NPASS Compound

Structure

CID37226 OpenBabel06191715362D 26 28 0 0 0 0 0 0 0 0999 V2000 -6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 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 -3.5491 -1.8090 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 3.0878 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 -5.2812 -1.8090 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 1.5878 -0.8090 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 -0.9511 -1.3090 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 -2.6831 -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 -0.9511 -0.3090 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 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.9230 0.0000 O 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 -1.8171 -2.8090 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 19 2 0 0 0 0 11 18 2 0 0 0 0 11 20 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 18 1 0 0 0 0 15 21 2 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	5.689
LogD:	3.748
LogS:	-3.564
# Rotatable Bonds:	5
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	2.724
Fsp3:	0.238
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:	-4.844
MDCK Permeability:	1.2829890692955814e-05
Pgp-inhibitor:	0.218
Pgp-substrate:	0.148
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.83
30% Bioavailability (F30%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	93.65287017822266%
Volume Distribution (VD):	0.911
Pgp-substrate:	9.814172744750977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.892
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.844
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	10.603
Half-life (T1/2):	0.322

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.699
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.701
Skin Sensitization:	0.673
Carcinogencity:	0.063
Eye Corrosion:	0.003
Eye Irritation:	0.631
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC37226

Natural Product ID:	NPC37226
*Common Name:**	Gancaonin I
IUPAC Name:	4-[4,6-dimethoxy-5-(3-methylbut-2-enyl)-1-benzofuran-2-yl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	DKVBYQAVNNRVNN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-12(2)5-7-15-18(24-3)11-20-16(21(15)25-4)10-19(26-20)14-8-6-13(22)9-17(14)23/h5-6,8-11,22-23H,7H2,1-4H3
SMILES:	COc1c(CC=C(C)C)c(OC)cc2c1cc(o2)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3808735
PubChem CID:	480777
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]
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]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
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]
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]
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]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO29384	Glycyrrhiza glabra	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]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	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
Ki	1
MIC	1
Others	12

Activity Type	# Activity
Cell Line	1
Individual Protein	3
Organism	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	90.0	%	PMID[491773]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3300.0	nM	PMID[491775]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	>	60.0	%	PMID[491775]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	80.0	%	PMID[491775]
NPT742	Organism	Influenza A virus	Influenza A virus	Activity	>	30.0	%	PMID[491773]
NPT2	Others	Unspecified		Activity	=	37.4	%	PMID[491774]
NPT2	Others	Unspecified		Activity	=	10.1	%	PMID[491774]
NPT2	Others	Unspecified		Activity	=	88.4	%	PMID[491774]
NPT2	Others	Unspecified		Activity	=	63.2	%	PMID[491774]
NPT2	Others	Unspecified		FC	=	0.8	n.a.	PMID[491774]
NPT2	Others	Unspecified		Ki	=	30900.0	nM	PMID[491774]
NPT2	Others	Unspecified		Inhibition	=	60.0	%	PMID[491774]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	5000.0	nM	PMID[491774]
NPT2	Others	Unspecified		Inhibition	>	40.0	%	PMID[491775]

☑ 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 NPC37226 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	387
0.1-0.2	1665
0.2-0.3	4074
0.3-0.4	10428
0.4-0.5	7807
0.5-0.6	3812
0.6-0.7	5646
0.7-0.8	4699
0.8-0.85	2002
0.85-0.9	1655
0.9-0.95	485
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC226644
0.9861	High Similarity	NPC170169
0.9859	High Similarity	NPC130581
0.9859	High Similarity	NPC12148
0.9792	High Similarity	NPC78335
0.9792	High Similarity	NPC230713
0.979	High Similarity	NPC135325
0.9789	High Similarity	NPC210826
0.9789	High Similarity	NPC300267
0.9789	High Similarity	NPC51641
0.9726	High Similarity	NPC1477
0.9726	High Similarity	NPC213608
0.9722	High Similarity	NPC178202
0.9722	High Similarity	NPC296030
0.9722	High Similarity	NPC39929
0.966	High Similarity	NPC148938
0.966	High Similarity	NPC198490
0.9658	High Similarity	NPC5871
0.9648	High Similarity	NPC225884
0.9648	High Similarity	NPC302181
0.9595	High Similarity	NPC160015
0.9595	High Similarity	NPC247677
0.9592	High Similarity	NPC472462
0.9592	High Similarity	NPC235333
0.9592	High Similarity	NPC183874
0.9586	High Similarity	NPC37208
0.9586	High Similarity	NPC221868
0.9583	High Similarity	NPC17816
0.958	High Similarity	NPC230943
0.9577	High Similarity	NPC53192
0.953	High Similarity	NPC164110
0.953	High Similarity	NPC260902
0.953	High Similarity	NPC212967
0.953	High Similarity	NPC246647
0.953	High Similarity	NPC96342
0.953	High Similarity	NPC296957
0.953	High Similarity	NPC65504
0.9527	High Similarity	NPC213936
0.9527	High Similarity	NPC297531
0.9524	High Similarity	NPC263676
0.9524	High Similarity	NPC207624
0.9521	High Similarity	NPC167576
0.9517	High Similarity	NPC272194
0.9467	High Similarity	NPC476350
0.9467	High Similarity	NPC476349
0.9467	High Similarity	NPC40583
0.9463	High Similarity	NPC180924
0.9459	High Similarity	NPC122365
0.9456	High Similarity	NPC23668
0.9456	High Similarity	NPC115324
0.9456	High Similarity	NPC58668
0.9456	High Similarity	NPC193976
0.9456	High Similarity	NPC106372
0.9456	High Similarity	NPC116604
0.9452	High Similarity	NPC317492
0.9444	High Similarity	NPC98926
0.9444	High Similarity	NPC155144
0.9404	High Similarity	NPC115432
0.9404	High Similarity	NPC260296
0.94	High Similarity	NPC268360
0.9392	High Similarity	NPC67654
0.9392	High Similarity	NPC142308
0.9384	High Similarity	NPC168085
0.9338	High Similarity	NPC244750
0.9329	High Similarity	NPC72370
0.9324	High Similarity	NPC156244
0.931	High Similarity	NPC234629
0.931	High Similarity	NPC311741
0.9281	High Similarity	NPC219861
0.9276	High Similarity	NPC304839
0.9276	High Similarity	NPC220582
0.9267	High Similarity	NPC99199
0.9262	High Similarity	NPC253872
0.9257	High Similarity	NPC472421
0.9252	High Similarity	NPC39195
0.9241	High Similarity	NPC166138
0.9241	High Similarity	NPC18585
0.9241	High Similarity	NPC106985
0.9241	High Similarity	NPC17262
0.9236	High Similarity	NPC110969
0.9231	High Similarity	NPC477956
0.9225	High Similarity	NPC472419
0.9221	High Similarity	NPC472581
0.9221	High Similarity	NPC155640
0.9216	High Similarity	NPC30655
0.9216	High Similarity	NPC45124
0.9216	High Similarity	NPC74854
0.9195	High Similarity	NPC472423
0.9195	High Similarity	NPC318424
0.9195	High Similarity	NPC474744
0.9195	High Similarity	NPC474772
0.9189	High Similarity	NPC266499
0.9184	High Similarity	NPC308200
0.9184	High Similarity	NPC198427
0.9178	High Similarity	NPC216538
0.9178	High Similarity	NPC273538
0.9172	High Similarity	NPC11561
0.9172	High Similarity	NPC470636
0.9172	High Similarity	NPC226636
0.9172	High Similarity	NPC144499
0.9172	High Similarity	NPC96791
0.9172	High Similarity	NPC226942
0.9167	High Similarity	NPC172986
0.9167	High Similarity	NPC261227
0.9167	High Similarity	NPC28337
0.9167	High Similarity	NPC270883
0.9167	High Similarity	NPC241100
0.9167	High Similarity	NPC69769
0.9167	High Similarity	NPC159275
0.9161	High Similarity	NPC21350
0.9161	High Similarity	NPC124269
0.9156	High Similarity	NPC193998
0.9155	High Similarity	NPC168105
0.9155	High Similarity	NPC477243
0.9155	High Similarity	NPC150399
0.9155	High Similarity	NPC98115
0.9155	High Similarity	NPC1486
0.9155	High Similarity	NPC477244
0.9155	High Similarity	NPC249606
0.9155	High Similarity	NPC477242
0.9155	High Similarity	NPC274109
0.9155	High Similarity	NPC186838
0.9155	High Similarity	NPC41461
0.9155	High Similarity	NPC66349
0.9155	High Similarity	NPC12165
0.9155	High Similarity	NPC25287
0.9145	High Similarity	NPC269495
0.9133	High Similarity	NPC473996
0.9133	High Similarity	NPC476238
0.9133	High Similarity	NPC327269
0.9133	High Similarity	NPC31627
0.9128	High Similarity	NPC148423
0.9128	High Similarity	NPC13282
0.9128	High Similarity	NPC321896
0.9128	High Similarity	NPC135303
0.9128	High Similarity	NPC472406
0.9128	High Similarity	NPC476185
0.9122	High Similarity	NPC37135
0.9122	High Similarity	NPC186397
0.9122	High Similarity	NPC266572
0.9122	High Similarity	NPC145467
0.9116	High Similarity	NPC472629
0.9116	High Similarity	NPC477955
0.9116	High Similarity	NPC5820
0.9116	High Similarity	NPC124729
0.9116	High Similarity	NPC178343
0.9116	High Similarity	NPC306488
0.9116	High Similarity	NPC299011
0.911	High Similarity	NPC175504
0.911	High Similarity	NPC257097
0.911	High Similarity	NPC143896
0.911	High Similarity	NPC68104
0.911	High Similarity	NPC169591
0.911	High Similarity	NPC262935
0.911	High Similarity	NPC150408
0.911	High Similarity	NPC190637
0.911	High Similarity	NPC149026
0.911	High Similarity	NPC164980
0.911	High Similarity	NPC212932
0.911	High Similarity	NPC221432
0.911	High Similarity	NPC251182
0.911	High Similarity	NPC293053
0.911	High Similarity	NPC9117
0.911	High Similarity	NPC39329
0.911	High Similarity	NPC172182
0.911	High Similarity	NPC75049
0.911	High Similarity	NPC310130
0.911	High Similarity	NPC91560
0.911	High Similarity	NPC24821
0.9103	High Similarity	NPC3188
0.9103	High Similarity	NPC26051
0.9103	High Similarity	NPC103362
0.9103	High Similarity	NPC205006
0.9103	High Similarity	NPC469404
0.9103	High Similarity	NPC321980
0.9103	High Similarity	NPC55832
0.9103	High Similarity	NPC470087
0.9103	High Similarity	NPC52789
0.9103	High Similarity	NPC470089
0.9103	High Similarity	NPC277480
0.9103	High Similarity	NPC268204
0.9103	High Similarity	NPC53640
0.9103	High Similarity	NPC147688
0.9103	High Similarity	NPC156590
0.9103	High Similarity	NPC64908
0.9103	High Similarity	NPC323137
0.9103	High Similarity	NPC282300
0.9103	High Similarity	NPC118840
0.9097	High Similarity	NPC216978
0.9097	High Similarity	NPC220062
0.9097	High Similarity	NPC78913
0.9097	High Similarity	NPC301217
0.9097	High Similarity	NPC303633
0.9097	High Similarity	NPC55018
0.9097	High Similarity	NPC18260
0.9097	High Similarity	NPC38591
0.9097	High Similarity	NPC137009
0.9097	High Similarity	NPC53181
0.9097	High Similarity	NPC109180
0.9097	High Similarity	NPC96565

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 NPC37226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	961
0.2-0.3	1507
0.3-0.4	2638
0.4-0.5	1936
0.5-0.6	1172
0.6-0.7	396
0.7-0.8	111
0.8-0.85	52
0.85-0.9	26
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8828	High Similarity	NPD2344	Approved
0.8803	High Similarity	NPD1240	Approved
0.88	High Similarity	NPD920	Approved
0.8774	High Similarity	NPD3749	Approved
0.8767	High Similarity	NPD1549	Phase 2
0.8707	High Similarity	NPD1243	Approved
0.8707	High Similarity	NPD2800	Approved
0.8701	High Similarity	NPD2393	Clinical (unspecified phase)
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.8693	High Similarity	NPD7411	Suspended
0.869	High Similarity	NPD1510	Phase 2
0.8681	High Similarity	NPD1607	Approved
0.8667	High Similarity	NPD642	Clinical (unspecified phase)
0.8645	High Similarity	NPD8443	Clinical (unspecified phase)
0.863	High Similarity	NPD2796	Approved
0.8627	High Similarity	NPD4380	Phase 2
0.8591	High Similarity	NPD2309	Approved
0.859	High Similarity	NPD3882	Suspended
0.8535	High Similarity	NPD7075	Discontinued
0.8533	High Similarity	NPD643	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD6559	Discontinued
0.8471	Intermediate Similarity	NPD7768	Phase 2
0.8462	Intermediate Similarity	NPD7819	Suspended
0.8462	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2801	Approved
0.8447	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1934	Approved
0.8375	Intermediate Similarity	NPD6959	Discontinued
0.8355	Intermediate Similarity	NPD6799	Approved
0.8355	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5494	Approved
0.8302	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2534	Approved
0.8301	Intermediate Similarity	NPD2532	Approved
0.8301	Intermediate Similarity	NPD2533	Approved
0.828	Intermediate Similarity	NPD6801	Discontinued
0.8272	Intermediate Similarity	NPD3926	Phase 2
0.8261	Intermediate Similarity	NPD1247	Approved
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8247	Intermediate Similarity	NPD1512	Approved
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.821	Intermediate Similarity	NPD6232	Discontinued
0.8188	Intermediate Similarity	NPD2799	Discontinued
0.8171	Intermediate Similarity	NPD7473	Discontinued
0.8158	Intermediate Similarity	NPD3750	Approved
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8137	Intermediate Similarity	NPD919	Approved
0.8133	Intermediate Similarity	NPD1551	Phase 2
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD5953	Discontinued
0.8079	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7286	Phase 2
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6651	Approved
0.8027	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2313	Discontinued
0.8026	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD2296	Approved
0.795	Intermediate Similarity	NPD3817	Phase 2
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3226	Approved
0.7857	Intermediate Similarity	NPD5844	Phase 1
0.7829	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD7074	Phase 3
0.7808	Intermediate Similarity	NPD1203	Approved
0.78	Intermediate Similarity	NPD943	Approved
0.7798	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7390	Discontinued
0.7751	Intermediate Similarity	NPD7054	Approved
0.7736	Intermediate Similarity	NPD5403	Approved
0.773	Intermediate Similarity	NPD5402	Approved
0.7727	Intermediate Similarity	NPD2346	Discontinued
0.7727	Intermediate Similarity	NPD1471	Phase 3
0.7716	Intermediate Similarity	NPD6279	Approved
0.7716	Intermediate Similarity	NPD6280	Approved
0.7714	Intermediate Similarity	NPD4287	Approved
0.7706	Intermediate Similarity	NPD1729	Discontinued
0.7706	Intermediate Similarity	NPD7472	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7665	Intermediate Similarity	NPD5710	Approved
0.7665	Intermediate Similarity	NPD5711	Approved
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7661	Intermediate Similarity	NPD6797	Phase 2
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.7628	Intermediate Similarity	NPD2654	Approved
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD5401	Approved
0.7603	Intermediate Similarity	NPD9717	Approved
0.7572	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7808	Phase 3
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.756	Intermediate Similarity	NPD6808	Phase 2
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3764	Approved
0.7548	Intermediate Similarity	NPD6099	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7534	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5760	Phase 2
0.7455	Intermediate Similarity	NPD5761	Phase 2
0.7444	Intermediate Similarity	NPD4360	Phase 2
0.7444	Intermediate Similarity	NPD4363	Phase 3
0.7439	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3268	Approved
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7415	Intermediate Similarity	NPD1610	Phase 2
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD2403	Approved
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD3972	Approved
0.7363	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7003	Approved
0.7333	Intermediate Similarity	NPD1164	Approved
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD5408	Approved
0.7325	Intermediate Similarity	NPD5405	Approved
0.7325	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD9545	Approved
0.7248	Intermediate Similarity	NPD1608	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9493	Approved
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2424	Discontinued
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1470	Approved
0.7216	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD411	Approved
0.7202	Intermediate Similarity	NPD4288	Approved
0.7193	Intermediate Similarity	NPD7199	Phase 2
0.719	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7179	Intermediate Similarity	NPD1933	Approved
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.717	Intermediate Similarity	NPD6004	Phase 3
0.717	Intermediate Similarity	NPD6002	Phase 3
0.717	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6005	Phase 3
0.717	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1241	Discontinued
0.7152	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6104	Discontinued
0.7118	Intermediate Similarity	NPD6971	Discontinued
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7115	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1613	Approved
0.711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD3267	Approved
0.7105	Intermediate Similarity	NPD7584	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7086	Intermediate Similarity	NPD7177	Discontinued
0.7083	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD37	Approved
0.7076	Intermediate Similarity	NPD6234	Discontinued
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7067	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD4967	Phase 2
0.7059	Intermediate Similarity	NPD4965	Approved
0.7059	Intermediate Similarity	NPD4966	Approved
0.7052	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD17	Approved
0.7041	Intermediate Similarity	NPD8455	Phase 2
0.7032	Intermediate Similarity	NPD3027	Phase 3
0.7031	Intermediate Similarity	NPD8151	Discontinued

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