NPASS Compound

Structure

CID221868 OpenBabel06191716012D 23 26 0 0 0 0 0 0 0 0999 V2000 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3147 1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 -0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3147 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8147 0.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.4067 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 16 2 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	317.024
LogP:	5.282
LogD:	4.098
LogS:	-3.193
# Rotatable Bonds:	1
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	2.877
Fsp3:	0.158
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:	-4.79
MDCK Permeability:	1.317530040978454e-05
Pgp-inhibitor:	0.215
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	100.54631042480469%
Volume Distribution (VD):	0.763
Pgp-substrate:	0.945304811000824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.776
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.95
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	6.092
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.783
Carcinogencity:	0.722
Eye Corrosion:	0.003
Eye Irritation:	0.596
Respiratory Toxicity:	0.78

Download Data

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

Natural Product: NPC221868

Natural Product ID:	NPC221868
*Common Name:**	8-(6-Hydroxy-1-Benzofuran-2-Yl)-2,2-Dimethylchromen-5-Ol
IUPAC Name:	8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol
Synonyms:
Standard InCHIKey:	SJIZTMNAKZAOTA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-19(2)8-7-13-15(21)6-5-14(18(13)23-19)17-9-11-3-4-12(20)10-16(11)22-17/h3-10,20-21H,1-2H3
SMILES:	Oc1ccc2c(c1)oc(c2)c1ccc(c2c1OC(C)(C)C=C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL233147
PubChem CID:	10542808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[12828487]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17517504]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Barks	n.a.	n.a.	PMID[18302333]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20934335]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022281]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	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
IC50	1
Others	9

Activity Type	# Activity
Cell Line	5
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	62700.0	nM	PMID[548333]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	1.3	%	PMID[548334]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	2.8	n.a.	PMID[548334]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	48.9	%	PMID[548334]
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	0.0	%	PMID[548334]
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	6.5	%	PMID[548334]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	9.7	%	PMID[548334]
NPT660	Cell Line	SW480	Homo sapiens	Inhibition	=	6.4	%	PMID[548334]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	12.5	%	PMID[548334]
NPT2	Others	Unspecified		Inhibition	=	32.2	%	PMID[548334]

☑ 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 NPC221868 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	409
0.1-0.2	1744
0.2-0.3	4232
0.3-0.4	11430
0.4-0.5	6688
0.5-0.6	4104
0.6-0.7	5996
0.7-0.8	4455
0.8-0.85	1977
0.85-0.9	1216
0.9-0.95	421
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37208
0.993	High Similarity	NPC272194
0.9789	High Similarity	NPC210826
0.9726	High Similarity	NPC472462
0.972	High Similarity	NPC130581
0.972	High Similarity	NPC12148
0.9653	High Similarity	NPC135325
0.965	High Similarity	NPC300267
0.965	High Similarity	NPC51641
0.9648	High Similarity	NPC225884
0.9586	High Similarity	NPC39929
0.9586	High Similarity	NPC296030
0.9586	High Similarity	NPC226644
0.9586	High Similarity	NPC37226
0.953	High Similarity	NPC65504
0.953	High Similarity	NPC268360
0.9521	High Similarity	NPC78335
0.9521	High Similarity	NPC230713
0.951	High Similarity	NPC17262
0.951	High Similarity	NPC302181
0.9507	High Similarity	NPC64908
0.9507	High Similarity	NPC118840
0.9507	High Similarity	NPC147688
0.9507	High Similarity	NPC156590
0.9507	High Similarity	NPC205006
0.9459	High Similarity	NPC1477
0.9459	High Similarity	NPC72370
0.9459	High Similarity	NPC213608
0.9459	High Similarity	NPC122365
0.9456	High Similarity	NPC170169
0.9452	High Similarity	NPC178202
0.9444	High Similarity	NPC234629
0.9444	High Similarity	NPC311741
0.9444	High Similarity	NPC230943
0.9441	High Similarity	NPC226636
0.9441	High Similarity	NPC53192
0.9441	High Similarity	NPC11561
0.9441	High Similarity	NPC144499
0.9437	High Similarity	NPC172986
0.9437	High Similarity	NPC235239
0.9437	High Similarity	NPC261227
0.9437	High Similarity	NPC305355
0.9437	High Similarity	NPC475680
0.9437	High Similarity	NPC270883
0.9396	High Similarity	NPC99199
0.9392	High Similarity	NPC5871
0.9384	High Similarity	NPC168085
0.9375	High Similarity	NPC106985
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC18585
0.9375	High Similarity	NPC38219
0.9375	High Similarity	NPC219915
0.9371	High Similarity	NPC103362
0.9371	High Similarity	NPC110969
0.9366	High Similarity	NPC220062
0.9366	High Similarity	NPC96565
0.9366	High Similarity	NPC301217
0.9366	High Similarity	NPC216978
0.9366	High Similarity	NPC303633
0.9366	High Similarity	NPC55018
0.9329	High Similarity	NPC235333
0.932	High Similarity	NPC317492
0.9315	High Similarity	NPC104406
0.9315	High Similarity	NPC79469
0.9315	High Similarity	NPC24673
0.9315	High Similarity	NPC97716
0.9315	High Similarity	NPC201731
0.9315	High Similarity	NPC237635
0.931	High Similarity	NPC257236
0.931	High Similarity	NPC278175
0.9306	High Similarity	NPC78803
0.9306	High Similarity	NPC299080
0.9306	High Similarity	NPC217083
0.9306	High Similarity	NPC214236
0.9306	High Similarity	NPC293852
0.9306	High Similarity	NPC62840
0.9306	High Similarity	NPC59739
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC69769
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC150522
0.9296	High Similarity	NPC201395
0.9281	High Similarity	NPC219861
0.9272	High Similarity	NPC296957
0.9272	High Similarity	NPC260902
0.9267	High Similarity	NPC213936
0.9267	High Similarity	NPC148938
0.9267	High Similarity	NPC297531
0.9267	High Similarity	NPC198490
0.9262	High Similarity	NPC476238
0.9262	High Similarity	NPC327269
0.9262	High Similarity	NPC285623
0.9262	High Similarity	NPC31627
0.9257	High Similarity	NPC167576
0.9252	High Similarity	NPC266572
0.9252	High Similarity	NPC6511
0.9247	High Similarity	NPC124729
0.9247	High Similarity	NPC477955
0.9241	High Similarity	NPC24821
0.9241	High Similarity	NPC293053
0.9241	High Similarity	NPC9117
0.9241	High Similarity	NPC212932
0.9241	High Similarity	NPC190637
0.9241	High Similarity	NPC11700
0.9236	High Similarity	NPC14871
0.9236	High Similarity	NPC282300
0.9231	High Similarity	NPC78913
0.9231	High Similarity	NPC18260
0.9231	High Similarity	NPC217186
0.9231	High Similarity	NPC53181
0.9225	High Similarity	NPC228661
0.9211	High Similarity	NPC244750
0.9211	High Similarity	NPC40583
0.9205	High Similarity	NPC247677
0.9205	High Similarity	NPC160015
0.92	High Similarity	NPC183874
0.9195	High Similarity	NPC472580
0.9195	High Similarity	NPC23668
0.9195	High Similarity	NPC471675
0.9195	High Similarity	NPC193976
0.9189	High Similarity	NPC65775
0.9189	High Similarity	NPC10027
0.9184	High Similarity	NPC166757
0.9184	High Similarity	NPC110303
0.9184	High Similarity	NPC473077
0.9184	High Similarity	NPC17816
0.9184	High Similarity	NPC14001
0.9184	High Similarity	NPC23728
0.9184	High Similarity	NPC296998
0.9178	High Similarity	NPC326500
0.9178	High Similarity	NPC155144
0.9178	High Similarity	NPC469953
0.9178	High Similarity	NPC216538
0.9178	High Similarity	NPC273538
0.9178	High Similarity	NPC209040
0.9172	High Similarity	NPC473042
0.9172	High Similarity	NPC200694
0.9167	High Similarity	NPC215311
0.9167	High Similarity	NPC80962
0.9167	High Similarity	NPC48624
0.9167	High Similarity	NPC326109
0.9167	High Similarity	NPC204985
0.9167	High Similarity	NPC28337
0.9167	High Similarity	NPC219917
0.9167	High Similarity	NPC213659
0.9167	High Similarity	NPC259166
0.9167	High Similarity	NPC144118
0.9167	High Similarity	NPC172250
0.9161	High Similarity	NPC470669
0.9161	High Similarity	NPC259007
0.9161	High Similarity	NPC21350
0.9161	High Similarity	NPC329215
0.9161	High Similarity	NPC470668
0.9161	High Similarity	NPC204088
0.9161	High Similarity	NPC131130
0.9155	High Similarity	NPC13408
0.915	High Similarity	NPC115432
0.915	High Similarity	NPC260296
0.9145	High Similarity	NPC212967
0.9145	High Similarity	NPC96342
0.9145	High Similarity	NPC246647
0.9145	High Similarity	NPC164110
0.9133	High Similarity	NPC142308
0.9133	High Similarity	NPC263676
0.9133	High Similarity	NPC477957
0.9133	High Similarity	NPC473996
0.9133	High Similarity	NPC207624
0.9128	High Similarity	NPC188403
0.9128	High Similarity	NPC472421
0.9128	High Similarity	NPC321896
0.9128	High Similarity	NPC61258
0.9128	High Similarity	NPC476185
0.9122	High Similarity	NPC244407
0.9122	High Similarity	NPC132592
0.9122	High Similarity	NPC160821
0.9122	High Similarity	NPC296869
0.9116	High Similarity	NPC195621
0.9116	High Similarity	NPC470647
0.9116	High Similarity	NPC246948
0.9116	High Similarity	NPC67805
0.9116	High Similarity	NPC176229
0.9116	High Similarity	NPC154217
0.9116	High Similarity	NPC5820
0.9116	High Similarity	NPC111786
0.9116	High Similarity	NPC88964
0.9116	High Similarity	NPC214774
0.9116	High Similarity	NPC301276
0.9116	High Similarity	NPC312973
0.9116	High Similarity	NPC220418
0.9116	High Similarity	NPC178343
0.9116	High Similarity	NPC20488
0.9116	High Similarity	NPC475052
0.9116	High Similarity	NPC83357
0.9116	High Similarity	NPC306488
0.9116	High Similarity	NPC267375
0.9116	High Similarity	NPC54577
0.9116	High Similarity	NPC142405
0.911	High Similarity	NPC214166
0.911	High Similarity	NPC39329
0.911	High Similarity	NPC143896

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 NPC221868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	973
0.2-0.3	1443
0.3-0.4	2683
0.4-0.5	1943
0.5-0.6	1172
0.6-0.7	366
0.7-0.8	123
0.8-0.85	41
0.85-0.9	22
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD7410	Clinical (unspecified phase)
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.8896	High Similarity	NPD3749	Approved
0.8836	High Similarity	NPD1243	Approved
0.8819	High Similarity	NPD1510	Phase 2
0.8767	High Similarity	NPD1549	Phase 2
0.8759	High Similarity	NPD2796	Approved
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.8699	High Similarity	NPD2344	Approved
0.8693	High Similarity	NPD7411	Suspended
0.8671	High Similarity	NPD1240	Approved
0.8645	High Similarity	NPD8443	Clinical (unspecified phase)
0.8627	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD2393	Clinical (unspecified phase)
0.8553	High Similarity	NPD920	Approved
0.8552	High Similarity	NPD1607	Approved
0.8535	High Similarity	NPD7075	Discontinued
0.8533	High Similarity	NPD643	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1511	Approved
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8467	Intermediate Similarity	NPD2309	Approved
0.8462	Intermediate Similarity	NPD7819	Suspended
0.8462	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2800	Approved
0.8447	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD3750	Approved
0.8397	Intermediate Similarity	NPD6801	Discontinued
0.8366	Intermediate Similarity	NPD1512	Approved
0.8364	Intermediate Similarity	NPD6559	Discontinued
0.8354	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1934	Approved
0.8261	Intermediate Similarity	NPD6959	Discontinued
0.8235	Intermediate Similarity	NPD6799	Approved
0.8137	Intermediate Similarity	NPD919	Approved
0.8121	Intermediate Similarity	NPD3818	Discontinued
0.8095	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD5494	Approved
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3748	Approved
0.8067	Intermediate Similarity	NPD2799	Discontinued
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8037	Intermediate Similarity	NPD1247	Approved
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8026	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD3817	Phase 2
0.7949	Intermediate Similarity	NPD2534	Approved
0.7949	Intermediate Similarity	NPD2532	Approved
0.7949	Intermediate Similarity	NPD2533	Approved
0.7933	Intermediate Similarity	NPD6651	Approved
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5953	Discontinued
0.7848	Intermediate Similarity	NPD5403	Approved
0.784	Intermediate Similarity	NPD2296	Approved
0.7829	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4287	Approved
0.7808	Intermediate Similarity	NPD1203	Approved
0.7806	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD7390	Discontinued
0.7755	Intermediate Similarity	NPD2798	Approved
0.7751	Intermediate Similarity	NPD7054	Approved
0.7751	Intermediate Similarity	NPD5844	Phase 1
0.7751	Intermediate Similarity	NPD7286	Phase 2
0.775	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5401	Approved
0.7712	Intermediate Similarity	NPD4308	Phase 3
0.7712	Intermediate Similarity	NPD7033	Discontinued
0.7706	Intermediate Similarity	NPD7472	Approved
0.7706	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD3764	Approved
0.7667	Intermediate Similarity	NPD3268	Approved
0.7661	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.7613	Intermediate Similarity	NPD1471	Phase 3
0.7603	Intermediate Similarity	NPD9717	Approved
0.7602	Intermediate Similarity	NPD1729	Discontinued
0.76	Intermediate Similarity	NPD4625	Phase 3
0.7598	Intermediate Similarity	NPD4361	Phase 2
0.7598	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7568	Intermediate Similarity	NPD2797	Approved
0.7534	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7533	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD6280	Approved
0.75	Intermediate Similarity	NPD6279	Approved
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7229	Phase 3
0.7455	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD4307	Phase 2
0.7444	Intermediate Similarity	NPD4363	Phase 3
0.7444	Intermediate Similarity	NPD4360	Phase 2
0.7436	Intermediate Similarity	NPD5406	Approved
0.7436	Intermediate Similarity	NPD5408	Approved
0.7436	Intermediate Similarity	NPD5404	Approved
0.7436	Intermediate Similarity	NPD5405	Approved
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.741	Intermediate Similarity	NPD4288	Approved
0.7403	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3225	Approved
0.7358	Intermediate Similarity	NPD7003	Approved
0.7356	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6808	Phase 2
0.7353	Intermediate Similarity	NPD5711	Approved
0.7353	Intermediate Similarity	NPD5710	Approved
0.7349	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD5761	Phase 2
0.7333	Intermediate Similarity	NPD3267	Approved
0.7333	Intermediate Similarity	NPD3266	Approved
0.7333	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6585	Discontinued
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD3972	Approved
0.7229	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1470	Approved
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD411	Approved
0.7208	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD4749	Approved
0.7196	Intermediate Similarity	NPD7584	Approved
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.719	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1201	Approved
0.7179	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1933	Approved
0.7168	Intermediate Similarity	NPD2403	Approved
0.7168	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5049	Phase 3
0.7126	Intermediate Similarity	NPD5890	Approved
0.7126	Intermediate Similarity	NPD5889	Approved
0.7124	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD9493	Approved
0.7118	Intermediate Similarity	NPD6971	Discontinued
0.711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2354	Approved
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD7177	Discontinued
0.7086	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD230	Phase 1
0.7049	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD17	Approved
0.7044	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD1876	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7034	Intermediate Similarity	NPD1241	Discontinued
0.7033	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3446	Phase 1
0.7022	Intermediate Similarity	NPD6104	Discontinued
0.7022	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1613	Approved
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6844	Discontinued
0.6982	Remote Similarity	NPD7577	Discontinued
0.698	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4377	Discontinued
0.6971	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7447	Phase 1
0.6962	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD4947	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data