NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	3.35
LogD:	3.156
LogS:	-4.792
# 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:	0.702
Synthetic Accessibility Score:	3.142
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.511
MDCK Permeability:	2.464711360516958e-05
Pgp-inhibitor:	0.621
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	96.77002716064453%
Volume Distribution (VD):	0.789
Pgp-substrate:	1.3663558959960938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.742
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.944
CYP2C9-substrate:	0.445
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	1.344
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.408
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.237
Carcinogencity:	0.901
Eye Corrosion:	0.009
Eye Irritation:	0.915
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC241851

Natural Product ID:	NPC241851
*Common Name:**	(3R)-Alpha-Dunnione
IUPAC Name:	(2R)-2,3,3-trimethyl-2H-benzo[f][1]benzofuran-4,9-dione
Synonyms:	(3R)-Alpha-Dunnione
Standard InCHIKey:	XWPLFOWMVZGBOX-MRVPVSSYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-8-15(2,3)11-12(16)9-6-4-5-7-10(9)13(17)14(11)18-8/h4-8H,1-3H3/t8-/m1/s1
SMILES:	O=C1c2ccccc2C(=O)C2=C1O[C@@H](C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668321
PubChem CID:	51354251
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	=	4500.0	nM	PMID[471415]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	4600.0	nM	PMID[471415]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5800.0	nM	PMID[471415]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[471415]

☑ 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 NPC241851 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	267
0.1-0.2	1309
0.2-0.3	2772
0.3-0.4	8980
0.4-0.5	13855
0.5-0.6	12319
0.6-0.7	2864
0.7-0.8	290
0.8-0.85	29
0.85-0.9	7
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC470764
0.9346	High Similarity	NPC137315
0.9035	High Similarity	NPC105709
0.8857	High Similarity	NPC112552
0.8807	High Similarity	NPC192577
0.8761	High Similarity	NPC226093
0.875	High Similarity	NPC326664
0.8716	High Similarity	NPC470391
0.8584	High Similarity	NPC477411
0.8583	High Similarity	NPC236405
0.8545	High Similarity	NPC203732
0.8519	High Similarity	NPC274443
0.8512	High Similarity	NPC81135
0.8482	Intermediate Similarity	NPC291799
0.8435	Intermediate Similarity	NPC62138
0.8426	Intermediate Similarity	NPC222390
0.8426	Intermediate Similarity	NPC244427
0.8421	Intermediate Similarity	NPC196075
0.8364	Intermediate Similarity	NPC172483
0.8333	Intermediate Similarity	NPC65627
0.8305	Intermediate Similarity	NPC204784
0.8293	Intermediate Similarity	NPC478162
0.8293	Intermediate Similarity	NPC478165
0.8291	Intermediate Similarity	NPC222968
0.8291	Intermediate Similarity	NPC80605
0.8291	Intermediate Similarity	NPC61651
0.8291	Intermediate Similarity	NPC323440
0.8264	Intermediate Similarity	NPC328107
0.8261	Intermediate Similarity	NPC67377
0.8235	Intermediate Similarity	NPC238861
0.8235	Intermediate Similarity	NPC77000
0.8174	Intermediate Similarity	NPC143768
0.8167	Intermediate Similarity	NPC144547
0.814	Intermediate Similarity	NPC38158
0.812	Intermediate Similarity	NPC135730
0.8115	Intermediate Similarity	NPC51079
0.8095	Intermediate Similarity	NPC476484
0.8087	Intermediate Similarity	NPC292834
0.8083	Intermediate Similarity	NPC289432
0.8083	Intermediate Similarity	NPC988
0.8067	Intermediate Similarity	NPC318173
0.8056	Intermediate Similarity	NPC156021
0.8017	Intermediate Similarity	NPC13784
0.7984	Intermediate Similarity	NPC23894
0.7984	Intermediate Similarity	NPC476599
0.7984	Intermediate Similarity	NPC328997
0.7984	Intermediate Similarity	NPC294050
0.7982	Intermediate Similarity	NPC145052
0.7967	Intermediate Similarity	NPC318067
0.7931	Intermediate Similarity	NPC212415
0.7903	Intermediate Similarity	NPC295664
0.7899	Intermediate Similarity	NPC469843
0.7881	Intermediate Similarity	NPC228936
0.7876	Intermediate Similarity	NPC134120
0.7863	Intermediate Similarity	NPC232996
0.7863	Intermediate Similarity	NPC469547
0.7857	Intermediate Similarity	NPC316553
0.7846	Intermediate Similarity	NPC474659
0.7823	Intermediate Similarity	NPC325740
0.781	Intermediate Similarity	NPC157778
0.7798	Intermediate Similarity	NPC12695
0.7739	Intermediate Similarity	NPC112903
0.7739	Intermediate Similarity	NPC470007
0.7731	Intermediate Similarity	NPC474408
0.7714	Intermediate Similarity	NPC43945
0.7712	Intermediate Similarity	NPC470253
0.7705	Intermediate Similarity	NPC476645
0.7705	Intermediate Similarity	NPC202015
0.7692	Intermediate Similarity	NPC210089
0.7692	Intermediate Similarity	NPC265513
0.7685	Intermediate Similarity	NPC59677
0.7672	Intermediate Similarity	NPC265407
0.7672	Intermediate Similarity	NPC83628
0.7667	Intermediate Similarity	NPC260886
0.7664	Intermediate Similarity	NPC110420
0.7664	Intermediate Similarity	NPC303967
0.7664	Intermediate Similarity	NPC67585
0.7664	Intermediate Similarity	NPC173413
0.7652	Intermediate Similarity	NPC100767
0.7642	Intermediate Similarity	NPC232958
0.7642	Intermediate Similarity	NPC473243
0.7638	Intermediate Similarity	NPC146239
0.7627	Intermediate Similarity	NPC280789
0.7627	Intermediate Similarity	NPC186128
0.7597	Intermediate Similarity	NPC471832
0.7593	Intermediate Similarity	NPC284475
0.7583	Intermediate Similarity	NPC474095
0.7581	Intermediate Similarity	NPC472981
0.7581	Intermediate Similarity	NPC50872
0.7568	Intermediate Similarity	NPC103048
0.7544	Intermediate Similarity	NPC247976
0.7542	Intermediate Similarity	NPC474057
0.7542	Intermediate Similarity	NPC474157
0.7541	Intermediate Similarity	NPC471553
0.7541	Intermediate Similarity	NPC268930
0.7523	Intermediate Similarity	NPC155232
0.7523	Intermediate Similarity	NPC188844
0.7523	Intermediate Similarity	NPC1682
0.7522	Intermediate Similarity	NPC473325
0.7519	Intermediate Similarity	NPC237225
0.75	Intermediate Similarity	NPC196673
0.75	Intermediate Similarity	NPC185763
0.75	Intermediate Similarity	NPC83409
0.75	Intermediate Similarity	NPC30594
0.75	Intermediate Similarity	NPC48992
0.75	Intermediate Similarity	NPC37622
0.75	Intermediate Similarity	NPC307651
0.75	Intermediate Similarity	NPC75724
0.75	Intermediate Similarity	NPC310662
0.75	Intermediate Similarity	NPC134882
0.7481	Intermediate Similarity	NPC173980
0.7479	Intermediate Similarity	NPC218855
0.7478	Intermediate Similarity	NPC329282
0.7456	Intermediate Similarity	NPC320891
0.7455	Intermediate Similarity	NPC238219
0.7444	Intermediate Similarity	NPC212207
0.7442	Intermediate Similarity	NPC115797
0.7442	Intermediate Similarity	NPC51448
0.7438	Intermediate Similarity	NPC215419
0.7438	Intermediate Similarity	NPC217111
0.7436	Intermediate Similarity	NPC211439
0.7434	Intermediate Similarity	NPC476042
0.7431	Intermediate Similarity	NPC133461
0.7424	Intermediate Similarity	NPC144257
0.7424	Intermediate Similarity	NPC477407
0.7419	Intermediate Similarity	NPC472708
0.7417	Intermediate Similarity	NPC272524
0.7417	Intermediate Similarity	NPC161611
0.7414	Intermediate Similarity	NPC209632
0.7411	Intermediate Similarity	NPC265220
0.7411	Intermediate Similarity	NPC239185
0.7407	Intermediate Similarity	NPC119542
0.7405	Intermediate Similarity	NPC27659
0.7405	Intermediate Similarity	NPC198305
0.7402	Intermediate Similarity	NPC135062
0.7398	Intermediate Similarity	NPC152812
0.7398	Intermediate Similarity	NPC94425
0.7377	Intermediate Similarity	NPC149691
0.7376	Intermediate Similarity	NPC476821
0.7368	Intermediate Similarity	NPC109514
0.7368	Intermediate Similarity	NPC476993
0.7368	Intermediate Similarity	NPC171968
0.7364	Intermediate Similarity	NPC153885
0.7364	Intermediate Similarity	NPC51292
0.7364	Intermediate Similarity	NPC51037
0.736	Intermediate Similarity	NPC476225
0.7357	Intermediate Similarity	NPC478160
0.7355	Intermediate Similarity	NPC130591
0.7355	Intermediate Similarity	NPC471721
0.7355	Intermediate Similarity	NPC308744
0.7355	Intermediate Similarity	NPC234637
0.735	Intermediate Similarity	NPC119271
0.7348	Intermediate Similarity	NPC477412
0.7344	Intermediate Similarity	NPC472694
0.7344	Intermediate Similarity	NPC472693
0.7339	Intermediate Similarity	NPC19256
0.7338	Intermediate Similarity	NPC478164
0.7333	Intermediate Similarity	NPC215008
0.7333	Intermediate Similarity	NPC471189
0.7328	Intermediate Similarity	NPC114594
0.7328	Intermediate Similarity	NPC49272
0.7328	Intermediate Similarity	NPC249067
0.7323	Intermediate Similarity	NPC164947
0.7299	Intermediate Similarity	NPC477408
0.7297	Intermediate Similarity	NPC289883
0.7295	Intermediate Similarity	NPC93181
0.7295	Intermediate Similarity	NPC474685
0.7293	Intermediate Similarity	NPC477406
0.7293	Intermediate Similarity	NPC309430
0.729	Intermediate Similarity	NPC307
0.729	Intermediate Similarity	NPC160339
0.7288	Intermediate Similarity	NPC56493
0.7279	Intermediate Similarity	NPC301341
0.7279	Intermediate Similarity	NPC284184
0.7273	Intermediate Similarity	NPC128368
0.7273	Intermediate Similarity	NPC471481
0.7273	Intermediate Similarity	NPC93287
0.7266	Intermediate Similarity	NPC182646
0.7265	Intermediate Similarity	NPC471186
0.7259	Intermediate Similarity	NPC217914
0.7259	Intermediate Similarity	NPC309056
0.7252	Intermediate Similarity	NPC165257
0.725	Intermediate Similarity	NPC167504
0.7241	Intermediate Similarity	NPC329556
0.7241	Intermediate Similarity	NPC60679
0.7241	Intermediate Similarity	NPC89886
0.7239	Intermediate Similarity	NPC254603
0.7232	Intermediate Similarity	NPC260233
0.7231	Intermediate Similarity	NPC177925
0.7231	Intermediate Similarity	NPC231774
0.7227	Intermediate Similarity	NPC10251
0.7227	Intermediate Similarity	NPC470252
0.7227	Intermediate Similarity	NPC474364
0.7227	Intermediate Similarity	NPC269023
0.7227	Intermediate Similarity	NPC99846
0.7227	Intermediate Similarity	NPC17417
0.7227	Intermediate Similarity	NPC469636
0.7227	Intermediate Similarity	NPC475282
0.7218	Intermediate Similarity	NPC205360
0.7209	Intermediate Similarity	NPC310540

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 NPC241851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	940
0.2-0.3	1298
0.3-0.4	3015
0.4-0.5	2421
0.5-0.6	1042
0.6-0.7	166
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD650	Approved
0.7593	Intermediate Similarity	NPD7609	Phase 3
0.7542	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7631	Approved
0.7458	Intermediate Similarity	NPD2067	Discontinued
0.744	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6858	Approved
0.7417	Intermediate Similarity	NPD7094	Approved
0.7411	Intermediate Similarity	NPD3495	Discontinued
0.7328	Intermediate Similarity	NPD1237	Approved
0.7241	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1929	Approved
0.7241	Intermediate Similarity	NPD1930	Approved
0.7227	Intermediate Similarity	NPD2182	Approved
0.7218	Intermediate Similarity	NPD7961	Discontinued
0.7179	Intermediate Similarity	NPD164	Approved
0.7165	Intermediate Similarity	NPD4879	Approved
0.7155	Intermediate Similarity	NPD1932	Approved
0.7154	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1471	Phase 3
0.7054	Intermediate Similarity	NPD1508	Approved
0.7018	Intermediate Similarity	NPD1989	Approved
0.7016	Intermediate Similarity	NPD5951	Approved
0.6983	Remote Similarity	NPD2066	Phase 3
0.6972	Remote Similarity	NPD7236	Approved
0.6947	Remote Similarity	NPD1876	Approved
0.6942	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2329	Discontinued
0.694	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7009	Phase 2
0.6923	Remote Similarity	NPD3972	Approved
0.688	Remote Similarity	NPD2629	Approved
0.687	Remote Similarity	NPD1843	Approved
0.685	Remote Similarity	NPD7610	Discontinued
0.6838	Remote Similarity	NPD1238	Approved
0.6822	Remote Similarity	NPD942	Approved
0.6822	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7008	Discontinued
0.68	Remote Similarity	NPD1241	Discontinued
0.6783	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1693	Approved
0.6772	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1087	Approved
0.6754	Remote Similarity	NPD1088	Approved
0.6735	Remote Similarity	NPD7239	Suspended
0.6718	Remote Similarity	NPD6287	Discontinued
0.6696	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4878	Approved
0.6642	Remote Similarity	NPD1470	Approved
0.6614	Remote Similarity	NPD4766	Approved
0.6613	Remote Similarity	NPD1317	Discontinued
0.6593	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3672	Approved
0.6579	Remote Similarity	NPD1086	Approved
0.6579	Remote Similarity	NPD3673	Approved
0.6579	Remote Similarity	NPD1089	Approved
0.6579	Remote Similarity	NPD1090	Approved
0.6565	Remote Similarity	NPD2932	Approved
0.6562	Remote Similarity	NPD3317	Approved
0.6552	Remote Similarity	NPD1563	Approved
0.6552	Remote Similarity	NPD1202	Approved
0.6529	Remote Similarity	NPD6647	Phase 2
0.6522	Remote Similarity	NPD1239	Approved
0.6518	Remote Similarity	NPD9257	Approved
0.6518	Remote Similarity	NPD9259	Approved
0.6503	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD7055	Discontinued
0.6491	Remote Similarity	NPD800	Approved
0.6489	Remote Similarity	NPD1651	Approved
0.6489	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD3024	Approved
0.6489	Remote Similarity	NPD3025	Approved
0.6486	Remote Similarity	NPD6273	Approved
0.6481	Remote Similarity	NPD9490	Approved
0.648	Remote Similarity	NPD1752	Approved
0.648	Remote Similarity	NPD4234	Approved
0.648	Remote Similarity	NPD1756	Approved
0.648	Remote Similarity	NPD4233	Approved
0.6475	Remote Similarity	NPD5909	Discontinued
0.6475	Remote Similarity	NPD7713	Phase 3
0.6471	Remote Similarity	NPD9495	Approved
0.6466	Remote Similarity	NPD1201	Approved
0.6463	Remote Similarity	NPD3950	Discontinued
0.6462	Remote Similarity	NPD6065	Approved
0.6457	Remote Similarity	NPD2607	Approved
0.6439	Remote Similarity	NPD3019	Approved
0.6429	Remote Similarity	NPD7058	Phase 2
0.6429	Remote Similarity	NPD7057	Phase 3
0.6422	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6010	Discontinued
0.6396	Remote Similarity	NPD9491	Approved
0.6391	Remote Similarity	NPD3023	Approved
0.6391	Remote Similarity	NPD3026	Approved
0.6389	Remote Similarity	NPD2346	Discontinued
0.6389	Remote Similarity	NPD225	Approved
0.6389	Remote Similarity	NPD227	Approved
0.6387	Remote Similarity	NPD1566	Phase 3
0.6387	Remote Similarity	NPD1564	Approved
0.6387	Remote Similarity	NPD1565	Approved
0.637	Remote Similarity	NPD4628	Phase 3
0.6357	Remote Similarity	NPD6663	Approved
0.635	Remote Similarity	NPD2788	Approved
0.6349	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1281	Approved
0.6316	Remote Similarity	NPD1282	Approved
0.6316	Remote Similarity	NPD2345	Approved
0.6316	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4198	Discontinued
0.6304	Remote Similarity	NPD7084	Phase 3
0.6304	Remote Similarity	NPD5736	Approved
0.6293	Remote Similarity	NPD9256	Approved
0.6293	Remote Similarity	NPD9258	Approved
0.6288	Remote Similarity	NPD9545	Approved
0.6286	Remote Similarity	NPD3764	Approved
0.6281	Remote Similarity	NPD7798	Approved
0.6276	Remote Similarity	NPD2344	Approved
0.6259	Remote Similarity	NPD7003	Approved
0.625	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7305	Phase 1
0.6241	Remote Similarity	NPD1245	Approved
0.6241	Remote Similarity	NPD8032	Phase 2
0.6232	Remote Similarity	NPD2798	Approved
0.6231	Remote Similarity	NPD1246	Approved
0.623	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD226	Approved
0.6216	Remote Similarity	NPD3887	Approved
0.6209	Remote Similarity	NPD6599	Discontinued
0.6207	Remote Similarity	NPD2796	Approved
0.6204	Remote Similarity	NPD1283	Approved
0.6176	Remote Similarity	NPD6637	Approved
0.617	Remote Similarity	NPD2313	Discontinued
0.6164	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.616	Remote Similarity	NPD1018	Approved
0.6154	Remote Similarity	NPD2652	Approved
0.6154	Remote Similarity	NPD2650	Approved
0.6149	Remote Similarity	NPD8166	Discontinued
0.6144	Remote Similarity	NPD3226	Approved
0.6139	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD2799	Discontinued
0.6138	Remote Similarity	NPD3748	Approved
0.6136	Remote Similarity	NPD4576	Approved
0.6136	Remote Similarity	NPD4574	Approved
0.6131	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5157	Phase 1
0.6131	Remote Similarity	NPD5159	Phase 2
0.6131	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5691	Approved
0.6111	Remote Similarity	NPD5704	Approved
0.6111	Remote Similarity	NPD5705	Approved
0.6111	Remote Similarity	NPD6685	Approved
0.6111	Remote Similarity	NPD5706	Approved
0.6107	Remote Similarity	NPD2309	Approved
0.6099	Remote Similarity	NPD6039	Approved
0.609	Remote Similarity	NPD2347	Approved
0.6087	Remote Similarity	NPD5667	Approved
0.6084	Remote Similarity	NPD2979	Phase 3
0.6084	Remote Similarity	NPD3142	Approved
0.6084	Remote Similarity	NPD3140	Approved
0.6083	Remote Similarity	NPD9260	Approved
0.6074	Remote Similarity	NPD7799	Discontinued
0.6074	Remote Similarity	NPD5306	Approved
0.6074	Remote Similarity	NPD5305	Approved
0.6074	Remote Similarity	NPD17	Approved
0.6054	Remote Similarity	NPD2353	Approved
0.6054	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2196	Discontinued
0.6048	Remote Similarity	NPD2193	Phase 2
0.6048	Remote Similarity	NPD2648	Phase 3
0.6042	Remote Similarity	NPD6355	Discontinued
0.6039	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6039	Remote Similarity	NPD7458	Discontinued
0.6036	Remote Similarity	NPD8434	Phase 2
0.6029	Remote Similarity	NPD4136	Approved
0.6029	Remote Similarity	NPD4106	Approved
0.6029	Remote Similarity	NPD4135	Approved
0.6028	Remote Similarity	NPD6832	Phase 2
0.6026	Remote Similarity	NPD8165	Discontinued
0.6015	Remote Similarity	NPD9493	Approved
0.6014	Remote Similarity	NPD2897	Discontinued
0.6014	Remote Similarity	NPD5327	Phase 3
0.6	Remote Similarity	NPD3357	Discontinued
0.6	Remote Similarity	NPD1607	Approved
0.6	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9261	Approved
0.5987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.5986	Remote Similarity	NPD2438	Suspended
0.5985	Remote Similarity	NPD2611	Approved
0.5985	Remote Similarity	NPD2612	Approved
0.5985	Remote Similarity	NPD4217	Approved
0.5985	Remote Similarity	NPD4806	Approved
0.5985	Remote Similarity	NPD4215	Approved
0.5985	Remote Similarity	NPD4807	Approved
0.5985	Remote Similarity	NPD4218	Approved
0.5985	Remote Similarity	NPD2609	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