NPASS Compound

Structure

NPC244338 OpenBabel07101718202D 22 24 0 0 0 0 0 0 0 0999 V2000 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 21 1 0 0 0 0 10 22 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.1
Volume:	296.116
LogP:	2.253
LogD:	2.383
LogS:	-3.955
# Rotatable Bonds:	4
TPSA:	65.07
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	2.91
Fsp3:	0.25
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:	-4.621
MDCK Permeability:	1.5617211829521693e-05
Pgp-inhibitor:	0.52
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.84

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	86.8510513305664%
Volume Distribution (VD):	0.499
Pgp-substrate:	13.516290664672852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.578
CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.717
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	12.242
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.066
Drug-inuced Liver Injury (DILI):	0.174
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.924
Carcinogencity:	0.959
Eye Corrosion:	0.017
Eye Irritation:	0.141
Respiratory Toxicity:	0.122

Download Data

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

Natural Product: NPC244338

Natural Product ID:	NPC244338
*Common Name:**	N-(3-Methoxy-4,5-Methylenedioxycinnamoyl)-Delta3-Pyridin-2-One
IUPAC Name:	1-[(E)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-enoyl]-2,3-dihydropyridin-6-one
Synonyms:
Standard InCHIKey:	SUHIRCMTPMDNGD-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C16H15NO5/c1-20-12-8-11(9-13-16(12)22-10-21-13)5-6-15(19)17-7-3-2-4-14(17)18/h2,4-6,8-9H,3,7,10H2,1H3/b6-5+
SMILES:	COc1cc(/C=C/C(=O)N2CCC=CC2=O)cc2c1OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509874
PubChem CID:	14707486
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids 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
NPO33320	piper aborescens	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[2089124]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.57	ug ml-1	PMID[453304]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.15	ug ml-1	PMID[453304]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.62	ug ml-1	PMID[453304]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.43	ug ml-1	PMID[453304]

☑ 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 NPC244338 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	241
0.1-0.2	1878
0.2-0.3	7947
0.3-0.4	11112
0.4-0.5	5206
0.5-0.6	10235
0.6-0.7	5550
0.7-0.8	493
0.8-0.85	11
0.85-0.9	20
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC113236
0.9412	High Similarity	NPC214036
0.931	High Similarity	NPC169742
0.8723	High Similarity	NPC470707
0.8714	High Similarity	NPC205178
0.8714	High Similarity	NPC73883
0.8714	High Similarity	NPC255817
0.8714	High Similarity	NPC136330
0.8714	High Similarity	NPC277042
0.8714	High Similarity	NPC251454
0.8714	High Similarity	NPC196609
0.8714	High Similarity	NPC230698
0.8652	High Similarity	NPC99078
0.8643	High Similarity	NPC45783
0.8643	High Similarity	NPC167096
0.8643	High Similarity	NPC103947
0.8643	High Similarity	NPC94280
0.8643	High Similarity	NPC159150
0.8643	High Similarity	NPC193673
0.8643	High Similarity	NPC328419
0.8633	High Similarity	NPC217574
0.8592	High Similarity	NPC252107
0.8592	High Similarity	NPC220923
0.8582	High Similarity	NPC96406
0.8521	High Similarity	NPC145446
0.8521	High Similarity	NPC469808
0.8521	High Similarity	NPC137172
0.8462	Intermediate Similarity	NPC248505
0.8462	Intermediate Similarity	NPC95366
0.8289	Intermediate Similarity	NPC270811
0.8289	Intermediate Similarity	NPC471073
0.8239	Intermediate Similarity	NPC318862
0.8194	Intermediate Similarity	NPC180647
0.8082	Intermediate Similarity	NPC225745
0.8074	Intermediate Similarity	NPC33271
0.7959	Intermediate Similarity	NPC194359
0.7959	Intermediate Similarity	NPC28641
0.7956	Intermediate Similarity	NPC119949
0.7905	Intermediate Similarity	NPC20796
0.7901	Intermediate Similarity	NPC473748
0.7899	Intermediate Similarity	NPC222175
0.7891	Intermediate Similarity	NPC240915
0.7857	Intermediate Similarity	NPC288238
0.7826	Intermediate Similarity	NPC69670
0.7823	Intermediate Similarity	NPC7163
0.781	Intermediate Similarity	NPC212643
0.781	Intermediate Similarity	NPC199209
0.7792	Intermediate Similarity	NPC59907
0.7792	Intermediate Similarity	NPC37144
0.7786	Intermediate Similarity	NPC310373
0.7786	Intermediate Similarity	NPC193484
0.7785	Intermediate Similarity	NPC231572
0.777	Intermediate Similarity	NPC73071
0.7746	Intermediate Similarity	NPC92869
0.7746	Intermediate Similarity	NPC191768
0.7746	Intermediate Similarity	NPC283170
0.773	Intermediate Similarity	NPC256167
0.773	Intermediate Similarity	NPC211231
0.7724	Intermediate Similarity	NPC228769
0.7724	Intermediate Similarity	NPC470633
0.7708	Intermediate Similarity	NPC194841
0.7688	Intermediate Similarity	NPC329640
0.7676	Intermediate Similarity	NPC108545
0.7671	Intermediate Similarity	NPC19242
0.7671	Intermediate Similarity	NPC63574
0.766	Intermediate Similarity	NPC114845
0.7651	Intermediate Similarity	NPC38101
0.7639	Intermediate Similarity	NPC127604
0.7619	Intermediate Similarity	NPC192255
0.7609	Intermediate Similarity	NPC111225
0.7609	Intermediate Similarity	NPC123948
0.76	Intermediate Similarity	NPC143895
0.7597	Intermediate Similarity	NPC297342
0.7597	Intermediate Similarity	NPC50696
0.7571	Intermediate Similarity	NPC57501
0.7569	Intermediate Similarity	NPC27352
0.7569	Intermediate Similarity	NPC300326
0.7569	Intermediate Similarity	NPC85830
0.7569	Intermediate Similarity	NPC58279
0.7566	Intermediate Similarity	NPC210478
0.7552	Intermediate Similarity	NPC238810
0.7551	Intermediate Similarity	NPC240722
0.7551	Intermediate Similarity	NPC244799
0.7548	Intermediate Similarity	NPC474158
0.7547	Intermediate Similarity	NPC470708
0.7531	Intermediate Similarity	NPC26353
0.7517	Intermediate Similarity	NPC241341
0.7517	Intermediate Similarity	NPC36437
0.7517	Intermediate Similarity	NPC471390
0.7517	Intermediate Similarity	NPC471391
0.7517	Intermediate Similarity	NPC136750
0.7517	Intermediate Similarity	NPC233018
0.7517	Intermediate Similarity	NPC266848
0.7517	Intermediate Similarity	NPC196937
0.7517	Intermediate Similarity	NPC473960
0.75	Intermediate Similarity	NPC296575
0.75	Intermediate Similarity	NPC118419
0.75	Intermediate Similarity	NPC203924
0.75	Intermediate Similarity	NPC231198
0.7484	Intermediate Similarity	NPC469978
0.7483	Intermediate Similarity	NPC11453
0.7483	Intermediate Similarity	NPC123127
0.7483	Intermediate Similarity	NPC27239
0.7481	Intermediate Similarity	NPC165386
0.7481	Intermediate Similarity	NPC127326
0.7467	Intermediate Similarity	NPC145769
0.7467	Intermediate Similarity	NPC11147
0.7466	Intermediate Similarity	NPC64948
0.7455	Intermediate Similarity	NPC474858
0.7455	Intermediate Similarity	NPC329717
0.745	Intermediate Similarity	NPC261812
0.745	Intermediate Similarity	NPC137669
0.745	Intermediate Similarity	NPC5423
0.745	Intermediate Similarity	NPC245120
0.745	Intermediate Similarity	NPC72046
0.745	Intermediate Similarity	NPC65183
0.7448	Intermediate Similarity	NPC152186
0.7448	Intermediate Similarity	NPC271985
0.7448	Intermediate Similarity	NPC182147
0.7448	Intermediate Similarity	NPC71105
0.7448	Intermediate Similarity	NPC170583
0.7448	Intermediate Similarity	NPC207541
0.7448	Intermediate Similarity	NPC246133
0.7447	Intermediate Similarity	NPC475961
0.7447	Intermediate Similarity	NPC254625
0.7439	Intermediate Similarity	NPC189782
0.7436	Intermediate Similarity	NPC476450
0.7434	Intermediate Similarity	NPC166184
0.7432	Intermediate Similarity	NPC184814
0.7421	Intermediate Similarity	NPC474560
0.7421	Intermediate Similarity	NPC218575
0.7417	Intermediate Similarity	NPC416184
0.7417	Intermediate Similarity	NPC189474
0.7417	Intermediate Similarity	NPC7018
0.7415	Intermediate Similarity	NPC109275
0.74	Intermediate Similarity	NPC58585
0.74	Intermediate Similarity	NPC284855
0.74	Intermediate Similarity	NPC473463
0.74	Intermediate Similarity	NPC282477
0.7397	Intermediate Similarity	NPC251466
0.7397	Intermediate Similarity	NPC156944
0.7396	Intermediate Similarity	NPC287152
0.7394	Intermediate Similarity	NPC180306
0.7391	Intermediate Similarity	NPC204120
0.7389	Intermediate Similarity	NPC472560
0.7389	Intermediate Similarity	NPC224687
0.7386	Intermediate Similarity	NPC226005
0.7383	Intermediate Similarity	NPC469698
0.7383	Intermediate Similarity	NPC473412
0.7379	Intermediate Similarity	NPC300955
0.7372	Intermediate Similarity	NPC475000
0.7368	Intermediate Similarity	NPC172818
0.7368	Intermediate Similarity	NPC25695
0.7365	Intermediate Similarity	NPC48315
0.7365	Intermediate Similarity	NPC262641
0.7362	Intermediate Similarity	NPC106786
0.7358	Intermediate Similarity	NPC283839
0.7358	Intermediate Similarity	NPC90896
0.7355	Intermediate Similarity	NPC210354
0.7355	Intermediate Similarity	NPC176586
0.7351	Intermediate Similarity	NPC111635
0.7351	Intermediate Similarity	NPC256776
0.7351	Intermediate Similarity	NPC185680
0.7351	Intermediate Similarity	NPC92830
0.7351	Intermediate Similarity	NPC145722
0.7351	Intermediate Similarity	NPC309953
0.7351	Intermediate Similarity	NPC31530
0.7347	Intermediate Similarity	NPC291449
0.7347	Intermediate Similarity	NPC191302
0.7347	Intermediate Similarity	NPC41331
0.7347	Intermediate Similarity	NPC99798
0.7347	Intermediate Similarity	NPC157740
0.7343	Intermediate Similarity	NPC166759
0.7343	Intermediate Similarity	NPC472596
0.7338	Intermediate Similarity	NPC278076
0.7333	Intermediate Similarity	NPC123954
0.7333	Intermediate Similarity	NPC162093
0.7333	Intermediate Similarity	NPC319969
0.733	Intermediate Similarity	NPC473716
0.733	Intermediate Similarity	NPC475597
0.7321	Intermediate Similarity	NPC75958
0.732	Intermediate Similarity	NPC195196
0.732	Intermediate Similarity	NPC185908
0.732	Intermediate Similarity	NPC196420
0.7312	Intermediate Similarity	NPC474852
0.7308	Intermediate Similarity	NPC474288
0.7303	Intermediate Similarity	NPC234865
0.7303	Intermediate Similarity	NPC150534
0.7303	Intermediate Similarity	NPC55040
0.7303	Intermediate Similarity	NPC49235
0.7303	Intermediate Similarity	NPC148893
0.7303	Intermediate Similarity	NPC25333
0.7299	Intermediate Similarity	NPC31279
0.7297	Intermediate Similarity	NPC210674
0.7297	Intermediate Similarity	NPC474623
0.7297	Intermediate Similarity	NPC246974
0.7297	Intermediate Similarity	NPC147247
0.7297	Intermediate Similarity	NPC474651
0.7296	Intermediate Similarity	NPC96294
0.7296	Intermediate Similarity	NPC477375

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 NPC244338 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	817
0.2-0.3	1471
0.3-0.4	2691
0.4-0.5	2321
0.5-0.6	1295
0.6-0.7	362
0.7-0.8	28
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8759	High Similarity	NPD5297	Approved
0.8714	High Similarity	NPD2492	Phase 1
0.7763	Intermediate Similarity	NPD2219	Phase 1
0.7662	Intermediate Similarity	NPD4357	Discontinued
0.7417	Intermediate Similarity	NPD6111	Discontinued
0.7407	Intermediate Similarity	NPD5353	Approved
0.7405	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7124	Phase 2
0.7308	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3705	Approved
0.7278	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3146	Approved
0.7267	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4210	Discontinued
0.7241	Intermediate Similarity	NPD2981	Phase 2
0.7192	Intermediate Similarity	NPD2983	Phase 2
0.7192	Intermediate Similarity	NPD2982	Phase 2
0.7183	Intermediate Similarity	NPD5536	Phase 2
0.7179	Intermediate Similarity	NPD4236	Phase 3
0.7179	Intermediate Similarity	NPD4237	Approved
0.717	Intermediate Similarity	NPD1424	Approved
0.7134	Intermediate Similarity	NPD4585	Approved
0.7126	Intermediate Similarity	NPD5677	Discontinued
0.7117	Intermediate Similarity	NPD6385	Approved
0.7117	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD5242	Approved
0.7099	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1653	Approved
0.7034	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1349	Approved
0.7019	Intermediate Similarity	NPD1351	Approved
0.7019	Intermediate Similarity	NPD1350	Approved
0.7012	Intermediate Similarity	NPD5090	Approved
0.7012	Intermediate Similarity	NPD5089	Approved
0.7	Intermediate Similarity	NPD3018	Phase 2
0.6994	Remote Similarity	NPD824	Approved
0.6989	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5718	Phase 2
0.6971	Remote Similarity	NPD7549	Discontinued
0.6968	Remote Similarity	NPD743	Approved
0.6966	Remote Similarity	NPD1357	Approved
0.6962	Remote Similarity	NPD2654	Approved
0.6951	Remote Similarity	NPD4678	Approved
0.6951	Remote Similarity	NPD4675	Approved
0.6951	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2978	Approved
0.6928	Remote Similarity	NPD2977	Approved
0.6914	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD5604	Discontinued
0.6897	Remote Similarity	NPD7534	Approved
0.6897	Remote Similarity	NPD7533	Approved
0.6897	Remote Similarity	NPD3885	Approved
0.6894	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3454	Phase 3
0.6868	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3383	Approved
0.6867	Remote Similarity	NPD3384	Approved
0.6867	Remote Similarity	NPD3382	Approved
0.6859	Remote Similarity	NPD6896	Approved
0.6859	Remote Similarity	NPD6895	Approved
0.6846	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6788	Approved
0.6836	Remote Similarity	NPD7280	Phase 3
0.6836	Remote Similarity	NPD7281	Phase 3
0.6835	Remote Similarity	NPD1375	Discontinued
0.6813	Remote Similarity	NPD5481	Discontinued
0.6807	Remote Similarity	NPD6873	Phase 2
0.6807	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7110	Phase 1
0.6795	Remote Similarity	NPD2653	Approved
0.6792	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5006	Approved
0.6791	Remote Similarity	NPD5005	Approved
0.6788	Remote Similarity	NPD4005	Discontinued
0.6783	Remote Similarity	NPD5283	Phase 1
0.6766	Remote Similarity	NPD37	Approved
0.675	Remote Similarity	NPD3060	Approved
0.6747	Remote Similarity	NPD6876	Approved
0.6747	Remote Similarity	NPD6875	Approved
0.674	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD1358	Approved
0.6709	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7466	Approved
0.6706	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2922	Phase 1
0.6686	Remote Similarity	NPD3818	Discontinued
0.6686	Remote Similarity	NPD5978	Approved
0.6686	Remote Similarity	NPD2563	Approved
0.6686	Remote Similarity	NPD5977	Approved
0.6686	Remote Similarity	NPD2560	Approved
0.6685	Remote Similarity	NPD6843	Phase 3
0.6685	Remote Similarity	NPD4157	Discontinued
0.6685	Remote Similarity	NPD6842	Approved
0.6685	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1670	Discontinued
0.6667	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4420	Approved
0.6647	Remote Similarity	NPD4965	Approved
0.6647	Remote Similarity	NPD4966	Approved
0.6647	Remote Similarity	NPD4967	Phase 2
0.6646	Remote Similarity	NPD3158	Phase 1
0.6646	Remote Similarity	NPD3157	Approved
0.6646	Remote Similarity	NPD4123	Phase 3
0.6627	Remote Similarity	NPD5773	Approved
0.6627	Remote Similarity	NPD3687	Approved
0.6627	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5772	Approved
0.6627	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3686	Approved
0.6623	Remote Similarity	NPD1421	Approved
0.6623	Remote Similarity	NPD1420	Approved
0.6623	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.66	Remote Similarity	NPD422	Phase 1
0.6596	Remote Similarity	NPD5457	Discontinued
0.6591	Remote Similarity	NPD8251	Approved
0.6591	Remote Similarity	NPD8099	Discontinued
0.6591	Remote Similarity	NPD8252	Approved
0.659	Remote Similarity	NPD7199	Phase 2
0.6587	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4481	Phase 3
0.657	Remote Similarity	NPD6234	Discontinued
0.657	Remote Similarity	NPD919	Approved
0.6566	Remote Similarity	NPD5976	Discontinued
0.6562	Remote Similarity	NPD3539	Phase 1
0.6559	Remote Similarity	NPD5582	Discontinued
0.6554	Remote Similarity	NPD8156	Discontinued
0.6552	Remote Similarity	NPD4166	Phase 2
0.655	Remote Similarity	NPD3882	Suspended
0.6545	Remote Similarity	NPD2335	Discontinued
0.6545	Remote Similarity	NPD4584	Approved
0.6545	Remote Similarity	NPD7447	Phase 1
0.6543	Remote Similarity	NPD4162	Approved
0.6543	Remote Similarity	NPD5177	Phase 3
0.6538	Remote Similarity	NPD3145	Approved
0.6538	Remote Similarity	NPD3144	Approved
0.6534	Remote Similarity	NPD3489	Phase 3
0.6528	Remote Similarity	NPD228	Approved
0.6525	Remote Similarity	NPD3134	Approved
0.6524	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7266	Discontinued
0.6522	Remote Similarity	NPD3656	Approved
0.6522	Remote Similarity	NPD3540	Phase 1
0.6519	Remote Similarity	NPD1933	Approved
0.6516	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4055	Discovery
0.6508	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3349	Phase 2
0.6497	Remote Similarity	NPD2674	Phase 3
0.6497	Remote Similarity	NPD2245	Discovery
0.6491	Remote Similarity	NPD3817	Phase 2
0.6485	Remote Similarity	NPD7212	Phase 2
0.6485	Remote Similarity	NPD7213	Phase 3
0.6481	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7263	Phase 2
0.6474	Remote Similarity	NPD3179	Approved
0.6474	Remote Similarity	NPD3180	Approved
0.6467	Remote Similarity	NPD2122	Discontinued
0.6467	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD3640	Phase 3
0.6467	Remote Similarity	NPD3641	Approved
0.6467	Remote Similarity	NPD2668	Approved
0.6467	Remote Similarity	NPD3639	Approved
0.6467	Remote Similarity	NPD2667	Approved
0.6463	Remote Similarity	NPD5241	Discontinued
0.6461	Remote Similarity	NPD7054	Approved
0.6457	Remote Similarity	NPD6071	Discontinued
0.6456	Remote Similarity	NPD2238	Phase 2
0.6456	Remote Similarity	NPD1613	Approved
0.6456	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3140	Approved
0.6456	Remote Similarity	NPD3142	Approved
0.6452	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4739	Approved
0.6438	Remote Similarity	NPD2200	Suspended
0.6437	Remote Similarity	NPD5494	Approved
0.6433	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD2801	Approved
0.6429	Remote Similarity	NPD6618	Phase 2
0.6425	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7472	Approved
0.6424	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3596	Phase 2
0.6416	Remote Similarity	NPD6971	Discontinued
0.6415	Remote Similarity	NPD230	Phase 1

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