NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.13
Volume:	248.552
LogP:	2.24
LogD:	2.316
LogS:	-2.46
# Rotatable Bonds:	3
TPSA:	45.75
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.877
Synthetic Accessibility Score:	2.262
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	3.514419586281292e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.469
Plasma Protein Binding (PPB):	92.0960922241211%
Volume Distribution (VD):	0.844
Pgp-substrate:	4.802818298339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.386
CYP1A2-substrate:	0.824
CYP2C19-inhibitor:	0.817
CYP2C19-substrate:	0.499
CYP2C9-inhibitor:	0.576
CYP2C9-substrate:	0.555
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	5.665
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.618
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.054
Carcinogencity:	0.199
Eye Corrosion:	0.003
Eye Irritation:	0.096
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC275467

Natural Product ID:	NPC275467
*Common Name:**	6-Benzyl-3-Isopropyl-1H-Pyrazin-2-One
IUPAC Name:	6-benzyl-3-propan-2-yl-1H-pyrazin-2-one
Synonyms:
Standard InCHIKey:	CZUORGWXUVRUMV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16N2O/c1-10(2)13-14(17)16-12(9-15-13)8-11-6-4-3-5-7-11/h3-7,9-10H,8H2,1-2H3,(H,16,17)
SMILES:	CC(c1ncc([nH]c1=O)Cc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL419498
PubChem CID:	10376483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001346] Diazines [CHEMONTID:0000067] Pyrazines

*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
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11551769]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1593278]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18232659]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21693706]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21939253]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22101040]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25730866]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5447649]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[809439]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[TCMID]
NPO6232	Streptomyces griseus	Species	Streptomycetaceae	Bacteria	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	2
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3579	Individual Protein	Calpain 1	Homo sapiens	IC50	=	1200.0	nM	PMID[542348]
NPT3579	Individual Protein	Calpain 1	Homo sapiens	Inhibition	=	0.0	%	PMID[542349]
NPT2	Others	Unspecified		IC50	=	1300.0	nM	PMID[542349]

☑ 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 NPC275467 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	451
0.1-0.2	7785
0.2-0.3	18169
0.3-0.4	10301
0.4-0.5	3123
0.5-0.6	1947
0.6-0.7	862
0.7-0.8	56
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8835	High Similarity	NPC473498
0.7885	Intermediate Similarity	NPC472258
0.7603	Intermediate Similarity	NPC474479
0.7456	Intermediate Similarity	NPC275410
0.7417	Intermediate Similarity	NPC71684
0.7414	Intermediate Similarity	NPC33742
0.7358	Intermediate Similarity	NPC161972
0.7358	Intermediate Similarity	NPC303045
0.7321	Intermediate Similarity	NPC327481
0.7311	Intermediate Similarity	NPC220698
0.7193	Intermediate Similarity	NPC77294
0.7168	Intermediate Similarity	NPC45033
0.7143	Intermediate Similarity	NPC14672
0.7143	Intermediate Similarity	NPC315276
0.7143	Intermediate Similarity	NPC470544
0.7143	Intermediate Similarity	NPC285926
0.7083	Intermediate Similarity	NPC470545
0.7075	Intermediate Similarity	NPC226438
0.7037	Intermediate Similarity	NPC256452
0.7034	Intermediate Similarity	NPC276949
0.7034	Intermediate Similarity	NPC35850
0.7025	Intermediate Similarity	NPC470546
0.6949	Remote Similarity	NPC474584
0.6939	Remote Similarity	NPC139658
0.693	Remote Similarity	NPC473418
0.6923	Remote Similarity	NPC319579
0.6909	Remote Similarity	NPC311242
0.6905	Remote Similarity	NPC474926
0.6857	Remote Similarity	NPC305602
0.6857	Remote Similarity	NPC17497
0.6857	Remote Similarity	NPC471638
0.6852	Remote Similarity	NPC473661
0.6818	Remote Similarity	NPC25565
0.6792	Remote Similarity	NPC12429
0.6789	Remote Similarity	NPC7067
0.6783	Remote Similarity	NPC143516
0.6774	Remote Similarity	NPC200964
0.6772	Remote Similarity	NPC101719
0.6762	Remote Similarity	NPC203076
0.6759	Remote Similarity	NPC245259
0.6757	Remote Similarity	NPC473501
0.6757	Remote Similarity	NPC475439
0.6754	Remote Similarity	NPC164859
0.6746	Remote Similarity	NPC175726
0.6746	Remote Similarity	NPC474082
0.6735	Remote Similarity	NPC122327
0.6735	Remote Similarity	NPC112609
0.6735	Remote Similarity	NPC113000
0.6731	Remote Similarity	NPC169016
0.6729	Remote Similarity	NPC470877
0.6724	Remote Similarity	NPC474973
0.6724	Remote Similarity	NPC474804
0.6724	Remote Similarity	NPC130898
0.6723	Remote Similarity	NPC329011
0.6721	Remote Similarity	NPC239357
0.6721	Remote Similarity	NPC2265
0.6699	Remote Similarity	NPC14326
0.6698	Remote Similarity	NPC473031
0.6693	Remote Similarity	NPC222466
0.6693	Remote Similarity	NPC22746
0.6667	Remote Similarity	NPC141139
0.6667	Remote Similarity	NPC121872
0.6667	Remote Similarity	NPC159178
0.6667	Remote Similarity	NPC329375
0.6667	Remote Similarity	NPC74936
0.6667	Remote Similarity	NPC471307
0.6667	Remote Similarity	NPC78041
0.6667	Remote Similarity	NPC209764
0.664	Remote Similarity	NPC27833
0.6639	Remote Similarity	NPC197470
0.6637	Remote Similarity	NPC12730
0.6636	Remote Similarity	NPC291070
0.6636	Remote Similarity	NPC71140
0.6636	Remote Similarity	NPC246757
0.6635	Remote Similarity	NPC474088
0.6615	Remote Similarity	NPC111428
0.6614	Remote Similarity	NPC6975
0.6613	Remote Similarity	NPC314992
0.6612	Remote Similarity	NPC314141
0.6609	Remote Similarity	NPC471317
0.6609	Remote Similarity	NPC202613
0.6598	Remote Similarity	NPC229235
0.6593	Remote Similarity	NPC132636
0.6591	Remote Similarity	NPC325479
0.6589	Remote Similarity	NPC477937
0.6587	Remote Similarity	NPC202521
0.6581	Remote Similarity	NPC471447
0.6535	Remote Similarity	NPC325662
0.6535	Remote Similarity	NPC290638
0.6535	Remote Similarity	NPC98269
0.6532	Remote Similarity	NPC313449
0.6518	Remote Similarity	NPC471320
0.6518	Remote Similarity	NPC471319
0.6514	Remote Similarity	NPC316108
0.6514	Remote Similarity	NPC78154
0.6514	Remote Similarity	NPC172128
0.6508	Remote Similarity	NPC179605
0.6508	Remote Similarity	NPC476990
0.6508	Remote Similarity	NPC279385
0.65	Remote Similarity	NPC276699
0.65	Remote Similarity	NPC119569
0.6496	Remote Similarity	NPC67043
0.6493	Remote Similarity	NPC141050
0.6489	Remote Similarity	NPC473322
0.6489	Remote Similarity	NPC313722
0.6486	Remote Similarity	NPC471309
0.6486	Remote Similarity	NPC469330
0.6484	Remote Similarity	NPC35996
0.6481	Remote Similarity	NPC262393
0.6476	Remote Similarity	NPC119677
0.6471	Remote Similarity	NPC12857
0.6466	Remote Similarity	NPC207428
0.6466	Remote Similarity	NPC40364
0.6465	Remote Similarity	NPC244738
0.646	Remote Similarity	NPC472788
0.6458	Remote Similarity	NPC473002
0.6457	Remote Similarity	NPC103292
0.6449	Remote Similarity	NPC258046
0.6441	Remote Similarity	NPC274089
0.6441	Remote Similarity	NPC191215
0.6439	Remote Similarity	NPC200589
0.6429	Remote Similarity	NPC58674
0.6429	Remote Similarity	NPC108339
0.6429	Remote Similarity	NPC473804
0.6423	Remote Similarity	NPC205652
0.6417	Remote Similarity	NPC470127
0.6414	Remote Similarity	NPC469903
0.6412	Remote Similarity	NPC319766
0.641	Remote Similarity	NPC113326
0.641	Remote Similarity	NPC194390
0.641	Remote Similarity	NPC88267
0.641	Remote Similarity	NPC224610
0.6406	Remote Similarity	NPC252878
0.6404	Remote Similarity	NPC322598
0.64	Remote Similarity	NPC192209
0.6391	Remote Similarity	NPC255447
0.6389	Remote Similarity	NPC53492
0.6371	Remote Similarity	NPC473573
0.6364	Remote Similarity	NPC476160
0.6357	Remote Similarity	NPC46427
0.6355	Remote Similarity	NPC3210
0.635	Remote Similarity	NPC287358
0.6346	Remote Similarity	NPC475289
0.6346	Remote Similarity	NPC475573
0.6345	Remote Similarity	NPC117032
0.6343	Remote Similarity	NPC53044
0.6343	Remote Similarity	NPC476689
0.6343	Remote Similarity	NPC476687
0.6343	Remote Similarity	NPC476685
0.6341	Remote Similarity	NPC187036
0.6339	Remote Similarity	NPC474974
0.6336	Remote Similarity	NPC119326
0.6333	Remote Similarity	NPC164802
0.6333	Remote Similarity	NPC302790
0.6333	Remote Similarity	NPC473676
0.6331	Remote Similarity	NPC2823
0.633	Remote Similarity	NPC325441
0.6324	Remote Similarity	NPC300299
0.6316	Remote Similarity	NPC300315
0.6316	Remote Similarity	NPC293628
0.6316	Remote Similarity	NPC122493
0.6316	Remote Similarity	NPC10781
0.6312	Remote Similarity	NPC136002
0.6309	Remote Similarity	NPC68650
0.629	Remote Similarity	NPC118202
0.629	Remote Similarity	NPC113099
0.6286	Remote Similarity	NPC231986
0.6283	Remote Similarity	NPC329430
0.6275	Remote Similarity	NPC271642
0.627	Remote Similarity	NPC254088
0.627	Remote Similarity	NPC169328
0.6269	Remote Similarity	NPC130309
0.6269	Remote Similarity	NPC126458
0.6262	Remote Similarity	NPC133162
0.625	Remote Similarity	NPC475168
0.625	Remote Similarity	NPC7817
0.6242	Remote Similarity	NPC469902
0.6242	Remote Similarity	NPC473003
0.6241	Remote Similarity	NPC469666
0.6232	Remote Similarity	NPC77992
0.6224	Remote Similarity	NPC470440
0.6222	Remote Similarity	NPC32858
0.6222	Remote Similarity	NPC194857
0.622	Remote Similarity	NPC310467
0.622	Remote Similarity	NPC237420
0.6218	Remote Similarity	NPC167336
0.6216	Remote Similarity	NPC258627
0.6214	Remote Similarity	NPC301760
0.6212	Remote Similarity	NPC322433
0.621	Remote Similarity	NPC296163
0.6194	Remote Similarity	NPC187231
0.619	Remote Similarity	NPC192623
0.6181	Remote Similarity	NPC13470
0.6179	Remote Similarity	NPC475013
0.6176	Remote Similarity	NPC98976
0.6176	Remote Similarity	NPC287401
0.6174	Remote Similarity	NPC469898
0.6174	Remote Similarity	NPC324569
0.6172	Remote Similarity	NPC177684
0.6172	Remote Similarity	NPC291962

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 NPC275467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	669
0.2-0.3	988
0.3-0.4	2040
0.4-0.5	2886
0.5-0.6	1803
0.6-0.7	474
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7333	Intermediate Similarity	NPD1812	Approved
0.7333	Intermediate Similarity	NPD1814	Approved
0.7281	Intermediate Similarity	NPD4063	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD787	Suspended
0.7232	Intermediate Similarity	NPD1765	Approved
0.7232	Intermediate Similarity	NPD1767	Approved
0.7232	Intermediate Similarity	NPD1766	Approved
0.7232	Intermediate Similarity	NPD1763	Approved
0.7232	Intermediate Similarity	NPD1761	Approved
0.7182	Intermediate Similarity	NPD5630	Phase 1
0.713	Intermediate Similarity	NPD1107	Approved
0.713	Intermediate Similarity	NPD1108	Approved
0.712	Intermediate Similarity	NPD3029	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD999	Phase 2
0.7069	Intermediate Similarity	NPD2583	Phase 2
0.7063	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD785	Approved
0.6992	Remote Similarity	NPD1079	Discontinued
0.6972	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.697	Remote Similarity	NPD296	Approved
0.697	Remote Similarity	NPD293	Approved
0.697	Remote Similarity	NPD295	Approved
0.6964	Remote Similarity	NPD4803	Discontinued
0.6961	Remote Similarity	NPD831	Approved
0.6961	Remote Similarity	NPD830	Approved
0.6929	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1036	Approved
0.69	Remote Similarity	NPD590	Approved
0.69	Remote Similarity	NPD589	Approved
0.6881	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1781	Discontinued
0.686	Remote Similarity	NPD1344	Phase 2
0.6857	Remote Similarity	NPD4146	Approved
0.6857	Remote Similarity	NPD4145	Approved
0.6829	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5915	Approved
0.6822	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD199	Approved
0.6789	Remote Similarity	NPD197	Approved
0.6783	Remote Similarity	NPD564	Approved
0.6783	Remote Similarity	NPD1018	Approved
0.6783	Remote Similarity	NPD563	Approved
0.6777	Remote Similarity	NPD1323	Discontinued
0.675	Remote Similarity	NPD5180	Approved
0.675	Remote Similarity	NPD5181	Approved
0.675	Remote Similarity	NPD1656	Phase 2
0.675	Remote Similarity	NPD5179	Approved
0.6735	Remote Similarity	NPD9591	Approved
0.6735	Remote Similarity	NPD9593	Approved
0.6735	Remote Similarity	NPD9594	Approved
0.6735	Remote Similarity	NPD9589	Approved
0.6735	Remote Similarity	NPD9590	Approved
0.6735	Remote Similarity	NPD9592	Approved
0.6735	Remote Similarity	NPD9588	Approved
0.6735	Remote Similarity	NPD80	Approved
0.6724	Remote Similarity	NPD990	Approved
0.6724	Remote Similarity	NPD993	Approved
0.672	Remote Similarity	NPD1123	Approved
0.672	Remote Similarity	NPD1124	Approved
0.6716	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD781	Approved
0.6698	Remote Similarity	NPD783	Approved
0.6698	Remote Similarity	NPD780	Approved
0.6698	Remote Similarity	NPD782	Approved
0.6697	Remote Similarity	NPD6690	Approved
0.6696	Remote Similarity	NPD4117	Approved
0.6696	Remote Similarity	NPD1026	Approved
0.6696	Remote Similarity	NPD466	Approved
0.6696	Remote Similarity	NPD1028	Approved
0.6694	Remote Similarity	NPD2319	Discontinued
0.6694	Remote Similarity	NPD851	Approved
0.6694	Remote Similarity	NPD853	Approved
0.6692	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2895	Discontinued
0.6667	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5716	Approved
0.6641	Remote Similarity	NPD5367	Discontinued
0.6641	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1348	Approved
0.6639	Remote Similarity	NPD3643	Approved
0.6639	Remote Similarity	NPD3644	Approved
0.6639	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3642	Approved
0.6636	Remote Similarity	NPD1080	Approved
0.6613	Remote Similarity	NPD2218	Phase 2
0.6613	Remote Similarity	NPD2217	Approved
0.6612	Remote Similarity	NPD1373	Approved
0.6612	Remote Similarity	NPD1371	Approved
0.6612	Remote Similarity	NPD1374	Approved
0.6612	Remote Similarity	NPD1370	Approved
0.6607	Remote Similarity	NPD1099	Approved
0.6607	Remote Similarity	NPD1100	Approved
0.6606	Remote Similarity	NPD517	Discontinued
0.6581	Remote Similarity	NPD1064	Approved
0.6581	Remote Similarity	NPD7130	Phase 3
0.6581	Remote Similarity	NPD1065	Approved
0.6579	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5554	Approved
0.6569	Remote Similarity	NPD1051	Approved
0.6569	Remote Similarity	NPD1052	Approved
0.6569	Remote Similarity	NPD1053	Approved
0.6555	Remote Similarity	NPD3581	Discontinued
0.6544	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD2002	Discontinued
0.6542	Remote Similarity	NPD3428	Approved
0.6542	Remote Similarity	NPD3426	Approved
0.6538	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4169	Approved
0.6538	Remote Similarity	NPD4170	Approved
0.6535	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4147	Approved
0.6535	Remote Similarity	NPD4144	Approved
0.6532	Remote Similarity	NPD7480	Approved
0.6532	Remote Similarity	NPD7481	Approved
0.6531	Remote Similarity	NPD292	Approved
0.6531	Remote Similarity	NPD294	Approved
0.6529	Remote Similarity	NPD480	Approved
0.6525	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD813	Approved
0.6522	Remote Similarity	NPD1417	Approved
0.6522	Remote Similarity	NPD708	Approved
0.6522	Remote Similarity	NPD707	Approved
0.6522	Remote Similarity	NPD1419	Approved
0.6522	Remote Similarity	NPD2841	Approved
0.6522	Remote Similarity	NPD4119	Approved
0.6515	Remote Similarity	NPD1619	Phase 3
0.6512	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD5578	Approved
0.6512	Remote Similarity	NPD2961	Approved
0.6512	Remote Similarity	NPD2031	Discontinued
0.6512	Remote Similarity	NPD2962	Approved
0.6496	Remote Similarity	NPD414	Discontinued
0.6496	Remote Similarity	NPD1040	Phase 2
0.6496	Remote Similarity	NPD5717	Approved
0.6493	Remote Similarity	NPD5272	Discontinued
0.6493	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD742	Approved
0.6484	Remote Similarity	NPD2584	Suspended
0.648	Remote Similarity	NPD998	Approved
0.6471	Remote Similarity	NPD79	Approved
0.6471	Remote Similarity	NPD6901	Phase 3
0.6471	Remote Similarity	NPD9564	Approved
0.6471	Remote Similarity	NPD2679	Approved
0.6471	Remote Similarity	NPD9563	Approved
0.6471	Remote Similarity	NPD2678	Approved
0.6466	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD9728	Phase 1
0.6462	Remote Similarity	NPD2840	Approved
0.646	Remote Similarity	NPD4655	Approved
0.646	Remote Similarity	NPD4657	Approved
0.646	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD4543	Discontinued
0.6449	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD305	Approved
0.6449	Remote Similarity	NPD304	Approved
0.6442	Remote Similarity	NPD3035	Approved
0.6442	Remote Similarity	NPD472	Approved
0.6441	Remote Similarity	NPD4778	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6729	Phase 2
0.6439	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD2371	Approved
0.6434	Remote Similarity	NPD4677	Discontinued
0.6429	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4094	Approved
0.6423	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD3551	Approved
0.6423	Remote Similarity	NPD5631	Phase 3
0.6422	Remote Similarity	NPD771	Phase 3
0.6418	Remote Similarity	NPD1316	Discontinued
0.6415	Remote Similarity	NPD2539	Approved
0.6415	Remote Similarity	NPD2538	Approved
0.6406	Remote Similarity	NPD2131	Approved
0.6404	Remote Similarity	NPD728	Approved
0.6397	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD1764	Approved
0.6393	Remote Similarity	NPD1762	Approved
0.6389	Remote Similarity	NPD187	Approved
0.6387	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD2171	Approved
0.6379	Remote Similarity	NPD6027	Approved
0.6379	Remote Similarity	NPD6024	Approved
0.6379	Remote Similarity	NPD2193	Phase 2
0.6379	Remote Similarity	NPD2648	Phase 3
0.6373	Remote Similarity	NPD603	Approved
0.6372	Remote Similarity	NPD2005	Discontinued
0.6372	Remote Similarity	NPD1738	Approved
0.6364	Remote Similarity	NPD2909	Phase 3
0.6364	Remote Similarity	NPD3626	Phase 3
0.6364	Remote Similarity	NPD4549	Discontinued
0.6364	Remote Similarity	NPD2908	Phase 3
0.6356	Remote Similarity	NPD1269	Approved
0.6356	Remote Similarity	NPD1268	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