NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	176.05
Volume:	177.592
LogP:	1.558
LogD:	1.915
LogS:	-3.022
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	2.317
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.635
MDCK Permeability:	1.5643159713363275e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.274

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	87.423095703125%
Volume Distribution (VD):	1.129
Pgp-substrate:	9.455471992492676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.995
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.683
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.121
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.922
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.647
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	11.72
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.175
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.844
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.128
Skin Sensitization:	0.911
Carcinogencity:	0.919
Eye Corrosion:	0.484
Eye Irritation:	0.975
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC111225

Natural Product ID:	NPC111225
*Common Name:**	(E)-3-(1,3-Benzodioxol-5-Yl)Prop-2-Enal
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)prop-2-enal
Synonyms:
Standard InCHIKey:	HZUFMSJUNLSDSZ-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C10H8O3/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h1-6H,7H2/b2-1+
SMILES:	C(=Cc1ccc2c(c1)OCO2)/C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2299415
PubChem CID:	5374493
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
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
MIC	14

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	350000.0	nM	PMID[564668]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2840000.0	nM	PMID[564668]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2840000.0	nM	PMID[564668]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	=	350000.0	nM	PMID[564668]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	1420000.0	nM	PMID[564668]
NPT1262	Organism	Aspergillus parasiticus	Aspergillus parasiticus	MIC	=	710000.0	nM	PMID[564668]
NPT1263	Organism	Aspergillus sydowii	Aspergillus sydowii	MIC	=	350000.0	nM	PMID[564668]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	350000.0	nM	PMID[564668]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	350000.0	nM	PMID[564668]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2840000.0	nM	PMID[564668]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2840000.0	nM	PMID[564668]
NPT1264	Organism	Burkholderia cepacia	Burkholderia cepacia	MIC	=	710000.0	nM	PMID[564668]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	1420000.0	nM	PMID[564668]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	=	1420000.0	nM	PMID[564668]

☑ 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 NPC111225 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	371
0.1-0.2	2302
0.2-0.3	7273
0.3-0.4	12254
0.4-0.5	3772
0.5-0.6	9973
0.6-0.7	5582
0.7-0.8	1073
0.8-0.85	76
0.85-0.9	12
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC212643
0.9375	High Similarity	NPC199209
0.9266	High Similarity	NPC179309
0.9211	High Similarity	NPC57501
0.9211	High Similarity	NPC69670
0.9174	High Similarity	NPC127326
0.9138	High Similarity	NPC114845
0.9091	High Similarity	NPC31279
0.8992	High Similarity	NPC120066
0.8974	High Similarity	NPC193484
0.8898	High Similarity	NPC256167
0.8707	High Similarity	NPC39793
0.8678	High Similarity	NPC85830
0.8609	High Similarity	NPC294941
0.8547	High Similarity	NPC33271
0.8537	High Similarity	NPC286683
0.8537	High Similarity	NPC64948
0.8532	High Similarity	NPC12714
0.8532	High Similarity	NPC310905
0.8475	Intermediate Similarity	NPC277460
0.844	Intermediate Similarity	NPC13755
0.8417	Intermediate Similarity	NPC295317
0.8403	Intermediate Similarity	NPC37858
0.8403	Intermediate Similarity	NPC119949
0.8378	Intermediate Similarity	NPC292792
0.8348	Intermediate Similarity	NPC245552
0.8333	Intermediate Similarity	NPC202474
0.8333	Intermediate Similarity	NPC344161
0.8319	Intermediate Similarity	NPC164706
0.8319	Intermediate Similarity	NPC272471
0.8319	Intermediate Similarity	NPC107588
0.8319	Intermediate Similarity	NPC137537
0.8319	Intermediate Similarity	NPC227894
0.8319	Intermediate Similarity	NPC124916
0.8319	Intermediate Similarity	NPC70744
0.8319	Intermediate Similarity	NPC212743
0.8319	Intermediate Similarity	NPC258171
0.8305	Intermediate Similarity	NPC268317
0.8295	Intermediate Similarity	NPC38101
0.8268	Intermediate Similarity	NPC217574
0.8264	Intermediate Similarity	NPC204466
0.8235	Intermediate Similarity	NPC280001
0.8235	Intermediate Similarity	NPC185738
0.8211	Intermediate Similarity	NPC108545
0.8205	Intermediate Similarity	NPC303522
0.8197	Intermediate Similarity	NPC80241
0.8197	Intermediate Similarity	NPC70752
0.8197	Intermediate Similarity	NPC301641
0.8189	Intermediate Similarity	NPC477694
0.8189	Intermediate Similarity	NPC477705
0.8182	Intermediate Similarity	NPC222175
0.8154	Intermediate Similarity	NPC469808
0.8154	Intermediate Similarity	NPC55040
0.814	Intermediate Similarity	NPC94280
0.814	Intermediate Similarity	NPC103947
0.814	Intermediate Similarity	NPC159150
0.814	Intermediate Similarity	NPC167096
0.814	Intermediate Similarity	NPC45783
0.814	Intermediate Similarity	NPC193673
0.814	Intermediate Similarity	NPC328419
0.813	Intermediate Similarity	NPC288238
0.8125	Intermediate Similarity	NPC179686
0.8125	Intermediate Similarity	NPC477706
0.8115	Intermediate Similarity	NPC471877
0.811	Intermediate Similarity	NPC476748
0.8103	Intermediate Similarity	NPC137685
0.8092	Intermediate Similarity	NPC230968
0.8092	Intermediate Similarity	NPC102260
0.8091	Intermediate Similarity	NPC175298
0.808	Intermediate Similarity	NPC473626
0.808	Intermediate Similarity	NPC271985
0.808	Intermediate Similarity	NPC87113
0.8077	Intermediate Similarity	NPC277042
0.8077	Intermediate Similarity	NPC255817
0.8077	Intermediate Similarity	NPC230698
0.8077	Intermediate Similarity	NPC251454
0.8077	Intermediate Similarity	NPC96406
0.8077	Intermediate Similarity	NPC73883
0.8077	Intermediate Similarity	NPC196609
0.8077	Intermediate Similarity	NPC205178
0.8077	Intermediate Similarity	NPC136330
0.8065	Intermediate Similarity	NPC249788
0.8049	Intermediate Similarity	NPC310373
0.8036	Intermediate Similarity	NPC84325
0.8034	Intermediate Similarity	NPC55300
0.8034	Intermediate Similarity	NPC78918
0.8034	Intermediate Similarity	NPC139617
0.8033	Intermediate Similarity	NPC2058
0.803	Intermediate Similarity	NPC166184
0.803	Intermediate Similarity	NPC20796
0.8017	Intermediate Similarity	NPC159916
0.8017	Intermediate Similarity	NPC36108
0.8017	Intermediate Similarity	NPC233731
0.8017	Intermediate Similarity	NPC7097
0.8017	Intermediate Similarity	NPC246358
0.8016	Intermediate Similarity	NPC40352
0.8016	Intermediate Similarity	NPC213711
0.8015	Intermediate Similarity	NPC99078
0.8015	Intermediate Similarity	NPC137172
0.8015	Intermediate Similarity	NPC145446
0.8	Intermediate Similarity	NPC300955
0.8	Intermediate Similarity	NPC146886
0.8	Intermediate Similarity	NPC246704
0.8	Intermediate Similarity	NPC191768
0.8	Intermediate Similarity	NPC92869
0.8	Intermediate Similarity	NPC283170
0.8	Intermediate Similarity	NPC60517
0.8	Intermediate Similarity	NPC20443
0.7984	Intermediate Similarity	NPC211231
0.7982	Intermediate Similarity	NPC128730
0.7982	Intermediate Similarity	NPC288760
0.797	Intermediate Similarity	NPC178290
0.797	Intermediate Similarity	NPC226005
0.7967	Intermediate Similarity	NPC225245
0.7967	Intermediate Similarity	NPC224814
0.7967	Intermediate Similarity	NPC14007
0.7967	Intermediate Similarity	NPC269843
0.7967	Intermediate Similarity	NPC189844
0.7967	Intermediate Similarity	NPC60962
0.7967	Intermediate Similarity	NPC109083
0.7966	Intermediate Similarity	NPC165646
0.7955	Intermediate Similarity	NPC95366
0.7955	Intermediate Similarity	NPC252107
0.7955	Intermediate Similarity	NPC220923
0.7955	Intermediate Similarity	NPC470707
0.7955	Intermediate Similarity	NPC248505
0.7953	Intermediate Similarity	NPC117237
0.7953	Intermediate Similarity	NPC203719
0.7953	Intermediate Similarity	NPC158737
0.7939	Intermediate Similarity	NPC45404
0.7939	Intermediate Similarity	NPC7163
0.7937	Intermediate Similarity	NPC17348
0.7937	Intermediate Similarity	NPC246133
0.7937	Intermediate Similarity	NPC170583
0.7937	Intermediate Similarity	NPC289459
0.7937	Intermediate Similarity	NPC152186
0.7937	Intermediate Similarity	NPC27352
0.7937	Intermediate Similarity	NPC71105
0.7937	Intermediate Similarity	NPC182147
0.7937	Intermediate Similarity	NPC207541
0.7923	Intermediate Similarity	NPC2190
0.792	Intermediate Similarity	NPC21238
0.7913	Intermediate Similarity	NPC19149
0.7913	Intermediate Similarity	NPC176971
0.7913	Intermediate Similarity	NPC326447
0.791	Intermediate Similarity	NPC210478
0.791	Intermediate Similarity	NPC278076
0.7895	Intermediate Similarity	NPC2518
0.7891	Intermediate Similarity	NPC226862
0.7891	Intermediate Similarity	NPC165128
0.7891	Intermediate Similarity	NPC57119
0.7891	Intermediate Similarity	NPC158471
0.7881	Intermediate Similarity	NPC257124
0.7881	Intermediate Similarity	NPC54626
0.7881	Intermediate Similarity	NPC8547
0.7881	Intermediate Similarity	NPC156840
0.7881	Intermediate Similarity	NPC203924
0.7881	Intermediate Similarity	NPC173746
0.7879	Intermediate Similarity	NPC240915
0.7874	Intermediate Similarity	NPC251466
0.7874	Intermediate Similarity	NPC473960
0.7874	Intermediate Similarity	NPC127604
0.7874	Intermediate Similarity	NPC274356
0.7874	Intermediate Similarity	NPC213552
0.7874	Intermediate Similarity	NPC120225
0.7874	Intermediate Similarity	NPC156944
0.7869	Intermediate Similarity	NPC205502
0.7863	Intermediate Similarity	NPC165386
0.7863	Intermediate Similarity	NPC205915
0.7846	Intermediate Similarity	NPC318862
0.7845	Intermediate Similarity	NPC151530
0.7845	Intermediate Similarity	NPC157473
0.784	Intermediate Similarity	NPC114298
0.784	Intermediate Similarity	NPC286573
0.7836	Intermediate Similarity	NPC318575
0.7833	Intermediate Similarity	NPC217472
0.7823	Intermediate Similarity	NPC158949
0.7823	Intermediate Similarity	NPC267064
0.782	Intermediate Similarity	NPC37468
0.782	Intermediate Similarity	NPC186418
0.782	Intermediate Similarity	NPC157554
0.7812	Intermediate Similarity	NPC157740
0.7812	Intermediate Similarity	NPC291449
0.7812	Intermediate Similarity	NPC191302
0.7812	Intermediate Similarity	NPC99798
0.7812	Intermediate Similarity	NPC41331
0.7812	Intermediate Similarity	NPC177167
0.7812	Intermediate Similarity	NPC100129
0.7803	Intermediate Similarity	NPC19890
0.7803	Intermediate Similarity	NPC110958
0.7795	Intermediate Similarity	NPC300326
0.7795	Intermediate Similarity	NPC58279
0.7787	Intermediate Similarity	NPC65791
0.7778	Intermediate Similarity	NPC470855
0.7778	Intermediate Similarity	NPC18984
0.7778	Intermediate Similarity	NPC164778
0.7778	Intermediate Similarity	NPC4181
0.7778	Intermediate Similarity	NPC160900
0.7778	Intermediate Similarity	NPC106659
0.7778	Intermediate Similarity	NPC238810

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 NPC111225 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1124
0.2-0.3	1877
0.3-0.4	2898
0.4-0.5	1566
0.5-0.6	996
0.6-0.7	342
0.7-0.8	19
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD1357	Approved
0.8235	Intermediate Similarity	NPD5536	Phase 2
0.8197	Intermediate Similarity	NPD3705	Approved
0.8158	Intermediate Similarity	NPD1358	Approved
0.8077	Intermediate Similarity	NPD2492	Phase 1
0.7953	Intermediate Similarity	NPD9494	Approved
0.7913	Intermediate Similarity	NPD3134	Approved
0.7881	Intermediate Similarity	NPD228	Approved
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5283	Phase 1
0.7576	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5691	Approved
0.7376	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1241	Discontinued
0.7227	Intermediate Similarity	NPD9697	Approved
0.719	Intermediate Similarity	NPD2684	Approved
0.7188	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD1653	Approved
0.7154	Intermediate Similarity	NPD2981	Phase 2
0.7099	Intermediate Similarity	NPD2982	Phase 2
0.7099	Intermediate Similarity	NPD2983	Phase 2
0.708	Intermediate Similarity	NPD1933	Approved
0.7075	Intermediate Similarity	NPD7028	Phase 2
0.7063	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1182	Approved
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6993	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD290	Approved
0.6963	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7843	Approved
0.6957	Remote Similarity	NPD447	Suspended
0.695	Remote Similarity	NPD7266	Discontinued
0.695	Remote Similarity	NPD1375	Discontinued
0.6947	Remote Similarity	NPD776	Approved
0.6929	Remote Similarity	NPD7157	Approved
0.6912	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD9296	Approved
0.6897	Remote Similarity	NPD5297	Approved
0.6889	Remote Similarity	NPD3018	Phase 2
0.688	Remote Similarity	NPD969	Suspended
0.6866	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD556	Approved
0.6846	Remote Similarity	NPD5585	Approved
0.6846	Remote Similarity	NPD1651	Approved
0.6833	Remote Similarity	NPD291	Approved
0.6825	Remote Similarity	NPD5535	Approved
0.6821	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1281	Approved
0.6818	Remote Similarity	NPD1091	Approved
0.6806	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4110	Phase 3
0.6797	Remote Similarity	NPD709	Approved
0.6794	Remote Similarity	NPD1778	Approved
0.6791	Remote Similarity	NPD1876	Approved
0.6791	Remote Similarity	NPD2922	Phase 1
0.6788	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2653	Approved
0.6783	Remote Similarity	NPD9365	Approved
0.6781	Remote Similarity	NPD4357	Discontinued
0.6767	Remote Similarity	NPD1840	Phase 2
0.6763	Remote Similarity	NPD3620	Phase 2
0.6763	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD37	Approved
0.6753	Remote Similarity	NPD919	Approved
0.6748	Remote Similarity	NPD968	Approved
0.6746	Remote Similarity	NPD1137	Approved
0.6746	Remote Similarity	NPD1139	Approved
0.6739	Remote Similarity	NPD3144	Approved
0.6739	Remote Similarity	NPD5111	Phase 2
0.6739	Remote Similarity	NPD5718	Phase 2
0.6739	Remote Similarity	NPD5110	Phase 2
0.6739	Remote Similarity	NPD5109	Approved
0.6739	Remote Similarity	NPD3145	Approved
0.6735	Remote Similarity	NPD4739	Approved
0.672	Remote Similarity	NPD5451	Approved
0.6714	Remote Similarity	NPD3657	Discovery
0.6693	Remote Similarity	NPD821	Approved
0.6693	Remote Similarity	NPD1138	Approved
0.6691	Remote Similarity	NPD2674	Phase 3
0.6667	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD1283	Approved
0.6643	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD4060	Phase 1
0.6643	Remote Similarity	NPD1613	Approved
0.6643	Remote Similarity	NPD2161	Phase 2
0.6642	Remote Similarity	NPD3972	Approved
0.6641	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD1894	Discontinued
0.6623	Remote Similarity	NPD4966	Approved
0.6623	Remote Similarity	NPD4967	Phase 2
0.6623	Remote Similarity	NPD4965	Approved
0.6621	Remote Similarity	NPD4236	Phase 3
0.6621	Remote Similarity	NPD4237	Approved
0.6601	Remote Similarity	NPD2977	Approved
0.6601	Remote Similarity	NPD2978	Approved
0.6601	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD230	Phase 1
0.6594	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5327	Phase 3
0.6593	Remote Similarity	NPD4359	Approved
0.6579	Remote Similarity	NPD6385	Approved
0.6579	Remote Similarity	NPD6386	Approved
0.6573	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2798	Approved
0.6567	Remote Similarity	NPD422	Phase 1
0.6567	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1247	Approved
0.6561	Remote Similarity	NPD7199	Phase 2
0.6556	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7095	Approved
0.6541	Remote Similarity	NPD6516	Phase 2
0.6541	Remote Similarity	NPD17	Approved
0.6541	Remote Similarity	NPD5846	Approved
0.6538	Remote Similarity	NPD6234	Discontinued
0.6525	Remote Similarity	NPD1558	Phase 1
0.6525	Remote Similarity	NPD4140	Approved
0.6522	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD3882	Suspended
0.6513	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3146	Approved
0.6507	Remote Similarity	NPD6674	Discontinued
0.6503	Remote Similarity	NPD6895	Approved
0.6503	Remote Similarity	NPD6896	Approved
0.6496	Remote Similarity	NPD987	Approved
0.6493	Remote Similarity	NPD3847	Discontinued
0.649	Remote Similarity	NPD4210	Discontinued
0.6479	Remote Similarity	NPD6355	Discontinued
0.6479	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD4340	Discontinued
0.6478	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6873	Phase 2
0.6471	Remote Similarity	NPD3685	Discontinued
0.6463	Remote Similarity	NPD6331	Phase 2
0.6458	Remote Similarity	NPD4108	Discontinued
0.6457	Remote Similarity	NPD3022	Approved
0.6457	Remote Similarity	NPD3021	Approved
0.6452	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD1019	Discontinued
0.6447	Remote Similarity	NPD824	Approved
0.6447	Remote Similarity	NPD7458	Discontinued
0.6444	Remote Similarity	NPD1611	Approved
0.6438	Remote Similarity	NPD7153	Discontinued
0.6434	Remote Similarity	NPD6653	Approved
0.6429	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2935	Discontinued
0.6414	Remote Similarity	NPD2438	Suspended
0.6414	Remote Similarity	NPD3539	Phase 1
0.6412	Remote Similarity	NPD6671	Approved
0.6408	Remote Similarity	NPD2979	Phase 3
0.6404	Remote Similarity	NPD111	Approved
0.6403	Remote Similarity	NPD2861	Phase 2
0.6402	Remote Similarity	NPD7685	Pre-registration
0.6397	Remote Similarity	NPD9717	Approved
0.6397	Remote Similarity	NPD1608	Approved
0.6395	Remote Similarity	NPD3060	Approved
0.6395	Remote Similarity	NPD4162	Approved
0.6392	Remote Similarity	NPD5494	Approved
0.6391	Remote Similarity	NPD1548	Phase 1
0.6389	Remote Similarity	NPD6111	Discontinued
0.6389	Remote Similarity	NPD7097	Phase 1
0.6383	Remote Similarity	NPD6798	Discontinued
0.6382	Remote Similarity	NPD3686	Approved
0.6382	Remote Similarity	NPD3687	Approved
0.6376	Remote Similarity	NPD643	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.637	Remote Similarity	NPD3540	Phase 1
0.6369	Remote Similarity	NPD5604	Discontinued
0.6364	Remote Similarity	NPD9493	Approved
0.6364	Remote Similarity	NPD3596	Phase 2
0.6358	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6832	Phase 2
0.6352	Remote Similarity	NPD8127	Discontinued
0.6351	Remote Similarity	NPD4628	Phase 3
0.6351	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.635	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.635	Remote Similarity	NPD1669	Approved
0.6346	Remote Similarity	NPD3817	Phase 2
0.6346	Remote Similarity	NPD5977	Approved
0.6346	Remote Similarity	NPD5978	Approved
0.6346	Remote Similarity	NPD5353	Approved
0.6341	Remote Similarity	NPD1242	Phase 1
0.6338	Remote Similarity	NPD4062	Phase 3
0.6338	Remote Similarity	NPD6233	Phase 2
0.6338	Remote Similarity	NPD8032	Phase 2
0.6331	Remote Similarity	NPD6584	Phase 3
0.6331	Remote Similarity	NPD4624	Approved
0.6331	Remote Similarity	NPD558	Phase 2
0.6327	Remote Similarity	NPD2424	Discontinued
0.6327	Remote Similarity	NPD2808	Discontinued
0.6327	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD9295	Approved
0.6324	Remote Similarity	NPD1535	Discovery
0.6324	Remote Similarity	NPD1610	Phase 2

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