NPASS Compound

Structure

CID135325 OpenBabel06191715492D 26 28 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 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -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 -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 -1.8171 -1.8090 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 3.0878 0.0570 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 -0.0000 -1.6180 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 -0.9511 -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 3.5878 -0.8090 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 -0.9511 -0.3090 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 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 0.9230 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 12 1 0 0 0 0 4 25 1 0 0 0 0 5 7 1 0 0 0 0 5 11 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 18 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 12 14 1 0 0 0 0 12 20 2 0 0 0 0 13 22 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 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:	5.668
LogD:	3.993
LogS:	-3.159
# Rotatable Bonds:	4
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	2.873
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.997
MDCK Permeability:	1.4318896319309715e-05
Pgp-inhibitor:	0.152
Pgp-substrate:	0.332
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.298

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.27096557617188%
Volume Distribution (VD):	0.722
Pgp-substrate:	4.14049768447876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.86
CYP3A4-inhibitor:	0.511
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	11.261
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.669
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.8
Skin Sensitization:	0.65
Carcinogencity:	0.071
Eye Corrosion:	0.003
Eye Irritation:	0.873
Respiratory Toxicity:	0.348

Download Data

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

Natural Product: NPC135325

Natural Product ID:	NPC135325
*Common Name:**	Glycybenzofuran
IUPAC Name:	4-(6-hydroxy-3-methyl-1-benzofuran-2-yl)-5-methoxy-6-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:	Glycybenzofuran
Standard InCHIKey:	OEIIVGQLDAYZNT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-11(2)5-7-15-16(23)10-17(24)19(21(15)25-4)20-12(3)14-8-6-13(22)9-18(14)26-20/h5-6,8-10,22-24H,7H2,1-4H3
SMILES:	COc1c(CC=C(C)C)c(O)cc(c1c1oc2c(c1C)ccc(c2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223582
PubChem CID:	46934435
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]
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]
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]
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]

☑ 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	6

Activity Type	# Activity
Individual Protein	7

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	=	25500.0	nM	PMID[557044]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Vmax	=	6.3	mM/hr	PMID[557044]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	3500.0	nM	PMID[557044]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	4200.0	nM	PMID[557044]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Km	=	5500.0	nM	PMID[557044]
NPT1211	Individual Protein	Dual specificity protein phosphatase 3	Homo sapiens	Inhibition	=	35.0	%	PMID[557045]
NPT1210	Individual Protein	T-cell protein-tyrosine phosphatase	Homo sapiens	Inhibition	=	4.0	%	PMID[557045]

☑ 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 NPC135325 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	383
0.1-0.2	1647
0.2-0.3	3932
0.3-0.4	10421
0.4-0.5	7891
0.5-0.6	3778
0.6-0.7	5794
0.7-0.8	4824
0.8-0.85	2085
0.85-0.9	1339
0.9-0.95	575
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC130581
0.9929	High Similarity	NPC12148
0.9858	High Similarity	NPC51641
0.9858	High Similarity	NPC300267
0.9858	High Similarity	NPC210826
0.979	High Similarity	NPC296030
0.979	High Similarity	NPC226644
0.979	High Similarity	NPC37226
0.979	High Similarity	NPC39929
0.9787	High Similarity	NPC230943
0.9716	High Similarity	NPC225884
0.9716	High Similarity	NPC302181
0.9658	High Similarity	NPC213608
0.9658	High Similarity	NPC1477
0.9655	High Similarity	NPC170169
0.9653	High Similarity	NPC221868
0.9653	High Similarity	NPC37208
0.9645	High Similarity	NPC53192
0.9592	High Similarity	NPC148938
0.9589	High Similarity	NPC5871
0.9586	High Similarity	NPC78335
0.9586	High Similarity	NPC230713
0.9583	High Similarity	NPC272194
0.9527	High Similarity	NPC160015
0.9527	High Similarity	NPC247677
0.9524	High Similarity	NPC235333
0.9524	High Similarity	NPC122365
0.9517	High Similarity	NPC178202
0.9463	High Similarity	NPC260902
0.9463	High Similarity	NPC96342
0.9463	High Similarity	NPC246647
0.9463	High Similarity	NPC296957
0.9463	High Similarity	NPC164110
0.9463	High Similarity	NPC65504
0.9463	High Similarity	NPC212967
0.9459	High Similarity	NPC297531
0.9459	High Similarity	NPC213936
0.9459	High Similarity	NPC198490
0.9456	High Similarity	NPC207624
0.94	High Similarity	NPC40583
0.94	High Similarity	NPC476350
0.94	High Similarity	NPC476349
0.9396	High Similarity	NPC180924
0.9392	High Similarity	NPC183874
0.9392	High Similarity	NPC472462
0.9388	High Similarity	NPC115324
0.9388	High Similarity	NPC23668
0.9388	High Similarity	NPC193976
0.9388	High Similarity	NPC58668
0.9388	High Similarity	NPC106372
0.9388	High Similarity	NPC156244
0.9379	High Similarity	NPC17816
0.9338	High Similarity	NPC115432
0.9338	High Similarity	NPC260296
0.9333	High Similarity	NPC268360
0.9324	High Similarity	NPC263676
0.9324	High Similarity	NPC142308
0.9324	High Similarity	NPC67654
0.932	High Similarity	NPC167576
0.9315	High Similarity	NPC168085
0.931	High Similarity	NPC477955
0.9306	High Similarity	NPC18585
0.9306	High Similarity	NPC106985
0.9306	High Similarity	NPC166138
0.9306	High Similarity	NPC17262
0.9301	High Similarity	NPC110969
0.9291	High Similarity	NPC62735
0.9272	High Similarity	NPC244750
0.9257	High Similarity	NPC116604
0.9252	High Similarity	NPC317492
0.9241	High Similarity	NPC271288
0.9241	High Similarity	NPC155144
0.9241	High Similarity	NPC311741
0.9241	High Similarity	NPC98926
0.9241	High Similarity	NPC234629
0.9236	High Similarity	NPC226636
0.9236	High Similarity	NPC144499
0.9236	High Similarity	NPC11561
0.9231	High Similarity	NPC28337
0.9231	High Similarity	NPC69769
0.9231	High Similarity	NPC270883
0.9231	High Similarity	NPC241100
0.9231	High Similarity	NPC159275
0.9231	High Similarity	NPC172986
0.9231	High Similarity	NPC261227
0.9231	High Similarity	NPC11056
0.9225	High Similarity	NPC21350
0.9225	High Similarity	NPC124269
0.922	High Similarity	NPC249606
0.922	High Similarity	NPC66349
0.922	High Similarity	NPC1486
0.922	High Similarity	NPC477243
0.922	High Similarity	NPC25287
0.922	High Similarity	NPC186838
0.922	High Similarity	NPC12165
0.922	High Similarity	NPC477242
0.922	High Similarity	NPC150399
0.922	High Similarity	NPC98115
0.922	High Similarity	NPC168105
0.922	High Similarity	NPC477244
0.922	High Similarity	NPC41461
0.922	High Similarity	NPC274109
0.92	High Similarity	NPC99199
0.9189	High Similarity	NPC476185
0.9189	High Similarity	NPC472421
0.9189	High Similarity	NPC321896
0.9184	High Similarity	NPC39195
0.9172	High Similarity	NPC175504
0.9172	High Similarity	NPC149026
0.9172	High Similarity	NPC143896
0.9172	High Similarity	NPC164980
0.9172	High Similarity	NPC150408
0.9172	High Similarity	NPC11700
0.9172	High Similarity	NPC169591
0.9172	High Similarity	NPC75049
0.9172	High Similarity	NPC91560
0.9172	High Similarity	NPC68104
0.9172	High Similarity	NPC39329
0.9172	High Similarity	NPC257097
0.9172	High Similarity	NPC221432
0.9172	High Similarity	NPC310130
0.9167	High Similarity	NPC3188
0.9167	High Similarity	NPC205006
0.9167	High Similarity	NPC103362
0.9167	High Similarity	NPC147688
0.9167	High Similarity	NPC64908
0.9167	High Similarity	NPC282300
0.9167	High Similarity	NPC156590
0.9167	High Similarity	NPC118840
0.9161	High Similarity	NPC301217
0.9161	High Similarity	NPC303633
0.9161	High Similarity	NPC96565
0.9161	High Similarity	NPC53181
0.9161	High Similarity	NPC216978
0.9161	High Similarity	NPC220062
0.9161	High Similarity	NPC18260
0.9161	High Similarity	NPC78913
0.9161	High Similarity	NPC472366
0.9161	High Similarity	NPC217186
0.9161	High Similarity	NPC477956
0.9161	High Similarity	NPC55018
0.9156	High Similarity	NPC155640
0.9155	High Similarity	NPC153979
0.9155	High Similarity	NPC188879
0.9155	High Similarity	NPC317119
0.9155	High Similarity	NPC472419
0.9149	High Similarity	NPC13575
0.9149	High Similarity	NPC156092
0.9149	High Similarity	NPC163029
0.9149	High Similarity	NPC131039
0.9133	High Similarity	NPC72370
0.9128	High Similarity	NPC474744
0.9128	High Similarity	NPC318424
0.9128	High Similarity	NPC472423
0.9128	High Similarity	NPC472580
0.9128	High Similarity	NPC474772
0.9116	High Similarity	NPC97716
0.9116	High Similarity	NPC237635
0.9116	High Similarity	NPC104406
0.9116	High Similarity	NPC24673
0.9116	High Similarity	NPC308200
0.9116	High Similarity	NPC201731
0.9116	High Similarity	NPC79469
0.9116	High Similarity	NPC10990
0.9116	High Similarity	NPC300988
0.911	High Similarity	NPC209040
0.911	High Similarity	NPC473013
0.911	High Similarity	NPC236766
0.911	High Similarity	NPC473015
0.911	High Similarity	NPC216538
0.911	High Similarity	NPC273538
0.911	High Similarity	NPC197252
0.9103	High Similarity	NPC226942
0.9103	High Similarity	NPC177354
0.9103	High Similarity	NPC1089
0.9103	High Similarity	NPC328164
0.9103	High Similarity	NPC228504
0.9103	High Similarity	NPC10937
0.9103	High Similarity	NPC220998
0.9103	High Similarity	NPC96791
0.9103	High Similarity	NPC32739
0.9103	High Similarity	NPC470636
0.9103	High Similarity	NPC265040
0.9103	High Similarity	NPC227579
0.9103	High Similarity	NPC296917
0.9103	High Similarity	NPC64915
0.9103	High Similarity	NPC324436
0.9103	High Similarity	NPC223500
0.9103	High Similarity	NPC324134
0.9103	High Similarity	NPC66515
0.9103	High Similarity	NPC182852
0.9103	High Similarity	NPC161506
0.9103	High Similarity	NPC107572
0.9103	High Similarity	NPC37496
0.9103	High Similarity	NPC78
0.9103	High Similarity	NPC166482
0.9103	High Similarity	NPC306829
0.9103	High Similarity	NPC76338
0.9103	High Similarity	NPC40833
0.9103	High Similarity	NPC202981

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 NPC135325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	967
0.2-0.3	1462
0.3-0.4	2586
0.4-0.5	1971
0.5-0.6	1197
0.6-0.7	425
0.7-0.8	119
0.8-0.85	51
0.85-0.9	25
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.911	High Similarity	NPD4378	Clinical (unspecified phase)
0.898	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD2344	Approved
0.8865	High Similarity	NPD1240	Approved
0.8831	High Similarity	NPD3749	Approved
0.8828	High Similarity	NPD1549	Phase 2
0.8824	High Similarity	NPD8443	Clinical (unspecified phase)
0.8767	High Similarity	NPD1243	Approved
0.8759	High Similarity	NPD1552	Clinical (unspecified phase)
0.8759	High Similarity	NPD1550	Clinical (unspecified phase)
0.875	High Similarity	NPD1510	Phase 2
0.875	High Similarity	NPD7411	Suspended
0.8741	High Similarity	NPD1607	Approved
0.869	High Similarity	NPD2796	Approved
0.8649	High Similarity	NPD2309	Approved
0.8645	High Similarity	NPD7768	Phase 2
0.8639	High Similarity	NPD2800	Approved
0.8636	High Similarity	NPD2393	Clinical (unspecified phase)
0.8636	High Similarity	NPD7819	Suspended
0.8616	High Similarity	NPD7852	Clinical (unspecified phase)
0.8609	High Similarity	NPD920	Approved
0.8591	High Similarity	NPD643	Clinical (unspecified phase)
0.859	High Similarity	NPD7075	Discontinued
0.8562	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD3882	Suspended
0.8516	High Similarity	NPD7096	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6959	Discontinued
0.8415	Intermediate Similarity	NPD6559	Discontinued
0.8411	Intermediate Similarity	NPD6799	Approved
0.8389	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD3750	Approved
0.8323	Intermediate Similarity	NPD3926	Phase 2
0.8323	Intermediate Similarity	NPD6599	Discontinued
0.8289	Intermediate Similarity	NPD1511	Approved
0.828	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD5494	Approved
0.8243	Intermediate Similarity	NPD2799	Discontinued
0.8239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2532	Approved
0.8235	Intermediate Similarity	NPD2533	Approved
0.8235	Intermediate Similarity	NPD2534	Approved
0.82	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2935	Discontinued
0.8188	Intermediate Similarity	NPD1551	Phase 2
0.8187	Intermediate Similarity	NPD919	Approved
0.8182	Intermediate Similarity	NPD1512	Approved
0.8148	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8108	Intermediate Similarity	NPD6651	Approved
0.8086	Intermediate Similarity	NPD1247	Approved
0.8082	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD3818	Discontinued
0.8049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD5953	Discontinued
0.8013	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2296	Approved
0.8	Intermediate Similarity	NPD3748	Approved
0.7959	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7286	Phase 2
0.7904	Intermediate Similarity	NPD5844	Phase 1
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7881	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1203	Approved
0.7857	Intermediate Similarity	NPD4628	Phase 3
0.7857	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2313	Discontinued
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7821	Intermediate Similarity	NPD7390	Discontinued
0.7799	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD1471	Phase 3
0.7764	Intermediate Similarity	NPD6280	Approved
0.7764	Intermediate Similarity	NPD6279	Approved
0.7759	Intermediate Similarity	NPD4287	Approved
0.7751	Intermediate Similarity	NPD7074	Phase 3
0.7751	Intermediate Similarity	NPD1729	Discontinued
0.7733	Intermediate Similarity	NPD943	Approved
0.7712	Intermediate Similarity	NPD6099	Approved
0.7712	Intermediate Similarity	NPD6100	Approved
0.7703	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD7054	Approved
0.7687	Intermediate Similarity	NPD2798	Approved
0.7677	Intermediate Similarity	NPD2654	Approved
0.7673	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7658	Intermediate Similarity	NPD5401	Approved
0.7655	Intermediate Similarity	NPD9717	Approved
0.7647	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD4361	Phase 2
0.764	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5711	Approved
0.7605	Intermediate Similarity	NPD6808	Phase 2
0.7605	Intermediate Similarity	NPD5710	Approved
0.7605	Intermediate Similarity	NPD7229	Phase 3
0.7602	Intermediate Similarity	NPD6797	Phase 2
0.76	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD3268	Approved
0.7586	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1610	Phase 2
0.7561	Intermediate Similarity	NPD5402	Approved
0.7558	Intermediate Similarity	NPD7251	Discontinued
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3972	Approved
0.7533	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD7003	Approved
0.7514	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD1164	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2797	Approved
0.7486	Intermediate Similarity	NPD4363	Phase 3
0.7486	Intermediate Similarity	NPD4360	Phase 2
0.7484	Intermediate Similarity	NPD5404	Approved
0.7484	Intermediate Similarity	NPD5408	Approved
0.7484	Intermediate Similarity	NPD5406	Approved
0.7484	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7419	Intermediate Similarity	NPD4308	Phase 3
0.7415	Intermediate Similarity	NPD1608	Approved
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5760	Phase 2
0.7394	Intermediate Similarity	NPD5761	Phase 2
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7349	Intermediate Similarity	NPD4288	Approved
0.7345	Intermediate Similarity	NPD8434	Phase 2
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7315	Intermediate Similarity	NPD1876	Approved
0.731	Intermediate Similarity	NPD9545	Approved
0.731	Intermediate Similarity	NPD2403	Approved
0.7292	Intermediate Similarity	NPD9493	Approved
0.7283	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD1470	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.7257	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD411	Approved
0.7251	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1201	Approved
0.7226	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7226	Intermediate Similarity	NPD6355	Discontinued
0.7226	Intermediate Similarity	NPD1933	Approved
0.7226	Intermediate Similarity	NPD5124	Phase 1
0.7226	Intermediate Similarity	NPD447	Suspended
0.7225	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7211	Intermediate Similarity	NPD17	Approved
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.72	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8312	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD6971	Discontinued
0.7159	Intermediate Similarity	NPD6104	Discontinued
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1651	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD4749	Approved
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1019	Discontinued
0.7101	Intermediate Similarity	NPD4947	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7073	Intermediate Similarity	NPD5049	Phase 3
0.7073	Intermediate Similarity	NPD6273	Approved
0.7066	Intermediate Similarity	NPD5890	Approved
0.7066	Intermediate Similarity	NPD5889	Approved
0.7063	Intermediate Similarity	NPD2424	Discontinued
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2861	Phase 2

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