NPASS Compound

Structure

CID53844 OpenBabel06191715392D 30 31 0 0 1 0 0 0 0 0999 V2000 7.2709 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1932 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3685 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7709 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2709 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0084 -2.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 8 16 2 0 0 0 0 9 11 2 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 29 1 0 0 0 0 12 17 2 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 30 1 0 0 0 0 18 26 2 0 0 0 0 19 21 1 0 0 0 0 19 24 2 0 0 0 0 20 24 1 0 0 0 0 20 25 1 1 0 0 0 21 27 1 6 0 0 0 22 13 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 28 2 0 0 0 0 23 29 1 0 0 0 0 25 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.26
Volume:	451.976
LogP:	3.226
LogD:	2.874
LogS:	-3.411
# Rotatable Bonds:	9
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	5.017
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	1.753129436110612e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.381

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.901
Plasma Protein Binding (PPB):	80.92575073242188%
Volume Distribution (VD):	0.98
Pgp-substrate:	14.294864654541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	7.29
Half-life (T1/2):	0.249

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.909
Carcinogencity:	0.233
Eye Corrosion:	0.873
Eye Irritation:	0.617
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC53844

Natural Product ID:	NPC53844
*Common Name:**	Neovibsanin I
IUPAC Name:	[(E)-2-[(3S,4R,5S,7R)-7-hydroxy-5-methyl-5-(4-methylpent-3-enyl)-3-(2-oxopropyl)-3,4,6,7-tetrahydro-1H-2-benzofuran-4-yl]ethenyl] 3-methylbut-2-enoate
Synonyms:	Neovibsanin I
Standard InCHIKey:	DOUGJCUAIIVOOP-RWHSQANCSA-N
Standard InCHI:	InChI=1S/C25H36O5/c1-16(2)8-7-10-25(6)14-21(27)19-15-30-22(13-18(5)26)24(19)20(25)9-11-29-23(28)12-17(3)4/h8-9,11-12,20-22,27H,7,10,13-15H2,1-6H3/b11-9+/t20-,21+,22-,25-/m0/s1
SMILES:	CC(=CCC[C@@]1(C)C[C@@H](O)C2=C([C@@H]1/C=C/OC(=O)C=C(C)C)[C@@H](OC2)CC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497442
PubChem CID:	10788065
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)83457-3]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843567]
NPO26482	Viburnum suspensum	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	PMID[12150795]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO26482	Viburnum suspensum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872155]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125219]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665952]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345641]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27592135]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33325237]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10806	Achillea roseoalba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24370	Crassocephalum crepidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6082	Centaurium pulchellum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5319	Ulmus thomasii	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3830	Euplotes rariseta	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6310	Ruta bracteosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7935	Strychnos angustiflora	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO149	Heliotropium europaeum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7766	Pericopsis schliebenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4516	Fasciospongia rimosa	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9228.1	Narcissus pseudonarcissus subsp. leonensis	Subspecies	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8103	Lecanora melanophthalma	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1355	Urechis caupo	Species	Urechidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9903	Engelhardia spicata	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8404	Isodon xerophilus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2304	Byssovorax cruenta	Species	Polyangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25481	Lonchocarpus oaxacensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7060	Ficus ruficaulis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2637	Agave rigidissima	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4979	Elysia grandifolia	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO276	Miscanthus sacchariflorus	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26482	Viburnum suspensum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5144	Berberis japonica	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15610	Citrus trifolia	Species	Rutaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	18000.0	nM	PMID[509486]

☑ 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 NPC53844 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	194
0.1-0.2	1031
0.2-0.3	4039
0.3-0.4	8224
0.4-0.5	14980
0.5-0.6	7531
0.6-0.7	5188
0.7-0.8	1429
0.8-0.85	70
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8958	High Similarity	NPC54705
0.8925	High Similarity	NPC115021
0.883	High Similarity	NPC53685
0.8791	High Similarity	NPC312561
0.871	High Similarity	NPC232426
0.871	High Similarity	NPC281942
0.8646	High Similarity	NPC242848
0.8617	High Similarity	NPC141831
0.8617	High Similarity	NPC177037
0.8617	High Similarity	NPC472814
0.8602	High Similarity	NPC5509
0.8571	High Similarity	NPC476299
0.8571	High Similarity	NPC474012
0.8557	High Similarity	NPC208094
0.8511	High Similarity	NPC51486
0.8511	High Similarity	NPC145666
0.8469	Intermediate Similarity	NPC316598
0.8462	Intermediate Similarity	NPC31086
0.8454	Intermediate Similarity	NPC240673
0.8454	Intermediate Similarity	NPC17578
0.8447	Intermediate Similarity	NPC137911
0.8447	Intermediate Similarity	NPC228477
0.8438	Intermediate Similarity	NPC474555
0.8431	Intermediate Similarity	NPC91034
0.8404	Intermediate Similarity	NPC174342
0.84	Intermediate Similarity	NPC476890
0.8384	Intermediate Similarity	NPC117685
0.8367	Intermediate Similarity	NPC475709
0.8352	Intermediate Similarity	NPC193198
0.8351	Intermediate Similarity	NPC209355
0.8351	Intermediate Similarity	NPC295347
0.835	Intermediate Similarity	NPC220155
0.8333	Intermediate Similarity	NPC139692
0.8333	Intermediate Similarity	NPC266570
0.8317	Intermediate Similarity	NPC473283
0.8317	Intermediate Similarity	NPC475526
0.8317	Intermediate Similarity	NPC476889
0.8317	Intermediate Similarity	NPC329345
0.8316	Intermediate Similarity	NPC477149
0.8316	Intermediate Similarity	NPC477147
0.83	Intermediate Similarity	NPC244456
0.83	Intermediate Similarity	NPC469657
0.83	Intermediate Similarity	NPC476888
0.83	Intermediate Similarity	NPC93744
0.83	Intermediate Similarity	NPC471075
0.8286	Intermediate Similarity	NPC324683
0.8265	Intermediate Similarity	NPC134072
0.8265	Intermediate Similarity	NPC234993
0.8247	Intermediate Similarity	NPC474554
0.8247	Intermediate Similarity	NPC65829
0.8218	Intermediate Similarity	NPC32577
0.8218	Intermediate Similarity	NPC40918
0.8218	Intermediate Similarity	NPC155332
0.8218	Intermediate Similarity	NPC114540
0.8211	Intermediate Similarity	NPC214387
0.8191	Intermediate Similarity	NPC171722
0.819	Intermediate Similarity	NPC29133
0.8182	Intermediate Similarity	NPC253826
0.8172	Intermediate Similarity	NPC189311
0.8155	Intermediate Similarity	NPC34768
0.8152	Intermediate Similarity	NPC474809
0.8144	Intermediate Similarity	NPC271652
0.8137	Intermediate Similarity	NPC72151
0.8132	Intermediate Similarity	NPC475944
0.8131	Intermediate Similarity	NPC122056
0.8125	Intermediate Similarity	NPC8062
0.8125	Intermediate Similarity	NPC78973
0.8119	Intermediate Similarity	NPC282524
0.8119	Intermediate Similarity	NPC115899
0.8113	Intermediate Similarity	NPC474315
0.8113	Intermediate Similarity	NPC470961
0.81	Intermediate Similarity	NPC57079
0.81	Intermediate Similarity	NPC108368
0.8095	Intermediate Similarity	NPC475065
0.8085	Intermediate Similarity	NPC322159
0.8085	Intermediate Similarity	NPC194417
0.8081	Intermediate Similarity	NPC476797
0.8081	Intermediate Similarity	NPC471153
0.8081	Intermediate Similarity	NPC202833
0.8081	Intermediate Similarity	NPC16967
0.8077	Intermediate Similarity	NPC473284
0.8077	Intermediate Similarity	NPC329048
0.8077	Intermediate Similarity	NPC330011
0.8077	Intermediate Similarity	NPC179380
0.8061	Intermediate Similarity	NPC470697
0.8061	Intermediate Similarity	NPC84893
0.8056	Intermediate Similarity	NPC67259
0.8056	Intermediate Similarity	NPC147912
0.8041	Intermediate Similarity	NPC252433
0.8039	Intermediate Similarity	NPC320447
0.8039	Intermediate Similarity	NPC476081
0.8037	Intermediate Similarity	NPC191620
0.8021	Intermediate Similarity	NPC470734
0.802	Intermediate Similarity	NPC266955
0.802	Intermediate Similarity	NPC477521
0.8	Intermediate Similarity	NPC318363
0.8	Intermediate Similarity	NPC473482
0.8	Intermediate Similarity	NPC475418
0.8	Intermediate Similarity	NPC478144
0.8	Intermediate Similarity	NPC2049
0.7982	Intermediate Similarity	NPC64318
0.798	Intermediate Similarity	NPC183012
0.798	Intermediate Similarity	NPC476488
0.798	Intermediate Similarity	NPC88310
0.798	Intermediate Similarity	NPC476487
0.7979	Intermediate Similarity	NPC179006
0.7979	Intermediate Similarity	NPC65661
0.7979	Intermediate Similarity	NPC471300
0.7979	Intermediate Similarity	NPC474860
0.7979	Intermediate Similarity	NPC474853
0.7979	Intermediate Similarity	NPC86316
0.7979	Intermediate Similarity	NPC106416
0.7979	Intermediate Similarity	NPC261380
0.7961	Intermediate Similarity	NPC112009
0.7961	Intermediate Similarity	NPC95899
0.7961	Intermediate Similarity	NPC120321
0.7961	Intermediate Similarity	NPC159533
0.7961	Intermediate Similarity	NPC475050
0.7959	Intermediate Similarity	NPC476598
0.7959	Intermediate Similarity	NPC476597
0.7957	Intermediate Similarity	NPC472377
0.7957	Intermediate Similarity	NPC311070
0.7941	Intermediate Similarity	NPC471412
0.7941	Intermediate Similarity	NPC224720
0.7941	Intermediate Similarity	NPC476240
0.7941	Intermediate Similarity	NPC303559
0.7941	Intermediate Similarity	NPC476223
0.7941	Intermediate Similarity	NPC472924
0.7938	Intermediate Similarity	NPC477782
0.7938	Intermediate Similarity	NPC161638
0.7938	Intermediate Similarity	NPC113393
0.7938	Intermediate Similarity	NPC473448
0.7935	Intermediate Similarity	NPC282293
0.7921	Intermediate Similarity	NPC222303
0.7921	Intermediate Similarity	NPC141191
0.7921	Intermediate Similarity	NPC478056
0.7917	Intermediate Similarity	NPC104560
0.7917	Intermediate Similarity	NPC226863
0.7917	Intermediate Similarity	NPC472378
0.7917	Intermediate Similarity	NPC472302
0.7917	Intermediate Similarity	NPC24816
0.7912	Intermediate Similarity	NPC471299
0.7909	Intermediate Similarity	NPC470492
0.7909	Intermediate Similarity	NPC140055
0.7909	Intermediate Similarity	NPC167606
0.7909	Intermediate Similarity	NPC286528
0.7909	Intermediate Similarity	NPC20302
0.7909	Intermediate Similarity	NPC470493
0.7909	Intermediate Similarity	NPC183580
0.7909	Intermediate Similarity	NPC312824
0.7905	Intermediate Similarity	NPC67321
0.7905	Intermediate Similarity	NPC302788
0.7905	Intermediate Similarity	NPC187435
0.79	Intermediate Similarity	NPC98874
0.79	Intermediate Similarity	NPC328371
0.79	Intermediate Similarity	NPC185553
0.79	Intermediate Similarity	NPC250757
0.79	Intermediate Similarity	NPC456
0.79	Intermediate Similarity	NPC301534
0.79	Intermediate Similarity	NPC184065
0.79	Intermediate Similarity	NPC472941
0.7895	Intermediate Similarity	NPC131813
0.7895	Intermediate Similarity	NPC220478
0.7895	Intermediate Similarity	NPC198761
0.7895	Intermediate Similarity	NPC261721
0.7885	Intermediate Similarity	NPC296950
0.7885	Intermediate Similarity	NPC118911
0.7885	Intermediate Similarity	NPC121099
0.7885	Intermediate Similarity	NPC146731
0.7879	Intermediate Similarity	NPC104925
0.7879	Intermediate Similarity	NPC298973
0.7879	Intermediate Similarity	NPC191521
0.7879	Intermediate Similarity	NPC476596
0.7879	Intermediate Similarity	NPC184870
0.7879	Intermediate Similarity	NPC167219
0.7872	Intermediate Similarity	NPC474865
0.787	Intermediate Similarity	NPC69291
0.787	Intermediate Similarity	NPC90952
0.7857	Intermediate Similarity	NPC2882
0.7857	Intermediate Similarity	NPC477783
0.785	Intermediate Similarity	NPC179642
0.7843	Intermediate Similarity	NPC306856
0.7843	Intermediate Similarity	NPC472644
0.7843	Intermediate Similarity	NPC476274
0.7843	Intermediate Similarity	NPC35751
0.7843	Intermediate Similarity	NPC201406
0.7843	Intermediate Similarity	NPC477720
0.7843	Intermediate Similarity	NPC471413
0.7843	Intermediate Similarity	NPC174314
0.7838	Intermediate Similarity	NPC50774
0.7838	Intermediate Similarity	NPC186525
0.7838	Intermediate Similarity	NPC709
0.7835	Intermediate Similarity	NPC168131
0.7835	Intermediate Similarity	NPC284561
0.7835	Intermediate Similarity	NPC218927
0.7835	Intermediate Similarity	NPC206001
0.783	Intermediate Similarity	NPC476802
0.783	Intermediate Similarity	NPC322903
0.783	Intermediate Similarity	NPC306265
0.783	Intermediate Similarity	NPC90946

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 NPC53844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1506
0.2-0.3	3495
0.3-0.4	2536
0.4-0.5	941
0.5-0.6	336
0.6-0.7	143
0.7-0.8	21
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7938	Intermediate Similarity	NPD5785	Approved
0.7909	Intermediate Similarity	NPD7115	Discovery
0.7745	Intermediate Similarity	NPD4225	Approved
0.767	Intermediate Similarity	NPD7640	Approved
0.767	Intermediate Similarity	NPD7639	Approved
0.766	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD1694	Approved
0.76	Intermediate Similarity	NPD5779	Approved
0.76	Intermediate Similarity	NPD5778	Approved
0.7579	Intermediate Similarity	NPD7154	Phase 3
0.7573	Intermediate Similarity	NPD7638	Approved
0.7525	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6411	Approved
0.7476	Intermediate Similarity	NPD6084	Phase 2
0.7476	Intermediate Similarity	NPD6083	Phase 2
0.7423	Intermediate Similarity	NPD5363	Approved
0.7419	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.7339	Intermediate Similarity	NPD6881	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7339	Intermediate Similarity	NPD6686	Approved
0.732	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6402	Approved
0.7315	Intermediate Similarity	NPD7128	Approved
0.7315	Intermediate Similarity	NPD5739	Approved
0.7315	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD7902	Approved
0.73	Intermediate Similarity	NPD6101	Approved
0.73	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4269	Approved
0.7292	Intermediate Similarity	NPD4270	Approved
0.7282	Intermediate Similarity	NPD5695	Phase 3
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7248	Intermediate Similarity	NPD5697	Approved
0.7232	Intermediate Similarity	NPD6053	Discontinued
0.7207	Intermediate Similarity	NPD6371	Approved
0.7207	Intermediate Similarity	NPD7290	Approved
0.7207	Intermediate Similarity	NPD6883	Approved
0.7207	Intermediate Similarity	NPD7102	Approved
0.72	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD5282	Discontinued
0.7182	Intermediate Similarity	NPD7320	Approved
0.7172	Intermediate Similarity	NPD5786	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.7157	Intermediate Similarity	NPD6079	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6869	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7129	Intermediate Similarity	NPD5328	Approved
0.7117	Intermediate Similarity	NPD6013	Approved
0.7117	Intermediate Similarity	NPD6373	Approved
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6372	Approved
0.7117	Intermediate Similarity	NPD6014	Approved
0.7117	Intermediate Similarity	NPD6012	Approved
0.7113	Intermediate Similarity	NPD5209	Approved
0.7097	Intermediate Similarity	NPD8039	Approved
0.7091	Intermediate Similarity	NPD5701	Approved
0.7083	Intermediate Similarity	NPD4252	Approved
0.708	Intermediate Similarity	NPD8297	Approved
0.708	Intermediate Similarity	NPD6882	Approved
0.7075	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD5362	Discontinued
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD7632	Discontinued
0.7027	Intermediate Similarity	NPD6011	Approved
0.7019	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5369	Approved
0.7	Intermediate Similarity	NPD4519	Discontinued
0.7	Intermediate Similarity	NPD4623	Approved
0.699	Remote Similarity	NPD5693	Phase 1
0.697	Remote Similarity	NPD4786	Approved
0.6961	Remote Similarity	NPD4753	Phase 2
0.6939	Remote Similarity	NPD6435	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6909	Remote Similarity	NPD5141	Approved
0.6907	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5286	Approved
0.6852	Remote Similarity	NPD4696	Approved
0.6852	Remote Similarity	NPD5285	Approved
0.6842	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5279	Phase 3
0.6827	Remote Similarity	NPD5281	Approved
0.6827	Remote Similarity	NPD5284	Approved
0.6827	Remote Similarity	NPD7983	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.6822	Remote Similarity	NPD4755	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD6904	Approved
0.6792	Remote Similarity	NPD5210	Approved
0.6792	Remote Similarity	NPD4629	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6412	Phase 2
0.6774	Remote Similarity	NPD7319	Approved
0.6765	Remote Similarity	NPD4251	Approved
0.6765	Remote Similarity	NPD3573	Approved
0.6765	Remote Similarity	NPD4250	Approved
0.6762	Remote Similarity	NPD4202	Approved
0.6752	Remote Similarity	NPD6868	Approved
0.6735	Remote Similarity	NPD4819	Approved
0.6735	Remote Similarity	NPD5368	Approved
0.6735	Remote Similarity	NPD4821	Approved
0.6735	Remote Similarity	NPD4820	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD4822	Approved
0.6729	Remote Similarity	NPD7839	Suspended
0.6729	Remote Similarity	NPD4697	Phase 3
0.6727	Remote Similarity	NPD5226	Approved
0.6727	Remote Similarity	NPD5225	Approved
0.6727	Remote Similarity	NPD5224	Approved
0.6727	Remote Similarity	NPD4633	Approved
0.6726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7100	Approved
0.6723	Remote Similarity	NPD7101	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.6701	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD4268	Approved
0.6697	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD6335	Approved
0.6637	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD5223	Approved
0.6635	Remote Similarity	NPD6051	Approved
0.6613	Remote Similarity	NPD7078	Approved
0.6612	Remote Similarity	NPD7503	Approved
0.661	Remote Similarity	NPD6274	Approved
0.6609	Remote Similarity	NPD4634	Approved
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6598	Remote Similarity	NPD4756	Discovery
0.6581	Remote Similarity	NPD4632	Approved
0.6571	Remote Similarity	NPD5692	Phase 3
0.6571	Remote Similarity	NPD5207	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5329	Approved
0.6569	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7736	Approved
0.6557	Remote Similarity	NPD6370	Approved
0.6555	Remote Similarity	NPD6317	Approved
0.6538	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD5331	Approved
0.6535	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD5332	Approved
0.6531	Remote Similarity	NPD3617	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6509	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD8035	Phase 2
0.6505	Remote Similarity	NPD5690	Phase 2
0.6505	Remote Similarity	NPD6098	Approved
0.6504	Remote Similarity	NPD8328	Phase 3
0.65	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD4790	Discontinued
0.65	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD5370	Suspended
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD6015	Approved
0.6475	Remote Similarity	NPD6909	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD6908	Approved
0.6475	Remote Similarity	NPD8513	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