NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.13
Volume:	293.391
LogP:	2.884
LogD:	2.414
LogS:	-3.36
# Rotatable Bonds:	6
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.289
Fsp3:	0.294
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:	-4.552
MDCK Permeability:	2.668678280315362e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.61
Plasma Protein Binding (PPB):	95.69861602783203%
Volume Distribution (VD):	1.145
Pgp-substrate:	2.2369959354400635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.853
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.494
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.638
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	9.139
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.867
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.948
Carcinogencity:	0.878
Eye Corrosion:	0.022
Eye Irritation:	0.438
Respiratory Toxicity:	0.483

Download Data

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

Natural Product: NPC77273

Natural Product ID:	NPC77273
*Common Name:**	R-Rugulactone
IUPAC Name:	(2R)-2-[(E)-4-oxo-6-phenylhex-2-enyl]-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	IRHVCJVCISOATN-KZJSRBBCSA-N
Standard InCHI:	InChI=1S/C17H18O3/c18-15(13-12-14-6-2-1-3-7-14)8-4-9-16-10-5-11-17(19)20-16/h1-8,11,16H,9-10,12-13H2/b8-4+/t16-/m1/s1
SMILES:	c1ccc(cc1)CCC(=O)/C=C/C[C@@H]1CC=CC(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1253688
PubChem CID:	52948504
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO9832	Cryptocarya rugulosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093800]
NPO9832	Cryptocarya rugulosa	Species	Lauraceae	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	2
MIC	6
Others	11

Activity Type	# Activity
Cell Line	5
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	21.66	%	PMID[512906]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	8.33	%	PMID[512906]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Activity	=	70.0	%	PMID[512906]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3592.0	nM	PMID[512906]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	3440.0	nM	PMID[512906]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[512904]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[512904]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	50.0	ug.mL-1	PMID[512904]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[512904]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[512904]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	25.0	ug.mL-1	PMID[512904]
NPT923	Organism	Rhizopus oryzae	Rhizopus oryzae	IZ	=	11.0	mm	PMID[512904]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	14.0	mm	PMID[512904]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	7.0	mm	PMID[512904]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	7.0	mm	PMID[512904]
NPT923	Organism	Rhizopus oryzae	Rhizopus oryzae	IZ	=	12.0	mm	PMID[512904]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IZ	=	16.0	mm	PMID[512904]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	8.0	mm	PMID[512904]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	8.0	mm	PMID[512904]

☑ 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 NPC77273 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	213
0.1-0.2	1594
0.2-0.3	3696
0.3-0.4	10463
0.4-0.5	15085
0.5-0.6	9868
0.6-0.7	1457
0.7-0.8	295
0.8-0.85	18
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8953	High Similarity	NPC308619
0.8953	High Similarity	NPC324835
0.8953	High Similarity	NPC127491
0.8687	High Similarity	NPC47536
0.8687	High Similarity	NPC20485
0.86	High Similarity	NPC40178
0.8539	High Similarity	NPC53299
0.8523	High Similarity	NPC243289
0.8523	High Similarity	NPC208183
0.8506	High Similarity	NPC89950
0.8372	Intermediate Similarity	NPC176228
0.8352	Intermediate Similarity	NPC169050
0.8352	Intermediate Similarity	NPC286608
0.8333	Intermediate Similarity	NPC270654
0.8295	Intermediate Similarity	NPC303245
0.8295	Intermediate Similarity	NPC71795
0.8283	Intermediate Similarity	NPC474365
0.8283	Intermediate Similarity	NPC301943
0.828	Intermediate Similarity	NPC240108
0.828	Intermediate Similarity	NPC213156
0.8276	Intermediate Similarity	NPC78517
0.8276	Intermediate Similarity	NPC167577
0.8211	Intermediate Similarity	NPC23453
0.8202	Intermediate Similarity	NPC99240
0.8191	Intermediate Similarity	NPC472319
0.8081	Intermediate Similarity	NPC42211
0.8077	Intermediate Similarity	NPC474157
0.8068	Intermediate Similarity	NPC139901
0.8068	Intermediate Similarity	NPC151405
0.8061	Intermediate Similarity	NPC35448
0.8061	Intermediate Similarity	NPC78701
0.8058	Intermediate Similarity	NPC469636
0.8046	Intermediate Similarity	NPC287790
0.8046	Intermediate Similarity	NPC3672
0.8039	Intermediate Similarity	NPC51174
0.798	Intermediate Similarity	NPC325497
0.798	Intermediate Similarity	NPC146351
0.798	Intermediate Similarity	NPC118343
0.7979	Intermediate Similarity	NPC9822
0.7959	Intermediate Similarity	NPC276775
0.7959	Intermediate Similarity	NPC289201
0.7959	Intermediate Similarity	NPC249912
0.7959	Intermediate Similarity	NPC92754
0.7957	Intermediate Similarity	NPC96625
0.7941	Intermediate Similarity	NPC269457
0.7935	Intermediate Similarity	NPC123476
0.7931	Intermediate Similarity	NPC175393
0.7925	Intermediate Similarity	NPC128368
0.7879	Intermediate Similarity	NPC225060
0.7843	Intermediate Similarity	NPC114594
0.7812	Intermediate Similarity	NPC119631
0.78	Intermediate Similarity	NPC98911
0.78	Intermediate Similarity	NPC472318
0.7789	Intermediate Similarity	NPC173443
0.7778	Intermediate Similarity	NPC210092
0.7767	Intermediate Similarity	NPC209632
0.7757	Intermediate Similarity	NPC272524
0.7755	Intermediate Similarity	NPC130398
0.7753	Intermediate Similarity	NPC76455
0.7753	Intermediate Similarity	NPC137847
0.7745	Intermediate Similarity	NPC60679
0.7742	Intermediate Similarity	NPC294134
0.7736	Intermediate Similarity	NPC476003
0.7736	Intermediate Similarity	NPC210089
0.7723	Intermediate Similarity	NPC70624
0.7714	Intermediate Similarity	NPC83628
0.7714	Intermediate Similarity	NPC474364
0.7714	Intermediate Similarity	NPC265407
0.7714	Intermediate Similarity	NPC17417
0.7714	Intermediate Similarity	NPC10251
0.7708	Intermediate Similarity	NPC303967
0.7708	Intermediate Similarity	NPC110420
0.7708	Intermediate Similarity	NPC67585
0.77	Intermediate Similarity	NPC179411
0.77	Intermediate Similarity	NPC135951
0.77	Intermediate Similarity	NPC154517
0.7692	Intermediate Similarity	NPC477251
0.7692	Intermediate Similarity	NPC73978
0.7685	Intermediate Similarity	NPC308744
0.7685	Intermediate Similarity	NPC307651
0.7684	Intermediate Similarity	NPC304760
0.767	Intermediate Similarity	NPC269644
0.7667	Intermediate Similarity	NPC272260
0.7667	Intermediate Similarity	NPC300205
0.7664	Intermediate Similarity	NPC158282
0.7642	Intermediate Similarity	NPC196246
0.7642	Intermediate Similarity	NPC214067
0.7642	Intermediate Similarity	NPC251854
0.7642	Intermediate Similarity	NPC93084
0.764	Intermediate Similarity	NPC329318
0.764	Intermediate Similarity	NPC9796
0.764	Intermediate Similarity	NPC245966
0.764	Intermediate Similarity	NPC179726
0.7636	Intermediate Similarity	NPC190298
0.7624	Intermediate Similarity	NPC80115
0.7619	Intermediate Similarity	NPC56493
0.7615	Intermediate Similarity	NPC474685
0.7609	Intermediate Similarity	NPC323103
0.7604	Intermediate Similarity	NPC220893
0.7604	Intermediate Similarity	NPC231591
0.7593	Intermediate Similarity	NPC161611
0.7593	Intermediate Similarity	NPC474176
0.7582	Intermediate Similarity	NPC71664
0.7582	Intermediate Similarity	NPC164086
0.7579	Intermediate Similarity	NPC89377
0.7579	Intermediate Similarity	NPC194326
0.7579	Intermediate Similarity	NPC69057
0.7573	Intermediate Similarity	NPC234305
0.7573	Intermediate Similarity	NPC89886
0.757	Intermediate Similarity	NPC305912
0.757	Intermediate Similarity	NPC1082
0.7556	Intermediate Similarity	NPC285470
0.7556	Intermediate Similarity	NPC2785
0.7556	Intermediate Similarity	NPC36342
0.7553	Intermediate Similarity	NPC475710
0.7547	Intermediate Similarity	NPC281604
0.7547	Intermediate Similarity	NPC99846
0.7547	Intermediate Similarity	NPC269023
0.7545	Intermediate Similarity	NPC149691
0.7527	Intermediate Similarity	NPC270507
0.7527	Intermediate Similarity	NPC288903
0.7527	Intermediate Similarity	NPC273758
0.7525	Intermediate Similarity	NPC329387
0.7525	Intermediate Similarity	NPC317280
0.7524	Intermediate Similarity	NPC119271
0.7524	Intermediate Similarity	NPC474376
0.7524	Intermediate Similarity	NPC475203
0.7524	Intermediate Similarity	NPC472316
0.7524	Intermediate Similarity	NPC472315
0.7524	Intermediate Similarity	NPC136962
0.7523	Intermediate Similarity	NPC474363
0.7522	Intermediate Similarity	NPC473243
0.7522	Intermediate Similarity	NPC475827
0.7522	Intermediate Similarity	NPC474223
0.75	Intermediate Similarity	NPC85977
0.75	Intermediate Similarity	NPC474689
0.75	Intermediate Similarity	NPC82899
0.75	Intermediate Similarity	NPC280616
0.75	Intermediate Similarity	NPC64340
0.75	Intermediate Similarity	NPC270699
0.75	Intermediate Similarity	NPC12936
0.75	Intermediate Similarity	NPC171831
0.75	Intermediate Similarity	NPC242913
0.75	Intermediate Similarity	NPC273033
0.7477	Intermediate Similarity	NPC174099
0.7476	Intermediate Similarity	NPC188895
0.7471	Intermediate Similarity	NPC74458
0.7453	Intermediate Similarity	NPC156648
0.7453	Intermediate Similarity	NPC470391
0.7451	Intermediate Similarity	NPC203925
0.7449	Intermediate Similarity	NPC476484
0.7434	Intermediate Similarity	NPC476096
0.7434	Intermediate Similarity	NPC204784
0.7419	Intermediate Similarity	NPC103387
0.7416	Intermediate Similarity	NPC32203
0.7416	Intermediate Similarity	NPC206800
0.7411	Intermediate Similarity	NPC469574
0.7411	Intermediate Similarity	NPC152812
0.7407	Intermediate Similarity	NPC167504
0.74	Intermediate Similarity	NPC5472
0.74	Intermediate Similarity	NPC206764
0.7391	Intermediate Similarity	NPC17408
0.7391	Intermediate Similarity	NPC190567
0.7391	Intermediate Similarity	NPC95868
0.7391	Intermediate Similarity	NPC285716
0.7391	Intermediate Similarity	NPC121800
0.7391	Intermediate Similarity	NPC477703
0.7387	Intermediate Similarity	NPC100353
0.7387	Intermediate Similarity	NPC471616
0.7386	Intermediate Similarity	NPC271437
0.7386	Intermediate Similarity	NPC285679
0.7368	Intermediate Similarity	NPC58616
0.7364	Intermediate Similarity	NPC87069
0.7364	Intermediate Similarity	NPC153053
0.7358	Intermediate Similarity	NPC37622
0.7358	Intermediate Similarity	NPC37115
0.7358	Intermediate Similarity	NPC30594
0.7353	Intermediate Similarity	NPC145052
0.7347	Intermediate Similarity	NPC108026
0.7347	Intermediate Similarity	NPC84288
0.7347	Intermediate Similarity	NPC185501
0.734	Intermediate Similarity	NPC44830
0.734	Intermediate Similarity	NPC215008
0.7339	Intermediate Similarity	NPC79496
0.7339	Intermediate Similarity	NPC321852
0.7339	Intermediate Similarity	NPC474314
0.7339	Intermediate Similarity	NPC234376
0.7333	Intermediate Similarity	NPC31786
0.7328	Intermediate Similarity	NPC474159
0.7328	Intermediate Similarity	NPC474254
0.7327	Intermediate Similarity	NPC30361
0.7327	Intermediate Similarity	NPC12695
0.732	Intermediate Similarity	NPC477693
0.732	Intermediate Similarity	NPC477704
0.7312	Intermediate Similarity	NPC145053
0.7308	Intermediate Similarity	NPC45613
0.7304	Intermediate Similarity	NPC50872
0.7303	Intermediate Similarity	NPC208075
0.73	Intermediate Similarity	NPC261181
0.7292	Intermediate Similarity	NPC318107

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 NPC77273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	944
0.2-0.3	1378
0.3-0.4	3206
0.4-0.5	2324
0.5-0.6	902
0.6-0.7	178
0.7-0.8	31
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
0.8352	Intermediate Similarity	NPD1282	Approved
0.798	Intermediate Similarity	NPD1238	Approved
0.7905	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD5909	Discontinued
0.781	Intermediate Similarity	NPD2067	Discontinued
0.7745	Intermediate Similarity	NPD6647	Phase 2
0.7714	Intermediate Similarity	NPD2182	Approved
0.7526	Intermediate Similarity	NPD3673	Approved
0.7526	Intermediate Similarity	NPD3672	Approved
0.7525	Intermediate Similarity	NPD5926	Approved
0.75	Intermediate Similarity	NPD942	Approved
0.75	Intermediate Similarity	NPD1989	Approved
0.7475	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2066	Phase 3
0.7451	Intermediate Similarity	NPD7798	Approved
0.7423	Intermediate Similarity	NPD689	Discontinued
0.7416	Intermediate Similarity	NPD9716	Approved
0.7391	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD225	Approved
0.7363	Intermediate Similarity	NPD227	Approved
0.734	Intermediate Similarity	NPD3971	Phase 1
0.7333	Intermediate Similarity	NPD164	Approved
0.73	Intermediate Similarity	NPD1202	Approved
0.7292	Intermediate Similarity	NPD9259	Approved
0.7292	Intermediate Similarity	NPD9257	Approved
0.7283	Intermediate Similarity	NPD9490	Approved
0.7273	Intermediate Similarity	NPD7609	Phase 3
0.7216	Intermediate Similarity	NPD650	Approved
0.72	Intermediate Similarity	NPD7631	Approved
0.7184	Intermediate Similarity	NPD9495	Approved
0.717	Intermediate Similarity	NPD1237	Approved
0.7158	Intermediate Similarity	NPD9491	Approved
0.7128	Intermediate Similarity	NPD226	Approved
0.7117	Intermediate Similarity	NPD6858	Approved
0.7117	Intermediate Similarity	NPD7094	Approved
0.7103	Intermediate Similarity	NPD5048	Discontinued
0.7094	Intermediate Similarity	NPD6287	Discontinued
0.7075	Intermediate Similarity	NPD1929	Approved
0.7075	Intermediate Similarity	NPD1930	Approved
0.7075	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1241	Discontinued
0.7054	Intermediate Similarity	NPD6010	Discontinued
0.7041	Intermediate Similarity	NPD1087	Approved
0.7041	Intermediate Similarity	NPD4793	Discontinued
0.7037	Intermediate Similarity	NPD3134	Approved
0.7034	Intermediate Similarity	NPD6637	Approved
0.7027	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9258	Approved
0.7	Intermediate Similarity	NPD9256	Approved
0.6991	Remote Similarity	NPD2629	Approved
0.6991	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1932	Approved
0.6957	Remote Similarity	NPD2347	Approved
0.6923	Remote Similarity	NPD3495	Discontinued
0.6917	Remote Similarity	NPD2198	Approved
0.6917	Remote Similarity	NPD2199	Approved
0.6916	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.69	Remote Similarity	NPD800	Approved
0.69	Remote Similarity	NPD5347	Phase 2
0.69	Remote Similarity	NPD5346	Phase 2
0.6893	Remote Similarity	NPD1693	Approved
0.6869	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1508	Approved
0.6832	Remote Similarity	NPD1090	Approved
0.6832	Remote Similarity	NPD1086	Approved
0.6832	Remote Similarity	NPD1089	Approved
0.6818	Remote Similarity	NPD1358	Approved
0.6765	Remote Similarity	NPD1239	Approved
0.6752	Remote Similarity	NPD1894	Discontinued
0.6752	Remote Similarity	NPD9545	Approved
0.6731	Remote Similarity	NPD9260	Approved
0.6723	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD1088	Approved
0.6696	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1843	Approved
0.6667	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7008	Discontinued
0.6639	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5667	Approved
0.6637	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD9697	Approved
0.6635	Remote Similarity	NPD1563	Approved
0.6607	Remote Similarity	NPD2329	Discontinued
0.6585	Remote Similarity	NPD3266	Approved
0.6585	Remote Similarity	NPD2797	Approved
0.6585	Remote Similarity	NPD3267	Approved
0.6581	Remote Similarity	NPD9493	Approved
0.6581	Remote Similarity	NPD4574	Approved
0.6581	Remote Similarity	NPD4576	Approved
0.6577	Remote Similarity	NPD6685	Approved
0.6571	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6049	Phase 2
0.6571	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5951	Approved
0.6549	Remote Similarity	NPD4234	Approved
0.6549	Remote Similarity	NPD4233	Approved
0.6549	Remote Similarity	NPD5239	Approved
0.6549	Remote Similarity	NPD5235	Approved
0.6549	Remote Similarity	NPD1752	Approved
0.6549	Remote Similarity	NPD1756	Approved
0.6549	Remote Similarity	NPD5236	Approved
0.6549	Remote Similarity	NPD5240	Approved
0.6549	Remote Similarity	NPD5237	Approved
0.6522	Remote Similarity	NPD2607	Approved
0.6514	Remote Similarity	NPD2648	Phase 3
0.6514	Remote Similarity	NPD2193	Phase 2
0.6514	Remote Similarity	NPD2171	Approved
0.6508	Remote Similarity	NPD6039	Approved
0.65	Remote Similarity	NPD5306	Approved
0.65	Remote Similarity	NPD5305	Approved
0.6496	Remote Similarity	NPD4198	Discontinued
0.6491	Remote Similarity	NPD2201	Approved
0.6484	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD3972	Approved
0.6466	Remote Similarity	NPD2650	Approved
0.6466	Remote Similarity	NPD2652	Approved
0.6462	Remote Similarity	NPD2569	Approved
0.6462	Remote Similarity	NPD2567	Approved
0.6457	Remote Similarity	NPD2313	Discontinued
0.6457	Remote Similarity	NPD3268	Approved
0.6455	Remote Similarity	NPD5765	Approved
0.6455	Remote Similarity	NPD9261	Approved
0.6449	Remote Similarity	NPD1564	Approved
0.6449	Remote Similarity	NPD1565	Approved
0.6449	Remote Similarity	NPD1099	Approved
0.6449	Remote Similarity	NPD1100	Approved
0.6449	Remote Similarity	NPD1566	Phase 3
0.6446	Remote Similarity	NPD4136	Approved
0.6446	Remote Similarity	NPD4135	Approved
0.6446	Remote Similarity	NPD4106	Approved
0.6439	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD969	Suspended
0.6429	Remote Similarity	NPD5706	Approved
0.6429	Remote Similarity	NPD5705	Approved
0.6429	Remote Similarity	NPD5704	Approved
0.6422	Remote Similarity	NPD2549	Approved
0.6422	Remote Similarity	NPD2550	Approved
0.6422	Remote Similarity	NPD2553	Approved
0.6422	Remote Similarity	NPD2558	Approved
0.6422	Remote Similarity	NPD2555	Approved
0.6422	Remote Similarity	NPD2552	Approved
0.6417	Remote Similarity	NPD5585	Approved
0.6415	Remote Similarity	NPD4094	Approved
0.6406	Remote Similarity	NPD7713	Phase 3
0.6404	Remote Similarity	NPD1317	Discontinued
0.64	Remote Similarity	NPD6085	Phase 2
0.64	Remote Similarity	NPD2798	Approved
0.64	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4807	Approved
0.6393	Remote Similarity	NPD4806	Approved
0.6387	Remote Similarity	NPD6065	Approved
0.6385	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5277	Phase 2
0.6378	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4188	Approved
0.6364	Remote Similarity	NPD2196	Discontinued
0.6364	Remote Similarity	NPD4189	Approved
0.6357	Remote Similarity	NPD3373	Approved
0.633	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6798	Discontinued
0.6321	Remote Similarity	NPD1066	Discontinued
0.632	Remote Similarity	NPD2625	Approved
0.632	Remote Similarity	NPD2627	Approved
0.632	Remote Similarity	NPD2626	Approved
0.632	Remote Similarity	NPD2159	Approved
0.632	Remote Similarity	NPD2628	Approved
0.632	Remote Similarity	NPD2160	Approved
0.6306	Remote Similarity	NPD3357	Discontinued
0.6303	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4655	Approved
0.6296	Remote Similarity	NPD4657	Approved
0.6293	Remote Similarity	NPD6912	Phase 3
0.629	Remote Similarity	NPD5157	Phase 1
0.629	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5159	Phase 2
0.6283	Remote Similarity	NPD467	Phase 1
0.6281	Remote Similarity	NPD4102	Approved
0.6281	Remote Similarity	NPD4105	Approved
0.6281	Remote Similarity	NPD5691	Approved
0.6279	Remote Similarity	NPD4062	Phase 3
0.6279	Remote Similarity	NPD6233	Phase 2
0.6273	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4766	Approved
0.627	Remote Similarity	NPD5647	Approved
0.627	Remote Similarity	NPD1019	Discontinued
0.626	Remote Similarity	NPD2609	Approved
0.626	Remote Similarity	NPD2612	Approved
0.626	Remote Similarity	NPD3132	Approved
0.626	Remote Similarity	NPD4215	Approved
0.626	Remote Similarity	NPD4218	Approved
0.626	Remote Similarity	NPD4216	Approved
0.626	Remote Similarity	NPD2608	Approved
0.626	Remote Similarity	NPD3131	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