NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	261.1
Volume:	258.006
LogP:	1.525
LogD:	2.348
LogS:	-3.467
# Rotatable Bonds:	3
TPSA:	48.0
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.149
Fsp3:	0.357
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:	-4.633
MDCK Permeability:	2.895873512898106e-05
Pgp-inhibitor:	0.198
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	83.86390686035156%
Volume Distribution (VD):	0.376
Pgp-substrate:	7.7675461769104%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.508
CYP2C19-inhibitor:	0.399
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.669
CYP2D6-substrate:	0.527
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.496
Half-life (T1/2):	0.834

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.377
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.76
Carcinogencity:	0.932
Eye Corrosion:	0.04
Eye Irritation:	0.371
Respiratory Toxicity:	0.052

Download Data

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

Natural Product: NPC469808

Natural Product ID:	NPC469808
*Common Name:**	Sid17403365
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-1-morpholin-4-ylprop-2-en-1-one
Synonyms:
Standard InCHIKey:	YGGASQPEKIGCKJ-DUXPYHPUSA-N
Standard InCHI:	InChI=1S/C14H15NO4/c16-14(15-5-7-17-8-6-15)4-2-11-1-3-12-13(9-11)19-10-18-12/h1-4,9H,5-8,10H2/b4-2+
SMILES:	O=C(N1CCOCC1)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL118703
PubChem CID:	682145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28928	Piper nigrum	Species	Piperaceae	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	4
Potency	12

Activity Type	# Activity
Individual Protein	11
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[488203]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	35481.3	nM	PMID[488203]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	31622.8	nM	PMID[488203]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[488203]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[488203]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	16944.1	nM	PMID[488203]
NPT1474	Individual Protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	31622.8	nM	PMID[488203]
NPT501	Individual Protein	Alpha-galactosidase A	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[488203]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	6390.0	nM	PMID[488204]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	>	100000.0	nM	PMID[488204]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	95780.0	nM	PMID[488201]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	96000.0	nM	PMID[488202]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	31622.8	nM	PMID[488203]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[488203]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[488203]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[488203]

☑ 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 NPC469808 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	239
0.1-0.2	1484
0.2-0.3	6590
0.3-0.4	12157
0.4-0.5	5585
0.5-0.6	12261
0.6-0.7	4041
0.7-0.8	301
0.8-0.85	9
0.85-0.9	16
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9242	High Similarity	NPC167096
0.9173	High Similarity	NPC251454
0.9173	High Similarity	NPC196609
0.9173	High Similarity	NPC230698
0.9173	High Similarity	NPC205178
0.9173	High Similarity	NPC73883
0.9173	High Similarity	NPC277042
0.9173	High Similarity	NPC255817
0.9173	High Similarity	NPC136330
0.9104	High Similarity	NPC99078
0.9037	High Similarity	NPC470707
0.9037	High Similarity	NPC220923
0.9037	High Similarity	NPC252107
0.8947	High Similarity	NPC217574
0.8815	High Similarity	NPC103947
0.8815	High Similarity	NPC94280
0.8815	High Similarity	NPC159150
0.8815	High Similarity	NPC193673
0.8815	High Similarity	NPC45783
0.8815	High Similarity	NPC328419
0.875	High Similarity	NPC96406
0.8686	High Similarity	NPC137172
0.8686	High Similarity	NPC145446
0.8623	High Similarity	NPC248505
0.8623	High Similarity	NPC95366
0.8613	High Similarity	NPC180647
0.8521	High Similarity	NPC244338
0.8489	Intermediate Similarity	NPC225745
0.8435	Intermediate Similarity	NPC270811
0.8435	Intermediate Similarity	NPC471073
0.8394	Intermediate Similarity	NPC318862
0.8154	Intermediate Similarity	NPC111225
0.8099	Intermediate Similarity	NPC194359
0.8099	Intermediate Similarity	NPC28641
0.8092	Intermediate Similarity	NPC199209
0.8092	Intermediate Similarity	NPC212643
0.806	Intermediate Similarity	NPC193484
0.806	Intermediate Similarity	NPC114845
0.8042	Intermediate Similarity	NPC231572
0.7972	Intermediate Similarity	NPC214036
0.7972	Intermediate Similarity	NPC113236
0.797	Intermediate Similarity	NPC69670
0.797	Intermediate Similarity	NPC57501
0.7961	Intermediate Similarity	NPC169742
0.7959	Intermediate Similarity	NPC469978
0.7902	Intermediate Similarity	NPC416184
0.7887	Intermediate Similarity	NPC284855
0.7887	Intermediate Similarity	NPC282477
0.7868	Intermediate Similarity	NPC256167
0.7834	Intermediate Similarity	NPC231198
0.7826	Intermediate Similarity	NPC85830
0.7778	Intermediate Similarity	NPC470708
0.7778	Intermediate Similarity	NPC7018
0.7752	Intermediate Similarity	NPC127326
0.7748	Intermediate Similarity	NPC470088
0.7692	Intermediate Similarity	NPC31279
0.763	Intermediate Similarity	NPC277460
0.7626	Intermediate Similarity	NPC300955
0.7589	Intermediate Similarity	NPC64948
0.7582	Intermediate Similarity	NPC223125
0.758	Intermediate Similarity	NPC329640
0.758	Intermediate Similarity	NPC106786
0.7571	Intermediate Similarity	NPC152186
0.7571	Intermediate Similarity	NPC182147
0.7571	Intermediate Similarity	NPC207541
0.7571	Intermediate Similarity	NPC246133
0.7571	Intermediate Similarity	NPC170583
0.7571	Intermediate Similarity	NPC71105
0.7557	Intermediate Similarity	NPC179309
0.7532	Intermediate Similarity	NPC474852
0.7518	Intermediate Similarity	NPC251466
0.7518	Intermediate Similarity	NPC156944
0.7517	Intermediate Similarity	NPC473463
0.7484	Intermediate Similarity	NPC223124
0.7483	Intermediate Similarity	NPC470706
0.7465	Intermediate Similarity	NPC157740
0.7465	Intermediate Similarity	NPC99798
0.7465	Intermediate Similarity	NPC191302
0.7465	Intermediate Similarity	NPC41331
0.7465	Intermediate Similarity	NPC291449
0.7463	Intermediate Similarity	NPC294941
0.7451	Intermediate Similarity	NPC475959
0.7447	Intermediate Similarity	NPC120066
0.7445	Intermediate Similarity	NPC37858
0.7438	Intermediate Similarity	NPC59567
0.7413	Intermediate Similarity	NPC469977
0.7413	Intermediate Similarity	NPC246974
0.7413	Intermediate Similarity	NPC147247
0.7391	Intermediate Similarity	NPC344161
0.7391	Intermediate Similarity	NPC202474
0.7383	Intermediate Similarity	NPC226005
0.7372	Intermediate Similarity	NPC124916
0.7365	Intermediate Similarity	NPC102260
0.7365	Intermediate Similarity	NPC230968
0.7361	Intermediate Similarity	NPC476748
0.7353	Intermediate Similarity	NPC471650
0.7353	Intermediate Similarity	NPC268317
0.7346	Intermediate Similarity	NPC329717
0.7346	Intermediate Similarity	NPC474858
0.7343	Intermediate Similarity	NPC286683
0.7338	Intermediate Similarity	NPC204466
0.7315	Intermediate Similarity	NPC20796
0.7315	Intermediate Similarity	NPC166184
0.731	Intermediate Similarity	NPC477694
0.731	Intermediate Similarity	NPC237579
0.731	Intermediate Similarity	NPC477705
0.7308	Intermediate Similarity	NPC119669
0.7299	Intermediate Similarity	NPC280001
0.7299	Intermediate Similarity	NPC33271
0.7299	Intermediate Similarity	NPC185738
0.7297	Intermediate Similarity	NPC55040
0.7289	Intermediate Similarity	NPC287152
0.7286	Intermediate Similarity	NPC70752
0.7286	Intermediate Similarity	NPC80241
0.7286	Intermediate Similarity	NPC301641
0.7284	Intermediate Similarity	NPC306669
0.7284	Intermediate Similarity	NPC247972
0.7273	Intermediate Similarity	NPC218323
0.7267	Intermediate Similarity	NPC178290
0.7266	Intermediate Similarity	NPC2058
0.7261	Intermediate Similarity	NPC148898
0.726	Intermediate Similarity	NPC118419
0.726	Intermediate Similarity	NPC477706
0.7256	Intermediate Similarity	NPC241055
0.7255	Intermediate Similarity	NPC110337
0.7254	Intermediate Similarity	NPC246704
0.7248	Intermediate Similarity	NPC37468
0.7248	Intermediate Similarity	NPC157554
0.7248	Intermediate Similarity	NPC186418
0.7246	Intermediate Similarity	NPC164706
0.7246	Intermediate Similarity	NPC272471
0.7246	Intermediate Similarity	NPC107588
0.7246	Intermediate Similarity	NPC137537
0.7246	Intermediate Similarity	NPC70744
0.7241	Intermediate Similarity	NPC160193
0.7239	Intermediate Similarity	NPC245552
0.7234	Intermediate Similarity	NPC288238
0.723	Intermediate Similarity	NPC11147
0.723	Intermediate Similarity	NPC7163
0.723	Intermediate Similarity	NPC138365
0.7226	Intermediate Similarity	NPC59907
0.7226	Intermediate Similarity	NPC37144
0.7222	Intermediate Similarity	NPC172403
0.7222	Intermediate Similarity	NPC158737
0.7222	Intermediate Similarity	NPC218614
0.7219	Intermediate Similarity	NPC278076
0.7214	Intermediate Similarity	NPC471877
0.7209	Intermediate Similarity	NPC12714
0.7209	Intermediate Similarity	NPC310905
0.7205	Intermediate Similarity	NPC158900
0.7203	Intermediate Similarity	NPC289459
0.7197	Intermediate Similarity	NPC258171
0.7194	Intermediate Similarity	NPC119949
0.7181	Intermediate Similarity	NPC240915
0.7178	Intermediate Similarity	NPC168409
0.7174	Intermediate Similarity	NPC39793
0.7172	Intermediate Similarity	NPC165128
0.7172	Intermediate Similarity	NPC226862
0.7172	Intermediate Similarity	NPC158471
0.7172	Intermediate Similarity	NPC57119
0.717	Intermediate Similarity	NPC138487
0.717	Intermediate Similarity	NPC93593
0.717	Intermediate Similarity	NPC41178
0.717	Intermediate Similarity	NPC78733
0.717	Intermediate Similarity	NPC216459
0.7162	Intermediate Similarity	NPC205915
0.7162	Intermediate Similarity	NPC29650
0.7153	Intermediate Similarity	NPC213711
0.7153	Intermediate Similarity	NPC40352
0.7153	Intermediate Similarity	NPC120225
0.7153	Intermediate Similarity	NPC213552
0.7152	Intermediate Similarity	NPC233029
0.7152	Intermediate Similarity	NPC210148
0.7152	Intermediate Similarity	NPC100389
0.7143	Intermediate Similarity	NPC222175
0.7143	Intermediate Similarity	NPC297342
0.7143	Intermediate Similarity	NPC110063
0.7143	Intermediate Similarity	NPC474470
0.7135	Intermediate Similarity	NPC116007
0.7135	Intermediate Similarity	NPC83511
0.7133	Intermediate Similarity	NPC254610
0.7133	Intermediate Similarity	NPC146886
0.7133	Intermediate Similarity	NPC20443
0.7133	Intermediate Similarity	NPC60517
0.7132	Intermediate Similarity	NPC303522
0.7126	Intermediate Similarity	NPC329992
0.7125	Intermediate Similarity	NPC146288
0.7125	Intermediate Similarity	NPC234392
0.7125	Intermediate Similarity	NPC31311
0.7122	Intermediate Similarity	NPC159916
0.7114	Intermediate Similarity	NPC110958
0.7114	Intermediate Similarity	NPC19890
0.7105	Intermediate Similarity	NPC210478
0.7105	Intermediate Similarity	NPC202700
0.7099	Intermediate Similarity	NPC292792
0.7099	Intermediate Similarity	NPC26353
0.7097	Intermediate Similarity	NPC83743
0.7097	Intermediate Similarity	NPC262182
0.7097	Intermediate Similarity	NPC287615
0.7097	Intermediate Similarity	NPC216819

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 NPC469808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	712
0.2-0.3	1258
0.3-0.4	2506
0.4-0.5	2428
0.5-0.6	1473
0.6-0.7	552
0.7-0.8	58
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9173	High Similarity	NPD2492	Phase 1
0.8027	Intermediate Similarity	NPD5297	Approved
0.7959	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3885	Approved
0.7616	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3146	Approved
0.7597	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4210	Discontinued
0.74	Intermediate Similarity	NPD4236	Phase 3
0.74	Intermediate Similarity	NPD4237	Approved
0.7379	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1357	Approved
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7297	Intermediate Similarity	NPD7119	Phase 2
0.7296	Intermediate Similarity	NPD5353	Approved
0.7292	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3705	Approved
0.7266	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1358	Approved
0.7192	Intermediate Similarity	NPD5718	Phase 2
0.719	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7135	Intermediate Similarity	NPD5457	Discontinued
0.7133	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3596	Phase 2
0.7089	Intermediate Similarity	NPD824	Approved
0.7086	Intermediate Similarity	NPD1725	Approved
0.7075	Intermediate Similarity	NPD1336	Approved
0.7063	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD776	Approved
0.7027	Intermediate Similarity	NPD3531	Approved
0.7027	Intermediate Similarity	NPD3532	Approved
0.7027	Intermediate Similarity	NPD3530	Approved
0.7025	Intermediate Similarity	NPD4124	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2978	Approved
0.7019	Intermediate Similarity	NPD2977	Approved
0.7006	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7110	Phase 1
0.7	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD6386	Approved
0.6993	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2219	Phase 1
0.6968	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD743	Approved
0.6948	Remote Similarity	NPD4162	Approved
0.6944	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4123	Phase 3
0.6929	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1102	Approved
0.6929	Remote Similarity	NPD1103	Approved
0.6928	Remote Similarity	NPD3656	Approved
0.6923	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5295	Discontinued
0.6918	Remote Similarity	NPD6584	Phase 3
0.6909	Remote Similarity	NPD5677	Discontinued
0.6908	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5604	Discontinued
0.6887	Remote Similarity	NPD2653	Approved
0.6884	Remote Similarity	NPD5283	Phase 1
0.6879	Remote Similarity	NPD6580	Approved
0.6879	Remote Similarity	NPD4357	Discontinued
0.6879	Remote Similarity	NPD6853	Approved
0.6879	Remote Similarity	NPD6581	Approved
0.6879	Remote Similarity	NPD6851	Approved
0.6871	Remote Similarity	NPD5978	Approved
0.6871	Remote Similarity	NPD5977	Approved
0.6867	Remote Similarity	NPD3142	Approved
0.6867	Remote Similarity	NPD3140	Approved
0.6866	Remote Similarity	NPD3134	Approved
0.6863	Remote Similarity	NPD6032	Approved
0.6853	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6895	Approved
0.6842	Remote Similarity	NPD6896	Approved
0.6839	Remote Similarity	NPD3060	Approved
0.6835	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4420	Approved
0.6831	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2595	Approved
0.6831	Remote Similarity	NPD2594	Approved
0.6829	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1341	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7281	Phase 3
0.6821	Remote Similarity	NPD7280	Phase 3
0.6816	Remote Similarity	NPD5582	Discontinued
0.6815	Remote Similarity	NPD5756	Phase 2
0.6803	Remote Similarity	NPD7018	Phase 2
0.6795	Remote Similarity	NPD5481	Discontinued
0.6795	Remote Similarity	NPD2085	Suspended
0.6795	Remote Similarity	NPD2086	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6873	Phase 2
0.6786	Remote Similarity	NPD2557	Approved
0.6786	Remote Similarity	NPD5242	Approved
0.6781	Remote Similarity	NPD2922	Phase 1
0.6779	Remote Similarity	NPD5746	Approved
0.6772	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6107	Approved
0.6763	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2237	Approved
0.6753	Remote Similarity	NPD3454	Phase 3
0.6752	Remote Similarity	NPD5241	Discontinued
0.675	Remote Similarity	NPD6030	Approved
0.675	Remote Similarity	NPD5976	Discontinued
0.675	Remote Similarity	NPD6031	Approved
0.6744	Remote Similarity	NPD6297	Approved
0.6739	Remote Similarity	NPD228	Approved
0.6733	Remote Similarity	NPD7294	Phase 1
0.6733	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5289	Phase 2
0.673	Remote Similarity	NPD4584	Approved
0.673	Remote Similarity	NPD4739	Approved
0.6728	Remote Similarity	NPD6876	Approved
0.6728	Remote Similarity	NPD6875	Approved
0.6728	Remote Similarity	NPD4678	Approved
0.6728	Remote Similarity	NPD4675	Approved
0.6726	Remote Similarity	NPD4166	Phase 2
0.6725	Remote Similarity	NPD5312	Approved
0.6725	Remote Similarity	NPD5313	Approved
0.6723	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6382	Discontinued
0.6712	Remote Similarity	NPD6543	Approved
0.6712	Remote Similarity	NPD6582	Phase 2
0.6712	Remote Similarity	NPD6542	Approved
0.6712	Remote Similarity	NPD6540	Phase 3
0.6712	Remote Similarity	NPD3685	Discontinued
0.6712	Remote Similarity	NPD1420	Approved
0.6712	Remote Similarity	NPD1421	Approved
0.6712	Remote Similarity	NPD6539	Approved
0.6712	Remote Similarity	NPD6583	Phase 3
0.6708	Remote Similarity	NPD3686	Approved
0.6708	Remote Similarity	NPD1653	Approved
0.6708	Remote Similarity	NPD3687	Approved
0.6707	Remote Similarity	NPD5773	Approved
0.6707	Remote Similarity	NPD5772	Approved
0.6689	Remote Similarity	NPD5745	Approved
0.6689	Remote Similarity	NPD2245	Discovery
0.6689	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4108	Discontinued
0.6687	Remote Similarity	NPD8031	Discontinued
0.6685	Remote Similarity	NPD5005	Approved
0.6685	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD2671	Approved
0.6667	Remote Similarity	NPD2673	Approved
0.6667	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1774	Approved
0.6667	Remote Similarity	NPD7037	Approved
0.6667	Remote Similarity	NPD7153	Discontinued
0.6647	Remote Similarity	NPD4481	Phase 3
0.6646	Remote Similarity	NPD7317	Phase 3
0.6646	Remote Similarity	NPD3641	Approved
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3640	Phase 3
0.6646	Remote Similarity	NPD2122	Discontinued
0.6646	Remote Similarity	NPD1670	Discontinued
0.6646	Remote Similarity	NPD3639	Approved
0.6644	Remote Similarity	NPD9494	Approved
0.6643	Remote Similarity	NPD7533	Approved
0.6643	Remote Similarity	NPD1182	Approved
0.6643	Remote Similarity	NPD7534	Approved
0.6625	Remote Similarity	NPD1424	Approved
0.6624	Remote Similarity	NPD5177	Phase 3
0.6623	Remote Similarity	NPD3145	Approved
0.6623	Remote Similarity	NPD3144	Approved
0.6622	Remote Similarity	NPD1817	Approved
0.6622	Remote Similarity	NPD1820	Approved
0.6622	Remote Similarity	NPD1818	Approved
0.6622	Remote Similarity	NPD1819	Approved
0.6607	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4622	Approved
0.6601	Remote Similarity	NPD4618	Approved
0.6601	Remote Similarity	NPD1933	Approved
0.6592	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6618	Phase 2
0.6588	Remote Similarity	NPD2388	Discontinued
0.6582	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4110	Phase 3
0.6579	Remote Similarity	NPD2674	Phase 3
0.6573	Remote Similarity	NPD4157	Discontinued
0.6573	Remote Similarity	NPD7291	Discontinued
0.6566	Remote Similarity	NPD7318	Phase 3
0.6564	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2897	Discontinued
0.6556	Remote Similarity	NPD3180	Approved
0.6556	Remote Similarity	NPD5163	Phase 2
0.6556	Remote Similarity	NPD3179	Approved
0.6554	Remote Similarity	NPD6541	Approved
0.6554	Remote Similarity	NPD2079	Discontinued
0.6554	Remote Similarity	NPD6538	Approved
0.655	Remote Similarity	NPD2898	Approved
0.6545	Remote Similarity	NPD3384	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