NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	272.449
LogP:	1.545
LogD:	0.92
LogS:	-3.44
# Rotatable Bonds:	0
TPSA:	71.59
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.285
Fsp3:	0.8
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:	-4.831
MDCK Permeability:	1.550111483084038e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.632
Plasma Protein Binding (PPB):	32.352664947509766%
Volume Distribution (VD):	1.278
Pgp-substrate:	61.43701171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	7.289
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.278
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.664
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.661
Carcinogencity:	0.1
Eye Corrosion:	0.874
Eye Irritation:	0.865
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC475881

Natural Product ID:	NPC475881
*Common Name:**	LWONQONPHFIJAL-LMGGXVIJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LWONQONPHFIJAL-LMGGXVIJSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-7-8-6-9(16)15(3)10(19-15)4-5-14(2)12(20-14)11(8)18-13(7)17/h8-12,16H,1,4-6H2,2-3H3/t8-,9+,10+,11-,12-,14+,15+/m0/s1
SMILES:	O=C1O[C@H]2[C@H](C1=C)C[C@@H](O)[C@@]1(C)O[C@@H]1CC[C@@]1([C@H]2O1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517917
PubChem CID:	44584231
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
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

Activity Type	# Activity
Cell Line	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT404	Cell Line	CCRF-CEM	Homo sapiens	ED50	=	1.44	ug ml-1	PMID[548487]
NPT112	Cell Line	MOLT-4	Homo sapiens	ED50	=	1.67	ug ml-1	PMID[548487]
NPT379	Cell Line	HOP-62	Homo sapiens	ED50	=	4.82	ug ml-1	PMID[548487]
NPT455	Cell Line	NCI-H522	Homo sapiens	ED50	=	1.53	ug ml-1	PMID[548487]
NPT393	Cell Line	HCT-116	Homo sapiens	ED50	=	4.96	ug ml-1	PMID[548487]
NPT323	Cell Line	SW-620	Homo sapiens	ED50	=	3.72	ug ml-1	PMID[548487]
NPT395	Cell Line	SF-268	Homo sapiens	ED50	=	13.47	ug ml-1	PMID[548487]
NPT392	Cell Line	SNB-75	Homo sapiens	ED50	=	20.75	ug ml-1	PMID[548487]
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[548487]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	=	3.28	ug ml-1	PMID[548487]
NPT381	Cell Line	OVCAR-8	Homo sapiens	ED50	=	9.72	ug ml-1	PMID[548487]
NPT369	Cell Line	ACHN	Homo sapiens	ED50	=	3.84	ug ml-1	PMID[548487]
NPT371	Cell Line	UO-31	Homo sapiens	ED50	=	4.76	ug ml-1	PMID[548487]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	7.59	ug ml-1	PMID[548487]
NPT90	Cell Line	DU-145	Homo sapiens	ED50	=	10.22	ug ml-1	PMID[548487]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	ED50	=	5.35	ug ml-1	PMID[548487]

☑ 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 NPC475881 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	271
0.1-0.2	2037
0.2-0.3	6554
0.3-0.4	14883
0.4-0.5	10794
0.5-0.6	5805
0.6-0.7	1957
0.7-0.8	322
0.8-0.85	55
0.85-0.9	13
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70251
0.9341	High Similarity	NPC474213
0.9176	High Similarity	NPC470238
0.9176	High Similarity	NPC138647
0.908	High Similarity	NPC5130
0.9	High Similarity	NPC212486
0.8901	High Similarity	NPC190294
0.8864	High Similarity	NPC186148
0.8851	High Similarity	NPC304509
0.8851	High Similarity	NPC47958
0.8851	High Similarity	NPC149725
0.8804	High Similarity	NPC270013
0.8804	High Similarity	NPC14961
0.8764	High Similarity	NPC58219
0.8764	High Similarity	NPC177629
0.875	High Similarity	NPC470242
0.8723	High Similarity	NPC473326
0.871	High Similarity	NPC39859
0.871	High Similarity	NPC76862
0.871	High Similarity	NPC158416
0.871	High Similarity	NPC470883
0.8696	High Similarity	NPC81386
0.8696	High Similarity	NPC474035
0.8696	High Similarity	NPC57405
0.8696	High Similarity	NPC303942
0.8681	High Similarity	NPC184463
0.8667	High Similarity	NPC92974
0.8617	High Similarity	NPC328562
0.8617	High Similarity	NPC323421
0.8587	High Similarity	NPC475912
0.8556	High Similarity	NPC202672
0.8542	High Similarity	NPC201718
0.8539	High Similarity	NPC474949
0.8539	High Similarity	NPC475019
0.8523	High Similarity	NPC474780
0.8511	High Similarity	NPC476315
0.8511	High Similarity	NPC31645
0.8511	High Similarity	NPC473859
0.8485	Intermediate Similarity	NPC477513
0.8478	Intermediate Similarity	NPC30515
0.8478	Intermediate Similarity	NPC12172
0.8478	Intermediate Similarity	NPC208886
0.8462	Intermediate Similarity	NPC151770
0.8462	Intermediate Similarity	NPC307411
0.8454	Intermediate Similarity	NPC471148
0.8444	Intermediate Similarity	NPC190753
0.8438	Intermediate Similarity	NPC471381
0.8438	Intermediate Similarity	NPC288876
0.8427	Intermediate Similarity	NPC329749
0.8404	Intermediate Similarity	NPC36954
0.8404	Intermediate Similarity	NPC475659
0.8387	Intermediate Similarity	NPC81419
0.8387	Intermediate Similarity	NPC179746
0.8387	Intermediate Similarity	NPC476300
0.837	Intermediate Similarity	NPC51004
0.837	Intermediate Similarity	NPC474323
0.837	Intermediate Similarity	NPC206614
0.8351	Intermediate Similarity	NPC476270
0.8333	Intermediate Similarity	NPC476015
0.8333	Intermediate Similarity	NPC45125
0.8333	Intermediate Similarity	NPC474762
0.8316	Intermediate Similarity	NPC476009
0.8316	Intermediate Similarity	NPC279621
0.8315	Intermediate Similarity	NPC475963
0.8315	Intermediate Similarity	NPC3464
0.8315	Intermediate Similarity	NPC151176
0.8298	Intermediate Similarity	NPC471147
0.8265	Intermediate Similarity	NPC320019
0.8265	Intermediate Similarity	NPC324017
0.8261	Intermediate Similarity	NPC173926
0.8256	Intermediate Similarity	NPC470014
0.8247	Intermediate Similarity	NPC186861
0.8242	Intermediate Similarity	NPC231889
0.8229	Intermediate Similarity	NPC471150
0.8222	Intermediate Similarity	NPC319795
0.8222	Intermediate Similarity	NPC50362
0.8222	Intermediate Similarity	NPC38468
0.8211	Intermediate Similarity	NPC475900
0.8202	Intermediate Similarity	NPC474472
0.8202	Intermediate Similarity	NPC257358
0.8191	Intermediate Similarity	NPC475838
0.8191	Intermediate Similarity	NPC125674
0.8191	Intermediate Similarity	NPC228451
0.8172	Intermediate Similarity	NPC474761
0.8172	Intermediate Similarity	NPC475748
0.8172	Intermediate Similarity	NPC473619
0.8172	Intermediate Similarity	NPC476004
0.8163	Intermediate Similarity	NPC473332
0.8163	Intermediate Similarity	NPC15993
0.8152	Intermediate Similarity	NPC473715
0.8152	Intermediate Similarity	NPC281516
0.8144	Intermediate Similarity	NPC208233
0.8137	Intermediate Similarity	NPC139838
0.8137	Intermediate Similarity	NPC59489
0.8125	Intermediate Similarity	NPC35498
0.8105	Intermediate Similarity	NPC473316
0.8105	Intermediate Similarity	NPC473330
0.8105	Intermediate Similarity	NPC474247
0.8085	Intermediate Similarity	NPC473321
0.8065	Intermediate Similarity	NPC474951
0.8065	Intermediate Similarity	NPC474032
0.8065	Intermediate Similarity	NPC166919
0.8061	Intermediate Similarity	NPC475949
0.8043	Intermediate Similarity	NPC118601
0.8021	Intermediate Similarity	NPC476053
0.8021	Intermediate Similarity	NPC471141
0.802	Intermediate Similarity	NPC243998
0.802	Intermediate Similarity	NPC44004
0.802	Intermediate Similarity	NPC54737
0.8	Intermediate Similarity	NPC295204
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC288240
0.8	Intermediate Similarity	NPC272814
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC128429
0.798	Intermediate Similarity	NPC477511
0.798	Intermediate Similarity	NPC474339
0.798	Intermediate Similarity	NPC164598
0.798	Intermediate Similarity	NPC47880
0.798	Intermediate Similarity	NPC264477
0.7979	Intermediate Similarity	NPC49342
0.7979	Intermediate Similarity	NPC65359
0.7979	Intermediate Similarity	NPC251385
0.7959	Intermediate Similarity	NPC471144
0.7957	Intermediate Similarity	NPC178875
0.7938	Intermediate Similarity	NPC230800
0.7935	Intermediate Similarity	NPC162071
0.7935	Intermediate Similarity	NPC50637
0.7921	Intermediate Similarity	NPC474741
0.7917	Intermediate Similarity	NPC71589
0.79	Intermediate Similarity	NPC474747
0.79	Intermediate Similarity	NPC149371
0.7895	Intermediate Similarity	NPC155215
0.7895	Intermediate Similarity	NPC469627
0.7895	Intermediate Similarity	NPC329952
0.7872	Intermediate Similarity	NPC215556
0.7865	Intermediate Similarity	NPC474981
0.7857	Intermediate Similarity	NPC471140
0.7857	Intermediate Similarity	NPC474313
0.7849	Intermediate Similarity	NPC248602
0.7843	Intermediate Similarity	NPC223450
0.7835	Intermediate Similarity	NPC472873
0.7835	Intermediate Similarity	NPC107476
0.7835	Intermediate Similarity	NPC471142
0.7826	Intermediate Similarity	NPC21469
0.7822	Intermediate Similarity	NPC475871
0.7822	Intermediate Similarity	NPC475945
0.7812	Intermediate Similarity	NPC258216
0.7802	Intermediate Similarity	NPC11620
0.78	Intermediate Similarity	NPC475958
0.7789	Intermediate Similarity	NPC475855
0.7789	Intermediate Similarity	NPC312042
0.7789	Intermediate Similarity	NPC216284
0.7778	Intermediate Similarity	NPC187268
0.7778	Intermediate Similarity	NPC279561
0.7766	Intermediate Similarity	NPC217983
0.7766	Intermediate Similarity	NPC153805
0.7766	Intermediate Similarity	NPC207114
0.7766	Intermediate Similarity	NPC79549
0.7755	Intermediate Similarity	NPC477921
0.7745	Intermediate Similarity	NPC100487
0.7745	Intermediate Similarity	NPC471143
0.7745	Intermediate Similarity	NPC477510
0.7742	Intermediate Similarity	NPC236692
0.7742	Intermediate Similarity	NPC309757
0.7742	Intermediate Similarity	NPC187661
0.7736	Intermediate Similarity	NPC475851
0.7736	Intermediate Similarity	NPC475924
0.7732	Intermediate Similarity	NPC140543
0.7717	Intermediate Similarity	NPC191476
0.7717	Intermediate Similarity	NPC114979
0.7717	Intermediate Similarity	NPC72464
0.7708	Intermediate Similarity	NPC470379
0.7708	Intermediate Similarity	NPC184063
0.7708	Intermediate Similarity	NPC131209
0.7708	Intermediate Similarity	NPC158061
0.7708	Intermediate Similarity	NPC470373
0.77	Intermediate Similarity	NPC70865
0.77	Intermediate Similarity	NPC477512
0.7684	Intermediate Similarity	NPC155935
0.7684	Intermediate Similarity	NPC295312
0.7684	Intermediate Similarity	NPC473564
0.7677	Intermediate Similarity	NPC181151
0.7677	Intermediate Similarity	NPC311904
0.767	Intermediate Similarity	NPC474101
0.766	Intermediate Similarity	NPC475703
0.766	Intermediate Similarity	NPC270270
0.7653	Intermediate Similarity	NPC163228
0.7653	Intermediate Similarity	NPC477922
0.7634	Intermediate Similarity	NPC474547
0.7634	Intermediate Similarity	NPC255307
0.7634	Intermediate Similarity	NPC137033
0.7629	Intermediate Similarity	NPC135776
0.7629	Intermediate Similarity	NPC153590
0.7624	Intermediate Similarity	NPC474742
0.7604	Intermediate Similarity	NPC246173
0.7604	Intermediate Similarity	NPC179394
0.7604	Intermediate Similarity	NPC62815
0.7604	Intermediate Similarity	NPC35809
0.7604	Intermediate Similarity	NPC54065

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 NPC475881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	2760
0.2-0.3	3738
0.3-0.4	1616
0.4-0.5	535
0.5-0.6	163
0.6-0.7	13
0.7-0.8	3
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
0.8222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6698	Approved
0.7604	Intermediate Similarity	NPD46	Approved
0.732	Intermediate Similarity	NPD1695	Approved
0.7245	Intermediate Similarity	NPD7838	Discovery
0.7129	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6818	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6686	Approved
0.6542	Remote Similarity	NPD6648	Approved
0.6449	Remote Similarity	NPD4225	Approved
0.6449	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6053	Discontinued
0.6339	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8517	Approved
0.6333	Remote Similarity	NPD8515	Approved
0.6333	Remote Similarity	NPD8516	Approved
0.6333	Remote Similarity	NPD8513	Phase 3
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6271	Remote Similarity	NPD7115	Discovery
0.6263	Remote Similarity	NPD6435	Approved
0.623	Remote Similarity	NPD7642	Approved
0.6226	Remote Similarity	NPD5282	Discontinued
0.62	Remote Similarity	NPD7154	Phase 3
0.6176	Remote Similarity	NPD4249	Approved
0.6154	Remote Similarity	NPD8133	Approved
0.6117	Remote Similarity	NPD4251	Approved
0.6117	Remote Similarity	NPD4250	Approved
0.6106	Remote Similarity	NPD6008	Approved
0.6098	Remote Similarity	NPD7829	Approved
0.6098	Remote Similarity	NPD7830	Approved
0.6095	Remote Similarity	NPD5785	Approved
0.608	Remote Similarity	NPD8074	Phase 3
0.6061	Remote Similarity	NPD5368	Approved
0.6019	Remote Similarity	NPD5786	Approved
0.6017	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD6101	Approved
0.5984	Remote Similarity	NPD6319	Approved
0.5963	Remote Similarity	NPD7839	Suspended
0.595	Remote Similarity	NPD7641	Discontinued
0.5935	Remote Similarity	NPD8268	Approved
0.5935	Remote Similarity	NPD8266	Approved
0.5935	Remote Similarity	NPD8269	Approved
0.5935	Remote Similarity	NPD8267	Approved
0.5922	Remote Similarity	NPD5363	Approved
0.5922	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4820	Approved
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4819	Approved
0.59	Remote Similarity	NPD4821	Approved
0.59	Remote Similarity	NPD4822	Approved
0.5888	Remote Similarity	NPD6411	Approved
0.5882	Remote Similarity	NPD5362	Discontinued
0.5873	Remote Similarity	NPD8273	Phase 1
0.5873	Remote Similarity	NPD8451	Approved
0.5859	Remote Similarity	NPD7319	Approved
0.5856	Remote Similarity	NPD7638	Approved
0.5827	Remote Similarity	NPD8448	Approved
0.5824	Remote Similarity	NPD7909	Approved
0.5806	Remote Similarity	NPD6921	Approved
0.5804	Remote Similarity	NPD7640	Approved
0.5804	Remote Similarity	NPD7639	Approved
0.5798	Remote Similarity	NPD8297	Approved
0.5794	Remote Similarity	NPD7492	Approved
0.5784	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4269	Approved
0.5784	Remote Similarity	NPD4270	Approved
0.5776	Remote Similarity	NPD6412	Phase 2
0.5776	Remote Similarity	NPD5697	Approved
0.5761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD1700	Approved
0.5748	Remote Similarity	NPD6616	Approved
0.5738	Remote Similarity	NPD6009	Approved
0.5738	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6899	Approved
0.5726	Remote Similarity	NPD6054	Approved
0.5726	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD7604	Phase 2
0.5714	Remote Similarity	NPD6650	Approved
0.5703	Remote Similarity	NPD7078	Approved
0.57	Remote Similarity	NPD4271	Approved
0.57	Remote Similarity	NPD4268	Approved
0.5692	Remote Similarity	NPD8392	Approved
0.5692	Remote Similarity	NPD8391	Approved
0.5692	Remote Similarity	NPD8390	Approved
0.569	Remote Similarity	NPD7128	Approved
0.569	Remote Similarity	NPD6402	Approved
0.569	Remote Similarity	NPD5739	Approved
0.569	Remote Similarity	NPD6675	Approved
0.5688	Remote Similarity	NPD6399	Phase 3
0.568	Remote Similarity	NPD5983	Phase 2
0.568	Remote Similarity	NPD8444	Approved
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD6016	Approved
0.5678	Remote Similarity	NPD6012	Approved
0.5678	Remote Similarity	NPD6373	Approved
0.5678	Remote Similarity	NPD6372	Approved
0.5678	Remote Similarity	NPD6013	Approved
0.5678	Remote Similarity	NPD6014	Approved
0.5669	Remote Similarity	NPD8340	Approved
0.5669	Remote Similarity	NPD8342	Approved
0.5669	Remote Similarity	NPD8299	Approved
0.5669	Remote Similarity	NPD8341	Approved
0.5659	Remote Similarity	NPD7736	Approved
0.5649	Remote Similarity	NPD7260	Phase 2
0.5648	Remote Similarity	NPD3168	Discontinued
0.5641	Remote Similarity	NPD5701	Approved
0.5635	Remote Similarity	NPD6370	Approved
0.5635	Remote Similarity	NPD5988	Approved
0.5635	Remote Similarity	NPD8080	Discontinued
0.563	Remote Similarity	NPD6883	Approved
0.563	Remote Similarity	NPD7102	Approved
0.563	Remote Similarity	NPD7290	Approved
0.561	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5606	Remote Similarity	NPD6845	Suspended
0.5603	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.56	Remote Similarity	NPD6059	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