NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.1
Volume:	273.408
LogP:	4.184
LogD:	3.91
LogS:	-4.762
# Rotatable Bonds:	3
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	2.102
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.612
MDCK Permeability:	3.1016745197121054e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.854
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	99.73912811279297%
Volume Distribution (VD):	0.655
Pgp-substrate:	0.8411483764648438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.869
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.733
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.67
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.347
CYP2D6-substrate:	0.454
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	10.331
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.111
Carcinogencity:	0.204
Eye Corrosion:	0.003
Eye Irritation:	0.101
Respiratory Toxicity:	0.214

Download Data

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

Natural Product: NPC270654

Natural Product ID:	NPC270654
*Common Name:**	Gymnoascolide A
IUPAC Name:	3-benzyl-4-phenyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	RTTHRDSFKNSBAG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O2/c18-17-16(14-9-5-2-6-10-14)15(12-19-17)11-13-7-3-1-4-8-13/h1-10H,11-12H2
SMILES:	c1ccc(cc1)CC1=C(c2ccccc2)C(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444485
PubChem CID:	11593998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	Australian	n.a.	PMID[16124766]
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	Australian	n.a.	PMID[16309319]
NPO33022	gymnoascus reessii	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17309300]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	LD99	=	13.0	mg/ml	PMID[479308]

☑ 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 NPC270654 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	224
0.1-0.2	1280
0.2-0.3	3244
0.3-0.4	9598
0.4-0.5	13023
0.5-0.6	12325
0.6-0.7	2628
0.7-0.8	316
0.8-0.85	39
0.85-0.9	16
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC42211
0.9011	High Similarity	NPC9822
0.898	High Similarity	NPC269644
0.8958	High Similarity	NPC118343
0.8913	High Similarity	NPC213156
0.8913	High Similarity	NPC240108
0.8812	High Similarity	NPC281604
0.8713	High Similarity	NPC156648
0.87	High Similarity	NPC269457
0.8617	High Similarity	NPC119631
0.8571	High Similarity	NPC294134
0.8557	High Similarity	NPC92754
0.8557	High Similarity	NPC249912
0.8557	High Similarity	NPC276775
0.8469	Intermediate Similarity	NPC35448
0.8469	Intermediate Similarity	NPC78701
0.8469	Intermediate Similarity	NPC225060
0.8384	Intermediate Similarity	NPC146351
0.8352	Intermediate Similarity	NPC288903
0.8351	Intermediate Similarity	NPC130398
0.8333	Intermediate Similarity	NPC77273
0.8333	Intermediate Similarity	NPC128249
0.8317	Intermediate Similarity	NPC301943
0.8317	Intermediate Similarity	NPC89886
0.8317	Intermediate Similarity	NPC474365
0.83	Intermediate Similarity	NPC70624
0.8269	Intermediate Similarity	NPC474364
0.8247	Intermediate Similarity	NPC261181
0.8211	Intermediate Similarity	NPC173443
0.8208	Intermediate Similarity	NPC158282
0.8208	Intermediate Similarity	NPC79496
0.82	Intermediate Similarity	NPC325497
0.8191	Intermediate Similarity	NPC89377
0.8152	Intermediate Similarity	NPC208183
0.8152	Intermediate Similarity	NPC243289
0.8137	Intermediate Similarity	NPC60679
0.8131	Intermediate Similarity	NPC128368
0.8095	Intermediate Similarity	NPC17417
0.8095	Intermediate Similarity	NPC10251
0.8095	Intermediate Similarity	NPC265407
0.8095	Intermediate Similarity	NPC83628
0.8095	Intermediate Similarity	NPC469636
0.8077	Intermediate Similarity	NPC119271
0.8058	Intermediate Similarity	NPC114594
0.8043	Intermediate Similarity	NPC323103
0.8039	Intermediate Similarity	NPC45613
0.8039	Intermediate Similarity	NPC188895
0.8022	Intermediate Similarity	NPC121800
0.8021	Intermediate Similarity	NPC220893
0.802	Intermediate Similarity	NPC203925
0.8019	Intermediate Similarity	NPC196246
0.8019	Intermediate Similarity	NPC214067
0.8019	Intermediate Similarity	NPC251854
0.8019	Intermediate Similarity	NPC93084
0.8	Intermediate Similarity	NPC289201
0.8	Intermediate Similarity	NPC56493
0.8	Intermediate Similarity	NPC96625
0.7981	Intermediate Similarity	NPC209632
0.7979	Intermediate Similarity	NPC58616
0.7957	Intermediate Similarity	NPC270507
0.7957	Intermediate Similarity	NPC285773
0.7944	Intermediate Similarity	NPC1082
0.7944	Intermediate Similarity	NPC474157
0.7944	Intermediate Similarity	NPC305912
0.7944	Intermediate Similarity	NPC210089
0.7944	Intermediate Similarity	NPC167504
0.7941	Intermediate Similarity	NPC473325
0.7925	Intermediate Similarity	NPC40178
0.7917	Intermediate Similarity	NPC304760
0.7912	Intermediate Similarity	NPC170484
0.7905	Intermediate Similarity	NPC37622
0.7905	Intermediate Similarity	NPC30594
0.7895	Intermediate Similarity	NPC318107
0.789	Intermediate Similarity	NPC87069
0.789	Intermediate Similarity	NPC307651
0.7885	Intermediate Similarity	NPC31786
0.7879	Intermediate Similarity	NPC23453
0.7876	Intermediate Similarity	NPC243059
0.7876	Intermediate Similarity	NPC280827
0.787	Intermediate Similarity	NPC82899
0.787	Intermediate Similarity	NPC474314
0.787	Intermediate Similarity	NPC270699
0.7857	Intermediate Similarity	NPC471033
0.7857	Intermediate Similarity	NPC311091
0.785	Intermediate Similarity	NPC174099
0.7849	Intermediate Similarity	NPC103387
0.783	Intermediate Similarity	NPC47536
0.783	Intermediate Similarity	NPC20485
0.7818	Intermediate Similarity	NPC210092
0.7802	Intermediate Similarity	NPC176228
0.7798	Intermediate Similarity	NPC272524
0.7798	Intermediate Similarity	NPC474176
0.7789	Intermediate Similarity	NPC475710
0.7788	Intermediate Similarity	NPC255676
0.7778	Intermediate Similarity	NPC476003
0.7778	Intermediate Similarity	NPC260818
0.7768	Intermediate Similarity	NPC469574
0.7766	Intermediate Similarity	NPC308619
0.7766	Intermediate Similarity	NPC127491
0.7766	Intermediate Similarity	NPC324835
0.7757	Intermediate Similarity	NPC269023
0.7757	Intermediate Similarity	NPC99846
0.7755	Intermediate Similarity	NPC185501
0.7748	Intermediate Similarity	NPC149691
0.7742	Intermediate Similarity	NPC165212
0.7736	Intermediate Similarity	NPC51174
0.7727	Intermediate Similarity	NPC308744
0.7727	Intermediate Similarity	NPC153053
0.7723	Intermediate Similarity	NPC12695
0.7717	Intermediate Similarity	NPC167577
0.7717	Intermediate Similarity	NPC78517
0.7706	Intermediate Similarity	NPC321852
0.7699	Intermediate Similarity	NPC293424
0.7692	Intermediate Similarity	NPC288945
0.7679	Intermediate Similarity	NPC190298
0.767	Intermediate Similarity	NPC472318
0.767	Intermediate Similarity	NPC98911
0.7664	Intermediate Similarity	NPC470391
0.7658	Intermediate Similarity	NPC474685
0.7658	Intermediate Similarity	NPC306740
0.7658	Intermediate Similarity	NPC474408
0.7653	Intermediate Similarity	NPC231591
0.7652	Intermediate Similarity	NPC50872
0.7647	Intermediate Similarity	NPC103048
0.7642	Intermediate Similarity	NPC105899
0.7636	Intermediate Similarity	NPC17693
0.7636	Intermediate Similarity	NPC161611
0.7634	Intermediate Similarity	NPC127343
0.7629	Intermediate Similarity	NPC286608
0.7629	Intermediate Similarity	NPC169050
0.7629	Intermediate Similarity	NPC322387
0.7624	Intermediate Similarity	NPC172925
0.7619	Intermediate Similarity	NPC329556
0.7619	Intermediate Similarity	NPC91820
0.7619	Intermediate Similarity	NPC160382
0.7619	Intermediate Similarity	NPC82426
0.7619	Intermediate Similarity	NPC234305
0.7611	Intermediate Similarity	NPC45104
0.7611	Intermediate Similarity	NPC228318
0.7604	Intermediate Similarity	NPC53299
0.7593	Intermediate Similarity	NPC85493
0.7589	Intermediate Similarity	NPC100353
0.7582	Intermediate Similarity	NPC175393
0.7579	Intermediate Similarity	NPC44830
0.7576	Intermediate Similarity	NPC84288
0.7576	Intermediate Similarity	NPC62765
0.7573	Intermediate Similarity	NPC175852
0.7573	Intermediate Similarity	NPC210529
0.7573	Intermediate Similarity	NPC229242
0.7573	Intermediate Similarity	NPC160548
0.7568	Intermediate Similarity	NPC237366
0.7568	Intermediate Similarity	NPC477411
0.7565	Intermediate Similarity	NPC473243
0.7565	Intermediate Similarity	NPC289432
0.7565	Intermediate Similarity	NPC988
0.7553	Intermediate Similarity	NPC303245
0.7553	Intermediate Similarity	NPC89950
0.7551	Intermediate Similarity	NPC329064
0.7547	Intermediate Similarity	NPC249067
0.7545	Intermediate Similarity	NPC474689
0.7525	Intermediate Similarity	NPC34243
0.7523	Intermediate Similarity	NPC79543
0.7523	Intermediate Similarity	NPC273837
0.75	Intermediate Similarity	NPC287790
0.75	Intermediate Similarity	NPC3672
0.75	Intermediate Similarity	NPC110704
0.75	Intermediate Similarity	NPC144547
0.75	Intermediate Similarity	NPC317645
0.75	Intermediate Similarity	NPC217621
0.7478	Intermediate Similarity	NPC204784
0.7476	Intermediate Similarity	NPC253423
0.7474	Intermediate Similarity	NPC99240
0.7458	Intermediate Similarity	NPC473942
0.7458	Intermediate Similarity	NPC14141
0.7455	Intermediate Similarity	NPC243355
0.7455	Intermediate Similarity	NPC183700
0.7451	Intermediate Similarity	NPC5472
0.7451	Intermediate Similarity	NPC206764
0.7438	Intermediate Similarity	NPC79332
0.7434	Intermediate Similarity	NPC226093
0.7431	Intermediate Similarity	NPC318327
0.7431	Intermediate Similarity	NPC206341
0.7423	Intermediate Similarity	NPC123476
0.7423	Intermediate Similarity	NPC95965
0.7414	Intermediate Similarity	NPC233282
0.7411	Intermediate Similarity	NPC474363
0.7407	Intermediate Similarity	NPC1065
0.7407	Intermediate Similarity	NPC477251
0.74	Intermediate Similarity	NPC274455
0.74	Intermediate Similarity	NPC70940
0.74	Intermediate Similarity	NPC86670
0.7395	Intermediate Similarity	NPC295664
0.7391	Intermediate Similarity	NPC64340
0.7387	Intermediate Similarity	NPC234376
0.7383	Intermediate Similarity	NPC171831
0.7383	Intermediate Similarity	NPC242913
0.7383	Intermediate Similarity	NPC280616
0.7383	Intermediate Similarity	NPC85977
0.7379	Intermediate Similarity	NPC61944
0.7368	Intermediate Similarity	NPC71795

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 NPC270654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	918
0.2-0.3	1018
0.3-0.4	2983
0.4-0.5	2473
0.5-0.6	1156
0.6-0.7	326
0.7-0.8	56
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8958	High Similarity	NPD1238	Approved
0.8454	Intermediate Similarity	NPD1989	Approved
0.8257	Intermediate Similarity	NPD2347	Approved
0.8247	Intermediate Similarity	NPD1202	Approved
0.819	Intermediate Similarity	NPD2067	Discontinued
0.8113	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD9490	Approved
0.8095	Intermediate Similarity	NPD2182	Approved
0.8058	Intermediate Similarity	NPD5909	Discontinued
0.7957	Intermediate Similarity	NPD9491	Approved
0.7921	Intermediate Similarity	NPD5926	Approved
0.7895	Intermediate Similarity	NPD9259	Approved
0.7895	Intermediate Similarity	NPD9257	Approved
0.7885	Intermediate Similarity	NPD164	Approved
0.7857	Intermediate Similarity	NPD1239	Approved
0.7802	Intermediate Similarity	NPD227	Approved
0.7802	Intermediate Similarity	NPD225	Approved
0.7755	Intermediate Similarity	NPD3672	Approved
0.7755	Intermediate Similarity	NPD3673	Approved
0.77	Intermediate Similarity	NPD1563	Approved
0.767	Intermediate Similarity	NPD7798	Approved
0.767	Intermediate Similarity	NPD2066	Phase 3
0.7629	Intermediate Similarity	NPD1282	Approved
0.7629	Intermediate Similarity	NPD1087	Approved
0.7624	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1929	Approved
0.7619	Intermediate Similarity	NPD1930	Approved
0.7576	Intermediate Similarity	NPD9258	Approved
0.7576	Intermediate Similarity	NPD9256	Approved
0.7573	Intermediate Similarity	NPD9495	Approved
0.7553	Intermediate Similarity	NPD226	Approved
0.7547	Intermediate Similarity	NPD1237	Approved
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD1565	Approved
0.7476	Intermediate Similarity	NPD1564	Approved
0.7476	Intermediate Similarity	NPD1566	Phase 3
0.7475	Intermediate Similarity	NPD800	Approved
0.7475	Intermediate Similarity	NPD689	Discontinued
0.7453	Intermediate Similarity	NPD6647	Phase 2
0.7436	Intermediate Similarity	NPD6287	Discontinued
0.74	Intermediate Similarity	NPD1086	Approved
0.74	Intermediate Similarity	NPD1089	Approved
0.74	Intermediate Similarity	NPD1090	Approved
0.7391	Intermediate Similarity	NPD1894	Discontinued
0.7364	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1932	Approved
0.7353	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD2629	Approved
0.7282	Intermediate Similarity	NPD1693	Approved
0.7282	Intermediate Similarity	NPD9260	Approved
0.7273	Intermediate Similarity	NPD4793	Discontinued
0.7273	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD1241	Discontinued
0.7255	Intermediate Similarity	NPD1088	Approved
0.7236	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4234	Approved
0.7207	Intermediate Similarity	NPD4233	Approved
0.7193	Intermediate Similarity	NPD5951	Approved
0.7188	Intermediate Similarity	NPD942	Approved
0.7168	Intermediate Similarity	NPD6858	Approved
0.7168	Intermediate Similarity	NPD7094	Approved
0.7156	Intermediate Similarity	NPD5048	Discontinued
0.7154	Intermediate Similarity	NPD6832	Phase 2
0.7129	Intermediate Similarity	NPD5347	Phase 2
0.7129	Intermediate Similarity	NPD5346	Phase 2
0.7107	Intermediate Similarity	NPD2198	Approved
0.7107	Intermediate Similarity	NPD5667	Approved
0.7107	Intermediate Similarity	NPD2199	Approved
0.7094	Intermediate Similarity	NPD9545	Approved
0.708	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4576	Approved
0.7069	Intermediate Similarity	NPD4574	Approved
0.7059	Intermediate Similarity	NPD4106	Approved
0.7059	Intermediate Similarity	NPD4136	Approved
0.7059	Intermediate Similarity	NPD4135	Approved
0.7054	Intermediate Similarity	NPD1756	Approved
0.7054	Intermediate Similarity	NPD5236	Approved
0.7054	Intermediate Similarity	NPD5239	Approved
0.7054	Intermediate Similarity	NPD5235	Approved
0.7054	Intermediate Similarity	NPD1752	Approved
0.7054	Intermediate Similarity	NPD5237	Approved
0.7054	Intermediate Similarity	NPD5240	Approved
0.7041	Intermediate Similarity	NPD3971	Phase 1
0.7018	Intermediate Similarity	NPD2607	Approved
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD17	Approved
0.6975	Remote Similarity	NPD5306	Approved
0.6975	Remote Similarity	NPD5305	Approved
0.6972	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2329	Discontinued
0.696	Remote Similarity	NPD7008	Discontinued
0.6957	Remote Similarity	NPD2652	Approved
0.6957	Remote Similarity	NPD2650	Approved
0.6937	Remote Similarity	NPD3134	Approved
0.693	Remote Similarity	NPD969	Suspended
0.6929	Remote Similarity	NPD3373	Approved
0.6923	Remote Similarity	NPD9493	Approved
0.6917	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD9716	Approved
0.6911	Remote Similarity	NPD3266	Approved
0.6911	Remote Similarity	NPD3267	Approved
0.6911	Remote Similarity	NPD2797	Approved
0.6905	Remote Similarity	NPD3764	Approved
0.6897	Remote Similarity	NPD4766	Approved
0.6891	Remote Similarity	NPD4102	Approved
0.6891	Remote Similarity	NPD4105	Approved
0.6891	Remote Similarity	NPD5585	Approved
0.686	Remote Similarity	NPD1281	Approved
0.686	Remote Similarity	NPD4807	Approved
0.686	Remote Similarity	NPD4806	Approved
0.6855	Remote Similarity	NPD2788	Approved
0.6838	Remote Similarity	NPD4198	Discontinued
0.6833	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD9261	Approved
0.681	Remote Similarity	NPD6010	Discontinued
0.6803	Remote Similarity	NPD1481	Phase 2
0.6803	Remote Similarity	NPD3972	Approved
0.6803	Remote Similarity	NPD1608	Approved
0.6803	Remote Similarity	NPD6637	Approved
0.68	Remote Similarity	NPD5204	Approved
0.6789	Remote Similarity	NPD2550	Approved
0.6789	Remote Similarity	NPD2549	Approved
0.6789	Remote Similarity	NPD2552	Approved
0.6789	Remote Similarity	NPD2553	Approved
0.6789	Remote Similarity	NPD2555	Approved
0.6789	Remote Similarity	NPD2558	Approved
0.6786	Remote Similarity	NPD5706	Approved
0.6786	Remote Similarity	NPD5704	Approved
0.6786	Remote Similarity	NPD5705	Approved
0.678	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1203	Approved
0.6772	Remote Similarity	NPD2313	Discontinued
0.6762	Remote Similarity	NPD1508	Approved
0.6744	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4189	Approved
0.6727	Remote Similarity	NPD4188	Approved
0.6726	Remote Similarity	NPD1358	Approved
0.6724	Remote Similarity	NPD5277	Phase 2
0.6724	Remote Similarity	NPD5535	Approved
0.6724	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6065	Approved
0.6721	Remote Similarity	NPD7437	Approved
0.6721	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7436	Approved
0.6721	Remote Similarity	NPD1535	Discovery
0.6696	Remote Similarity	NPD9697	Approved
0.6696	Remote Similarity	NPD2201	Approved
0.6694	Remote Similarity	NPD1283	Approved
0.6693	Remote Similarity	NPD6039	Approved
0.6692	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4619	Approved
0.6641	Remote Similarity	NPD6798	Discontinued
0.6641	Remote Similarity	NPD2569	Approved
0.6641	Remote Similarity	NPD3268	Approved
0.6641	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2567	Approved
0.6641	Remote Similarity	NPD4621	Approved
0.664	Remote Similarity	NPD2625	Approved
0.664	Remote Similarity	NPD2627	Approved
0.664	Remote Similarity	NPD2159	Approved
0.664	Remote Similarity	NPD2160	Approved
0.664	Remote Similarity	NPD2626	Approved
0.664	Remote Similarity	NPD552	Approved
0.664	Remote Similarity	NPD553	Approved
0.664	Remote Similarity	NPD9567	Approved
0.664	Remote Similarity	NPD2628	Approved
0.6639	Remote Similarity	NPD1889	Phase 1
0.6639	Remote Similarity	NPD3847	Discontinued
0.6638	Remote Similarity	NPD9508	Approved
0.6637	Remote Similarity	NPD6685	Approved
0.6637	Remote Similarity	NPD467	Phase 1
0.6617	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4618	Approved
0.6615	Remote Similarity	NPD1933	Approved
0.6615	Remote Similarity	NPD6355	Discontinued
0.6615	Remote Similarity	NPD4622	Approved
0.6614	Remote Similarity	NPD4620	Approved
0.6614	Remote Similarity	NPD5201	Approved
0.6614	Remote Similarity	NPD4617	Approved
0.6614	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5203	Approved
0.6613	Remote Similarity	NPD4359	Approved
0.661	Remote Similarity	NPD1246	Approved
0.6607	Remote Similarity	NPD3046	Approved
0.6607	Remote Similarity	NPD3047	Approved
0.6607	Remote Similarity	NPD3048	Approved
0.6602	Remote Similarity	NPD650	Approved
0.6598	Remote Similarity	NPD9294	Approved
0.6589	Remote Similarity	NPD7713	Phase 3
0.6589	Remote Similarity	NPD6233	Phase 2

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