NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	162.07
Volume:	171.438
LogP:	1.17
LogD:	1.27
LogS:	-2.172
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	2.555
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.554
MDCK Permeability:	1.9580718799261376e-05
Pgp-inhibitor:	0.128
Pgp-substrate:	0.855
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.74
Plasma Protein Binding (PPB):	30.435077667236328%
Volume Distribution (VD):	0.682
Pgp-substrate:	65.01939392089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.343
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.174
CYP2C19-substrate:	0.339
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.43
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.379

ADMET: Excretion

Clearance (CL):	10.286
Half-life (T1/2):	0.641

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.121
Carcinogencity:	0.871
Eye Corrosion:	0.069
Eye Irritation:	0.927
Respiratory Toxicity:	0.416

Download Data

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

Natural Product: NPC211439

Natural Product ID:	NPC211439
*Common Name:**	(-)-4-Hydroxy-Alpha-Tetralone
IUPAC Name:	(4S)-4-hydroxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	BGPJTIXJFAGUIF-VIFPVBQESA-N
Standard InCHI:	InChI=1S/C10H10O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-4,9,11H,5-6H2/t9-/m0/s1
SMILES:	c1ccc2c(c1)[C@H](CCC2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2281757
PubChem CID:	11240662
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444709]
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9599266]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26892	Juglans mandshurica	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20411	Engelhardia roxburghiana	Species	Juglandaceae	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
MIC	7
Others	1

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	50.0	ug.mL-1	PMID[495104]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	4.0	ug.mL-1	PMID[495104]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	250.0	ug.mL-1	PMID[495105]
NPT19	Organism	Escherichia coli	Escherichia coli	FC	=	4.0	n.a.	PMID[495105]

☑ 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 NPC211439 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	234
0.1-0.2	1176
0.2-0.3	2930
0.3-0.4	8474
0.4-0.5	12037
0.5-0.6	11184
0.6-0.7	5726
0.7-0.8	890
0.8-0.85	35
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8932	High Similarity	NPC249067
0.8716	High Similarity	NPC196673
0.8673	High Similarity	NPC473662
0.8673	High Similarity	NPC7151
0.8673	High Similarity	NPC216297
0.8654	High Similarity	NPC255676
0.8529	High Similarity	NPC289201
0.8448	Intermediate Similarity	NPC217756
0.8447	Intermediate Similarity	NPC329387
0.8447	Intermediate Similarity	NPC229242
0.8447	Intermediate Similarity	NPC317280
0.844	Intermediate Similarity	NPC474057
0.8435	Intermediate Similarity	NPC472981
0.8305	Intermediate Similarity	NPC234890
0.8305	Intermediate Similarity	NPC74507
0.8304	Intermediate Similarity	NPC186933
0.8288	Intermediate Similarity	NPC272524
0.8286	Intermediate Similarity	NPC282895
0.8257	Intermediate Similarity	NPC318327
0.8208	Intermediate Similarity	NPC25458
0.8208	Intermediate Similarity	NPC284477
0.8198	Intermediate Similarity	NPC158282
0.8165	Intermediate Similarity	NPC141523
0.8165	Intermediate Similarity	NPC34715
0.8158	Intermediate Similarity	NPC108288
0.8151	Intermediate Similarity	NPC152525
0.8151	Intermediate Similarity	NPC68756
0.8148	Intermediate Similarity	NPC105899
0.8115	Intermediate Similarity	NPC262819
0.8108	Intermediate Similarity	NPC260818
0.8099	Intermediate Similarity	NPC470841
0.8091	Intermediate Similarity	NPC85493
0.8037	Intermediate Similarity	NPC304873
0.8036	Intermediate Similarity	NPC66208
0.8036	Intermediate Similarity	NPC321852
0.8036	Intermediate Similarity	NPC471188
0.8034	Intermediate Similarity	NPC206778
0.8034	Intermediate Similarity	NPC285829
0.8033	Intermediate Similarity	NPC247250
0.8033	Intermediate Similarity	NPC767
0.8019	Intermediate Similarity	NPC217621
0.8017	Intermediate Similarity	NPC169913
0.8	Intermediate Similarity	NPC158157
0.8	Intermediate Similarity	NPC156021
0.8	Intermediate Similarity	NPC253423
0.7983	Intermediate Similarity	NPC300274
0.7982	Intermediate Similarity	NPC306740
0.7982	Intermediate Similarity	NPC134120
0.7982	Intermediate Similarity	NPC474685
0.7967	Intermediate Similarity	NPC27712
0.7965	Intermediate Similarity	NPC128368
0.7965	Intermediate Similarity	NPC231717
0.7941	Intermediate Similarity	NPC62765
0.7934	Intermediate Similarity	NPC275576
0.7928	Intermediate Similarity	NPC83628
0.7928	Intermediate Similarity	NPC265407
0.7925	Intermediate Similarity	NPC160548
0.7925	Intermediate Similarity	NPC175852
0.7925	Intermediate Similarity	NPC210529
0.7917	Intermediate Similarity	NPC375356
0.7905	Intermediate Similarity	NPC61944
0.7903	Intermediate Similarity	NPC31799
0.7903	Intermediate Similarity	NPC136588
0.7903	Intermediate Similarity	NPC199253
0.7899	Intermediate Similarity	NPC120545
0.7895	Intermediate Similarity	NPC237366
0.7895	Intermediate Similarity	NPC477411
0.7895	Intermediate Similarity	NPC153053
0.7881	Intermediate Similarity	NPC133302
0.7876	Intermediate Similarity	NPC114682
0.7876	Intermediate Similarity	NPC212718
0.787	Intermediate Similarity	NPC222390
0.787	Intermediate Similarity	NPC244427
0.7863	Intermediate Similarity	NPC41567
0.7863	Intermediate Similarity	NPC249435
0.7851	Intermediate Similarity	NPC142956
0.7845	Intermediate Similarity	NPC477453
0.784	Intermediate Similarity	NPC93015
0.7833	Intermediate Similarity	NPC223351
0.7833	Intermediate Similarity	NPC307174
0.7833	Intermediate Similarity	NPC91478
0.7818	Intermediate Similarity	NPC163734
0.781	Intermediate Similarity	NPC206764
0.7798	Intermediate Similarity	NPC60679
0.7798	Intermediate Similarity	NPC274443
0.7798	Intermediate Similarity	NPC329556
0.7798	Intermediate Similarity	NPC89886
0.7797	Intermediate Similarity	NPC476645
0.7797	Intermediate Similarity	NPC473767
0.7797	Intermediate Similarity	NPC232178
0.7797	Intermediate Similarity	NPC472708
0.7788	Intermediate Similarity	NPC210089
0.7788	Intermediate Similarity	NPC476003
0.7788	Intermediate Similarity	NPC265513
0.7788	Intermediate Similarity	NPC474157
0.7787	Intermediate Similarity	NPC103540
0.7778	Intermediate Similarity	NPC42211
0.7778	Intermediate Similarity	NPC110609
0.7778	Intermediate Similarity	NPC246693
0.7778	Intermediate Similarity	NPC17843
0.7778	Intermediate Similarity	NPC70622
0.7778	Intermediate Similarity	NPC242358
0.7768	Intermediate Similarity	NPC224584
0.7768	Intermediate Similarity	NPC17525
0.776	Intermediate Similarity	NPC147757
0.7759	Intermediate Similarity	NPC226093
0.7759	Intermediate Similarity	NPC322197
0.7759	Intermediate Similarity	NPC240163
0.7759	Intermediate Similarity	NPC149691
0.7759	Intermediate Similarity	NPC161304
0.775	Intermediate Similarity	NPC18785
0.7748	Intermediate Similarity	NPC119271
0.7748	Intermediate Similarity	NPC185763
0.7748	Intermediate Similarity	NPC83409
0.7739	Intermediate Similarity	NPC474363
0.7739	Intermediate Similarity	NPC196075
0.7739	Intermediate Similarity	NPC307651
0.7727	Intermediate Similarity	NPC31786
0.7727	Intermediate Similarity	NPC114594
0.7724	Intermediate Similarity	NPC474106
0.7724	Intermediate Similarity	NPC96915
0.7724	Intermediate Similarity	NPC51037
0.7724	Intermediate Similarity	NPC3224
0.7717	Intermediate Similarity	NPC52407
0.7714	Intermediate Similarity	NPC261181
0.7712	Intermediate Similarity	NPC318173
0.7705	Intermediate Similarity	NPC310540
0.7692	Intermediate Similarity	NPC110704
0.7686	Intermediate Similarity	NPC46634
0.7686	Intermediate Similarity	NPC65627
0.7685	Intermediate Similarity	NPC118343
0.7679	Intermediate Similarity	NPC112903
0.7679	Intermediate Similarity	NPC56493
0.7679	Intermediate Similarity	NPC249811
0.7679	Intermediate Similarity	NPC470391
0.7679	Intermediate Similarity	NPC226699
0.7672	Intermediate Similarity	NPC476357
0.7672	Intermediate Similarity	NPC285350
0.7672	Intermediate Similarity	NPC93181
0.7672	Intermediate Similarity	NPC274839
0.7667	Intermediate Similarity	NPC190971
0.7667	Intermediate Similarity	NPC216216
0.7661	Intermediate Similarity	NPC115797
0.7661	Intermediate Similarity	NPC51448
0.7658	Intermediate Similarity	NPC172483
0.7658	Intermediate Similarity	NPC209632
0.7656	Intermediate Similarity	NPC474659
0.7656	Intermediate Similarity	NPC23894
0.7652	Intermediate Similarity	NPC470253
0.7652	Intermediate Similarity	NPC13784
0.7647	Intermediate Similarity	NPC194326
0.7642	Intermediate Similarity	NPC167055
0.7642	Intermediate Similarity	NPC472592
0.7642	Intermediate Similarity	NPC236405
0.7642	Intermediate Similarity	NPC240744
0.7638	Intermediate Similarity	NPC478190
0.7636	Intermediate Similarity	NPC160382
0.7636	Intermediate Similarity	NPC247976
0.7632	Intermediate Similarity	NPC133308
0.7632	Intermediate Similarity	NPC116842
0.7627	Intermediate Similarity	NPC323440
0.7627	Intermediate Similarity	NPC125252
0.7627	Intermediate Similarity	NPC222968
0.7627	Intermediate Similarity	NPC269414
0.7627	Intermediate Similarity	NPC80605
0.7623	Intermediate Similarity	NPC275145
0.7623	Intermediate Similarity	NPC228739
0.7623	Intermediate Similarity	NPC135062
0.7623	Intermediate Similarity	NPC85511
0.7615	Intermediate Similarity	NPC112552
0.7611	Intermediate Similarity	NPC475282
0.7611	Intermediate Similarity	NPC17417
0.7611	Intermediate Similarity	NPC10251
0.7607	Intermediate Similarity	NPC135730
0.7607	Intermediate Similarity	NPC62138
0.7603	Intermediate Similarity	NPC198336
0.7603	Intermediate Similarity	NPC167323
0.7603	Intermediate Similarity	NPC295034
0.7603	Intermediate Similarity	NPC269923
0.76	Intermediate Similarity	NPC172984
0.76	Intermediate Similarity	NPC48248
0.76	Intermediate Similarity	NPC165257
0.76	Intermediate Similarity	NPC237225
0.76	Intermediate Similarity	NPC282923
0.7589	Intermediate Similarity	NPC30594
0.7589	Intermediate Similarity	NPC95178
0.7589	Intermediate Similarity	NPC187913
0.7589	Intermediate Similarity	NPC29989
0.7589	Intermediate Similarity	NPC6984
0.7589	Intermediate Similarity	NPC69332
0.7589	Intermediate Similarity	NPC37622
0.7586	Intermediate Similarity	NPC11824
0.7586	Intermediate Similarity	NPC308744
0.7583	Intermediate Similarity	NPC472680
0.7583	Intermediate Similarity	NPC472679
0.7583	Intermediate Similarity	NPC133389
0.7583	Intermediate Similarity	NPC473243
0.7583	Intermediate Similarity	NPC234337
0.7583	Intermediate Similarity	NPC183339
0.7581	Intermediate Similarity	NPC231774

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 NPC211439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	886
0.2-0.3	1329
0.3-0.4	2672
0.4-0.5	2406
0.5-0.6	1262
0.6-0.7	311
0.7-0.8	51
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8932	High Similarity	NPD1237	Approved
0.8158	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD9256	Approved
0.7941	Intermediate Similarity	NPD9258	Approved
0.7925	Intermediate Similarity	NPD9495	Approved
0.7826	Intermediate Similarity	NPD5951	Approved
0.7798	Intermediate Similarity	NPD1930	Approved
0.7798	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1929	Approved
0.7788	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD1470	Approved
0.775	Intermediate Similarity	NPD1201	Approved
0.7727	Intermediate Similarity	NPD164	Approved
0.7714	Intermediate Similarity	NPD1202	Approved
0.7706	Intermediate Similarity	NPD1932	Approved
0.7685	Intermediate Similarity	NPD1238	Approved
0.7611	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2182	Approved
0.7565	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD9259	Approved
0.7549	Intermediate Similarity	NPD9257	Approved
0.7541	Intermediate Similarity	NPD4878	Approved
0.7523	Intermediate Similarity	NPD2066	Phase 3
0.7521	Intermediate Similarity	NPD2629	Approved
0.748	Intermediate Similarity	NPD5159	Phase 2
0.748	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5157	Phase 1
0.7477	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD7008	Discontinued
0.7321	Intermediate Similarity	NPD6647	Phase 2
0.7308	Intermediate Similarity	NPD650	Approved
0.7304	Intermediate Similarity	NPD2329	Discontinued
0.7302	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD9491	Approved
0.7228	Intermediate Similarity	NPD942	Approved
0.7217	Intermediate Similarity	NPD9264	Approved
0.7217	Intermediate Similarity	NPD9263	Approved
0.7217	Intermediate Similarity	NPD9267	Approved
0.7196	Intermediate Similarity	NPD1239	Approved
0.7172	Intermediate Similarity	NPD9294	Approved
0.7168	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD74	Approved
0.7155	Intermediate Similarity	NPD9266	Approved
0.713	Intermediate Similarity	NPD1508	Approved
0.7119	Intermediate Similarity	NPD9508	Approved
0.7107	Intermediate Similarity	NPD9493	Approved
0.7087	Intermediate Similarity	NPD1164	Approved
0.7077	Intermediate Similarity	NPD3764	Approved
0.7073	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD226	Approved
0.704	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7609	Phase 3
0.7016	Intermediate Similarity	NPD3019	Approved
0.7016	Intermediate Similarity	NPD2932	Approved
0.7015	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1876	Approved
0.7	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1693	Approved
0.7	Intermediate Similarity	NPD9260	Approved
0.6992	Remote Similarity	NPD9545	Approved
0.6972	Remote Similarity	NPD7631	Approved
0.697	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD1089	Approved
0.6944	Remote Similarity	NPD1086	Approved
0.6944	Remote Similarity	NPD1090	Approved
0.6942	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1843	Approved
0.6929	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5277	Phase 2
0.6912	Remote Similarity	NPD2346	Discontinued
0.6911	Remote Similarity	NPD7610	Discontinued
0.6906	Remote Similarity	NPD7236	Approved
0.6899	Remote Similarity	NPD2798	Approved
0.6899	Remote Similarity	NPD4980	Approved
0.6889	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3317	Approved
0.6875	Remote Similarity	NPD1565	Approved
0.6875	Remote Similarity	NPD1564	Approved
0.6875	Remote Similarity	NPD3495	Discontinued
0.6875	Remote Similarity	NPD1566	Phase 3
0.687	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.687	Remote Similarity	NPD9261	Approved
0.6866	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9490	Approved
0.686	Remote Similarity	NPD1241	Discontinued
0.6852	Remote Similarity	NPD800	Approved
0.6838	Remote Similarity	NPD5405	Approved
0.6838	Remote Similarity	NPD5404	Approved
0.6838	Remote Similarity	NPD5406	Approved
0.6838	Remote Similarity	NPD5408	Approved
0.6825	Remote Similarity	NPD4879	Approved
0.6818	Remote Similarity	NPD2313	Discontinued
0.6818	Remote Similarity	NPD1088	Approved
0.681	Remote Similarity	NPD5909	Discontinued
0.6807	Remote Similarity	NPD1317	Discontinued
0.6803	Remote Similarity	NPD9281	Approved
0.6796	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1989	Approved
0.6772	Remote Similarity	NPD6287	Discontinued
0.6765	Remote Similarity	NPD1510	Phase 2
0.6765	Remote Similarity	NPD227	Approved
0.6765	Remote Similarity	NPD225	Approved
0.6762	Remote Similarity	NPD3971	Phase 1
0.6752	Remote Similarity	NPD5048	Discontinued
0.6746	Remote Similarity	NPD5305	Approved
0.6746	Remote Similarity	NPD2345	Approved
0.6746	Remote Similarity	NPD5306	Approved
0.6744	Remote Similarity	NPD1283	Approved
0.6741	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2651	Approved
0.6736	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2649	Approved
0.672	Remote Similarity	NPD7009	Phase 2
0.6719	Remote Similarity	NPD3972	Approved
0.6718	Remote Similarity	NPD9494	Approved
0.6716	Remote Similarity	NPD1240	Approved
0.6693	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4135	Approved
0.6693	Remote Similarity	NPD4136	Approved
0.6693	Remote Similarity	NPD4106	Approved
0.6692	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD1087	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD7239	Suspended
0.6643	Remote Similarity	NPD3750	Approved
0.6643	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7003	Approved
0.6643	Remote Similarity	NPD6273	Approved
0.6643	Remote Similarity	NPD4628	Phase 3
0.6642	Remote Similarity	NPD6663	Approved
0.6642	Remote Similarity	NPD2799	Discontinued
0.6642	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6085	Phase 2
0.6641	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4807	Approved
0.6641	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4806	Approved
0.6639	Remote Similarity	NPD2342	Discontinued
0.6621	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1549	Phase 2
0.6618	Remote Similarity	NPD1607	Approved
0.6615	Remote Similarity	NPD1888	Phase 1
0.6614	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3020	Approved
0.6607	Remote Similarity	NPD1563	Approved
0.6594	Remote Similarity	NPD2935	Discontinued
0.6593	Remote Similarity	NPD4453	Approved
0.6593	Remote Similarity	NPD4452	Approved
0.6593	Remote Similarity	NPD4445	Approved
0.6591	Remote Similarity	NPD5736	Approved
0.6589	Remote Similarity	NPD9717	Approved
0.6587	Remote Similarity	NPD3091	Approved
0.6579	Remote Similarity	NPD288	Approved
0.6573	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD3023	Approved
0.6562	Remote Similarity	NPD3026	Approved
0.6552	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3300	Phase 2
0.6549	Remote Similarity	NPD2933	Approved
0.6549	Remote Similarity	NPD2934	Approved
0.6547	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1471	Phase 3
0.6538	Remote Similarity	NPD1755	Approved
0.6535	Remote Similarity	NPD4105	Approved
0.6535	Remote Similarity	NPD3025	Approved
0.6535	Remote Similarity	NPD3024	Approved
0.6535	Remote Similarity	NPD9268	Approved
0.6535	Remote Similarity	NPD4102	Approved
0.6532	Remote Similarity	NPD1246	Approved
0.6529	Remote Similarity	NPD2067	Discontinued
0.6522	Remote Similarity	NPD9612	Approved
0.6522	Remote Similarity	NPD7305	Phase 1
0.6522	Remote Similarity	NPD9609	Approved
0.6522	Remote Similarity	NPD9611	Approved
0.6519	Remote Similarity	NPD7713	Phase 3
0.6519	Remote Similarity	NPD520	Approved
0.6519	Remote Similarity	NPD7715	Approved
0.6519	Remote Similarity	NPD7714	Approved
0.6519	Remote Similarity	NPD7961	Discontinued
0.6514	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4793	Discontinued
0.6512	Remote Similarity	NPD1281	Approved
0.6507	Remote Similarity	NPD3226	Approved
0.6504	Remote Similarity	NPD7635	Approved
0.6504	Remote Similarity	NPD6858	Approved
0.6504	Remote Similarity	NPD7094	Approved
0.65	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6039	Approved
0.6493	Remote Similarity	NPD6966	Discovery
0.6491	Remote Similarity	NPD2860	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