved
0.629	Remote Similarity	NPD8273	Phase 1
0.625	Remote Similarity	NPD7641	Discontinued
0.6238	Remote Similarity	NPD6110	Phase 1
0.6238	Remote Similarity	NPD5331	Approved
0.6238	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD7637	Suspended
0.6226	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD4790	Discontinued
0.6196	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4632	Approved
0.6183	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8451	Approved
0.6148	Remote Similarity	NPD6319	Approved
0.6142	Remote Similarity	NPD7319	Approved
0.6139	Remote Similarity	NPD5209	Approved
0.6111	Remote Similarity	NPD8448	Approved
0.6102	Remote Similarity	NPD8297	Approved
0.6098	Remote Similarity	NPD8444	Approved
0.6087	Remote Similarity	NPD5697	Approved
0.608	Remote Similarity	NPD8340	Approved
0.608	Remote Similarity	NPD8342	Approved
0.608	Remote Similarity	NPD8341	Approved
0.608	Remote Similarity	NPD8299	Approved
0.608	Remote Similarity	NPD7492	Approved
0.6047	Remote Similarity	NPD7260	Phase 2
0.6038	Remote Similarity	NPD5370	Suspended
0.6034	Remote Similarity	NPD6899	Approved
0.6034	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD6009	Approved
0.6032	Remote Similarity	NPD6616	Approved
0.6019	Remote Similarity	NPD6399	Phase 3
0.6017	Remote Similarity	NPD6650	Approved
0.6017	Remote Similarity	NPD6649	Approved
0.6017	Remote Similarity	NPD2204	Approved
0.6016	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD7078	Approved
0.5983	Remote Similarity	NPD6014	Approved
0.5983	Remote Similarity	NPD6372	Approved
0.5983	Remote Similarity	NPD6012	Approved
0.5983	Remote Similarity	NPD6013	Approved
0.5983	Remote Similarity	NPD6373	Approved
0.5969	Remote Similarity	NPD8392	Approved
0.5969	Remote Similarity	NPD8390	Approved
0.5969	Remote Similarity	NPD8391	Approved
0.5968	Remote Similarity	NPD6015	Approved
0.5968	Remote Similarity	NPD6016	Approved
0.5968	Remote Similarity	NPD5983	Phase 2
0.596	Remote Similarity	NPD4756	Discovery
0.5948	Remote Similarity	NPD6412	Phase 2
0.5948	Remote Similarity	NPD5701	Approved
0.5938	Remote Similarity	NPD7736	Approved
0.5932	Remote Similarity	NPD7290	Approved
0.5932	Remote Similarity	NPD6421	Discontinued
0.5932	Remote Similarity	NPD7102	Approved
0.5932	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.592	Remote Similarity	NPD5988	Approved
0.592	Remote Similarity	NPD6370	Approved
0.5918	Remote Similarity	NPD8039	Approved
0.5914	Remote Similarity	NPD7331	Phase 2
0.5905	Remote Similarity	NPD6422	Discontinued
0.5902	Remote Similarity	NPD7500	Approved
0.5897	Remote Similarity	NPD7320	Approved
0.5897	Remote Similarity	NPD6011	Approved
0.5887	Remote Similarity	NPD6059	Approved
0.5882	Remote Similarity	NPD6617	Approved
0.5882	Remote Similarity	NPD8130	Phase 1
0.5882	Remote Similarity	NPD6847	Approved
0.5882	Remote Similarity	NPD6869	Approved
0.5878	Remote Similarity	NPD6845	Suspended
0.5877	Remote Similarity	NPD7632	Discontinued
0.5877	Remote Similarity	NPD5211	Phase 2
0.5865	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8293	Discontinued
0.5849	Remote Similarity	NPD7524	Approved
0.5833	Remote Similarity	NPD6882	Approved
0.581	Remote Similarity	NPD1696	Phase 3
0.5804	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD6084	Phase 2
0.5785	Remote Similarity	NPD8133	Approved
0.5781	Remote Similarity	NPD6336	Discontinued
0.5776	Remote Similarity	NPD5141	Approved
0.5772	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6695	Phase 3
0.5766	Remote Similarity	NPD5695	Phase 3
0.5752	Remote Similarity	NPD5696	Approved
0.575	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD8328	Phase 3
0.5726	Remote Similarity	NPD7328	Approved
0.5726	Remote Similarity	NPD5048	Discontinued
0.5726	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD8269	Approved
0.5714	Remote Similarity	NPD8267	Approved
0.5714	Remote Similarity	NPD8268	Approved
0.5714	Remote Similarity	NPD8266	Approved
0.5714	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7503	Approved
0.5714	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD5285	Approved
0.5702	Remote Similarity	NPD5286	Approved
0.5702	Remote Similarity	NPD4696	Approved
0.5699	Remote Similarity	NPD3197	Phase 1
0.5691	Remote Similarity	NPD6274	Approved
0.5688	Remote Similarity	NPD3168	Discontinued
0.568	Remote Similarity	NPD7516	Approved
0.5673	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD8080	Discontinued
0.5667	Remote Similarity	NPD2067	Discontinued
0.5667	Remote Similarity	NPD4634	Approved
0.5664	Remote Similarity	NPD4755	Approved
0.5664	Remote Similarity	NPD7902	Approved
0.5652	Remote Similarity	NPD368	Approved
0.5645	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7341	Phase 2
0.5635	Remote Similarity	NPD8377	Approved
0.5635	Remote Similarity	NPD8294	Approved
0.563	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.562	Remote Similarity	NPD1719	Phase 1
0.5606	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD5226	Approved
0.5603	Remote Similarity	NPD4633	Approved
0.5603	Remote Similarity	NPD5225	Approved
0.5603	Remote Similarity	NPD5224	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