NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.03
Volume:	145.636
LogP:	0.651
LogD:	1.101
LogS:	-1.847
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	2.705
Fsp3:	0.125
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:	-4.818
MDCK Permeability:	1.4237532923289109e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.828
Plasma Protein Binding (PPB):	44.569210052490234%
Volume Distribution (VD):	1.175
Pgp-substrate:	44.89436340332031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.309
CYP1A2-substrate:	0.291
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.653
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.548
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	5.192
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.587
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.108
Skin Sensitization:	0.213
Carcinogencity:	0.402
Eye Corrosion:	0.012
Eye Irritation:	0.975
Respiratory Toxicity:	0.225

Download Data

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

Natural Product: NPC237366

Natural Product ID:	NPC237366
*Common Name:**	3-Hydroxy-3H-2-Benzofuran-1-One
IUPAC Name:	3-hydroxy-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	JKNKNWJNCOJPLI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4,7,9H
SMILES:	O=C1OC(c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL234051
PubChem CID:	3804259
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	IC50	=	25000.0	nM	PMID[554512]

☑ 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 NPC237366 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	265
0.1-0.2	1313
0.2-0.3	3359
0.3-0.4	9087
0.4-0.5	11658
0.5-0.6	12063
0.6-0.7	4539
0.7-0.8	357
0.8-0.85	42
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC89886
0.8991	High Similarity	NPC260818
0.8909	High Similarity	NPC321852
0.8807	High Similarity	NPC85493
0.8774	High Similarity	NPC45613
0.875	High Similarity	NPC153053
0.8636	High Similarity	NPC83628
0.8636	High Similarity	NPC265407
0.8624	High Similarity	NPC119271
0.8545	High Similarity	NPC56493
0.8509	High Similarity	NPC306740
0.8505	High Similarity	NPC282895
0.8496	Intermediate Similarity	NPC272524
0.8468	Intermediate Similarity	NPC17417
0.8468	Intermediate Similarity	NPC10251
0.8455	Intermediate Similarity	NPC37622
0.8455	Intermediate Similarity	NPC30594
0.844	Intermediate Similarity	NPC31786
0.8421	Intermediate Similarity	NPC307651
0.8393	Intermediate Similarity	NPC174099
0.8393	Intermediate Similarity	NPC93084
0.8393	Intermediate Similarity	NPC196246
0.8393	Intermediate Similarity	NPC251854
0.8393	Intermediate Similarity	NPC214067
0.8349	Intermediate Similarity	NPC60679
0.8319	Intermediate Similarity	NPC1082
0.8319	Intermediate Similarity	NPC305912
0.8318	Intermediate Similarity	NPC229242
0.8246	Intermediate Similarity	NPC158282
0.8246	Intermediate Similarity	NPC82899
0.8246	Intermediate Similarity	NPC270699
0.8224	Intermediate Similarity	NPC276775
0.8224	Intermediate Similarity	NPC249912
0.8224	Intermediate Similarity	NPC92754
0.819	Intermediate Similarity	NPC474685
0.8165	Intermediate Similarity	NPC42211
0.8158	Intermediate Similarity	NPC476003
0.8148	Intermediate Similarity	NPC225060
0.8148	Intermediate Similarity	NPC78701
0.8148	Intermediate Similarity	NPC35448
0.812	Intermediate Similarity	NPC149691
0.8108	Intermediate Similarity	NPC114594
0.8091	Intermediate Similarity	NPC284477
0.8087	Intermediate Similarity	NPC474314
0.8073	Intermediate Similarity	NPC146351
0.8073	Intermediate Similarity	NPC118343
0.8049	Intermediate Similarity	NPC246166
0.8037	Intermediate Similarity	NPC130398
0.8036	Intermediate Similarity	NPC209632
0.8018	Intermediate Similarity	NPC255676
0.8	Intermediate Similarity	NPC474157
0.8	Intermediate Similarity	NPC210089
0.8	Intermediate Similarity	NPC70624
0.8	Intermediate Similarity	NPC62765
0.8	Intermediate Similarity	NPC167504
0.7949	Intermediate Similarity	NPC474363
0.7931	Intermediate Similarity	NPC79496
0.7895	Intermediate Similarity	NPC211439
0.7886	Intermediate Similarity	NPC223351
0.7874	Intermediate Similarity	NPC27712
0.7857	Intermediate Similarity	NPC474365
0.7857	Intermediate Similarity	NPC301943
0.7826	Intermediate Similarity	NPC99846
0.7826	Intermediate Similarity	NPC269023
0.7798	Intermediate Similarity	NPC61944
0.7797	Intermediate Similarity	NPC308744
0.7778	Intermediate Similarity	NPC169913
0.7768	Intermediate Similarity	NPC188895
0.7768	Intermediate Similarity	NPC304873
0.7748	Intermediate Similarity	NPC217621
0.7748	Intermediate Similarity	NPC325497
0.7748	Intermediate Similarity	NPC203925
0.7742	Intermediate Similarity	NPC46634
0.7731	Intermediate Similarity	NPC210092
0.7731	Intermediate Similarity	NPC81808
0.7727	Intermediate Similarity	NPC253423
0.7719	Intermediate Similarity	NPC269457
0.7712	Intermediate Similarity	NPC474176
0.7698	Intermediate Similarity	NPC275576
0.7698	Intermediate Similarity	NPC9180
0.7698	Intermediate Similarity	NPC100402
0.7692	Intermediate Similarity	NPC243355
0.768	Intermediate Similarity	NPC228739
0.7679	Intermediate Similarity	NPC473325
0.7672	Intermediate Similarity	NPC318327
0.7672	Intermediate Similarity	NPC474364
0.7672	Intermediate Similarity	NPC469636
0.7667	Intermediate Similarity	NPC100353
0.7656	Intermediate Similarity	NPC301857
0.7647	Intermediate Similarity	NPC477411
0.7638	Intermediate Similarity	NPC114096
0.7634	Intermediate Similarity	NPC38420
0.7634	Intermediate Similarity	NPC136608
0.7627	Intermediate Similarity	NPC185840
0.7619	Intermediate Similarity	NPC318107
0.7615	Intermediate Similarity	NPC7012
0.7611	Intermediate Similarity	NPC25458
0.7589	Intermediate Similarity	NPC228435
0.7586	Intermediate Similarity	NPC249811
0.7578	Intermediate Similarity	NPC148026
0.757	Intermediate Similarity	NPC173443
0.7568	Intermediate Similarity	NPC270654
0.7565	Intermediate Similarity	NPC105899
0.7563	Intermediate Similarity	NPC128368
0.7544	Intermediate Similarity	NPC82426
0.7544	Intermediate Similarity	NPC91820
0.7544	Intermediate Similarity	NPC160382
0.7541	Intermediate Similarity	NPC240664
0.754	Intermediate Similarity	NPC471466
0.7521	Intermediate Similarity	NPC226093
0.75	Intermediate Similarity	NPC87069
0.75	Intermediate Similarity	NPC160548
0.75	Intermediate Similarity	NPC210529
0.75	Intermediate Similarity	NPC196075
0.75	Intermediate Similarity	NPC474476
0.75	Intermediate Similarity	NPC175852
0.748	Intermediate Similarity	NPC295664
0.748	Intermediate Similarity	NPC27633
0.748	Intermediate Similarity	NPC94298
0.748	Intermediate Similarity	NPC94637
0.7479	Intermediate Similarity	NPC66208
0.7478	Intermediate Similarity	NPC249067
0.746	Intermediate Similarity	NPC472703
0.7436	Intermediate Similarity	NPC277788
0.7431	Intermediate Similarity	NPC110704
0.7419	Intermediate Similarity	NPC90522
0.7419	Intermediate Similarity	NPC328459
0.7419	Intermediate Similarity	NPC204784
0.7417	Intermediate Similarity	NPC161611
0.7407	Intermediate Similarity	NPC475195
0.7402	Intermediate Similarity	NPC472704
0.7383	Intermediate Similarity	NPC89377
0.7368	Intermediate Similarity	NPC114116
0.7364	Intermediate Similarity	NPC472706
0.736	Intermediate Similarity	NPC233282
0.736	Intermediate Similarity	NPC72977
0.7355	Intermediate Similarity	NPC196673
0.735	Intermediate Similarity	NPC187913
0.735	Intermediate Similarity	NPC37115
0.7348	Intermediate Similarity	NPC233692
0.7333	Intermediate Similarity	NPC471345
0.7333	Intermediate Similarity	NPC212415
0.7328	Intermediate Similarity	NPC82712
0.7328	Intermediate Similarity	NPC242913
0.7328	Intermediate Similarity	NPC272946
0.7328	Intermediate Similarity	NPC280616
0.7328	Intermediate Similarity	NPC171831
0.7323	Intermediate Similarity	NPC217756
0.7317	Intermediate Similarity	NPC128825
0.7317	Intermediate Similarity	NPC131192
0.7317	Intermediate Similarity	NPC128249
0.7313	Intermediate Similarity	NPC473399
0.7313	Intermediate Similarity	NPC477893
0.7313	Intermediate Similarity	NPC232888
0.7313	Intermediate Similarity	NPC477367
0.7313	Intermediate Similarity	NPC477896
0.7313	Intermediate Similarity	NPC473216
0.7308	Intermediate Similarity	NPC51448
0.7308	Intermediate Similarity	NPC115797
0.7308	Intermediate Similarity	NPC472707
0.7302	Intermediate Similarity	NPC50872
0.7299	Intermediate Similarity	NPC77493
0.7297	Intermediate Similarity	NPC261181
0.7295	Intermediate Similarity	NPC186933
0.7295	Intermediate Similarity	NPC476357
0.7293	Intermediate Similarity	NPC477364
0.7288	Intermediate Similarity	NPC470391
0.7288	Intermediate Similarity	NPC156648
0.7287	Intermediate Similarity	NPC121272
0.7287	Intermediate Similarity	NPC470765
0.7287	Intermediate Similarity	NPC476033
0.7287	Intermediate Similarity	NPC79608
0.7286	Intermediate Similarity	NPC469513
0.728	Intermediate Similarity	NPC472708
0.7273	Intermediate Similarity	NPC17693
0.7273	Intermediate Similarity	NPC13784
0.7273	Intermediate Similarity	NPC72915
0.7273	Intermediate Similarity	NPC119631
0.7266	Intermediate Similarity	NPC478250
0.7258	Intermediate Similarity	NPC228318
0.725	Intermediate Similarity	NPC474057
0.7248	Intermediate Similarity	NPC220893
0.7246	Intermediate Similarity	NPC477537
0.7241	Intermediate Similarity	NPC291426
0.7239	Intermediate Similarity	NPC477368
0.7239	Intermediate Similarity	NPC203486
0.7239	Intermediate Similarity	NPC329913
0.7239	Intermediate Similarity	NPC28836
0.7239	Intermediate Similarity	NPC126516
0.7239	Intermediate Similarity	NPC311492
0.7239	Intermediate Similarity	NPC48929
0.7236	Intermediate Similarity	NPC210531
0.7236	Intermediate Similarity	NPC135730
0.7234	Intermediate Similarity	NPC208293
0.7231	Intermediate Similarity	NPC51292
0.7231	Intermediate Similarity	NPC470753
0.7231	Intermediate Similarity	NPC475236
0.7231	Intermediate Similarity	NPC473220
0.7231	Intermediate Similarity	NPC110211
0.7227	Intermediate Similarity	NPC469511

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 NPC237366 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	872
0.2-0.3	1506
0.3-0.4	2916
0.4-0.5	2256
0.5-0.6	1087
0.6-0.7	253
0.7-0.8	23
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8482	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD2182	Approved
0.844	Intermediate Similarity	NPD164	Approved
0.8073	Intermediate Similarity	NPD1238	Approved
0.8	Intermediate Similarity	NPD9258	Approved
0.8	Intermediate Similarity	NPD9256	Approved
0.7874	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9257	Approved
0.7619	Intermediate Similarity	NPD9259	Approved
0.757	Intermediate Similarity	NPD689	Discontinued
0.75	Intermediate Similarity	NPD9495	Approved
0.748	Intermediate Similarity	NPD9545	Approved
0.7479	Intermediate Similarity	NPD969	Suspended
0.7478	Intermediate Similarity	NPD1237	Approved
0.7438	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3764	Approved
0.7373	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD9493	Approved
0.7297	Intermediate Similarity	NPD1202	Approved
0.7295	Intermediate Similarity	NPD5951	Approved
0.7241	Intermediate Similarity	NPD6647	Phase 2
0.7197	Intermediate Similarity	NPD7008	Discontinued
0.717	Intermediate Similarity	NPD9491	Approved
0.7109	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9260	Approved
0.7025	Intermediate Similarity	NPD2067	Discontinued
0.7	Intermediate Similarity	NPD9267	Approved
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9263	Approved
0.7	Intermediate Similarity	NPD9264	Approved
0.6978	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9490	Approved
0.6949	Remote Similarity	NPD1929	Approved
0.6949	Remote Similarity	NPD1930	Approved
0.6949	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD74	Approved
0.6942	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9717	Approved
0.6911	Remote Similarity	NPD9508	Approved
0.6905	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5909	Discontinued
0.688	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD1089	Approved
0.6875	Remote Similarity	NPD1090	Approved
0.6875	Remote Similarity	NPD1086	Approved
0.6864	Remote Similarity	NPD1932	Approved
0.6855	Remote Similarity	NPD5277	Phase 2
0.6838	Remote Similarity	NPD2066	Phase 3
0.6822	Remote Similarity	NPD226	Approved
0.6814	Remote Similarity	NPD1239	Approved
0.6807	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD800	Approved
0.6783	Remote Similarity	NPD1693	Approved
0.6767	Remote Similarity	NPD1203	Approved
0.6765	Remote Similarity	NPD2313	Discontinued
0.6754	Remote Similarity	NPD1088	Approved
0.6742	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD230	Phase 1
0.6738	Remote Similarity	NPD2346	Discontinued
0.6736	Remote Similarity	NPD7236	Approved
0.6724	Remote Similarity	NPD1989	Approved
0.6718	Remote Similarity	NPD6287	Discontinued
0.6716	Remote Similarity	NPD6085	Phase 2
0.6716	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD9261	Approved
0.6641	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD447	Suspended
0.6614	Remote Similarity	NPD9281	Approved
0.6607	Remote Similarity	NPD1087	Approved
0.6604	Remote Similarity	NPD9294	Approved
0.6599	Remote Similarity	NPD6273	Approved
0.6597	Remote Similarity	NPD4628	Phase 3
0.6593	Remote Similarity	NPD1019	Discontinued
0.6593	Remote Similarity	NPD2798	Approved
0.6579	Remote Similarity	NPD3673	Approved
0.6579	Remote Similarity	NPD3672	Approved
0.6567	Remote Similarity	NPD2198	Approved
0.6567	Remote Similarity	NPD2199	Approved
0.6567	Remote Similarity	NPD1283	Approved
0.6567	Remote Similarity	NPD1876	Approved
0.6565	Remote Similarity	NPD5305	Approved
0.6565	Remote Similarity	NPD5125	Phase 3
0.6565	Remote Similarity	NPD5306	Approved
0.6565	Remote Similarity	NPD5126	Approved
0.656	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD227	Approved
0.6542	Remote Similarity	NPD225	Approved
0.6541	Remote Similarity	NPD4878	Approved
0.6541	Remote Similarity	NPD1481	Phase 2
0.6532	Remote Similarity	NPD2329	Discontinued
0.6531	Remote Similarity	NPD2532	Approved
0.6531	Remote Similarity	NPD2533	Approved
0.6531	Remote Similarity	NPD2534	Approved
0.6525	Remote Similarity	NPD1565	Approved
0.6525	Remote Similarity	NPD1564	Approved
0.6525	Remote Similarity	NPD1566	Phase 3
0.6522	Remote Similarity	NPD411	Approved
0.6519	Remote Similarity	NPD2628	Approved
0.6519	Remote Similarity	NPD2160	Approved
0.6519	Remote Similarity	NPD2159	Approved
0.6519	Remote Similarity	NPD2626	Approved
0.6519	Remote Similarity	NPD2625	Approved
0.6519	Remote Similarity	NPD553	Approved
0.6519	Remote Similarity	NPD552	Approved
0.6519	Remote Similarity	NPD9567	Approved
0.6519	Remote Similarity	NPD2797	Approved
0.6519	Remote Similarity	NPD2627	Approved
0.6515	Remote Similarity	NPD4106	Approved
0.6515	Remote Similarity	NPD4136	Approved
0.6515	Remote Similarity	NPD4135	Approved
0.651	Remote Similarity	NPD7239	Suspended
0.6503	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6832	Phase 2
0.6484	Remote Similarity	NPD1246	Approved
0.6483	Remote Similarity	NPD7003	Approved
0.6483	Remote Similarity	NPD3750	Approved
0.6479	Remote Similarity	NPD2799	Discontinued
0.6471	Remote Similarity	NPD5647	Approved
0.6467	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1535	Discovery
0.6466	Remote Similarity	NPD4806	Approved
0.6466	Remote Similarity	NPD4807	Approved
0.6462	Remote Similarity	NPD2347	Approved
0.646	Remote Similarity	NPD4793	Discontinued
0.6458	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1104	Approved
0.6439	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1551	Phase 2
0.6434	Remote Similarity	NPD4198	Discontinued
0.6434	Remote Similarity	NPD2935	Discontinued
0.6423	Remote Similarity	NPD9494	Approved
0.6423	Remote Similarity	NPD3662	Phase 3
0.6423	Remote Similarity	NPD5204	Approved
0.6423	Remote Similarity	NPD3663	Approved
0.6423	Remote Similarity	NPD3664	Approved
0.6423	Remote Similarity	NPD3661	Approved
0.6418	Remote Similarity	NPD1608	Approved
0.6418	Remote Similarity	NPD1877	Discontinued
0.6415	Remote Similarity	NPD9716	Approved
0.6414	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD2569	Approved
0.6408	Remote Similarity	NPD2567	Approved
0.6406	Remote Similarity	NPD2650	Approved
0.6406	Remote Similarity	NPD2652	Approved
0.6397	Remote Similarity	NPD1164	Approved
0.6397	Remote Similarity	NPD1470	Approved
0.6396	Remote Similarity	NPD3971	Phase 1
0.6395	Remote Similarity	NPD7440	Discontinued
0.6391	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2344	Approved
0.6389	Remote Similarity	NPD6004	Phase 3
0.6389	Remote Similarity	NPD6002	Phase 3
0.6389	Remote Similarity	NPD6005	Phase 3
0.6389	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7799	Discontinued
0.6371	Remote Similarity	NPD3134	Approved
0.6371	Remote Similarity	NPD6685	Approved
0.637	Remote Similarity	NPD5159	Phase 2
0.637	Remote Similarity	NPD5157	Phase 1
0.637	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4308	Phase 3
0.6364	Remote Similarity	NPD1245	Approved
0.6364	Remote Similarity	NPD4105	Approved
0.6364	Remote Similarity	NPD4102	Approved
0.6364	Remote Similarity	NPD9268	Approved
0.6358	Remote Similarity	NPD7458	Discontinued
0.6358	Remote Similarity	NPD3226	Approved
0.6357	Remote Similarity	NPD520	Approved
0.6351	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD1317	Discontinued
0.6348	Remote Similarity	NPD5347	Phase 2
0.6348	Remote Similarity	NPD5346	Phase 2
0.6343	Remote Similarity	NPD1281	Approved
0.6343	Remote Similarity	NPD1201	Approved
0.632	Remote Similarity	NPD1358	Approved
0.6316	Remote Similarity	NPD650	Approved
0.6316	Remote Similarity	NPD9272	Approved
0.6316	Remote Similarity	NPD1282	Approved
0.6316	Remote Similarity	NPD4626	Approved
0.6312	Remote Similarity	NPD3373	Approved
0.6304	Remote Similarity	NPD454	Approved
0.6296	Remote Similarity	NPD9269	Phase 2
0.6296	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3972	Approved
0.629	Remote Similarity	NPD9697	Approved
0.629	Remote Similarity	NPD5048	Discontinued

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