NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	462.15
Volume:	441.585
LogP:	1.312
LogD:	0.932
LogS:	-4.263
# Rotatable Bonds:	7
TPSA:	130.26
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.257
Synthetic Accessibility Score:	5.639
Fsp3:	0.565
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:	-5.234
MDCK Permeability:	0.0001382923364872113
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.194
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	29.80603790283203%
Volume Distribution (VD):	1.247
Pgp-substrate:	47.829559326171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.323
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	8.446
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.923
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.724
Skin Sensitization:	0.826
Carcinogencity:	0.117
Eye Corrosion:	0.487
Eye Irritation:	0.088
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC477510

Natural Product ID:	NPC477510
*Common Name:**	methyl (1S,2R,4S,5Z,7E,9R,10S,11R)-9-acetyloxy-10-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradeca-5,7-diene-8-carboxylate
IUPAC Name:	methyl (1S,2R,4S,5Z,7E,9R,10S,11R)-9-acetyloxy-10-[(2S,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradeca-5,7-diene-8-carboxylate
Synonyms:
Standard InCHIKey:	OHHDXIRXYVPFMP-RXVUQRMFSA-N
Standard InCHI:	InChI=1S/C23H26O10/c1-10-14-16(31-21(27)23(5)11(2)32-23)15(29-12(3)24)13(20(26)28-6)8-7-9-22(4)18(33-22)17(14)30-19(10)25/h7-9,11,14-18H,1H2,2-6H3/b9-7-,13-8+/t11-,14+,15+,16-,17-,18+,22-,23-/m0/s1
SMILES:	C[C@H]1[C@@](O1)(C)C(=O)O[C@H]2[C@@H]3[C@@H]([C@@H]4[C@@](O4)(/C=C\C=C(/[C@H]2OC(=O)C)\C(=O)OC)C)OC(=O)C3=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178694
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO18602	Melampodium leucanthum	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	6
Others	1

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1700	nM	PMID[25685941]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	1800	nM	PMID[25685941]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1700	nM	PMID[25685941]
NPT2657	Cell Line	A10	Rattus norvegicus	IC50	=	1700	nM	PMID[25685941]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	570000	nM	PMID[25685941]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	1400000	nM	PMID[25685941]
NPT146	Cell Line	SK-OV-3	Homo sapiens	Ratio IC50	=	2.5	n.a.	PMID[25685941]

☑ 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 NPC477510 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	281
0.1-0.2	1580
0.2-0.3	5599
0.3-0.4	10305
0.4-0.5	15541
0.5-0.6	6397
0.6-0.7	2396
0.7-0.8	470
0.8-0.85	96
0.85-0.9	18
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471143
0.9688	High Similarity	NPC264477
0.9688	High Similarity	NPC477511
0.9583	High Similarity	NPC477512
0.9375	High Similarity	NPC471140
0.9271	High Similarity	NPC17585
0.9208	High Similarity	NPC477513
0.9062	High Similarity	NPC471147
0.8889	High Similarity	NPC208233
0.8878	High Similarity	NPC35498
0.8812	High Similarity	NPC149371
0.8812	High Similarity	NPC471148
0.8713	High Similarity	NPC164598
0.8713	High Similarity	NPC47880
0.8713	High Similarity	NPC474339
0.8673	High Similarity	NPC473330
0.8673	High Similarity	NPC473316
0.8673	High Similarity	NPC140543
0.866	High Similarity	NPC20713
0.8646	High Similarity	NPC166919
0.8646	High Similarity	NPC151770
0.8614	High Similarity	NPC475949
0.8614	High Similarity	NPC288876
0.8586	High Similarity	NPC475659
0.8557	High Similarity	NPC475748
0.8529	High Similarity	NPC201718
0.8515	High Similarity	NPC471144
0.85	High Similarity	NPC473859
0.8485	Intermediate Similarity	NPC476267
0.8462	Intermediate Similarity	NPC474741
0.8438	Intermediate Similarity	NPC266957
0.8438	Intermediate Similarity	NPC231889
0.8384	Intermediate Similarity	NPC165383
0.8333	Intermediate Similarity	NPC50637
0.8317	Intermediate Similarity	NPC476275
0.8317	Intermediate Similarity	NPC230800
0.8317	Intermediate Similarity	NPC279621
0.8241	Intermediate Similarity	NPC281624
0.8229	Intermediate Similarity	NPC319795
0.8229	Intermediate Similarity	NPC50362
0.8229	Intermediate Similarity	NPC38468
0.8218	Intermediate Similarity	NPC474947
0.8218	Intermediate Similarity	NPC471142
0.8208	Intermediate Similarity	NPC16313
0.8208	Intermediate Similarity	NPC9303
0.8208	Intermediate Similarity	NPC475802
0.819	Intermediate Similarity	NPC19239
0.819	Intermediate Similarity	NPC475945
0.819	Intermediate Similarity	NPC475871
0.819	Intermediate Similarity	NPC474166
0.8182	Intermediate Similarity	NPC251385
0.8182	Intermediate Similarity	NPC49342
0.8182	Intermediate Similarity	NPC329857
0.8182	Intermediate Similarity	NPC469718
0.8182	Intermediate Similarity	NPC312042
0.8173	Intermediate Similarity	NPC474742
0.8173	Intermediate Similarity	NPC476270
0.8165	Intermediate Similarity	NPC475495
0.8163	Intermediate Similarity	NPC475902
0.8155	Intermediate Similarity	NPC279561
0.8155	Intermediate Similarity	NPC474213
0.8155	Intermediate Similarity	NPC473326
0.8148	Intermediate Similarity	NPC38154
0.8137	Intermediate Similarity	NPC476315
0.8131	Intermediate Similarity	NPC194620
0.8131	Intermediate Similarity	NPC326994
0.8131	Intermediate Similarity	NPC324327
0.8131	Intermediate Similarity	NPC469558
0.8131	Intermediate Similarity	NPC474421
0.8131	Intermediate Similarity	NPC474716
0.8131	Intermediate Similarity	NPC72813
0.8119	Intermediate Similarity	NPC474247
0.8119	Intermediate Similarity	NPC57405
0.8119	Intermediate Similarity	NPC303942
0.8095	Intermediate Similarity	NPC472754
0.8095	Intermediate Similarity	NPC474747
0.8091	Intermediate Similarity	NPC477093
0.8091	Intermediate Similarity	NPC473522
0.8091	Intermediate Similarity	NPC475277
0.8081	Intermediate Similarity	NPC475971
0.8073	Intermediate Similarity	NPC473843
0.8073	Intermediate Similarity	NPC473975
0.8073	Intermediate Similarity	NPC474586
0.8073	Intermediate Similarity	NPC473594
0.8061	Intermediate Similarity	NPC475703
0.8056	Intermediate Similarity	NPC233379
0.8056	Intermediate Similarity	NPC14862
0.8056	Intermediate Similarity	NPC55972
0.8056	Intermediate Similarity	NPC327286
0.8056	Intermediate Similarity	NPC474664
0.8056	Intermediate Similarity	NPC169888
0.8041	Intermediate Similarity	NPC474547
0.8039	Intermediate Similarity	NPC14961
0.8039	Intermediate Similarity	NPC471141
0.8039	Intermediate Similarity	NPC270013
0.8036	Intermediate Similarity	NPC477509
0.8021	Intermediate Similarity	NPC272814
0.802	Intermediate Similarity	NPC125674
0.802	Intermediate Similarity	NPC475838
0.802	Intermediate Similarity	NPC228451
0.802	Intermediate Similarity	NPC212486
0.802	Intermediate Similarity	NPC476300
0.8019	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC194619
0.8	Intermediate Similarity	NPC15993
0.8	Intermediate Similarity	NPC472753
0.8	Intermediate Similarity	NPC62815
0.7982	Intermediate Similarity	NPC15218
0.7981	Intermediate Similarity	NPC161855
0.7965	Intermediate Similarity	NPC471146
0.7965	Intermediate Similarity	NPC471145
0.7963	Intermediate Similarity	NPC470192
0.7963	Intermediate Similarity	NPC475587
0.7963	Intermediate Similarity	NPC475510
0.7961	Intermediate Similarity	NPC301596
0.7961	Intermediate Similarity	NPC172998
0.7961	Intermediate Similarity	NPC299396
0.7959	Intermediate Similarity	NPC204048
0.7944	Intermediate Similarity	NPC472756
0.7941	Intermediate Similarity	NPC81386
0.7941	Intermediate Similarity	NPC474035
0.7938	Intermediate Similarity	NPC138647
0.7938	Intermediate Similarity	NPC470238
0.7925	Intermediate Similarity	NPC320019
0.7925	Intermediate Similarity	NPC324017
0.7905	Intermediate Similarity	NPC469551
0.789	Intermediate Similarity	NPC473939
0.789	Intermediate Similarity	NPC473595
0.7879	Intermediate Similarity	NPC5130
0.7864	Intermediate Similarity	NPC234339
0.7864	Intermediate Similarity	NPC273197
0.7864	Intermediate Similarity	NPC477922
0.7864	Intermediate Similarity	NPC36954
0.785	Intermediate Similarity	NPC475873
0.785	Intermediate Similarity	NPC4620
0.7843	Intermediate Similarity	NPC475912
0.7835	Intermediate Similarity	NPC170377
0.783	Intermediate Similarity	NPC128733
0.783	Intermediate Similarity	NPC133907
0.783	Intermediate Similarity	NPC185141
0.783	Intermediate Similarity	NPC110443
0.783	Intermediate Similarity	NPC46998
0.7822	Intermediate Similarity	NPC179394
0.7822	Intermediate Similarity	NPC473619
0.7822	Intermediate Similarity	NPC475855
0.7822	Intermediate Similarity	NPC144133
0.7822	Intermediate Similarity	NPC51004
0.7818	Intermediate Similarity	NPC475922
0.7812	Intermediate Similarity	NPC141810
0.7807	Intermediate Similarity	NPC475305
0.78	Intermediate Similarity	NPC471047
0.78	Intermediate Similarity	NPC469653
0.78	Intermediate Similarity	NPC469628
0.78	Intermediate Similarity	NPC469631
0.78	Intermediate Similarity	NPC475906
0.7788	Intermediate Similarity	NPC477921
0.7788	Intermediate Similarity	NPC158416
0.7788	Intermediate Similarity	NPC470883
0.7788	Intermediate Similarity	NPC473291
0.7788	Intermediate Similarity	NPC39859
0.7788	Intermediate Similarity	NPC76862
0.7778	Intermediate Similarity	NPC475676
0.7778	Intermediate Similarity	NPC220964
0.7768	Intermediate Similarity	NPC66108
0.7767	Intermediate Similarity	NPC190294
0.7757	Intermediate Similarity	NPC105725
0.7748	Intermediate Similarity	NPC161816
0.7748	Intermediate Similarity	NPC115257
0.7745	Intermediate Similarity	NPC184463
0.7745	Intermediate Similarity	NPC30515
0.7745	Intermediate Similarity	NPC70251
0.7745	Intermediate Similarity	NPC475881
0.7745	Intermediate Similarity	NPC473321
0.7739	Intermediate Similarity	NPC475401
0.7723	Intermediate Similarity	NPC307411
0.7723	Intermediate Similarity	NPC474032
0.7719	Intermediate Similarity	NPC474333
0.7714	Intermediate Similarity	NPC40812
0.7708	Intermediate Similarity	NPC474510
0.7706	Intermediate Similarity	NPC223450
0.77	Intermediate Similarity	NPC471739
0.7692	Intermediate Similarity	NPC107476
0.7679	Intermediate Similarity	NPC179798
0.7679	Intermediate Similarity	NPC304180
0.7677	Intermediate Similarity	NPC197903
0.7677	Intermediate Similarity	NPC99395
0.7672	Intermediate Similarity	NPC477092
0.767	Intermediate Similarity	NPC475302
0.767	Intermediate Similarity	NPC288240
0.767	Intermediate Similarity	NPC273579
0.767	Intermediate Similarity	NPC162205
0.767	Intermediate Similarity	NPC81419
0.767	Intermediate Similarity	NPC179746
0.767	Intermediate Similarity	NPC295204
0.7658	Intermediate Similarity	NPC471934
0.7653	Intermediate Similarity	NPC474703
0.7653	Intermediate Similarity	NPC128429
0.7652	Intermediate Similarity	NPC296822
0.7642	Intermediate Similarity	NPC261377
0.7642	Intermediate Similarity	NPC308567

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 NPC477510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	2036
0.2-0.3	3891
0.3-0.4	2001
0.4-0.5	715
0.5-0.6	225
0.6-0.7	31
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8229	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD7838	Discovery
0.7404	Intermediate Similarity	NPD7983	Approved
0.7308	Intermediate Similarity	NPD46	Approved
0.7308	Intermediate Similarity	NPD6698	Approved
0.7212	Intermediate Similarity	NPD1695	Approved
0.7091	Intermediate Similarity	NPD6648	Approved
0.7037	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6371	Approved
0.6847	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5282	Discontinued
0.678	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5344	Discontinued
0.6724	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5209	Approved
0.6697	Remote Similarity	NPD5779	Approved
0.6697	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8515	Approved
0.6694	Remote Similarity	NPD8516	Approved
0.6694	Remote Similarity	NPD8517	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6587	Remote Similarity	NPD7830	Approved
0.6587	Remote Similarity	NPD7829	Approved
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7839	Suspended
0.648	Remote Similarity	NPD6319	Approved
0.6457	Remote Similarity	NPD7642	Approved
0.6434	Remote Similarity	NPD8074	Phase 3
0.6404	Remote Similarity	NPD4225	Approved
0.6387	Remote Similarity	NPD6686	Approved
0.6371	Remote Similarity	NPD7115	Discovery
0.6364	Remote Similarity	NPD5785	Approved
0.6364	Remote Similarity	NPD7260	Phase 2
0.6356	Remote Similarity	NPD6008	Approved
0.6355	Remote Similarity	NPD1694	Approved
0.6333	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD2067	Discontinued
0.6279	Remote Similarity	NPD7492	Approved
0.6273	Remote Similarity	NPD6101	Approved
0.6273	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6616	Approved
0.6231	Remote Similarity	NPD8451	Approved
0.6231	Remote Similarity	NPD8273	Phase 1
0.6226	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6054	Approved
0.6204	Remote Similarity	NPD5363	Approved
0.6183	Remote Similarity	NPD8448	Approved
0.6183	Remote Similarity	NPD7078	Approved
0.6179	Remote Similarity	NPD6053	Discontinued
0.6179	Remote Similarity	NPD8297	Approved
0.6172	Remote Similarity	NPD6016	Approved
0.6172	Remote Similarity	NPD6015	Approved
0.6161	Remote Similarity	NPD6411	Approved
0.6147	Remote Similarity	NPD5786	Approved
0.6136	Remote Similarity	NPD7736	Approved
0.6124	Remote Similarity	NPD6370	Approved
0.6124	Remote Similarity	NPD5988	Approved
0.6116	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6650	Approved
0.6098	Remote Similarity	NPD6649	Approved
0.6074	Remote Similarity	NPD6845	Suspended
0.6063	Remote Similarity	NPD7641	Discontinued
0.6047	Remote Similarity	NPD8444	Approved
0.6045	Remote Similarity	NPD8392	Approved
0.6045	Remote Similarity	NPD8391	Approved
0.6045	Remote Similarity	NPD8390	Approved
0.6033	Remote Similarity	NPD5697	Approved
0.6031	Remote Similarity	NPD8299	Approved
0.6031	Remote Similarity	NPD8342	Approved
0.6031	Remote Similarity	NPD8341	Approved
0.6031	Remote Similarity	NPD8340	Approved
0.6019	Remote Similarity	NPD8039	Approved
0.6019	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4632	Approved
0.5984	Remote Similarity	NPD6881	Approved
0.5984	Remote Similarity	NPD6899	Approved
0.5984	Remote Similarity	NPD6009	Approved
0.5984	Remote Similarity	NPD7500	Approved
0.5981	Remote Similarity	NPD5369	Approved
0.597	Remote Similarity	NPD7319	Approved
0.5969	Remote Similarity	NPD6059	Approved
0.5954	Remote Similarity	NPD8328	Phase 3
0.5954	Remote Similarity	NPD7604	Phase 2
0.5946	Remote Similarity	NPD4250	Approved
0.5946	Remote Similarity	NPD4251	Approved
0.594	Remote Similarity	NPD8293	Discontinued
0.5935	Remote Similarity	NPD6372	Approved
0.5935	Remote Similarity	NPD6013	Approved
0.5935	Remote Similarity	NPD6012	Approved
0.5935	Remote Similarity	NPD6014	Approved
0.5935	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD6435	Approved
0.5926	Remote Similarity	NPD4269	Approved
0.5926	Remote Similarity	NPD4270	Approved
0.5923	Remote Similarity	NPD5983	Phase 2
0.592	Remote Similarity	NPD6882	Approved
0.5905	Remote Similarity	NPD4756	Discovery
0.5887	Remote Similarity	NPD7102	Approved
0.5887	Remote Similarity	NPD7290	Approved
0.5887	Remote Similarity	NPD6883	Approved
0.5878	Remote Similarity	NPD8080	Discontinued
0.5877	Remote Similarity	NPD5694	Approved
0.5877	Remote Similarity	NPD5693	Phase 1
0.5877	Remote Similarity	NPD7637	Suspended
0.5865	Remote Similarity	NPD7507	Approved
0.5854	Remote Similarity	NPD6011	Approved
0.584	Remote Similarity	NPD6847	Approved
0.584	Remote Similarity	NPD8130	Phase 1
0.584	Remote Similarity	NPD2204	Approved
0.584	Remote Similarity	NPD6617	Approved
0.584	Remote Similarity	NPD6869	Approved
0.582	Remote Similarity	NPD6402	Approved
0.582	Remote Similarity	NPD7128	Approved
0.582	Remote Similarity	NPD5739	Approved
0.582	Remote Similarity	NPD6675	Approved
0.5789	Remote Similarity	NPD5692	Phase 3
0.578	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD5701	Approved
0.576	Remote Similarity	NPD4634	Approved
0.5752	Remote Similarity	NPD6672	Approved
0.5752	Remote Similarity	NPD5737	Approved
0.5746	Remote Similarity	NPD6336	Discontinued
0.5741	Remote Similarity	NPD4822	Approved
0.5741	Remote Similarity	NPD5368	Approved
0.5741	Remote Similarity	NPD4820	Approved
0.5741	Remote Similarity	NPD4252	Approved
0.5741	Remote Similarity	NPD4821	Approved
0.5741	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4819	Approved
0.5739	Remote Similarity	NPD6050	Approved
0.5736	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD5362	Discontinued
0.5727	Remote Similarity	NPD6110	Phase 1
0.5726	Remote Similarity	NPD5695	Phase 3
0.5726	Remote Similarity	NPD7320	Approved
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5682	Remote Similarity	NPD6921	Approved
0.5682	Remote Similarity	NPD7503	Approved
0.5682	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7639	Approved
0.5667	Remote Similarity	NPD7640	Approved
0.5652	Remote Similarity	NPD5207	Approved
0.5643	Remote Similarity	NPD8415	Approved
0.563	Remote Similarity	NPD6084	Phase 2
0.563	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD8387	Clinical (unspecified phase)

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