NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	245.08
Volume:	233.981
LogP:	0.579
LogD:	0.706
LogS:	-2.734
# Rotatable Bonds:	2
TPSA:	74.98
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	2.989
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:	-4.718
MDCK Permeability:	1.3882250641472638e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.115
30% Bioavailability (F30%):	0.143

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	76.52433776855469%
Volume Distribution (VD):	0.823
Pgp-substrate:	23.58576774597168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.796
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.525
CYP2C19-substrate:	0.841
CYP2C9-inhibitor:	0.34
CYP2C9-substrate:	0.666
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.589

ADMET: Excretion

Clearance (CL):	8.392
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.85
Drug-inuced Liver Injury (DILI):	0.794
AMES Toxicity:	0.714
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.264
Carcinogencity:	0.958
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.479

Download Data

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

Natural Product: NPC474852

Natural Product ID:	NPC474852
*Common Name:**	Leucettamine B
IUPAC Name:	(5Z)-2-amino-5-(1,3-benzodioxol-5-ylmethylidene)-3-methylimidazol-4-one
Synonyms:
Standard InCHIKey:	PKEDBIGNILOTHW-YWEYNIOJSA-N
Standard InCHI:	InChI=1S/C12H11N3O3/c1-15-11(16)8(14-12(15)13)4-7-2-3-9-10(5-7)18-6-17-9/h2-5H,6H2,1H3,(H2,13,14)/b8-4-
SMILES:	N=C1N/C(=Cc2ccc3c(c2)OCO3)/C(=O)N1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485053
PubChem CID:	10037501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino 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
NPO18731	Leucetta microraphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691722]
NPO18731	Leucetta microraphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8383730]
NPO18731	Leucetta microraphis	Species	Leucettidae	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	34
Ki	1

Activity Type	# Activity
Individual Protein	22
Others	3
PROTEIN COMPLEX	8
Protein Family	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3068	Individual Protein	Leukotriene B4 receptor 1	Homo sapiens	Ki	=	100000.0	nM	PMID[468219]
NPT3399	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Homo sapiens	IC50	=	1500.0	nM	PMID[468221]
NPT3932	Individual Protein	Dual specificity protein kinase CLK1	Mus musculus	IC50	=	400.0	nM	PMID[468221]
NPT3931	Individual Protein	Dual specificity protein kinase CLK3	Mus musculus	IC50	=	6400.0	nM	PMID[468221]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	>	10000.0	nM	PMID[468221]
NPT1265	Individual Protein	Serine/threonine-protein kinase PIM1	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT5345	Individual Protein	Mitogen-activated protein kinase 1	Rattus norvegicus	IC50	>	10000.0	nM	PMID[468222]
NPT3459	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 4	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT3460	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 3	Homo sapiens	IC50	=	1400.0	nM	PMID[468222]
NPT3399	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 2	Homo sapiens	IC50	=	2000.0	nM	PMID[468222]
NPT3274	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	Homo sapiens	IC50	=	4100.0	nM	PMID[468222]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	950.0	nM	PMID[468222]
NPT3114	Individual Protein	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	Homo sapiens	IC50	=	600.0	nM	PMID[468222]
NPT5346	Individual Protein	Dual specificity protein kinase CLK4	Mus musculus	IC50	=	150.0	nM	PMID[468222]
NPT3931	Individual Protein	Dual specificity protein kinase CLK3	Mus musculus	IC50	=	1800.0	nM	PMID[468222]
NPT5347	Individual Protein	Dual specificity protein kinase CLK2	Mus musculus	IC50	=	2100.0	nM	PMID[468222]
NPT3932	Individual Protein	Dual specificity protein kinase CLK1	Mus musculus	IC50	=	66.0	nM	PMID[468222]
NPT24788	PROTEIN COMPLEX	Casein kinase I isoform alpha/subunit beta	Homo sapiens	IC50	>	100000.0	nM	PMID[468220]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	>	100000.0	nM	PMID[468220]
NPT1572	Protein Family	Glycogen synthase kinase-3	Homo sapiens	IC50	=	15000.0	nM	PMID[468220]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	IC50	=	2800.0	nM	PMID[468221]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	>	10000.0	nM	PMID[468221]
NPT22078	PROTEIN FAMILY	Glycogen synthase kinase-3	Sus scrofa	IC50	>	10000.0	nM	PMID[468221]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[468221]
NPT22078	PROTEIN FAMILY	Glycogen synthase kinase-3	Sus scrofa	IC50	=	2900.0	nM	PMID[468222]
NPT676	Individual Protein	Glycogen synthase kinase-3 alpha	Homo sapiens	IC50	=	7700.0	nM	PMID[468222]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	IC50	=	900.0	nM	PMID[468222]
NPT84	Individual Protein	Dual specificity tyrosine-phosphorylation-regulated kinase 1A	Rattus norvegicus	IC50	=	920.0	nM	PMID[468222]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[468222]
NPT4092	Protein Complex	CDK9/cyclin T1	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT4090	Protein Complex	Cyclin-dependent kinase 7/ cyclin H	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT1509	Protein Complex	Cyclin-dependent kinase 5/CDK5 activator 1	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]
NPT3814	Protein Complex	Cyclin-dependent kinase 2/cyclin A	Homo sapiens	IC50	>	10000.0	nM	PMID[468222]

☑ 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 NPC474852 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	274
0.1-0.2	2633
0.2-0.3	11641
0.3-0.4	6968
0.4-0.5	13993
0.5-0.6	6485
0.6-0.7	666
0.7-0.8	30
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8133	Intermediate Similarity	NPC181905
0.8095	Intermediate Similarity	NPC217574
0.7987	Intermediate Similarity	NPC328419
0.7987	Intermediate Similarity	NPC193673
0.7987	Intermediate Similarity	NPC45783
0.7987	Intermediate Similarity	NPC94280
0.7987	Intermediate Similarity	NPC159150
0.7987	Intermediate Similarity	NPC103947
0.7933	Intermediate Similarity	NPC96406
0.7881	Intermediate Similarity	NPC145446
0.7881	Intermediate Similarity	NPC137172
0.7875	Intermediate Similarity	NPC292003
0.7829	Intermediate Similarity	NPC95366
0.7829	Intermediate Similarity	NPC248505
0.7632	Intermediate Similarity	NPC167096
0.7616	Intermediate Similarity	NPC318862
0.7597	Intermediate Similarity	NPC470707
0.7582	Intermediate Similarity	NPC73883
0.7582	Intermediate Similarity	NPC255817
0.7582	Intermediate Similarity	NPC136330
0.7582	Intermediate Similarity	NPC230698
0.7582	Intermediate Similarity	NPC196609
0.7582	Intermediate Similarity	NPC205178
0.7582	Intermediate Similarity	NPC277042
0.7582	Intermediate Similarity	NPC251454
0.7532	Intermediate Similarity	NPC469808
0.7532	Intermediate Similarity	NPC99078
0.7484	Intermediate Similarity	NPC220923
0.7484	Intermediate Similarity	NPC252107
0.7372	Intermediate Similarity	NPC28641
0.7372	Intermediate Similarity	NPC194359
0.7362	Intermediate Similarity	NPC13397
0.7312	Intermediate Similarity	NPC244338
0.731	Intermediate Similarity	NPC199209
0.731	Intermediate Similarity	NPC212643
0.7241	Intermediate Similarity	NPC111225
0.7211	Intermediate Similarity	NPC69670
0.7134	Intermediate Similarity	NPC180647
0.7113	Intermediate Similarity	NPC127326
0.7095	Intermediate Similarity	NPC57501
0.7067	Intermediate Similarity	NPC114845
0.7044	Intermediate Similarity	NPC225745
0.7039	Intermediate Similarity	NPC300955
0.702	Intermediate Similarity	NPC256167
0.6993	Remote Similarity	NPC182147
0.6993	Remote Similarity	NPC246133
0.6993	Remote Similarity	NPC170583
0.6993	Remote Similarity	NPC71105
0.6993	Remote Similarity	NPC207541
0.6993	Remote Similarity	NPC152186
0.6968	Remote Similarity	NPC469977
0.6962	Remote Similarity	NPC29650
0.6954	Remote Similarity	NPC193484
0.6948	Remote Similarity	NPC156944
0.6948	Remote Similarity	NPC251466
0.6944	Remote Similarity	NPC31279
0.6918	Remote Similarity	NPC138365
0.6903	Remote Similarity	NPC157740
0.6903	Remote Similarity	NPC99798
0.6903	Remote Similarity	NPC191302
0.6903	Remote Similarity	NPC41331
0.6903	Remote Similarity	NPC291449
0.69	Remote Similarity	NPC17305
0.6882	Remote Similarity	NPC169742
0.6864	Remote Similarity	NPC471073
0.6864	Remote Similarity	NPC270811
0.6859	Remote Similarity	NPC246974
0.6859	Remote Similarity	NPC147247
0.6855	Remote Similarity	NPC282477
0.6855	Remote Similarity	NPC473463
0.6855	Remote Similarity	NPC284855
0.6845	Remote Similarity	NPC223125
0.6834	Remote Similarity	NPC467439
0.6832	Remote Similarity	NPC113236
0.6832	Remote Similarity	NPC214036
0.6828	Remote Similarity	NPC179309
0.6824	Remote Similarity	NPC470708
0.6815	Remote Similarity	NPC470706
0.6813	Remote Similarity	NPC237227
0.6795	Remote Similarity	NPC286683
0.6795	Remote Similarity	NPC64948
0.679	Remote Similarity	NPC231572
0.6786	Remote Similarity	NPC470088
0.6782	Remote Similarity	NPC247251
0.6774	Remote Similarity	NPC85830
0.6765	Remote Similarity	NPC223124
0.6757	Remote Similarity	NPC294941
0.6747	Remote Similarity	NPC469978
0.6733	Remote Similarity	NPC33271
0.6732	Remote Similarity	NPC301641
0.6732	Remote Similarity	NPC80241
0.6721	Remote Similarity	NPC102760
0.6705	Remote Similarity	NPC231198
0.6688	Remote Similarity	NPC298486
0.6667	Remote Similarity	NPC7018
0.6667	Remote Similarity	NPC120066
0.6667	Remote Similarity	NPC4669
0.6667	Remote Similarity	NPC416184
0.6645	Remote Similarity	NPC119949
0.6625	Remote Similarity	NPC118419
0.6623	Remote Similarity	NPC120075
0.662	Remote Similarity	NPC310905
0.662	Remote Similarity	NPC12714
0.661	Remote Similarity	NPC306669
0.6604	Remote Similarity	NPC476748
0.6601	Remote Similarity	NPC344161
0.6596	Remote Similarity	NPC79213
0.6585	Remote Similarity	NPC166184
0.6579	Remote Similarity	NPC137537
0.6579	Remote Similarity	NPC272471
0.6579	Remote Similarity	NPC107588
0.6579	Remote Similarity	NPC70744
0.6579	Remote Similarity	NPC277460
0.6579	Remote Similarity	NPC124916
0.6579	Remote Similarity	NPC164706
0.6571	Remote Similarity	NPC106786
0.6556	Remote Similarity	NPC268317
0.6554	Remote Similarity	NPC245552
0.6545	Remote Similarity	NPC178290
0.6536	Remote Similarity	NPC37858
0.6535	Remote Similarity	NPC12100
0.6528	Remote Similarity	NPC292792
0.6524	Remote Similarity	NPC102260
0.6524	Remote Similarity	NPC230968
0.6524	Remote Similarity	NPC471650
0.6513	Remote Similarity	NPC185738
0.6513	Remote Similarity	NPC280001
0.6513	Remote Similarity	NPC39793
0.6506	Remote Similarity	NPC275150
0.6506	Remote Similarity	NPC278076
0.6505	Remote Similarity	NPC83511
0.6503	Remote Similarity	NPC11147
0.6494	Remote Similarity	NPC93593
0.6494	Remote Similarity	NPC78733
0.6494	Remote Similarity	NPC222175
0.6494	Remote Similarity	NPC202474
0.6494	Remote Similarity	NPC76079
0.6478	Remote Similarity	NPC177167
0.6478	Remote Similarity	NPC158737
0.6467	Remote Similarity	NPC303522
0.6461	Remote Similarity	NPC59567
0.646	Remote Similarity	NPC477694
0.646	Remote Similarity	NPC477705
0.6452	Remote Similarity	NPC471877
0.6452	Remote Similarity	NPC204466
0.6452	Remote Similarity	NPC183262
0.6448	Remote Similarity	NPC287152
0.6442	Remote Similarity	NPC205915
0.6438	Remote Similarity	NPC165128
0.6438	Remote Similarity	NPC158471
0.6438	Remote Similarity	NPC226862
0.6438	Remote Similarity	NPC57119
0.6433	Remote Similarity	NPC475959
0.6433	Remote Similarity	NPC249788
0.6429	Remote Similarity	NPC254053
0.6424	Remote Similarity	NPC254610
0.6424	Remote Similarity	NPC193528
0.642	Remote Similarity	NPC477706
0.6417	Remote Similarity	NPC116007
0.6415	Remote Similarity	NPC40352
0.6415	Remote Similarity	NPC213711
0.6413	Remote Similarity	NPC5167
0.6413	Remote Similarity	NPC85613
0.641	Remote Similarity	NPC310373
0.641	Remote Similarity	NPC70752
0.6405	Remote Similarity	NPC323948
0.6395	Remote Similarity	NPC469539
0.6395	Remote Similarity	NPC258171
0.6395	Remote Similarity	NPC470082
0.6395	Remote Similarity	NPC227894
0.6395	Remote Similarity	NPC469540
0.6392	Remote Similarity	NPC92869
0.6392	Remote Similarity	NPC283170
0.6392	Remote Similarity	NPC191768
0.6387	Remote Similarity	NPC2058
0.6386	Remote Similarity	NPC20796
0.6379	Remote Similarity	NPC233029
0.6379	Remote Similarity	NPC210148
0.6379	Remote Similarity	NPC148898
0.6375	Remote Similarity	NPC172403
0.6369	Remote Similarity	NPC211231
0.6369	Remote Similarity	NPC288238
0.6364	Remote Similarity	NPC174754
0.6364	Remote Similarity	NPC38101
0.6364	Remote Similarity	NPC240915
0.6359	Remote Similarity	NPC25897
0.6358	Remote Similarity	NPC233224
0.6358	Remote Similarity	NPC271208
0.6353	Remote Similarity	NPC15743
0.6353	Remote Similarity	NPC327623
0.6353	Remote Similarity	NPC50696
0.6353	Remote Similarity	NPC145304
0.6352	Remote Similarity	NPC17348
0.6347	Remote Similarity	NPC226005
0.6347	Remote Similarity	NPC318575
0.6346	Remote Similarity	NPC295317
0.6346	Remote Similarity	NPC14007
0.6346	Remote Similarity	NPC224814
0.6346	Remote Similarity	NPC60962
0.6346	Remote Similarity	NPC189844

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 NPC474852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	691
0.2-0.3	1170
0.3-0.4	2598
0.4-0.5	3206
0.5-0.6	1207
0.6-0.7	107
0.7-0.8	2
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
0.7582	Intermediate Similarity	NPD2492	Phase 1
0.7329	Intermediate Similarity	NPD5297	Approved
0.7233	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4157	Discontinued
0.7161	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1351	Approved
0.6826	Remote Similarity	NPD1350	Approved
0.6826	Remote Similarity	NPD1349	Approved
0.6766	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7280	Phase 3
0.6758	Remote Similarity	NPD7281	Phase 3
0.6645	Remote Similarity	NPD1357	Approved
0.6627	Remote Similarity	NPD5481	Discontinued
0.6625	Remote Similarity	NPD2245	Discovery
0.6587	Remote Similarity	NPD2219	Phase 1
0.6587	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3631	Phase 3
0.6548	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5536	Phase 2
0.6464	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5718	Phase 2
0.646	Remote Similarity	NPD1039	Discontinued
0.6436	Remote Similarity	NPD3349	Phase 2
0.642	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3705	Approved
0.6407	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD2653	Approved
0.64	Remote Similarity	NPD4048	Approved
0.6389	Remote Similarity	NPD4166	Phase 2
0.6375	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2186	Approved
0.6335	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6297	Approved
0.6322	Remote Similarity	NPD824	Approved
0.6316	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4357	Discontinued
0.6296	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2922	Phase 1
0.6284	Remote Similarity	NPD1358	Approved
0.6284	Remote Similarity	NPD3489	Phase 3
0.6279	Remote Similarity	NPD1424	Approved
0.6276	Remote Similarity	NPD6612	Phase 2
0.6273	Remote Similarity	NPD455	Discontinued
0.6273	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2978	Approved
0.6271	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2977	Approved
0.627	Remote Similarity	NPD3885	Approved
0.6269	Remote Similarity	NPD4917	Discontinued
0.6269	Remote Similarity	NPD3592	Approved
0.6269	Remote Similarity	NPD6493	Phase 3
0.6269	Remote Similarity	NPD3591	Approved
0.6265	Remote Similarity	NPD743	Approved
0.6264	Remote Similarity	NPD4210	Discontinued
0.6257	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5604	Discontinued
0.6244	Remote Similarity	NPD3441	Approved
0.6244	Remote Similarity	NPD3442	Approved
0.6235	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1421	Approved
0.6226	Remote Similarity	NPD1420	Approved
0.6226	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD228	Approved
0.6218	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD5720	Discontinued
0.6214	Remote Similarity	NPD2530	Phase 2
0.6207	Remote Similarity	NPD6030	Approved
0.6207	Remote Similarity	NPD6031	Approved
0.6201	Remote Similarity	NPD19	Approved
0.6201	Remote Similarity	NPD1742	Approved
0.6201	Remote Similarity	NPD1743	Approved
0.6198	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5746	Approved
0.6193	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.619	Remote Similarity	NPD729	Discontinued
0.619	Remote Similarity	NPD6853	Approved
0.619	Remote Similarity	NPD6851	Approved
0.6186	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD4739	Approved
0.6185	Remote Similarity	NPD3146	Approved
0.6185	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4236	Phase 3
0.6176	Remote Similarity	NPD4237	Approved
0.6171	Remote Similarity	NPD5267	Discontinued
0.6166	Remote Similarity	NPD3634	Approved
0.6166	Remote Similarity	NPD3633	Approved
0.6159	Remote Similarity	NPD3145	Approved
0.6159	Remote Similarity	NPD3144	Approved
0.6154	Remote Similarity	NPD1375	Discontinued
0.6154	Remote Similarity	NPD5582	Discontinued
0.615	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5967	Approved
0.6144	Remote Similarity	NPD5283	Phase 1
0.614	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4796	Discontinued
0.6127	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD2674	Phase 3
0.6121	Remote Similarity	NPD5745	Approved
0.6118	Remote Similarity	NPD7153	Discontinued
0.6114	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5457	Discontinued
0.6108	Remote Similarity	NPD7032	Approved
0.6107	Remote Similarity	NPD3134	Approved
0.6105	Remote Similarity	NPD6618	Phase 2
0.6101	Remote Similarity	NPD776	Approved
0.6096	Remote Similarity	NPD2325	Approved
0.6095	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD3156	Discontinued
0.6091	Remote Similarity	NPD5071	Phase 2
0.6089	Remote Similarity	NPD5772	Approved
0.6089	Remote Similarity	NPD4585	Approved
0.6089	Remote Similarity	NPD5773	Approved
0.6087	Remote Similarity	NPD5561	Approved
0.6087	Remote Similarity	NPD5562	Approved
0.6074	Remote Similarity	NPD9494	Approved
0.6071	Remote Similarity	NPD6896	Approved
0.6071	Remote Similarity	NPD6895	Approved
0.6069	Remote Similarity	NPD2120	Phase 2
0.6067	Remote Similarity	NPD6385	Approved
0.6067	Remote Similarity	NPD6873	Phase 2
0.6067	Remote Similarity	NPD6386	Approved
0.6066	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3983	Phase 3
0.6061	Remote Similarity	NPD5110	Phase 2
0.6061	Remote Similarity	NPD5109	Approved
0.6061	Remote Similarity	NPD5111	Phase 2
0.6059	Remote Similarity	NPD4859	Phase 1
0.6057	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1391	Approved
0.6023	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1670	Discontinued
0.6011	Remote Similarity	NPD5677	Discontinued
0.601	Remote Similarity	NPD6877	Discontinued
0.601	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2161	Phase 2
0.6	Remote Similarity	NPD2335	Discontinued
0.5991	Remote Similarity	NPD4885	Approved
0.599	Remote Similarity	NPD3964	Approved
0.5989	Remote Similarity	NPD2883	Discontinued
0.5989	Remote Similarity	NPD3686	Approved
0.5989	Remote Similarity	NPD3687	Approved
0.5988	Remote Similarity	NPD4162	Approved
0.5988	Remote Similarity	NPD3060	Approved
0.5978	Remote Similarity	NPD7110	Phase 1
0.5978	Remote Similarity	NPD2821	Approved
0.5978	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4993	Discontinued
0.5976	Remote Similarity	NPD6111	Discontinued
0.5967	Remote Similarity	NPD5978	Approved
0.5967	Remote Similarity	NPD5977	Approved
0.5962	Remote Similarity	NPD709	Approved
0.5961	Remote Similarity	NPD2060	Approved
0.5956	Remote Similarity	NPD2190	Approved
0.5951	Remote Similarity	NPD1819	Approved
0.5951	Remote Similarity	NPD1818	Approved
0.5951	Remote Similarity	NPD1817	Approved
0.5951	Remote Similarity	NPD1820	Approved
0.5949	Remote Similarity	NPD7668	Phase 2
0.5941	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD2122	Discontinued
0.5932	Remote Similarity	NPD5976	Discontinued
0.5928	Remote Similarity	NPD481	Phase 3
0.5928	Remote Similarity	NPD1423	Approved
0.5928	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD2644	Approved
0.5922	Remote Similarity	NPD6876	Approved
0.5922	Remote Similarity	NPD1009	Approved
0.5922	Remote Similarity	NPD7028	Phase 2
0.5922	Remote Similarity	NPD6875	Approved
0.592	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4083	Discontinued
0.5912	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6419	Discontinued
0.5909	Remote Similarity	NPD4123	Phase 3
0.5904	Remote Similarity	NPD5163	Phase 2
0.5902	Remote Similarity	NPD1307	Phase 2
0.5902	Remote Similarity	NPD1309	Phase 2
0.5899	Remote Similarity	NPD4124	Clinical (unspecified phase)

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