NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	484.32
Volume:	518.059
LogP:	4.528
LogD:	3.617
LogS:	-4.693
# Rotatable Bonds:	1
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	5.562
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.27
MDCK Permeability:	1.997354229388293e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.877
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.624
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	83.04650115966797%
Volume Distribution (VD):	1.95
Pgp-substrate:	10.49258804321289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.657
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	12.093
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.585
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.275
Carcinogencity:	0.262
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC60679

Natural Product ID:	NPC60679
*Common Name:**	Isocoumarin
IUPAC Name:	isochromen-1-one
Synonyms:	Isocoumarin
Standard InCHIKey:	IQZZFVDIZRWADY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O2/c10-9-8-4-2-1-3-7(8)5-6-11-9/h1-6H
SMILES:	O=c1occc2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457811
PubChem CID:	68108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*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
NPO18980	Haldina cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26649	Colchicum decaisnei	Species	Colchicaceae	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
EC50	1
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	>	200.0	ug.mL-1	PMID[479812]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	83.0	ug.mL-1	PMID[479812]

☑ 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 NPC60679 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	518
0.1-0.2	2497
0.2-0.3	5970
0.3-0.4	12167
0.4-0.5	5186
0.5-0.6	8542
0.6-0.7	6888
0.7-0.8	895
0.8-0.85	19
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.949	High Similarity	NPC114594
0.9394	High Similarity	NPC209632
0.9314	High Similarity	NPC474157
0.9192	High Similarity	NPC89886
0.9135	High Similarity	NPC272524
0.9118	High Similarity	NPC269023
0.9118	High Similarity	NPC99846
0.9048	High Similarity	NPC308744
0.899	High Similarity	NPC42211
0.8962	High Similarity	NPC210092
0.8962	High Similarity	NPC474685
0.8942	High Similarity	NPC243355
0.8922	High Similarity	NPC30594
0.8922	High Similarity	NPC37622
0.8922	High Similarity	NPC119271
0.8911	High Similarity	NPC31786
0.89	High Similarity	NPC45613
0.8889	High Similarity	NPC118343
0.8878	High Similarity	NPC249912
0.8878	High Similarity	NPC276775
0.8878	High Similarity	NPC92754
0.8866	High Similarity	NPC130398
0.8835	High Similarity	NPC56493
0.8788	High Similarity	NPC78701
0.8788	High Similarity	NPC35448
0.8788	High Similarity	NPC225060
0.8762	High Similarity	NPC210089
0.8762	High Similarity	NPC167504
0.875	High Similarity	NPC265407
0.875	High Similarity	NPC17417
0.875	High Similarity	NPC83628
0.875	High Similarity	NPC10251
0.87	High Similarity	NPC146351
0.8679	High Similarity	NPC79496
0.8667	High Similarity	NPC174099
0.8667	High Similarity	NPC214067
0.8667	High Similarity	NPC196246
0.8667	High Similarity	NPC93084
0.8667	High Similarity	NPC251854
0.8614	High Similarity	NPC70624
0.8585	High Similarity	NPC305912
0.8585	High Similarity	NPC1082
0.8585	High Similarity	NPC260818
0.8571	High Similarity	NPC85493
0.8532	High Similarity	NPC149691
0.8529	High Similarity	NPC188895
0.8519	High Similarity	NPC196075
0.8515	High Similarity	NPC203925
0.8505	High Similarity	NPC321852
0.8505	High Similarity	NPC270699
0.8505	High Similarity	NPC82899
0.8462	Intermediate Similarity	NPC269457
0.8447	Intermediate Similarity	NPC301943
0.8447	Intermediate Similarity	NPC474365
0.844	Intermediate Similarity	NPC306740
0.8426	Intermediate Similarity	NPC13784
0.8421	Intermediate Similarity	NPC318107
0.8416	Intermediate Similarity	NPC229242
0.8396	Intermediate Similarity	NPC474364
0.8364	Intermediate Similarity	NPC100353
0.8349	Intermediate Similarity	NPC477411
0.8349	Intermediate Similarity	NPC237366
0.8349	Intermediate Similarity	NPC307651
0.8349	Intermediate Similarity	NPC153053
0.8333	Intermediate Similarity	NPC212415
0.8333	Intermediate Similarity	NPC325497
0.8302	Intermediate Similarity	NPC470391
0.8273	Intermediate Similarity	NPC228936
0.8269	Intermediate Similarity	NPC255676
0.8257	Intermediate Similarity	NPC128368
0.8252	Intermediate Similarity	NPC282895
0.8224	Intermediate Similarity	NPC469636
0.82	Intermediate Similarity	NPC261181
0.8198	Intermediate Similarity	NPC226093
0.8173	Intermediate Similarity	NPC284477
0.8165	Intermediate Similarity	NPC158282
0.8165	Intermediate Similarity	NPC474314
0.8163	Intermediate Similarity	NPC173443
0.8137	Intermediate Similarity	NPC270654
0.8091	Intermediate Similarity	NPC161611
0.8081	Intermediate Similarity	NPC62765
0.8036	Intermediate Similarity	NPC135730
0.8018	Intermediate Similarity	NPC279916
0.8	Intermediate Similarity	NPC119631
0.7959	Intermediate Similarity	NPC89377
0.7949	Intermediate Similarity	NPC46634
0.7946	Intermediate Similarity	NPC474408
0.7928	Intermediate Similarity	NPC474176
0.7909	Intermediate Similarity	NPC476003
0.7909	Intermediate Similarity	NPC291799
0.7905	Intermediate Similarity	NPC112552
0.7895	Intermediate Similarity	NPC228318
0.7895	Intermediate Similarity	NPC45104
0.789	Intermediate Similarity	NPC318327
0.7864	Intermediate Similarity	NPC61944
0.7845	Intermediate Similarity	NPC473243
0.783	Intermediate Similarity	NPC304873
0.7818	Intermediate Similarity	NPC273837
0.7815	Intermediate Similarity	NPC246166
0.7815	Intermediate Similarity	NPC295664
0.781	Intermediate Similarity	NPC98911
0.781	Intermediate Similarity	NPC472318
0.781	Intermediate Similarity	NPC217621
0.78	Intermediate Similarity	NPC220893
0.7798	Intermediate Similarity	NPC211439
0.7797	Intermediate Similarity	NPC223351
0.7788	Intermediate Similarity	NPC474095
0.7788	Intermediate Similarity	NPC253423
0.7778	Intermediate Similarity	NPC96625
0.7778	Intermediate Similarity	NPC144547
0.7778	Intermediate Similarity	NPC105899
0.7778	Intermediate Similarity	NPC50872
0.7759	Intermediate Similarity	NPC204784
0.7755	Intermediate Similarity	NPC58616
0.7755	Intermediate Similarity	NPC294134
0.7745	Intermediate Similarity	NPC77273
0.7739	Intermediate Similarity	NPC217423
0.7736	Intermediate Similarity	NPC473325
0.7732	Intermediate Similarity	NPC288903
0.7727	Intermediate Similarity	NPC40178
0.7723	Intermediate Similarity	NPC213156
0.7723	Intermediate Similarity	NPC240108
0.7719	Intermediate Similarity	NPC188907
0.7719	Intermediate Similarity	NPC220540
0.7706	Intermediate Similarity	NPC1065
0.77	Intermediate Similarity	NPC304760
0.7699	Intermediate Similarity	NPC474363
0.7692	Intermediate Similarity	NPC289432
0.7692	Intermediate Similarity	NPC988
0.7685	Intermediate Similarity	NPC269644
0.7679	Intermediate Similarity	NPC66208
0.7679	Intermediate Similarity	NPC23332
0.767	Intermediate Similarity	NPC23453
0.7667	Intermediate Similarity	NPC107846
0.7667	Intermediate Similarity	NPC265910
0.7667	Intermediate Similarity	NPC91475
0.7664	Intermediate Similarity	NPC25458
0.7652	Intermediate Similarity	NPC190298
0.7647	Intermediate Similarity	NPC110704
0.7642	Intermediate Similarity	NPC228435
0.7636	Intermediate Similarity	NPC47536
0.7632	Intermediate Similarity	NPC470764
0.7632	Intermediate Similarity	NPC81808
0.7624	Intermediate Similarity	NPC9822
0.7619	Intermediate Similarity	NPC156021
0.7607	Intermediate Similarity	NPC201284
0.7596	Intermediate Similarity	NPC5472
0.7593	Intermediate Similarity	NPC234305
0.7589	Intermediate Similarity	NPC183648
0.7589	Intermediate Similarity	NPC137315
0.7586	Intermediate Similarity	NPC469574
0.7586	Intermediate Similarity	NPC240664
0.7583	Intermediate Similarity	NPC228739
0.7568	Intermediate Similarity	NPC281604
0.7544	Intermediate Similarity	NPC53953
0.7544	Intermediate Similarity	NPC87069
0.7542	Intermediate Similarity	NPC238861
0.7542	Intermediate Similarity	NPC77000
0.7542	Intermediate Similarity	NPC232958
0.7542	Intermediate Similarity	NPC233282
0.7541	Intermediate Similarity	NPC51292
0.7523	Intermediate Similarity	NPC249067
0.7523	Intermediate Similarity	NPC85977
0.7522	Intermediate Similarity	NPC54626
0.7522	Intermediate Similarity	NPC57879
0.7521	Intermediate Similarity	NPC94298
0.7521	Intermediate Similarity	NPC94637
0.7521	Intermediate Similarity	NPC470163
0.7521	Intermediate Similarity	NPC27633
0.7521	Intermediate Similarity	NPC470162
0.75	Intermediate Similarity	NPC131192
0.75	Intermediate Similarity	NPC234639
0.75	Intermediate Similarity	NPC470860
0.75	Intermediate Similarity	NPC128825
0.75	Intermediate Similarity	NPC217756
0.748	Intermediate Similarity	NPC181715
0.7478	Intermediate Similarity	NPC186933
0.7477	Intermediate Similarity	NPC249811
0.7477	Intermediate Similarity	NPC203732
0.7477	Intermediate Similarity	NPC156648
0.7459	Intermediate Similarity	NPC476599
0.7459	Intermediate Similarity	NPC470765
0.7459	Intermediate Similarity	NPC121272
0.7459	Intermediate Similarity	NPC275576
0.7458	Intermediate Similarity	NPC90522
0.7458	Intermediate Similarity	NPC328459
0.7458	Intermediate Similarity	NPC61779
0.7458	Intermediate Similarity	NPC137710
0.744	Intermediate Similarity	NPC473271
0.744	Intermediate Similarity	NPC475478
0.7438	Intermediate Similarity	NPC182646
0.7436	Intermediate Similarity	NPC469954
0.7431	Intermediate Similarity	NPC82426
0.7431	Intermediate Similarity	NPC91820
0.7426	Intermediate Similarity	NPC286608
0.7426	Intermediate Similarity	NPC169050
0.7411	Intermediate Similarity	NPC192577
0.7398	Intermediate Similarity	NPC470753
0.7398	Intermediate Similarity	NPC473220
0.7398	Intermediate Similarity	NPC169913

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 NPC60679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	483
0.1-0.2	987
0.2-0.3	1454
0.3-0.4	2863
0.4-0.5	1956
0.5-0.6	1040
0.6-0.7	303
0.7-0.8	63
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8911	High Similarity	NPD164	Approved
0.8889	High Similarity	NPD1238	Approved
0.875	High Similarity	NPD2182	Approved
0.8585	High Similarity	NPD2181	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD9259	Approved
0.8421	Intermediate Similarity	NPD9257	Approved
0.8333	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD1202	Approved
0.8081	Intermediate Similarity	NPD9256	Approved
0.8081	Intermediate Similarity	NPD9258	Approved
0.7767	Intermediate Similarity	NPD9260	Approved
0.7684	Intermediate Similarity	NPD9490	Approved
0.7632	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1241	Discontinued
0.7542	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD5909	Discontinued
0.7523	Intermediate Similarity	NPD1237	Approved
0.7521	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7478	Intermediate Similarity	NPD5951	Approved
0.7431	Intermediate Similarity	NPD9261	Approved
0.7426	Intermediate Similarity	NPD1282	Approved
0.7383	Intermediate Similarity	NPD9495	Approved
0.7377	Intermediate Similarity	NPD1876	Approved
0.7374	Intermediate Similarity	NPD9491	Approved
0.736	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7008	Discontinued
0.7358	Intermediate Similarity	NPD1989	Approved
0.7345	Intermediate Similarity	NPD2067	Discontinued
0.7297	Intermediate Similarity	NPD9697	Approved
0.728	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD1929	Approved
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1930	Approved
0.7273	Intermediate Similarity	NPD1281	Approved
0.7273	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6287	Discontinued
0.7264	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1087	Approved
0.7216	Intermediate Similarity	NPD227	Approved
0.7216	Intermediate Similarity	NPD225	Approved
0.7213	Intermediate Similarity	NPD3972	Approved
0.7168	Intermediate Similarity	NPD9267	Approved
0.7168	Intermediate Similarity	NPD9264	Approved
0.7168	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD9263	Approved
0.7165	Intermediate Similarity	NPD3764	Approved
0.7156	Intermediate Similarity	NPD2066	Phase 3
0.7143	Intermediate Similarity	NPD1239	Approved
0.712	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1019	Discontinued
0.7107	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD74	Approved
0.7105	Intermediate Similarity	NPD9266	Approved
0.7099	Intermediate Similarity	NPD3748	Approved
0.7097	Intermediate Similarity	NPD2199	Approved
0.7097	Intermediate Similarity	NPD2198	Approved
0.7097	Intermediate Similarity	NPD1283	Approved
0.7087	Intermediate Similarity	NPD650	Approved
0.7083	Intermediate Similarity	NPD1894	Discontinued
0.708	Intermediate Similarity	NPD3134	Approved
0.7073	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3673	Approved
0.7048	Intermediate Similarity	NPD3672	Approved
0.7048	Intermediate Similarity	NPD1089	Approved
0.7048	Intermediate Similarity	NPD1086	Approved
0.7048	Intermediate Similarity	NPD1090	Approved
0.704	Intermediate Similarity	NPD1203	Approved
0.7031	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD1932	Approved
0.7018	Intermediate Similarity	NPD1358	Approved
0.7009	Intermediate Similarity	NPD1563	Approved
0.7	Intermediate Similarity	NPD226	Approved
0.6967	Remote Similarity	NPD17	Approved
0.6952	Remote Similarity	NPD800	Approved
0.6923	Remote Similarity	NPD9508	Approved
0.6923	Remote Similarity	NPD4307	Phase 2
0.6916	Remote Similarity	NPD1088	Approved
0.6905	Remote Similarity	NPD553	Approved
0.6905	Remote Similarity	NPD3266	Approved
0.6905	Remote Similarity	NPD2797	Approved
0.6905	Remote Similarity	NPD9567	Approved
0.6905	Remote Similarity	NPD552	Approved
0.6905	Remote Similarity	NPD3267	Approved
0.6885	Remote Similarity	NPD1651	Approved
0.6885	Remote Similarity	NPD5691	Approved
0.687	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2346	Discontinued
0.6864	Remote Similarity	NPD5277	Phase 2
0.686	Remote Similarity	NPD2347	Approved
0.6852	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD3750	Approved
0.6838	Remote Similarity	NPD7003	Approved
0.6832	Remote Similarity	NPD942	Approved
0.6822	Remote Similarity	NPD7609	Phase 3
0.6818	Remote Similarity	NPD1565	Approved
0.6818	Remote Similarity	NPD1566	Phase 3
0.6818	Remote Similarity	NPD1564	Approved
0.6815	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6647	Phase 2
0.68	Remote Similarity	NPD6637	Approved
0.68	Remote Similarity	NPD1608	Approved
0.6794	Remote Similarity	NPD3373	Approved
0.6794	Remote Similarity	NPD2979	Phase 3
0.6789	Remote Similarity	NPD1693	Approved
0.6759	Remote Similarity	NPD1508	Approved
0.6759	Remote Similarity	NPD7631	Approved
0.6757	Remote Similarity	NPD5926	Approved
0.675	Remote Similarity	NPD2629	Approved
0.675	Remote Similarity	NPD9281	Approved
0.6748	Remote Similarity	NPD5585	Approved
0.6746	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1933	Approved
0.6716	Remote Similarity	NPD4308	Phase 3
0.6716	Remote Similarity	NPD2799	Discontinued
0.6715	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4628	Phase 3
0.6714	Remote Similarity	NPD6273	Approved
0.6699	Remote Similarity	NPD3971	Phase 1
0.6695	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4626	Approved
0.6693	Remote Similarity	NPD5667	Approved
0.6692	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2329	Discontinued
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD1551	Phase 2
0.6642	Remote Similarity	NPD2567	Approved
0.6642	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2569	Approved
0.6641	Remote Similarity	NPD3268	Approved
0.6641	Remote Similarity	NPD411	Approved
0.6641	Remote Similarity	NPD1164	Approved
0.664	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD969	Suspended
0.6619	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1756	Approved
0.661	Remote Similarity	NPD5235	Approved
0.661	Remote Similarity	NPD5240	Approved
0.661	Remote Similarity	NPD5237	Approved
0.661	Remote Similarity	NPD1752	Approved
0.661	Remote Similarity	NPD5236	Approved
0.661	Remote Similarity	NPD5239	Approved
0.6604	Remote Similarity	NPD4793	Discontinued
0.6593	Remote Similarity	NPD1510	Phase 2
0.6591	Remote Similarity	NPD7713	Phase 3
0.6587	Remote Similarity	NPD1535	Discovery
0.6587	Remote Similarity	NPD1201	Approved
0.6577	Remote Similarity	NPD1843	Approved
0.6573	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD9716	Approved
0.6565	Remote Similarity	NPD6039	Approved
0.656	Remote Similarity	NPD5306	Approved
0.656	Remote Similarity	NPD5305	Approved
0.6557	Remote Similarity	NPD4198	Discontinued
0.6555	Remote Similarity	NPD2201	Approved
0.6549	Remote Similarity	NPD7798	Approved
0.6547	Remote Similarity	NPD3887	Approved
0.6544	Remote Similarity	NPD2796	Approved
0.6544	Remote Similarity	NPD2531	Phase 2
0.6544	Remote Similarity	NPD4476	Approved
0.6544	Remote Similarity	NPD2438	Suspended
0.6544	Remote Similarity	NPD4477	Approved
0.6541	Remote Similarity	NPD1240	Approved
0.6538	Remote Similarity	NPD454	Approved
0.6538	Remote Similarity	NPD9494	Approved
0.6535	Remote Similarity	NPD1877	Discontinued
0.6525	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5401	Approved
0.6518	Remote Similarity	NPD3495	Discontinued
0.6515	Remote Similarity	NPD1296	Phase 2
0.6512	Remote Similarity	NPD1470	Approved
0.6508	Remote Similarity	NPD3847	Discontinued
0.6508	Remote Similarity	NPD1889	Phase 1
0.6508	Remote Similarity	NPD4106	Approved
0.6508	Remote Similarity	NPD4135	Approved
0.6508	Remote Similarity	NPD4136	Approved
0.6504	Remote Similarity	NPD694	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7236	Approved
0.65	Remote Similarity	NPD7440	Discontinued
0.6496	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD2353	Approved
0.6496	Remote Similarity	NPD1471	Phase 3
0.6493	Remote Similarity	NPD447	Suspended
0.6493	Remote Similarity	NPD230	Phase 1
0.6493	Remote Similarity	NPD4622	Approved
0.6493	Remote Similarity	NPD4618	Approved
0.6484	Remote Similarity	NPD4359	Approved
0.6481	Remote Similarity	NPD5346	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