NPASS Compound

Structure

NPC210826 OpenBabel07101718312D 23 25 0 0 0 0 0 0 0 0999 V2000 -4.5878 4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 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 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 2.5411 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 6 1 0 0 0 0 3 11 2 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 19 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.12
Volume:	325.58
LogP:	5.398
LogD:	3.267
LogS:	-3.456
# Rotatable Bonds:	3
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	2.648
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:	-4.896
MDCK Permeability:	1.4304109754448291e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.381
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	99.72998046875%
Volume Distribution (VD):	1.144
Pgp-substrate:	2.4990649223327637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.682
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.886
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.151

ADMET: Excretion

Clearance (CL):	11.366
Half-life (T1/2):	0.549

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.445
Drug-inuced Liver Injury (DILI):	0.642
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.241
Maximum Recommended Daily Dose:	0.344
Skin Sensitization:	0.928
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.834
Respiratory Toxicity:	0.368

Download Data

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

Natural Product: NPC210826

Natural Product ID:	NPC210826
*Common Name:**	2'-O-Demethylbidwillol B
IUPAC Name:	4-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:	2'-O-demethylbidwillol B
Standard InCHIKey:	JTWAOWXXBMXCGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O4/c1-11(2)3-6-14-16(21)8-7-15(19(14)22)18-9-12-4-5-13(20)10-17(12)23-18/h3-5,7-10,20-22H,6H2,1-2H3
SMILES:	CC(=CCc1c(ccc(c2cc3ccc(cc3o2)O)c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL232935
PubChem CID:	23655080
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
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]
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]
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]
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]
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]
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]
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[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]
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]
NPO27387	Erythrina addisoniae	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]

☑ 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	3
Others	11

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

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	=	13600.0	nM	PMID[499813]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	16.0	%	PMID[499814]
NPT660	Cell Line	SW480	Homo sapiens	GI	=	36.0	%	PMID[499814]
NPT65	Cell Line	HepG2	Homo sapiens	GI	=	8.0	%	PMID[499814]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	32.0	%	PMID[499814]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	24.0	%	PMID[499814]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	FC	=	4.34	n.a.	PMID[499815]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	9200.0	nM	PMID[499816]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[499816]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[499816]
NPT2	Others	Unspecified		Inhibition	=	42.0	%	PMID[499814]
NPT2	Others	Unspecified		Inhibition	=	12.0	%	PMID[499814]
NPT2	Others	Unspecified		IC50	=	8600.0	nM	PMID[499816]
NPT2	Others	Unspecified		Inhibition	=	61.7	%	PMID[499816]

☑ 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 NPC210826 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	398
0.1-0.2	1729
0.2-0.3	4411
0.3-0.4	11620
0.4-0.5	6361
0.5-0.6	4145
0.6-0.7	5903
0.7-0.8	4538
0.8-0.85	1992
0.85-0.9	1179
0.9-0.95	391
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC12148
0.9929	High Similarity	NPC130581
0.9858	High Similarity	NPC135325
0.9857	High Similarity	NPC51641
0.9857	High Similarity	NPC300267
0.9856	High Similarity	NPC225884
0.9789	High Similarity	NPC37208
0.9789	High Similarity	NPC296030
0.9789	High Similarity	NPC37226
0.9789	High Similarity	NPC221868
0.9789	High Similarity	NPC39929
0.9789	High Similarity	NPC226644
0.972	High Similarity	NPC78335
0.972	High Similarity	NPC230713
0.9718	High Similarity	NPC272194
0.9714	High Similarity	NPC302181
0.9653	High Similarity	NPC170169
0.965	High Similarity	NPC178202
0.9645	High Similarity	NPC230943
0.9643	High Similarity	NPC53192
0.9521	High Similarity	NPC122365
0.9521	High Similarity	NPC213608
0.9521	High Similarity	NPC1477
0.9521	High Similarity	NPC472462
0.9521	High Similarity	NPC235333
0.9456	High Similarity	NPC297531
0.9456	High Similarity	NPC213936
0.9456	High Similarity	NPC148938
0.9456	High Similarity	NPC198490
0.9452	High Similarity	NPC5871
0.9448	High Similarity	NPC167576
0.9392	High Similarity	NPC160015
0.9392	High Similarity	NPC247677
0.9388	High Similarity	NPC183874
0.9384	High Similarity	NPC193976
0.9384	High Similarity	NPC23668
0.9375	High Similarity	NPC17816
0.9371	High Similarity	NPC155144
0.9366	High Similarity	NPC144499
0.9362	High Similarity	NPC69769
0.9362	High Similarity	NPC270883
0.9362	High Similarity	NPC261227
0.9362	High Similarity	NPC28337
0.9362	High Similarity	NPC172986
0.9329	High Similarity	NPC96342
0.9329	High Similarity	NPC246647
0.9329	High Similarity	NPC296957
0.9329	High Similarity	NPC268360
0.9329	High Similarity	NPC164110
0.9329	High Similarity	NPC212967
0.9329	High Similarity	NPC260902
0.9329	High Similarity	NPC65504
0.932	High Similarity	NPC263676
0.932	High Similarity	NPC207624
0.932	High Similarity	NPC142308
0.931	High Similarity	NPC168085
0.9301	High Similarity	NPC18585
0.9301	High Similarity	NPC106985
0.9301	High Similarity	NPC17262
0.9301	High Similarity	NPC166138
0.9296	High Similarity	NPC110969
0.9296	High Similarity	NPC205006
0.9296	High Similarity	NPC118840
0.9296	High Similarity	NPC64908
0.9296	High Similarity	NPC147688
0.9296	High Similarity	NPC156590
0.9291	High Similarity	NPC301217
0.9291	High Similarity	NPC303633
0.9291	High Similarity	NPC96565
0.9291	High Similarity	NPC216978
0.9291	High Similarity	NPC220062
0.9291	High Similarity	NPC55018
0.9286	High Similarity	NPC62735
0.9281	High Similarity	NPC163029
0.9267	High Similarity	NPC244750
0.9267	High Similarity	NPC40583
0.9267	High Similarity	NPC476349
0.9267	High Similarity	NPC476350
0.9262	High Similarity	NPC180924
0.9257	High Similarity	NPC72370
0.9252	High Similarity	NPC106372
0.9252	High Similarity	NPC156244
0.9252	High Similarity	NPC58668
0.9252	High Similarity	NPC116604
0.9252	High Similarity	NPC115324
0.9247	High Similarity	NPC317492
0.9236	High Similarity	NPC311741
0.9236	High Similarity	NPC98926
0.9236	High Similarity	NPC234629
0.9231	High Similarity	NPC226636
0.9231	High Similarity	NPC11561
0.9225	High Similarity	NPC235239
0.9225	High Similarity	NPC241100
0.9225	High Similarity	NPC305355
0.9225	High Similarity	NPC159275
0.9225	High Similarity	NPC475680
0.922	High Similarity	NPC21350
0.922	High Similarity	NPC201395
0.922	High Similarity	NPC124269
0.9214	High Similarity	NPC150399
0.9214	High Similarity	NPC1486
0.9214	High Similarity	NPC477242
0.9214	High Similarity	NPC274109
0.9214	High Similarity	NPC186838
0.9214	High Similarity	NPC168105
0.9214	High Similarity	NPC66349
0.9214	High Similarity	NPC477243
0.9214	High Similarity	NPC249606
0.9214	High Similarity	NPC98115
0.9214	High Similarity	NPC12165
0.9214	High Similarity	NPC41461
0.9214	High Similarity	NPC477244
0.9214	High Similarity	NPC25287
0.9205	High Similarity	NPC260296
0.9205	High Similarity	NPC115432
0.9195	High Similarity	NPC99199
0.9189	High Similarity	NPC67654
0.9184	High Similarity	NPC472421
0.9172	High Similarity	NPC477955
0.9167	High Similarity	NPC39329
0.9167	High Similarity	NPC212932
0.9167	High Similarity	NPC310130
0.9167	High Similarity	NPC169591
0.9167	High Similarity	NPC38219
0.9167	High Similarity	NPC221432
0.9167	High Similarity	NPC164980
0.9167	High Similarity	NPC190637
0.9167	High Similarity	NPC175504
0.9167	High Similarity	NPC143896
0.9167	High Similarity	NPC149026
0.9167	High Similarity	NPC257097
0.9167	High Similarity	NPC24821
0.9167	High Similarity	NPC150408
0.9167	High Similarity	NPC11700
0.9167	High Similarity	NPC9117
0.9167	High Similarity	NPC91560
0.9167	High Similarity	NPC68104
0.9167	High Similarity	NPC293053
0.9167	High Similarity	NPC75049
0.9167	High Similarity	NPC219915
0.9161	High Similarity	NPC3188
0.9161	High Similarity	NPC103362
0.9161	High Similarity	NPC282300
0.9161	High Similarity	NPC14871
0.9155	High Similarity	NPC18260
0.9155	High Similarity	NPC53181
0.9155	High Similarity	NPC78913
0.9155	High Similarity	NPC217186
0.9155	High Similarity	NPC477956
0.9149	High Similarity	NPC472419
0.9149	High Similarity	NPC317119
0.9149	High Similarity	NPC228661
0.9149	High Similarity	NPC153979
0.9149	High Similarity	NPC188879
0.9143	High Similarity	NPC13575
0.9143	High Similarity	NPC156092
0.9143	High Similarity	NPC131039
0.9122	High Similarity	NPC472423
0.9122	High Similarity	NPC474744
0.9122	High Similarity	NPC318424
0.9122	High Similarity	NPC474772
0.9122	High Similarity	NPC472580
0.911	High Similarity	NPC97716
0.911	High Similarity	NPC237635
0.911	High Similarity	NPC79469
0.911	High Similarity	NPC24673
0.911	High Similarity	NPC201731
0.911	High Similarity	NPC104406
0.9103	High Similarity	NPC326500
0.9103	High Similarity	NPC209040
0.9103	High Similarity	NPC273538
0.9103	High Similarity	NPC278175
0.9103	High Similarity	NPC197252
0.9103	High Similarity	NPC236766
0.9103	High Similarity	NPC257236
0.9103	High Similarity	NPC271288
0.9103	High Similarity	NPC216538
0.9103	High Similarity	NPC473013
0.9103	High Similarity	NPC473015
0.9097	High Similarity	NPC62840
0.9097	High Similarity	NPC148757
0.9097	High Similarity	NPC166934
0.9097	High Similarity	NPC1089
0.9097	High Similarity	NPC125855
0.9097	High Similarity	NPC177354
0.9097	High Similarity	NPC324134
0.9097	High Similarity	NPC306829
0.9097	High Similarity	NPC167624
0.9097	High Similarity	NPC96791
0.9097	High Similarity	NPC59739
0.9097	High Similarity	NPC76372
0.9097	High Similarity	NPC293852
0.9097	High Similarity	NPC161506
0.9097	High Similarity	NPC32739
0.9097	High Similarity	NPC227579
0.9097	High Similarity	NPC37496
0.9097	High Similarity	NPC299080
0.9097	High Similarity	NPC78
0.9097	High Similarity	NPC166482
0.9097	High Similarity	NPC228504

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 NPC210826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	975
0.2-0.3	1457
0.3-0.4	2704
0.4-0.5	1903
0.5-0.6	1179
0.6-0.7	368
0.7-0.8	117
0.8-0.85	49
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD4378	Clinical (unspecified phase)
0.9103	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD1243	Approved
0.8881	High Similarity	NPD2344	Approved
0.8857	High Similarity	NPD1240	Approved
0.8824	High Similarity	NPD3749	Approved
0.8819	High Similarity	NPD1549	Phase 2
0.875	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1552	Clinical (unspecified phase)
0.8742	High Similarity	NPD7411	Suspended
0.8741	High Similarity	NPD1510	Phase 2
0.8732	High Similarity	NPD1607	Approved
0.8693	High Similarity	NPD8443	Clinical (unspecified phase)
0.8681	High Similarity	NPD2796	Approved
0.8639	High Similarity	NPD2309	Approved
0.863	High Similarity	NPD2800	Approved
0.8627	High Similarity	NPD2393	Clinical (unspecified phase)
0.86	High Similarity	NPD920	Approved
0.8581	High Similarity	NPD643	Clinical (unspecified phase)
0.8581	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD4380	Phase 2
0.8516	High Similarity	NPD3882	Suspended
0.8516	High Similarity	NPD7768	Phase 2
0.8506	High Similarity	NPD7096	Clinical (unspecified phase)
0.8506	High Similarity	NPD7819	Suspended
0.8491	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD6559	Discontinued
0.84	Intermediate Similarity	NPD1511	Approved
0.84	Intermediate Similarity	NPD6799	Approved
0.8378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD1934	Approved
0.8322	Intermediate Similarity	NPD3750	Approved
0.8302	Intermediate Similarity	NPD6959	Discontinued
0.8289	Intermediate Similarity	NPD1512	Approved
0.8269	Intermediate Similarity	NPD2801	Approved
0.8231	Intermediate Similarity	NPD2799	Discontinued
0.8228	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3926	Phase 2
0.8194	Intermediate Similarity	NPD6599	Discontinued
0.8176	Intermediate Similarity	NPD1551	Phase 2
0.8176	Intermediate Similarity	NPD919	Approved
0.8176	Intermediate Similarity	NPD2935	Discontinued
0.8125	Intermediate Similarity	NPD5494	Approved
0.8105	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2534	Approved
0.8095	Intermediate Similarity	NPD6651	Approved
0.8075	Intermediate Similarity	NPD1247	Approved
0.8069	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8037	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6166	Phase 2
0.8025	Intermediate Similarity	NPD6232	Discontinued
0.8024	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD3748	Approved
0.7987	Intermediate Similarity	NPD2296	Approved
0.7972	Intermediate Similarity	NPD1203	Approved
0.7945	Intermediate Similarity	NPD2313	Discontinued
0.7892	Intermediate Similarity	NPD7286	Phase 2
0.7881	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3817	Phase 2
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD943	Approved
0.7826	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7390	Discontinued
0.7785	Intermediate Similarity	NPD3226	Approved
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD5403	Approved
0.7763	Intermediate Similarity	NPD1471	Phase 3
0.7762	Intermediate Similarity	NPD9717	Approved
0.7746	Intermediate Similarity	NPD4287	Approved
0.7738	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD1729	Discontinued
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6099	Approved
0.7697	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD4908	Phase 1
0.7687	Intermediate Similarity	NPD6832	Phase 2
0.7679	Intermediate Similarity	NPD7054	Approved
0.7671	Intermediate Similarity	NPD2798	Approved
0.7662	Intermediate Similarity	NPD2654	Approved
0.7658	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD5401	Approved
0.764	Intermediate Similarity	NPD6279	Approved
0.764	Intermediate Similarity	NPD6280	Approved
0.7633	Intermediate Similarity	NPD7472	Approved
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6797	Phase 2
0.7584	Intermediate Similarity	NPD3764	Approved
0.7584	Intermediate Similarity	NPD3268	Approved
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7569	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5402	Approved
0.7544	Intermediate Similarity	NPD7251	Discontinued
0.7528	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4361	Phase 2
0.7517	Intermediate Similarity	NPD4625	Phase 3
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD6808	Phase 2
0.7483	Intermediate Similarity	NPD1164	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7448	Intermediate Similarity	NPD1610	Phase 2
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1548	Phase 1
0.7399	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3972	Approved
0.7397	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7003	Approved
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4360	Phase 2
0.7374	Intermediate Similarity	NPD4363	Phase 3
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD411	Approved
0.7346	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4288	Approved
0.732	Intermediate Similarity	NPD447	Suspended
0.732	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3225	Approved
0.7294	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9545	Approved
0.7273	Intermediate Similarity	NPD5761	Phase 2
0.7273	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD5760	Phase 2
0.7256	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4307	Phase 2
0.7248	Intermediate Similarity	NPD1470	Approved
0.7248	Intermediate Similarity	NPD3267	Approved
0.7248	Intermediate Similarity	NPD3266	Approved
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7232	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7199	Phase 2
0.7211	Intermediate Similarity	NPD1201	Approved
0.7208	Intermediate Similarity	NPD5124	Phase 1
0.7208	Intermediate Similarity	NPD1933	Approved
0.7208	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7193	Intermediate Similarity	NPD2403	Approved
0.7192	Intermediate Similarity	NPD17	Approved
0.7183	Intermediate Similarity	NPD1241	Discontinued
0.7181	Intermediate Similarity	NPD1876	Approved
0.7179	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2354	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7123	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4749	Approved
0.711	Intermediate Similarity	NPD7177	Discontinued
0.7097	Intermediate Similarity	NPD6355	Discontinued
0.7091	Intermediate Similarity	NPD6585	Discontinued
0.7089	Intermediate Similarity	NPD6002	Phase 3
0.7089	Intermediate Similarity	NPD6005	Phase 3
0.7089	Intermediate Similarity	NPD6004	Phase 3
0.7089	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1019	Discontinued
0.7083	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8312	Approved
0.7062	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5890	Approved
0.7048	Intermediate Similarity	NPD5889	Approved
0.7047	Intermediate Similarity	NPD1481	Phase 2
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7037	Intermediate Similarity	NPD7584	Approved
0.7032	Intermediate Similarity	NPD1613	Approved
0.7032	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4476	Approved
0.7025	Intermediate Similarity	NPD4477	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