NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.04
Volume:	186.382
LogP:	1.751
LogD:	1.616
LogS:	-3.249
# Rotatable Bonds:	2
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	2.0
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.681
MDCK Permeability:	1.3309382666193414e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.41
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	87.06903076171875%
Volume Distribution (VD):	0.242
Pgp-substrate:	7.173671722412109%

ADMET: Metabolism

CYP1A2-inhibitor:	0.627
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.603
CYP2D6-inhibitor:	0.374
CYP2D6-substrate:	0.253
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	9.164
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.791
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.835
Carcinogencity:	0.864
Eye Corrosion:	0.52
Eye Irritation:	0.967
Respiratory Toxicity:	0.541

Download Data

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

Natural Product: NPC57501

Natural Product ID:	NPC57501
*Common Name:**	(E)-3-(1,3-Benzodioxol-5-Yl)Prop-2-Enoic Acid
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)prop-2-enoic acid
Synonyms:	3,4-(Methylenedioxy)Cinnamic Acid; 3,4-Methylenedioxy Cinnamic Acid
Standard InCHIKey:	QFQYZMGOKIROEC-DUXPYHPUSA-N
Standard InCHI:	InChI=1S/C10H8O4/c11-10(12)4-2-7-1-3-8-9(5-7)14-6-13-8/h1-5H,6H2,(H,11,12)/b4-2+
SMILES:	OC(=O)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173153
PubChem CID:	643181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric 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
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28218	Asplenium adiantum-nigrum	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28392	Macrosiphum liriodendri	Species	Aphididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28510	Aspergillus pseudodeflectus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28036	Distemonanthus benthamianus	Species	Fabaceae	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
EC50	1
GI50	1
IC50	8
MIC	3
Others	8
Potency	1

Activity Type	# Activity
Cell Line	2
Individual Protein	5
NON-MOLECULAR	3
Organism	6
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT525	Individual Protein	Hydroxycarboxylic acid receptor 2	Homo sapiens	Activity	=	7.0	%	PMID[515120]
NPT3485	Individual Protein	Neuraminidase	Influenza A virus (strain A/Wilson-Smith/1933 H1N1) (Influenza A virus(strain A/WS/1933 H1N1))	IC50	>	100000.0	nM	PMID[515122]
NPT113	Cell Line	RAW264.7	Mus musculus	GI50	=	2774000.0	nM	PMID[515124]
NPT65	Cell Line	HepG2	Homo sapiens	CC50	=	503460.0	nM	PMID[515125]
NPT4582	Individual Protein	Transitional endoplasmic reticulum ATPase	Homo sapiens	IC50	>	30000.0	nM	PMID[515127]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	deltaA	=	0.19	n.a.	PMID[515119]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[515121]
NPT742	Organism	Influenza A virus	Influenza A virus	EC50	>	100000.0	nM	PMID[515122]
NPT2	Others	Unspecified		Inhibition	=	79.7	%	PMID[515123]
NPT2	Others	Unspecified		IC50	=	28800.0	nM	PMID[515123]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>	600000.0	nM	PMID[515124]
NPT2	Others	Unspecified		Selectivity Index	=	8.8	n.a.	PMID[515124]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	416000.0	nM	PMID[515124]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	312000.0	nM	PMID[515124]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	526250.0	nM	PMID[515125]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.16	n.a.	PMID[515125]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	433150.0	nM	PMID[515125]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	0.96	n.a.	PMID[515125]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	90000.0	nM	PMID[515126]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	>	90000.0	nM	PMID[515126]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[515127]

☑ 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 NPC57501 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	297
0.1-0.2	1958
0.2-0.3	5710
0.3-0.4	12723
0.4-0.5	4447
0.5-0.6	7854
0.6-0.7	7779
0.7-0.8	1739
0.8-0.85	148
0.85-0.9	28
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC199209
0.9643	High Similarity	NPC212643
0.9474	High Similarity	NPC69670
0.9375	High Similarity	NPC294941
0.9231	High Similarity	NPC114845
0.9211	High Similarity	NPC111225
0.9068	High Similarity	NPC193484
0.9052	High Similarity	NPC70744
0.9052	High Similarity	NPC137537
0.9052	High Similarity	NPC164706
0.9052	High Similarity	NPC272471
0.9052	High Similarity	NPC107588
0.9052	High Similarity	NPC124916
0.8974	High Similarity	NPC37858
0.8929	High Similarity	NPC127326
0.8898	High Similarity	NPC202474
0.885	High Similarity	NPC31279
0.8833	High Similarity	NPC256167
0.8824	High Similarity	NPC204466
0.877	High Similarity	NPC85830
0.875	High Similarity	NPC70752
0.875	High Similarity	NPC310373
0.8739	High Similarity	NPC2058
0.8644	High Similarity	NPC280001
0.8594	High Similarity	NPC45404
0.8571	High Similarity	NPC277460
0.8571	High Similarity	NPC288760
0.8537	High Similarity	NPC146886
0.8537	High Similarity	NPC20443
0.8537	High Similarity	NPC60517
0.8537	High Similarity	NPC246704
0.8522	High Similarity	NPC179309
0.8487	Intermediate Similarity	NPC39793
0.8482	Intermediate Similarity	NPC2518
0.848	Intermediate Similarity	NPC64948
0.8473	Intermediate Similarity	NPC318575
0.8473	Intermediate Similarity	NPC226005
0.8468	Intermediate Similarity	NPC300326
0.8468	Intermediate Similarity	NPC58279
0.8468	Intermediate Similarity	NPC289459
0.8448	Intermediate Similarity	NPC245552
0.8448	Intermediate Similarity	NPC226250
0.843	Intermediate Similarity	NPC222175
0.8425	Intermediate Similarity	NPC477705
0.8425	Intermediate Similarity	NPC477694
0.8421	Intermediate Similarity	NPC227894
0.8417	Intermediate Similarity	NPC205502
0.84	Intermediate Similarity	NPC213552
0.84	Intermediate Similarity	NPC120225
0.839	Intermediate Similarity	NPC217472
0.8372	Intermediate Similarity	NPC284855
0.8372	Intermediate Similarity	NPC282477
0.8361	Intermediate Similarity	NPC109083
0.8361	Intermediate Similarity	NPC269843
0.8361	Intermediate Similarity	NPC224814
0.8361	Intermediate Similarity	NPC60962
0.8361	Intermediate Similarity	NPC471877
0.8361	Intermediate Similarity	NPC14007
0.8361	Intermediate Similarity	NPC189844
0.8359	Intermediate Similarity	NPC477706
0.8333	Intermediate Similarity	NPC33271
0.8333	Intermediate Similarity	NPC286683
0.8333	Intermediate Similarity	NPC65791
0.8321	Intermediate Similarity	NPC157554
0.8321	Intermediate Similarity	NPC37468
0.8321	Intermediate Similarity	NPC186418
0.832	Intermediate Similarity	NPC27352
0.832	Intermediate Similarity	NPC120066
0.8306	Intermediate Similarity	NPC249788
0.8305	Intermediate Similarity	NPC303522
0.8305	Intermediate Similarity	NPC95381
0.8304	Intermediate Similarity	NPC310905
0.8304	Intermediate Similarity	NPC12714
0.8293	Intermediate Similarity	NPC177291
0.8293	Intermediate Similarity	NPC194416
0.8279	Intermediate Similarity	NPC344161
0.8276	Intermediate Similarity	NPC246358
0.8276	Intermediate Similarity	NPC233731
0.8276	Intermediate Similarity	NPC36108
0.8276	Intermediate Similarity	NPC7097
0.8268	Intermediate Similarity	NPC110313
0.8268	Intermediate Similarity	NPC109275
0.8268	Intermediate Similarity	NPC478215
0.8254	Intermediate Similarity	NPC274356
0.825	Intermediate Similarity	NPC268317
0.8244	Intermediate Similarity	NPC477301
0.824	Intermediate Similarity	NPC300955
0.8235	Intermediate Similarity	NPC33749
0.8235	Intermediate Similarity	NPC328593
0.8235	Intermediate Similarity	NPC261453
0.8226	Intermediate Similarity	NPC288238
0.8226	Intermediate Similarity	NPC286573
0.822	Intermediate Similarity	NPC131530
0.8211	Intermediate Similarity	NPC158949
0.8203	Intermediate Similarity	NPC476748
0.8203	Intermediate Similarity	NPC48315
0.8203	Intermediate Similarity	NPC83062
0.8197	Intermediate Similarity	NPC119949
0.8195	Intermediate Similarity	NPC100389
0.8182	Intermediate Similarity	NPC230968
0.8182	Intermediate Similarity	NPC102260
0.8182	Intermediate Similarity	NPC185738
0.8175	Intermediate Similarity	NPC152186
0.8175	Intermediate Similarity	NPC207541
0.8175	Intermediate Similarity	NPC71105
0.8175	Intermediate Similarity	NPC182147
0.8175	Intermediate Similarity	NPC170583
0.8175	Intermediate Similarity	NPC246133
0.8174	Intermediate Similarity	NPC294902
0.8174	Intermediate Similarity	NPC1075
0.8174	Intermediate Similarity	NPC1786
0.8168	Intermediate Similarity	NPC7163
0.8167	Intermediate Similarity	NPC474967
0.8167	Intermediate Similarity	NPC233669
0.8162	Intermediate Similarity	NPC297342
0.8162	Intermediate Similarity	NPC110063
0.816	Intermediate Similarity	NPC238810
0.816	Intermediate Similarity	NPC160900
0.816	Intermediate Similarity	NPC18984
0.816	Intermediate Similarity	NPC106659
0.816	Intermediate Similarity	NPC229084
0.8158	Intermediate Similarity	NPC292792
0.8145	Intermediate Similarity	NPC301641
0.8145	Intermediate Similarity	NPC80241
0.814	Intermediate Similarity	NPC285776
0.8136	Intermediate Similarity	NPC139617
0.8136	Intermediate Similarity	NPC8547
0.8136	Intermediate Similarity	NPC173746
0.8136	Intermediate Similarity	NPC257124
0.8136	Intermediate Similarity	NPC78918
0.8136	Intermediate Similarity	NPC55300
0.8136	Intermediate Similarity	NPC156840
0.8134	Intermediate Similarity	NPC202700
0.812	Intermediate Similarity	NPC20796
0.8115	Intermediate Similarity	NPC159916
0.8115	Intermediate Similarity	NPC212743
0.8115	Intermediate Similarity	NPC275519
0.811	Intermediate Similarity	NPC156944
0.811	Intermediate Similarity	NPC40352
0.811	Intermediate Similarity	NPC251466
0.811	Intermediate Similarity	NPC473960
0.811	Intermediate Similarity	NPC213711
0.8106	Intermediate Similarity	NPC240915
0.8102	Intermediate Similarity	NPC262182
0.8102	Intermediate Similarity	NPC287615
0.8102	Intermediate Similarity	NPC83743
0.8102	Intermediate Similarity	NPC216819
0.8099	Intermediate Similarity	NPC281277
0.8092	Intermediate Similarity	NPC473463
0.8087	Intermediate Similarity	NPC227255
0.808	Intermediate Similarity	NPC114298
0.8077	Intermediate Similarity	NPC219677
0.8077	Intermediate Similarity	NPC217574
0.8074	Intermediate Similarity	NPC28398
0.807	Intermediate Similarity	NPC179686
0.8067	Intermediate Similarity	NPC165646
0.8065	Intermediate Similarity	NPC307253
0.8062	Intermediate Similarity	NPC228769
0.8062	Intermediate Similarity	NPC470633
0.8051	Intermediate Similarity	NPC137685
0.8047	Intermediate Similarity	NPC41331
0.8047	Intermediate Similarity	NPC291449
0.8047	Intermediate Similarity	NPC157740
0.8047	Intermediate Similarity	NPC99798
0.8045	Intermediate Similarity	NPC90431
0.8043	Intermediate Similarity	NPC189054
0.8031	Intermediate Similarity	NPC280767
0.8031	Intermediate Similarity	NPC271985
0.8016	Intermediate Similarity	NPC257976
0.8016	Intermediate Similarity	NPC164778
0.8016	Intermediate Similarity	NPC242372
0.8016	Intermediate Similarity	NPC4181
0.8016	Intermediate Similarity	NPC21238
0.8015	Intermediate Similarity	NPC140502
0.8015	Intermediate Similarity	NPC157816
0.8015	Intermediate Similarity	NPC5423
0.8015	Intermediate Similarity	NPC245120
0.8015	Intermediate Similarity	NPC473924
0.8015	Intermediate Similarity	NPC111888
0.8	Intermediate Similarity	NPC275950
0.8	Intermediate Similarity	NPC63574
0.8	Intermediate Similarity	NPC184814
0.8	Intermediate Similarity	NPC109637
0.7985	Intermediate Similarity	NPC231719
0.7985	Intermediate Similarity	NPC52968
0.7984	Intermediate Similarity	NPC232880
0.7984	Intermediate Similarity	NPC246974
0.7984	Intermediate Similarity	NPC147247
0.7984	Intermediate Similarity	NPC469977
0.7982	Intermediate Similarity	NPC94343
0.797	Intermediate Similarity	NPC73071
0.797	Intermediate Similarity	NPC469808
0.797	Intermediate Similarity	NPC55040
0.7969	Intermediate Similarity	NPC154275
0.7969	Intermediate Similarity	NPC127604
0.7969	Intermediate Similarity	NPC276014
0.7967	Intermediate Similarity	NPC309434
0.7967	Intermediate Similarity	NPC203124
0.7956	Intermediate Similarity	NPC478239
0.7955	Intermediate Similarity	NPC283823

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 NPC57501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	1057
0.2-0.3	1759
0.3-0.4	2854
0.4-0.5	1683
0.5-0.6	1082
0.6-0.7	439
0.7-0.8	27
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD1357	Approved
0.8261	Intermediate Similarity	NPD1358	Approved
0.8182	Intermediate Similarity	NPD5536	Phase 2
0.816	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD228	Approved
0.8	Intermediate Similarity	NPD3705	Approved
0.7971	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2492	Phase 1
0.7863	Intermediate Similarity	NPD3134	Approved
0.7769	Intermediate Similarity	NPD9494	Approved
0.7705	Intermediate Similarity	NPD5283	Phase 1
0.7698	Intermediate Similarity	NPD4626	Approved
0.7622	Intermediate Similarity	NPD1653	Approved
0.7556	Intermediate Similarity	NPD447	Suspended
0.7552	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.741	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5691	Approved
0.7333	Intermediate Similarity	NPD9697	Approved
0.7299	Intermediate Similarity	NPD1933	Approved
0.7279	Intermediate Similarity	NPD7028	Phase 2
0.7258	Intermediate Similarity	NPD969	Suspended
0.7197	Intermediate Similarity	NPD2983	Phase 2
0.7197	Intermediate Similarity	NPD2982	Phase 2
0.7181	Intermediate Similarity	NPD37	Approved
0.7155	Intermediate Similarity	NPD9296	Approved
0.7154	Intermediate Similarity	NPD2684	Approved
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4110	Phase 3
0.7133	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3027	Phase 3
0.7121	Intermediate Similarity	NPD2981	Phase 2
0.7103	Intermediate Similarity	NPD4357	Discontinued
0.7101	Intermediate Similarity	NPD4060	Phase 1
0.7063	Intermediate Similarity	NPD7843	Approved
0.7063	Intermediate Similarity	NPD5535	Approved
0.705	Intermediate Similarity	NPD230	Phase 1
0.7045	Intermediate Similarity	NPD422	Phase 1
0.7045	Intermediate Similarity	NPD1091	Approved
0.7042	Intermediate Similarity	NPD1375	Discontinued
0.7039	Intermediate Similarity	NPD4966	Approved
0.7039	Intermediate Similarity	NPD4965	Approved
0.7039	Intermediate Similarity	NPD4967	Phase 2
0.7031	Intermediate Similarity	NPD7157	Approved
0.7023	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1283	Approved
0.7008	Intermediate Similarity	NPD1241	Discontinued
0.7007	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.7	Intermediate Similarity	NPD2653	Approved
0.6992	Remote Similarity	NPD9717	Approved
0.6985	Remote Similarity	NPD3018	Phase 2
0.6972	Remote Similarity	NPD2935	Discontinued
0.697	Remote Similarity	NPD3847	Discontinued
0.696	Remote Similarity	NPD556	Approved
0.6957	Remote Similarity	NPD3144	Approved
0.6957	Remote Similarity	NPD3145	Approved
0.6948	Remote Similarity	NPD6234	Discontinued
0.6942	Remote Similarity	NPD291	Approved
0.6939	Remote Similarity	NPD4739	Approved
0.6935	Remote Similarity	NPD290	Approved
0.6934	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4340	Discontinued
0.6917	Remote Similarity	NPD1281	Approved
0.6917	Remote Similarity	NPD776	Approved
0.6917	Remote Similarity	NPD1535	Discovery
0.6906	Remote Similarity	NPD2674	Phase 3
0.6899	Remote Similarity	NPD709	Approved
0.6879	Remote Similarity	NPD6653	Approved
0.6871	Remote Similarity	NPD5297	Approved
0.687	Remote Similarity	NPD1894	Discontinued
0.687	Remote Similarity	NPD1182	Approved
0.6867	Remote Similarity	NPD7458	Discontinued
0.6866	Remote Similarity	NPD1481	Phase 2
0.6861	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7199	Phase 2
0.6857	Remote Similarity	NPD1613	Approved
0.6857	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3620	Phase 2
0.6857	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3818	Discontinued
0.6855	Remote Similarity	NPD968	Approved
0.6849	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9493	Approved
0.6838	Remote Similarity	NPD1203	Approved
0.6838	Remote Similarity	NPD987	Approved
0.6835	Remote Similarity	NPD411	Approved
0.6825	Remote Similarity	NPD3022	Approved
0.6825	Remote Similarity	NPD3021	Approved
0.6818	Remote Similarity	NPD5585	Approved
0.6818	Remote Similarity	NPD9268	Approved
0.6809	Remote Similarity	NPD6355	Discontinued
0.6803	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3687	Approved
0.68	Remote Similarity	NPD3686	Approved
0.6797	Remote Similarity	NPD2978	Approved
0.6797	Remote Similarity	NPD1138	Approved
0.6797	Remote Similarity	NPD2977	Approved
0.679	Remote Similarity	NPD7685	Pre-registration
0.6781	Remote Similarity	NPD4628	Phase 3
0.6772	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2922	Phase 1
0.6765	Remote Similarity	NPD3225	Approved
0.6755	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD9365	Approved
0.6741	Remote Similarity	NPD9269	Phase 2
0.6741	Remote Similarity	NPD1608	Approved
0.6738	Remote Similarity	NPD1558	Phase 1
0.6738	Remote Similarity	NPD4140	Approved
0.6735	Remote Similarity	NPD6190	Approved
0.6732	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1139	Approved
0.6719	Remote Similarity	NPD1137	Approved
0.6714	Remote Similarity	NPD5110	Phase 2
0.6714	Remote Similarity	NPD3764	Approved
0.6714	Remote Similarity	NPD5111	Phase 2
0.6714	Remote Similarity	NPD6798	Discontinued
0.6714	Remote Similarity	NPD5109	Approved
0.6713	Remote Similarity	NPD7097	Phase 1
0.6712	Remote Similarity	NPD4236	Phase 3
0.6712	Remote Similarity	NPD4237	Approved
0.671	Remote Similarity	NPD3882	Suspended
0.6692	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1651	Approved
0.6691	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6873	Phase 2
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD111	Approved
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD821	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD6386	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6646	Remote Similarity	NPD2821	Approved
0.6646	Remote Similarity	NPD7228	Approved
0.6646	Remote Similarity	NPD8127	Discontinued
0.6645	Remote Similarity	NPD3817	Phase 2
0.6645	Remote Similarity	NPD824	Approved
0.6645	Remote Similarity	NPD3111	Phase 1
0.6644	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1876	Approved
0.6642	Remote Similarity	NPD17	Approved
0.6642	Remote Similarity	NPD196	Phase 1
0.6641	Remote Similarity	NPD6671	Approved
0.6627	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD919	Approved
0.6622	Remote Similarity	NPD2219	Phase 1
0.6621	Remote Similarity	NPD2161	Phase 2
0.6618	Remote Similarity	NPD1840	Phase 2
0.6603	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3146	Approved
0.66	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD6674	Discontinued
0.6599	Remote Similarity	NPD3060	Approved
0.6596	Remote Similarity	NPD5718	Phase 2
0.6596	Remote Similarity	NPD1048	Approved
0.6594	Remote Similarity	NPD2797	Approved
0.6585	Remote Similarity	NPD1242	Phase 1
0.6581	Remote Similarity	NPD689	Discontinued
0.6581	Remote Similarity	NPD9295	Approved
0.6575	Remote Similarity	NPD5763	Approved
0.6575	Remote Similarity	NPD5762	Approved
0.6573	Remote Similarity	NPD3657	Discovery
0.6573	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2614	Approved
0.6569	Remote Similarity	NPD4359	Approved
0.6569	Remote Similarity	NPD3685	Discontinued
0.6562	Remote Similarity	NPD5451	Approved
0.6561	Remote Similarity	NPD5604	Discontinued
0.6552	Remote Similarity	NPD2799	Discontinued
0.6552	Remote Similarity	NPD4108	Discontinued
0.6549	Remote Similarity	NPD259	Phase 1
0.6547	Remote Similarity	NPD258	Approved
0.6547	Remote Similarity	NPD1019	Discontinued
0.6547	Remote Similarity	NPD257	Approved
0.6545	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD9377	Approved
0.6538	Remote Similarity	NPD9379	Approved
0.6536	Remote Similarity	NPD3455	Phase 2
0.6533	Remote Similarity	NPD1511	Approved
0.6528	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5846	Approved
0.6519	Remote Similarity	NPD6516	Phase 2
0.6516	Remote Similarity	NPD1934	Approved
0.6512	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6032	Approved
0.6507	Remote Similarity	NPD1551	Phase 2
0.6507	Remote Similarity	NPD2438	Suspended
0.6503	Remote Similarity	NPD825	Approved
0.6503	Remote Similarity	NPD2979	Phase 3

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