NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	146.04
Volume:	151.506
LogP:	2.145
LogD:	2.246
LogS:	-3.053
# Rotatable Bonds:	1
TPSA:	30.21
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	2.241
Fsp3:	0.0
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:	-4.441
MDCK Permeability:	1.4748177818546537e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.716
Plasma Protein Binding (PPB):	91.72310638427734%
Volume Distribution (VD):	0.923
Pgp-substrate:	11.403532028198242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.475
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.518
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.612
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	7.411
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.183
Rat Oral Acute Toxicity:	0.405
Maximum Recommended Daily Dose:	0.191
Skin Sensitization:	0.181
Carcinogencity:	0.843
Eye Corrosion:	0.935
Eye Irritation:	0.994
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC50583

Natural Product ID:	NPC50583
*Common Name:**	Benzofuran-5-Carbaldehyde
IUPAC Name:	1-benzofuran-5-carbaldehyde
Synonyms:
Standard InCHIKey:	LLLBDLDNTMMZHL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H6O2/c10-6-7-1-2-9-8(5-7)3-4-11-9/h1-6H
SMILES:	O=Cc1ccc2c(c1)cco2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358215
PubChem CID:	2773875
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16378372]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	flower	n.a.	PMID[16378372]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30570	Tetrapanax papyriferus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	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	2
Ki	3
Others	1

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Ki	=	5500.0	nM	PMID[548918]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Ki	=	70.0	nM	PMID[548918]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	400.0	nM	PMID[548918]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	IC50	=	50.0	nM	PMID[548918]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Ki	=	2400.0	nM	PMID[548918]
NPT240	Individual Protein	Cytochrome P450 2A6	Homo sapiens	Kinact	=	0.08	/min	PMID[548918]

☑ 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 NPC50583 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	611
0.1-0.2	2594
0.2-0.3	6232
0.3-0.4	11902
0.4-0.5	4552
0.5-0.6	6851
0.6-0.7	7217
0.7-0.8	2626
0.8-0.85	95
0.85-0.9	15
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9113	High Similarity	NPC141252
0.9113	High Similarity	NPC11799
0.9091	High Similarity	NPC206007
0.8968	High Similarity	NPC470858
0.8788	High Similarity	NPC209858
0.8731	High Similarity	NPC29638
0.8705	High Similarity	NPC190572
0.8692	High Similarity	NPC170546
0.8692	High Similarity	NPC939
0.8692	High Similarity	NPC66246
0.8686	High Similarity	NPC27220
0.8643	High Similarity	NPC198427
0.8626	High Similarity	NPC282230
0.8626	High Similarity	NPC183348
0.8623	High Similarity	NPC166858
0.8623	High Similarity	NPC51146
0.8605	High Similarity	NPC237868
0.8582	High Similarity	NPC306788
0.8561	High Similarity	NPC196979
0.8561	High Similarity	NPC470976
0.8561	High Similarity	NPC470977
0.8561	High Similarity	NPC15083
0.856	High Similarity	NPC137710
0.8529	High Similarity	NPC233707
0.8519	High Similarity	NPC163029
0.8507	High Similarity	NPC324117
0.85	High Similarity	NPC246903
0.8496	Intermediate Similarity	NPC470859
0.8492	Intermediate Similarity	NPC246214
0.8462	Intermediate Similarity	NPC135303
0.8462	Intermediate Similarity	NPC148423
0.8462	Intermediate Similarity	NPC472406
0.8455	Intermediate Similarity	NPC252004
0.8421	Intermediate Similarity	NPC279596
0.8403	Intermediate Similarity	NPC116604
0.8403	Intermediate Similarity	NPC472407
0.8394	Intermediate Similarity	NPC62735
0.8369	Intermediate Similarity	NPC208584
0.8357	Intermediate Similarity	NPC117674
0.8346	Intermediate Similarity	NPC245395
0.8345	Intermediate Similarity	NPC38361
0.8345	Intermediate Similarity	NPC130015
0.8345	Intermediate Similarity	NPC263676
0.8345	Intermediate Similarity	NPC28337
0.8322	Intermediate Similarity	NPC266743
0.8321	Intermediate Similarity	NPC141059
0.8298	Intermediate Similarity	NPC27798
0.8298	Intermediate Similarity	NPC93241
0.8288	Intermediate Similarity	NPC41719
0.8281	Intermediate Similarity	NPC115859
0.8264	Intermediate Similarity	NPC88445
0.8252	Intermediate Similarity	NPC74539
0.8252	Intermediate Similarity	NPC304443
0.8248	Intermediate Similarity	NPC64157
0.8248	Intermediate Similarity	NPC278832
0.8244	Intermediate Similarity	NPC83301
0.8235	Intermediate Similarity	NPC247743
0.8231	Intermediate Similarity	NPC233776
0.8219	Intermediate Similarity	NPC253872
0.8219	Intermediate Similarity	NPC10429
0.8211	Intermediate Similarity	NPC57879
0.8211	Intermediate Similarity	NPC23332
0.8207	Intermediate Similarity	NPC191104
0.8195	Intermediate Similarity	NPC59502
0.8182	Intermediate Similarity	NPC281398
0.8169	Intermediate Similarity	NPC290038
0.8169	Intermediate Similarity	NPC17262
0.8156	Intermediate Similarity	NPC254010
0.8143	Intermediate Similarity	NPC262635
0.813	Intermediate Similarity	NPC183648
0.812	Intermediate Similarity	NPC293387
0.8112	Intermediate Similarity	NPC478166
0.811	Intermediate Similarity	NPC469954
0.8106	Intermediate Similarity	NPC165556
0.8102	Intermediate Similarity	NPC265793
0.8099	Intermediate Similarity	NPC158871
0.8099	Intermediate Similarity	NPC313036
0.8095	Intermediate Similarity	NPC205523
0.8082	Intermediate Similarity	NPC155882
0.8077	Intermediate Similarity	NPC314329
0.8074	Intermediate Similarity	NPC475092
0.806	Intermediate Similarity	NPC125887
0.8056	Intermediate Similarity	NPC51641
0.8056	Intermediate Similarity	NPC300267
0.8042	Intermediate Similarity	NPC225884
0.8041	Intermediate Similarity	NPC122365
0.8041	Intermediate Similarity	NPC290927
0.8041	Intermediate Similarity	NPC473194
0.8041	Intermediate Similarity	NPC131725
0.8031	Intermediate Similarity	NPC79202
0.8031	Intermediate Similarity	NPC59035
0.8031	Intermediate Similarity	NPC316062
0.8031	Intermediate Similarity	NPC470860
0.803	Intermediate Similarity	NPC473885
0.803	Intermediate Similarity	NPC471074
0.8028	Intermediate Similarity	NPC22467
0.8015	Intermediate Similarity	NPC473982
0.8014	Intermediate Similarity	NPC137009
0.8014	Intermediate Similarity	NPC296030
0.8014	Intermediate Similarity	NPC39929
0.8	Intermediate Similarity	NPC265181
0.8	Intermediate Similarity	NPC130581
0.8	Intermediate Similarity	NPC12148
0.7985	Intermediate Similarity	NPC37512
0.7984	Intermediate Similarity	NPC201284
0.7984	Intermediate Similarity	NPC35744
0.7972	Intermediate Similarity	NPC53192
0.7969	Intermediate Similarity	NPC312525
0.7969	Intermediate Similarity	NPC217180
0.7961	Intermediate Similarity	NPC109238
0.7961	Intermediate Similarity	NPC264293
0.7961	Intermediate Similarity	NPC304387
0.7959	Intermediate Similarity	NPC144010
0.7958	Intermediate Similarity	NPC470856
0.7956	Intermediate Similarity	NPC183103
0.7955	Intermediate Similarity	NPC118853
0.7947	Intermediate Similarity	NPC250076
0.7945	Intermediate Similarity	NPC95526
0.7945	Intermediate Similarity	NPC135325
0.7941	Intermediate Similarity	NPC109778
0.7937	Intermediate Similarity	NPC279916
0.7937	Intermediate Similarity	NPC90903
0.7937	Intermediate Similarity	NPC53953
0.7933	Intermediate Similarity	NPC160015
0.7933	Intermediate Similarity	NPC247677
0.7931	Intermediate Similarity	NPC210826
0.7929	Intermediate Similarity	NPC222633
0.7929	Intermediate Similarity	NPC130976
0.7929	Intermediate Similarity	NPC177262
0.7919	Intermediate Similarity	NPC179170
0.7917	Intermediate Similarity	NPC302181
0.7917	Intermediate Similarity	NPC245522
0.7917	Intermediate Similarity	NPC114513
0.791	Intermediate Similarity	NPC474737
0.7908	Intermediate Similarity	NPC193998
0.7908	Intermediate Similarity	NPC473196
0.7907	Intermediate Similarity	NPC243704
0.7907	Intermediate Similarity	NPC32298
0.7905	Intermediate Similarity	NPC145830
0.7905	Intermediate Similarity	NPC156244
0.7899	Intermediate Similarity	NPC229646
0.7895	Intermediate Similarity	NPC107846
0.7891	Intermediate Similarity	NPC37226
0.7891	Intermediate Similarity	NPC472298
0.7891	Intermediate Similarity	NPC226644
0.7887	Intermediate Similarity	NPC37206
0.7881	Intermediate Similarity	NPC269495
0.7881	Intermediate Similarity	NPC296957
0.7881	Intermediate Similarity	NPC260902
0.7868	Intermediate Similarity	NPC473019
0.7867	Intermediate Similarity	NPC278010
0.7867	Intermediate Similarity	NPC473193
0.7867	Intermediate Similarity	NPC250769
0.7867	Intermediate Similarity	NPC295608
0.7863	Intermediate Similarity	NPC216216
0.7863	Intermediate Similarity	NPC97566
0.7862	Intermediate Similarity	NPC230943
0.7857	Intermediate Similarity	NPC307401
0.7857	Intermediate Similarity	NPC65846
0.7852	Intermediate Similarity	NPC67654
0.7852	Intermediate Similarity	NPC60211
0.7846	Intermediate Similarity	NPC54243
0.7842	Intermediate Similarity	NPC292998
0.7836	Intermediate Similarity	NPC2771
0.7836	Intermediate Similarity	NPC473626
0.7836	Intermediate Similarity	NPC52035
0.7832	Intermediate Similarity	NPC263337
0.7829	Intermediate Similarity	NPC476349
0.7829	Intermediate Similarity	NPC33320
0.7829	Intermediate Similarity	NPC228501
0.7829	Intermediate Similarity	NPC476350
0.7826	Intermediate Similarity	NPC293253
0.7823	Intermediate Similarity	NPC272194
0.782	Intermediate Similarity	NPC65735
0.782	Intermediate Similarity	NPC178382
0.782	Intermediate Similarity	NPC188377
0.7817	Intermediate Similarity	NPC148374
0.7817	Intermediate Similarity	NPC473988
0.7812	Intermediate Similarity	NPC28054
0.7806	Intermediate Similarity	NPC38914
0.7805	Intermediate Similarity	NPC42471
0.7803	Intermediate Similarity	NPC295034
0.7801	Intermediate Similarity	NPC254741
0.78	Intermediate Similarity	NPC1477
0.78	Intermediate Similarity	NPC213608
0.7794	Intermediate Similarity	NPC2401
0.7786	Intermediate Similarity	NPC217914
0.7786	Intermediate Similarity	NPC204592
0.7785	Intermediate Similarity	NPC98028
0.7785	Intermediate Similarity	NPC170169
0.7778	Intermediate Similarity	NPC177925
0.7778	Intermediate Similarity	NPC49009
0.7778	Intermediate Similarity	NPC171870
0.7778	Intermediate Similarity	NPC474264
0.7778	Intermediate Similarity	NPC169
0.7778	Intermediate Similarity	NPC243509
0.7778	Intermediate Similarity	NPC54626
0.777	Intermediate Similarity	NPC37208
0.777	Intermediate Similarity	NPC221868
0.777	Intermediate Similarity	NPC287533

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 NPC50583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	531
0.1-0.2	1027
0.2-0.3	1614
0.3-0.4	2788
0.4-0.5	1770
0.5-0.6	1014
0.6-0.7	322
0.7-0.8	76
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD643	Clinical (unspecified phase)
0.85	High Similarity	NPD642	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD920	Approved
0.8143	Intermediate Similarity	NPD1243	Approved
0.8129	Intermediate Similarity	NPD2344	Approved
0.808	Intermediate Similarity	NPD1241	Discontinued
0.8077	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1471	Phase 3
0.7961	Intermediate Similarity	NPD1247	Approved
0.7902	Intermediate Similarity	NPD2309	Approved
0.7829	Intermediate Similarity	NPD919	Approved
0.7801	Intermediate Similarity	NPD2796	Approved
0.7744	Intermediate Similarity	NPD3972	Approved
0.763	Intermediate Similarity	NPD1876	Approved
0.7616	Intermediate Similarity	NPD6280	Approved
0.7616	Intermediate Similarity	NPD6279	Approved
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7569	Intermediate Similarity	NPD1549	Phase 2
0.7554	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1510	Phase 2
0.7452	Intermediate Similarity	NPD6808	Phase 2
0.7447	Intermediate Similarity	NPD3142	Approved
0.7447	Intermediate Similarity	NPD3140	Approved
0.7447	Intermediate Similarity	NPD1240	Approved
0.7445	Intermediate Similarity	NPD3267	Approved
0.7445	Intermediate Similarity	NPD3266	Approved
0.7444	Intermediate Similarity	NPD1651	Approved
0.7434	Intermediate Similarity	NPD7411	Suspended
0.741	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3748	Approved
0.7343	Intermediate Similarity	NPD1607	Approved
0.7338	Intermediate Similarity	NPD9494	Approved
0.729	Intermediate Similarity	NPD2296	Approved
0.729	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1281	Approved
0.7266	Intermediate Similarity	NPD2798	Approved
0.7266	Intermediate Similarity	NPD1019	Discontinued
0.7259	Intermediate Similarity	NPD17	Approved
0.7239	Intermediate Similarity	NPD9545	Approved
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7819	Suspended
0.7226	Intermediate Similarity	NPD9717	Approved
0.7215	Intermediate Similarity	NPD5494	Approved
0.7203	Intermediate Similarity	NPD4307	Phase 2
0.72	Intermediate Similarity	NPD6799	Approved
0.7197	Intermediate Similarity	NPD3749	Approved
0.7194	Intermediate Similarity	NPD1203	Approved
0.7192	Intermediate Similarity	NPD1551	Phase 2
0.7192	Intermediate Similarity	NPD2935	Discontinued
0.7185	Intermediate Similarity	NPD5691	Approved
0.7183	Intermediate Similarity	NPD3268	Approved
0.7181	Intermediate Similarity	NPD3887	Approved
0.7165	Intermediate Similarity	NPD9697	Approved
0.7164	Intermediate Similarity	NPD9092	Discovery
0.7153	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7134	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1283	Approved
0.7115	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD3750	Approved
0.7111	Intermediate Similarity	NPD1894	Discontinued
0.7101	Intermediate Similarity	NPD1608	Approved
0.7091	Intermediate Similarity	NPD6559	Discontinued
0.7089	Intermediate Similarity	NPD7075	Discontinued
0.7081	Intermediate Similarity	NPD3926	Phase 2
0.7078	Intermediate Similarity	NPD7458	Discontinued
0.7078	Intermediate Similarity	NPD3226	Approved
0.7075	Intermediate Similarity	NPD4476	Approved
0.7075	Intermediate Similarity	NPD4477	Approved
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3869	Phase 3
0.7059	Intermediate Similarity	NPD3873	Phase 3
0.7051	Intermediate Similarity	NPD6801	Discontinued
0.7047	Intermediate Similarity	NPD2800	Approved
0.7034	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD6599	Discontinued
0.7025	Intermediate Similarity	NPD3882	Suspended
0.7007	Intermediate Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD6273	Approved
0.6987	Remote Similarity	NPD5890	Approved
0.6987	Remote Similarity	NPD5889	Approved
0.6977	Remote Similarity	NPD3134	Approved
0.6974	Remote Similarity	NPD1511	Approved
0.6968	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2354	Approved
0.6951	Remote Similarity	NPD2163	Approved
0.695	Remote Similarity	NPD2797	Approved
0.6948	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD411	Approved
0.6944	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD1934	Approved
0.6934	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1358	Approved
0.6918	Remote Similarity	NPD7768	Phase 2
0.6918	Remote Similarity	NPD1933	Approved
0.6894	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4626	Approved
0.6884	Remote Similarity	NPD1778	Approved
0.6883	Remote Similarity	NPD1512	Approved
0.6883	Remote Similarity	NPD5049	Phase 3
0.6875	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2684	Approved
0.6867	Remote Similarity	NPD2424	Discontinued
0.6857	Remote Similarity	NPD1481	Phase 2
0.6842	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9493	Approved
0.6831	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1164	Approved
0.6828	Remote Similarity	NPD1296	Phase 2
0.6828	Remote Similarity	NPD3764	Approved
0.6821	Remote Similarity	NPD2654	Approved
0.6818	Remote Similarity	NPD2533	Approved
0.6818	Remote Similarity	NPD4662	Approved
0.6818	Remote Similarity	NPD4661	Approved
0.6818	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD2534	Approved
0.6815	Remote Similarity	NPD6585	Discontinued
0.681	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD447	Suspended
0.6794	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5535	Approved
0.6788	Remote Similarity	NPD5536	Phase 2
0.6786	Remote Similarity	NPD1611	Approved
0.6786	Remote Similarity	NPD1535	Discovery
0.6781	Remote Similarity	NPD8032	Phase 2
0.6772	Remote Similarity	NPD1238	Approved
0.6767	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1729	Discontinued
0.6763	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3225	Approved
0.6755	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3817	Phase 2
0.6748	Remote Similarity	NPD6959	Discontinued
0.6747	Remote Similarity	NPD3818	Discontinued
0.6744	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9261	Approved
0.6736	Remote Similarity	NPD454	Approved
0.6733	Remote Similarity	NPD2531	Phase 2
0.6733	Remote Similarity	NPD2438	Suspended
0.673	Remote Similarity	NPD7577	Discontinued
0.6714	Remote Similarity	NPD3496	Discontinued
0.6711	Remote Similarity	NPD743	Approved
0.671	Remote Similarity	NPD5401	Approved
0.671	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5844	Phase 1
0.6691	Remote Similarity	NPD5585	Approved
0.6689	Remote Similarity	NPD6002	Phase 3
0.6689	Remote Similarity	NPD4618	Approved
0.6689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4622	Approved
0.6689	Remote Similarity	NPD6005	Phase 3
0.6689	Remote Similarity	NPD6004	Phase 3
0.6688	Remote Similarity	NPD957	Approved
0.6688	Remote Similarity	NPD7440	Discontinued
0.6687	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2801	Approved
0.6686	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD1610	Phase 2
0.6667	Remote Similarity	NPD7843	Approved
0.6667	Remote Similarity	NPD290	Approved
0.6647	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2897	Discontinued
0.6645	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7157	Approved
0.6627	Remote Similarity	NPD3823	Discontinued
0.6627	Remote Similarity	NPD5953	Discontinued
0.6626	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5403	Approved
0.6624	Remote Similarity	NPD7427	Discontinued
0.6622	Remote Similarity	NPD4060	Phase 1
0.6619	Remote Similarity	NPD1182	Approved
0.6619	Remote Similarity	NPD1548	Phase 1
0.6607	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5688	Approved
0.66	Remote Similarity	NPD5689	Approved
0.6594	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD968	Approved
0.6588	Remote Similarity	NPD6764	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