NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	3.405
LogD:	3.31
LogS:	-4.973
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.176
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.489
MDCK Permeability:	2.623476211738307e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.698

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.13257598876953%
Volume Distribution (VD):	0.67
Pgp-substrate:	1.2355709075927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.736
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.613
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	2.603
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.657
AMES Toxicity:	0.532
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.218
Carcinogencity:	0.889
Eye Corrosion:	0.018
Eye Irritation:	0.838
Respiratory Toxicity:	0.088

Download Data

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

Natural Product: NPC226093

Natural Product ID:	NPC226093
*Common Name:**	(3R)-Dunnione
IUPAC Name:	(2R)-2,3,3-trimethyl-2H-benzo[g][1]benzofuran-4,5-dione
Synonyms:	(3R)-Dunnione
Standard InCHIKey:	WGENOABUKBFVAA-MRVPVSSYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-8-15(2,3)11-13(17)12(16)9-6-4-5-7-10(9)14(11)18-8/h4-8H,1-3H3/t8-/m1/s1
SMILES:	C[C@@H]1C(C)(C)C2=C(c3ccccc3C(=O)C2=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668320
PubChem CID:	53322969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174407]
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT845	Cell Line	BT-474	Homo sapiens	IC50	=	1000.0	nM	PMID[522373]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	1900.0	nM	PMID[522373]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2300.0	nM	PMID[522373]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5000.0	nM	PMID[522373]

☑ 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 NPC226093 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	278
0.1-0.2	1366
0.2-0.3	2842
0.3-0.4	8004
0.4-0.5	12093
0.5-0.6	10011
0.6-0.7	7283
0.7-0.8	743
0.8-0.85	54
0.85-0.9	17
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9813	High Similarity	NPC477411
0.945	High Similarity	NPC196075
0.9091	High Similarity	NPC212415
0.8879	High Similarity	NPC238861
0.8879	High Similarity	NPC77000
0.885	High Similarity	NPC470764
0.8839	High Similarity	NPC13784
0.8803	High Similarity	NPC144547
0.8772	High Similarity	NPC135730
0.8761	High Similarity	NPC241851
0.8718	High Similarity	NPC289432
0.8718	High Similarity	NPC988
0.8684	High Similarity	NPC228936
0.8649	High Similarity	NPC83628
0.8649	High Similarity	NPC265407
0.8583	High Similarity	NPC51079
0.8559	High Similarity	NPC470391
0.8496	Intermediate Similarity	NPC210089
0.8496	Intermediate Similarity	NPC474157
0.8468	Intermediate Similarity	NPC37622
0.8468	Intermediate Similarity	NPC30594
0.8378	Intermediate Similarity	NPC209632
0.8348	Intermediate Similarity	NPC272524
0.8333	Intermediate Similarity	NPC137315
0.8288	Intermediate Similarity	NPC114594
0.8276	Intermediate Similarity	NPC308744
0.8276	Intermediate Similarity	NPC307651
0.8268	Intermediate Similarity	NPC477407
0.825	Intermediate Similarity	NPC232958
0.8211	Intermediate Similarity	NPC295664
0.8205	Intermediate Similarity	NPC474095
0.8205	Intermediate Similarity	NPC474685
0.8203	Intermediate Similarity	NPC310662
0.8198	Intermediate Similarity	NPC89886
0.8198	Intermediate Similarity	NPC60679
0.8189	Intermediate Similarity	NPC477412
0.8182	Intermediate Similarity	NPC50872
0.8174	Intermediate Similarity	NPC291799
0.8167	Intermediate Similarity	NPC204784
0.8158	Intermediate Similarity	NPC474364
0.8158	Intermediate Similarity	NPC99846
0.8158	Intermediate Similarity	NPC469636
0.8158	Intermediate Similarity	NPC269023
0.8145	Intermediate Similarity	NPC236405
0.8145	Intermediate Similarity	NPC476599
0.8142	Intermediate Similarity	NPC119271
0.8136	Intermediate Similarity	NPC149691
0.8125	Intermediate Similarity	NPC477406
0.8099	Intermediate Similarity	NPC105709
0.8092	Intermediate Similarity	NPC119542
0.807	Intermediate Similarity	NPC56493
0.8051	Intermediate Similarity	NPC210092
0.8051	Intermediate Similarity	NPC474408
0.8034	Intermediate Similarity	NPC128368
0.8018	Intermediate Similarity	NPC112552
0.8017	Intermediate Similarity	NPC167504
0.8	Intermediate Similarity	NPC10251
0.8	Intermediate Similarity	NPC192577
0.8	Intermediate Similarity	NPC17417
0.7983	Intermediate Similarity	NPC471616
0.7983	Intermediate Similarity	NPC100353
0.7965	Intermediate Similarity	NPC31786
0.7951	Intermediate Similarity	NPC473243
0.7949	Intermediate Similarity	NPC82899
0.7949	Intermediate Similarity	NPC79496
0.7949	Intermediate Similarity	NPC270699
0.7946	Intermediate Similarity	NPC45613
0.7937	Intermediate Similarity	NPC81135
0.7937	Intermediate Similarity	NPC51292
0.7931	Intermediate Similarity	NPC174099
0.7931	Intermediate Similarity	NPC93084
0.7931	Intermediate Similarity	NPC196246
0.7931	Intermediate Similarity	NPC214067
0.7931	Intermediate Similarity	NPC251854
0.792	Intermediate Similarity	NPC246166
0.7909	Intermediate Similarity	NPC276775
0.7909	Intermediate Similarity	NPC249912
0.7909	Intermediate Similarity	NPC92754
0.7903	Intermediate Similarity	NPC223351
0.7886	Intermediate Similarity	NPC472981
0.7881	Intermediate Similarity	NPC474176
0.7881	Intermediate Similarity	NPC161611
0.7879	Intermediate Similarity	NPC38158
0.7879	Intermediate Similarity	NPC232996
0.7876	Intermediate Similarity	NPC474365
0.7876	Intermediate Similarity	NPC301943
0.7863	Intermediate Similarity	NPC305912
0.7863	Intermediate Similarity	NPC23894
0.7863	Intermediate Similarity	NPC260818
0.7863	Intermediate Similarity	NPC1082
0.7857	Intermediate Similarity	NPC42211
0.7857	Intermediate Similarity	NPC70624
0.7851	Intermediate Similarity	NPC61651
0.7846	Intermediate Similarity	NPC472656
0.784	Intermediate Similarity	NPC228739
0.7838	Intermediate Similarity	NPC225060
0.7838	Intermediate Similarity	NPC35448
0.7838	Intermediate Similarity	NPC78701
0.7815	Intermediate Similarity	NPC326664
0.7797	Intermediate Similarity	NPC474314
0.7797	Intermediate Similarity	NPC321852
0.7797	Intermediate Similarity	NPC23332
0.7795	Intermediate Similarity	NPC177925
0.7786	Intermediate Similarity	NPC329913
0.7769	Intermediate Similarity	NPC279596
0.7769	Intermediate Similarity	NPC190298
0.7768	Intermediate Similarity	NPC146351
0.7768	Intermediate Similarity	NPC118343
0.776	Intermediate Similarity	NPC65627
0.7759	Intermediate Similarity	NPC211439
0.7752	Intermediate Similarity	NPC82712
0.7752	Intermediate Similarity	NPC471832
0.775	Intermediate Similarity	NPC306740
0.7727	Intermediate Similarity	NPC130398
0.7719	Intermediate Similarity	NPC274443
0.7717	Intermediate Similarity	NPC294050
0.7717	Intermediate Similarity	NPC328997
0.7712	Intermediate Similarity	NPC183648
0.7712	Intermediate Similarity	NPC243355
0.7712	Intermediate Similarity	NPC474057
0.7705	Intermediate Similarity	NPC469954
0.7698	Intermediate Similarity	NPC182646
0.7698	Intermediate Similarity	NPC11799
0.7698	Intermediate Similarity	NPC141252
0.7698	Intermediate Similarity	NPC472704
0.7692	Intermediate Similarity	NPC85493
0.7674	Intermediate Similarity	NPC59502
0.7667	Intermediate Similarity	NPC153053
0.7661	Intermediate Similarity	NPC476225
0.7652	Intermediate Similarity	NPC126516
0.7652	Intermediate Similarity	NPC203486
0.7638	Intermediate Similarity	NPC472693
0.7638	Intermediate Similarity	NPC472694
0.7634	Intermediate Similarity	NPC472394
0.7634	Intermediate Similarity	NPC239134
0.7632	Intermediate Similarity	NPC188895
0.7632	Intermediate Similarity	NPC244427
0.7632	Intermediate Similarity	NPC222390
0.7619	Intermediate Similarity	NPC472703
0.7619	Intermediate Similarity	NPC217756
0.7615	Intermediate Similarity	NPC272946
0.7615	Intermediate Similarity	NPC42234
0.7611	Intermediate Similarity	NPC325497
0.7611	Intermediate Similarity	NPC203925
0.7607	Intermediate Similarity	NPC470007
0.7607	Intermediate Similarity	NPC203732
0.7597	Intermediate Similarity	NPC115797
0.7597	Intermediate Similarity	NPC51448
0.7597	Intermediate Similarity	NPC316553
0.7594	Intermediate Similarity	NPC212207
0.7594	Intermediate Similarity	NPC474659
0.7586	Intermediate Similarity	NPC172483
0.7578	Intermediate Similarity	NPC121272
0.7578	Intermediate Similarity	NPC470858
0.7568	Intermediate Similarity	NPC5472
0.7561	Intermediate Similarity	NPC152812
0.7559	Intermediate Similarity	NPC325740
0.7557	Intermediate Similarity	NPC470278
0.7541	Intermediate Similarity	NPC62138
0.7521	Intermediate Similarity	NPC196673
0.7521	Intermediate Similarity	NPC237366
0.7521	Intermediate Similarity	NPC474363
0.7519	Intermediate Similarity	NPC472706
0.7519	Intermediate Similarity	NPC470753
0.7519	Intermediate Similarity	NPC473220
0.7519	Intermediate Similarity	NPC59459
0.7519	Intermediate Similarity	NPC474737
0.7519	Intermediate Similarity	NPC169913
0.75	Intermediate Similarity	NPC164295
0.75	Intermediate Similarity	NPC158282
0.75	Intermediate Similarity	NPC30216
0.75	Intermediate Similarity	NPC57879
0.75	Intermediate Similarity	NPC471074
0.75	Intermediate Similarity	NPC249067
0.75	Intermediate Similarity	NPC477360
0.75	Intermediate Similarity	NPC473885
0.7481	Intermediate Similarity	NPC147561
0.7463	Intermediate Similarity	NPC311339
0.7462	Intermediate Similarity	NPC478165
0.7462	Intermediate Similarity	NPC45537
0.7462	Intermediate Similarity	NPC478162
0.7462	Intermediate Similarity	NPC428300
0.746	Intermediate Similarity	NPC97566
0.7459	Intermediate Similarity	NPC252004
0.7444	Intermediate Similarity	NPC183103
0.7444	Intermediate Similarity	NPC477364
0.7444	Intermediate Similarity	NPC476644
0.7442	Intermediate Similarity	NPC470765
0.7442	Intermediate Similarity	NPC275576
0.744	Intermediate Similarity	NPC137710
0.744	Intermediate Similarity	NPC472708
0.7436	Intermediate Similarity	NPC269457
0.7434	Intermediate Similarity	NPC156021
0.7434	Intermediate Similarity	NPC270654
0.7426	Intermediate Similarity	NPC284184
0.7426	Intermediate Similarity	NPC301341
0.7424	Intermediate Similarity	NPC72915
0.7422	Intermediate Similarity	NPC85511
0.7422	Intermediate Similarity	NPC328107
0.7419	Intermediate Similarity	NPC323440

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 NPC226093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	961
0.2-0.3	1129
0.3-0.4	2679
0.4-0.5	2479
0.5-0.6	1262
0.6-0.7	354
0.7-0.8	27
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD1609	Clinical (unspecified phase)
0.8879	High Similarity	NPD3412	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2182	Approved
0.7965	Intermediate Similarity	NPD164	Approved
0.7903	Intermediate Similarity	NPD3972	Approved
0.7768	Intermediate Similarity	NPD1238	Approved
0.7667	Intermediate Similarity	NPD1241	Discontinued
0.7603	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1876	Approved
0.75	Intermediate Similarity	NPD1237	Approved
0.7481	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD2067	Discontinued
0.746	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6287	Discontinued
0.7348	Intermediate Similarity	NPD7008	Discontinued
0.725	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD650	Approved
0.7246	Intermediate Similarity	NPD1471	Phase 3
0.7239	Intermediate Similarity	NPD7713	Phase 3
0.7234	Intermediate Similarity	NPD7236	Approved
0.7222	Intermediate Similarity	NPD9545	Approved
0.7177	Intermediate Similarity	NPD5951	Approved
0.7143	Intermediate Similarity	NPD7609	Phase 3
0.7131	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3495	Discontinued
0.7092	Intermediate Similarity	NPD4628	Phase 3
0.708	Intermediate Similarity	NPD7631	Approved
0.7077	Intermediate Similarity	NPD4878	Approved
0.7031	Intermediate Similarity	NPD1651	Approved
0.7018	Intermediate Similarity	NPD1202	Approved
0.7016	Intermediate Similarity	NPD6858	Approved
0.7016	Intermediate Similarity	NPD7094	Approved
0.7	Intermediate Similarity	NPD9259	Approved
0.7	Intermediate Similarity	NPD9257	Approved
0.6986	Remote Similarity	NPD7239	Suspended
0.6977	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6273	Approved
0.6934	Remote Similarity	NPD3142	Approved
0.6934	Remote Similarity	NPD3140	Approved
0.6929	Remote Similarity	NPD2796	Approved
0.6929	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5909	Discontinued
0.6912	Remote Similarity	NPD3764	Approved
0.6899	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1989	Approved
0.6879	Remote Similarity	NPD2344	Approved
0.6879	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.687	Remote Similarity	NPD518	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1281	Approved
0.6866	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2798	Approved
0.6864	Remote Similarity	NPD2066	Phase 3
0.6846	Remote Similarity	NPD17	Approved
0.6838	Remote Similarity	NPD6039	Approved
0.6835	Remote Similarity	NPD1607	Approved
0.6833	Remote Similarity	NPD1929	Approved
0.6833	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1930	Approved
0.6825	Remote Similarity	NPD6010	Discontinued
0.6812	Remote Similarity	NPD1240	Approved
0.6797	Remote Similarity	NPD9493	Approved
0.6786	Remote Similarity	NPD1282	Approved
0.6783	Remote Similarity	NPD1508	Approved
0.6772	Remote Similarity	NPD2629	Approved
0.6765	Remote Similarity	NPD6832	Phase 2
0.6754	Remote Similarity	NPD9256	Approved
0.6754	Remote Similarity	NPD9258	Approved
0.675	Remote Similarity	NPD1932	Approved
0.6741	Remote Similarity	NPD2788	Approved
0.6739	Remote Similarity	NPD8032	Phase 2
0.6738	Remote Similarity	NPD3748	Approved
0.6736	Remote Similarity	NPD7003	Approved
0.6718	Remote Similarity	NPD2932	Approved
0.6716	Remote Similarity	NPD2199	Approved
0.6716	Remote Similarity	NPD2198	Approved
0.6716	Remote Similarity	NPD1283	Approved
0.6713	Remote Similarity	NPD1549	Phase 2
0.6697	Remote Similarity	NPD942	Approved
0.6694	Remote Similarity	NPD6647	Phase 2
0.6692	Remote Similarity	NPD1608	Approved
0.6691	Remote Similarity	NPD9494	Approved
0.669	Remote Similarity	NPD3887	Approved
0.669	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD7057	Phase 3
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7058	Phase 2
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6643	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7055	Discontinued
0.6641	Remote Similarity	NPD3024	Approved
0.6641	Remote Similarity	NPD3025	Approved
0.6641	Remote Similarity	NPD5691	Approved
0.6639	Remote Similarity	NPD3047	Approved
0.6639	Remote Similarity	NPD3046	Approved
0.6639	Remote Similarity	NPD3048	Approved
0.6639	Remote Similarity	NPD9495	Approved
0.6638	Remote Similarity	NPD1088	Approved
0.6637	Remote Similarity	NPD1087	Approved
0.662	Remote Similarity	NPD1510	Phase 2
0.662	Remote Similarity	NPD2799	Discontinued
0.6618	Remote Similarity	NPD1019	Discontinued
0.6617	Remote Similarity	NPD1201	Approved
0.661	Remote Similarity	NPD1843	Approved
0.66	Remote Similarity	NPD7458	Discontinued
0.6591	Remote Similarity	NPD3019	Approved
0.6589	Remote Similarity	NPD3317	Approved
0.6589	Remote Similarity	NPD4198	Discontinued
0.6581	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4307	Phase 2
0.6571	Remote Similarity	NPD2979	Phase 3
0.6567	Remote Similarity	NPD9717	Approved
0.6565	Remote Similarity	NPD7009	Phase 2
0.656	Remote Similarity	NPD2329	Discontinued
0.6552	Remote Similarity	NPD2800	Approved
0.6549	Remote Similarity	NPD2569	Approved
0.6549	Remote Similarity	NPD2567	Approved
0.6541	Remote Similarity	NPD4879	Approved
0.6541	Remote Similarity	NPD3026	Approved
0.6541	Remote Similarity	NPD3023	Approved
0.6532	Remote Similarity	NPD3134	Approved
0.6528	Remote Similarity	NPD2353	Approved
0.6528	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD9260	Approved
0.6519	Remote Similarity	NPD5159	Phase 2
0.6519	Remote Similarity	NPD5327	Phase 3
0.6519	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5157	Phase 1
0.6515	Remote Similarity	NPD5585	Approved
0.6507	Remote Similarity	NPD3750	Approved
0.6507	Remote Similarity	NPD8166	Discontinued
0.6503	Remote Similarity	NPD7305	Phase 1
0.65	Remote Similarity	NPD6663	Approved
0.649	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2651	Approved
0.649	Remote Similarity	NPD3226	Approved
0.649	Remote Similarity	NPD2649	Approved
0.6489	Remote Similarity	NPD7610	Discontinued
0.6489	Remote Similarity	NPD2347	Approved
0.6483	Remote Similarity	NPD970	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1358	Approved
0.648	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5667	Approved
0.6471	Remote Similarity	NPD6280	Approved
0.6471	Remote Similarity	NPD6279	Approved
0.6467	Remote Similarity	NPD920	Approved
0.6466	Remote Similarity	NPD1778	Approved
0.6466	Remote Similarity	NPD1089	Approved
0.6466	Remote Similarity	NPD1086	Approved
0.6466	Remote Similarity	NPD3672	Approved
0.6466	Remote Similarity	NPD3673	Approved
0.6466	Remote Similarity	NPD1090	Approved
0.6458	Remote Similarity	NPD2438	Suspended
0.6449	Remote Similarity	NPD5736	Approved
0.6444	Remote Similarity	NPD6637	Approved
0.6443	Remote Similarity	NPD2532	Approved
0.6443	Remote Similarity	NPD2534	Approved
0.6443	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD2533	Approved
0.6441	Remote Similarity	NPD1563	Approved
0.6439	Remote Similarity	NPD1894	Discontinued
0.6438	Remote Similarity	NPD1243	Approved
0.6429	Remote Similarity	NPD7819	Suspended
0.6429	Remote Similarity	NPD3268	Approved
0.6423	Remote Similarity	NPD2797	Approved
0.6423	Remote Similarity	NPD9261	Approved
0.6423	Remote Similarity	NPD1203	Approved
0.6419	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD694	Clinical (unspecified phase)
0.641	Remote Similarity	NPD1239	Approved
0.6408	Remote Similarity	NPD230	Phase 1
0.6408	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD969	Suspended
0.6393	Remote Similarity	NPD2553	Approved
0.6393	Remote Similarity	NPD2549	Approved
0.6393	Remote Similarity	NPD2552	Approved
0.6393	Remote Similarity	NPD2558	Approved
0.6393	Remote Similarity	NPD2550	Approved
0.6393	Remote Similarity	NPD2555	Approved
0.6389	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4308	Phase 3
0.6387	Remote Similarity	NPD5977	Approved
0.6387	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5978	Approved
0.6387	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7961	Discontinued
0.6382	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD800	Approved
0.6378	Remote Similarity	NPD1752	Approved
0.6378	Remote Similarity	NPD4233	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