NPASS Compound

Structure

CID103116 OpenBabel06191715452D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5289 1.1002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 3.4641 0.0000 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 21 1 0 0 0 0 2 26 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 1 0 0 0 0 5 13 1 0 0 0 0 6 21 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.12
Volume:	377.986
LogP:	2.927
LogD:	2.537
LogS:	-4.025
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	3.426
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.809
MDCK Permeability:	1.538007018098142e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.522

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	97.10767364501953%
Volume Distribution (VD):	0.503
Pgp-substrate:	3.959064483642578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.896
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.353
CYP2C9-substrate:	0.872
CYP2D6-inhibitor:	0.595
CYP2D6-substrate:	0.777
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	9.37
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.707
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.408
Skin Sensitization:	0.369
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC103116

Natural Product ID:	NPC103116
*Common Name:**	Licopyranocoumarin
IUPAC Name:	7-(2,4-dihydroxyphenyl)-2-(hydroxymethyl)-5-methoxy-2-methyl-3,4-dihydropyrano[3,2-g]chromen-8-one
Synonyms:	Licopyranocoumarin
Standard InCHIKey:	MOBCUWLJOZHPQL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O7/c1-21(10-22)6-5-13-18(28-21)9-17-15(19(13)26-2)8-14(20(25)27-17)12-4-3-11(23)7-16(12)24/h3-4,7-9,22-24H,5-6,10H2,1-2H3
SMILES:	CC1(CCc2c(cc3c(cc(c4ccc(cc4O)O)c(=O)o3)c2OC)O1)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL597425
PubChem CID:	122851
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0004154] Hydroxyisoflavonoids

*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]
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]
NPO1698	Glycyrrhiza inflata	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]
NPO29384	Glycyrrhiza glabra	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]
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]
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]
NPO29384	Glycyrrhiza glabra	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]
NPO1698	Glycyrrhiza inflata	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[490274]

☑ 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 NPC103116 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	374
0.1-0.2	1602
0.2-0.3	3726
0.3-0.4	8478
0.4-0.5	9932
0.5-0.6	3990
0.6-0.7	5515
0.7-0.8	4335
0.8-0.85	3010
0.85-0.9	1481
0.9-0.95	244
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9648	High Similarity	NPC295696
0.9366	High Similarity	NPC310370
0.9366	High Similarity	NPC183642
0.9241	High Similarity	NPC71739
0.9231	High Similarity	NPC195357
0.9231	High Similarity	NPC170812
0.9231	High Similarity	NPC152771
0.9161	High Similarity	NPC71903
0.9161	High Similarity	NPC312881
0.9097	High Similarity	NPC287286
0.9091	High Similarity	NPC151946
0.9091	High Similarity	NPC279573
0.9091	High Similarity	NPC211110
0.9073	High Similarity	NPC7989
0.9073	High Similarity	NPC223701
0.9073	High Similarity	NPC469405
0.9073	High Similarity	NPC472583
0.906	High Similarity	NPC100818
0.9041	High Similarity	NPC471824
0.9021	High Similarity	NPC155963
0.9021	High Similarity	NPC232246
0.9021	High Similarity	NPC153818
0.9021	High Similarity	NPC281014
0.9021	High Similarity	NPC294456
0.9021	High Similarity	NPC212124
0.9021	High Similarity	NPC184861
0.9021	High Similarity	NPC225106
0.9007	High Similarity	NPC256141
0.898	High Similarity	NPC469701
0.8951	High Similarity	NPC224543
0.8951	High Similarity	NPC26954
0.8951	High Similarity	NPC188380
0.8951	High Similarity	NPC78746
0.8951	High Similarity	NPC38099
0.8944	High Similarity	NPC131950
0.894	High Similarity	NPC263384
0.894	High Similarity	NPC472420
0.894	High Similarity	NPC472422
0.894	High Similarity	NPC471676
0.894	High Similarity	NPC244577
0.8889	High Similarity	NPC217706
0.8889	High Similarity	NPC476169
0.8889	High Similarity	NPC304207
0.8889	High Similarity	NPC108937
0.8889	High Similarity	NPC477530
0.8889	High Similarity	NPC48579
0.8889	High Similarity	NPC471069
0.8889	High Similarity	NPC477958
0.8889	High Similarity	NPC207809
0.8889	High Similarity	NPC279218
0.8889	High Similarity	NPC471068
0.8889	High Similarity	NPC470681
0.8889	High Similarity	NPC259710
0.8882	High Similarity	NPC475790
0.8882	High Similarity	NPC150123
0.8882	High Similarity	NPC56232
0.8882	High Similarity	NPC161881
0.8882	High Similarity	NPC10807
0.8882	High Similarity	NPC244583
0.8881	High Similarity	NPC472525
0.8874	High Similarity	NPC180351
0.8861	High Similarity	NPC471823
0.8846	High Similarity	NPC97812
0.8844	High Similarity	NPC229916
0.8831	High Similarity	NPC471787
0.8831	High Similarity	NPC474609
0.8831	High Similarity	NPC474738
0.8831	High Similarity	NPC109967
0.8831	High Similarity	NPC78554
0.8831	High Similarity	NPC475797
0.8831	High Similarity	NPC469936
0.8831	High Similarity	NPC129053
0.8831	High Similarity	NPC321372
0.8828	High Similarity	NPC471070
0.8828	High Similarity	NPC221046
0.8828	High Similarity	NPC471072
0.8828	High Similarity	NPC471071
0.8824	High Similarity	NPC248793
0.8824	High Similarity	NPC180301
0.8819	High Similarity	NPC283019
0.8819	High Similarity	NPC149320
0.8819	High Similarity	NPC177281
0.8819	High Similarity	NPC476455
0.8819	High Similarity	NPC128529
0.8819	High Similarity	NPC471630
0.8819	High Similarity	NPC223616
0.8819	High Similarity	NPC55615
0.8819	High Similarity	NPC160727
0.8816	High Similarity	NPC471677
0.8816	High Similarity	NPC474021
0.8816	High Similarity	NPC209846
0.8816	High Similarity	NPC328740
0.8816	High Similarity	NPC289774
0.8816	High Similarity	NPC474023
0.8816	High Similarity	NPC477897
0.8811	High Similarity	NPC267412
0.8811	High Similarity	NPC287182
0.8811	High Similarity	NPC260265
0.8811	High Similarity	NPC50896
0.8811	High Similarity	NPC47163
0.8811	High Similarity	NPC213173
0.8811	High Similarity	NPC84894
0.8811	High Similarity	NPC100986
0.8811	High Similarity	NPC180716
0.8811	High Similarity	NPC195343
0.8811	High Similarity	NPC319859
0.8811	High Similarity	NPC326600
0.8811	High Similarity	NPC224475
0.8811	High Similarity	NPC204353
0.8811	High Similarity	NPC62366
0.8811	High Similarity	NPC164269
0.8811	High Similarity	NPC127888
0.8811	High Similarity	NPC166672
0.8811	High Similarity	NPC18804
0.8811	High Similarity	NPC198381
0.8811	High Similarity	NPC74655
0.8803	High Similarity	NPC307289
0.88	High Similarity	NPC14875
0.88	High Similarity	NPC142863
0.88	High Similarity	NPC140120
0.8782	High Similarity	NPC24164
0.8782	High Similarity	NPC471976
0.8776	High Similarity	NPC184053
0.8766	High Similarity	NPC304745
0.8766	High Similarity	NPC111341
0.8758	High Similarity	NPC476238
0.8758	High Similarity	NPC285623
0.8758	High Similarity	NPC171651
0.8758	High Similarity	NPC243171
0.8758	High Similarity	NPC327269
0.8758	High Similarity	NPC474656
0.8758	High Similarity	NPC31627
0.8758	High Similarity	NPC210597
0.8758	High Similarity	NPC35567
0.8758	High Similarity	NPC473996
0.875	High Similarity	NPC474735
0.875	High Similarity	NPC29777
0.875	High Similarity	NPC471625
0.875	High Similarity	NPC124478
0.875	High Similarity	NPC281241
0.875	High Similarity	NPC471115
0.875	High Similarity	NPC472424
0.875	High Similarity	NPC177308
0.875	High Similarity	NPC471909
0.875	High Similarity	NPC86892
0.8742	High Similarity	NPC266572
0.8742	High Similarity	NPC6511
0.8742	High Similarity	NPC13481
0.8742	High Similarity	NPC207575
0.8741	High Similarity	NPC296624
0.8741	High Similarity	NPC133956
0.8741	High Similarity	NPC167111
0.8741	High Similarity	NPC92805
0.8741	High Similarity	NPC207002
0.8741	High Similarity	NPC31849
0.8741	High Similarity	NPC318400
0.8741	High Similarity	NPC471910
0.8733	High Similarity	NPC87950
0.8733	High Similarity	NPC471764
0.8733	High Similarity	NPC476347
0.8726	High Similarity	NPC3629
0.8725	High Similarity	NPC85624
0.8725	High Similarity	NPC226722
0.871	High Similarity	NPC78492
0.871	High Similarity	NPC208152
0.8707	High Similarity	NPC155552
0.8701	High Similarity	NPC268193
0.8701	High Similarity	NPC112701
0.8701	High Similarity	NPC109594
0.8701	High Similarity	NPC100134
0.8701	High Similarity	NPC311579
0.8701	High Similarity	NPC293286
0.8701	High Similarity	NPC326592
0.8701	High Similarity	NPC209760
0.8701	High Similarity	NPC236756
0.8699	High Similarity	NPC278600
0.8699	High Similarity	NPC144512
0.8699	High Similarity	NPC137262
0.8699	High Similarity	NPC35501
0.8699	High Similarity	NPC37428
0.8699	High Similarity	NPC47040
0.8693	High Similarity	NPC319910
0.8693	High Similarity	NPC278476
0.8693	High Similarity	NPC472636
0.8693	High Similarity	NPC262039
0.8693	High Similarity	NPC471229
0.8693	High Similarity	NPC471675
0.8693	High Similarity	NPC472580
0.8693	High Similarity	NPC262038
0.8693	High Similarity	NPC474772
0.8693	High Similarity	NPC474744
0.8693	High Similarity	NPC254412
0.8693	High Similarity	NPC472423
0.8684	High Similarity	NPC89442
0.8684	High Similarity	NPC19238
0.8684	High Similarity	NPC5173
0.8684	High Similarity	NPC472628
0.8684	High Similarity	NPC164299
0.8684	High Similarity	NPC164205
0.8684	High Similarity	NPC104236

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 NPC103116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	908
0.2-0.3	1723
0.3-0.4	2573
0.4-0.5	1938
0.5-0.6	1074
0.6-0.7	359
0.7-0.8	144
0.8-0.85	52
0.85-0.9	22
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4380	Phase 2
0.8654	High Similarity	NPD7075	Discontinued
0.859	High Similarity	NPD4868	Clinical (unspecified phase)
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8535	High Similarity	NPD4381	Clinical (unspecified phase)
0.8523	High Similarity	NPD3750	Approved
0.8516	High Similarity	NPD6801	Discontinued
0.8483	Intermediate Similarity	NPD5124	Phase 1
0.8483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7411	Suspended
0.8421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD5403	Approved
0.8301	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD5402	Approved
0.8276	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6799	Approved
0.8228	Intermediate Similarity	NPD7819	Suspended
0.8212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD3748	Approved
0.8182	Intermediate Similarity	NPD5401	Approved
0.8165	Intermediate Similarity	NPD1934	Approved
0.8158	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4628	Phase 3
0.8151	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1549	Phase 2
0.8144	Intermediate Similarity	NPD6559	Discontinued
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8113	Intermediate Similarity	NPD2801	Approved
0.811	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1652	Phase 2
0.8084	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD3749	Approved
0.8067	Intermediate Similarity	NPD1510	Phase 2
0.8063	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD3817	Phase 2
0.8056	Intermediate Similarity	NPD2797	Approved
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8028	Intermediate Similarity	NPD422	Phase 1
0.8014	Intermediate Similarity	NPD4908	Phase 1
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD2935	Discontinued
0.8013	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7054	Approved
0.7962	Intermediate Similarity	NPD920	Approved
0.7947	Intermediate Similarity	NPD4308	Phase 3
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1613	Approved
0.7919	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7911	Intermediate Similarity	NPD1653	Approved
0.7905	Intermediate Similarity	NPD3268	Approved
0.7905	Intermediate Similarity	NPD6798	Discontinued
0.7905	Intermediate Similarity	NPD2313	Discontinued
0.7901	Intermediate Similarity	NPD3882	Suspended
0.7885	Intermediate Similarity	NPD1511	Approved
0.7879	Intermediate Similarity	NPD6232	Discontinued
0.787	Intermediate Similarity	NPD6797	Phase 2
0.7866	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD3225	Approved
0.7834	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD7033	Discontinued
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.78	Intermediate Similarity	NPD1240	Approved
0.7792	Intermediate Similarity	NPD2424	Discontinued
0.7785	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6355	Discontinued
0.7746	Intermediate Similarity	NPD1548	Phase 1
0.7742	Intermediate Similarity	NPD1243	Approved
0.7738	Intermediate Similarity	NPD7473	Discontinued
0.7733	Intermediate Similarity	NPD6233	Phase 2
0.7722	Intermediate Similarity	NPD2534	Approved
0.7722	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2532	Approved
0.7722	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD37	Approved
0.7711	Intermediate Similarity	NPD6959	Discontinued
0.7707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1607	Approved
0.7697	Intermediate Similarity	NPD6234	Discontinued
0.7692	Intermediate Similarity	NPD7228	Approved
0.7687	Intermediate Similarity	NPD1203	Approved
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7682	Intermediate Similarity	NPD4060	Phase 1
0.7682	Intermediate Similarity	NPD4307	Phase 2
0.7677	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1296	Phase 2
0.7661	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD7286	Phase 2
0.7647	Intermediate Similarity	NPD7097	Phase 1
0.7643	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD3226	Approved
0.7632	Intermediate Similarity	NPD230	Phase 1
0.763	Intermediate Similarity	NPD8312	Approved
0.763	Intermediate Similarity	NPD8313	Approved
0.7627	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD7585	Approved
0.7613	Intermediate Similarity	NPD2346	Discontinued
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD4625	Phase 3
0.76	Intermediate Similarity	NPD3027	Phase 3
0.759	Intermediate Similarity	NPD919	Approved
0.7588	Intermediate Similarity	NPD3751	Discontinued
0.7568	Intermediate Similarity	NPD7583	Approved
0.7568	Intermediate Similarity	NPD3266	Approved
0.7568	Intermediate Similarity	NPD3267	Approved
0.756	Intermediate Similarity	NPD7229	Phase 3
0.7556	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3764	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7548	Intermediate Similarity	NPD6099	Approved
0.7543	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7458	Discontinued
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6005	Phase 3
0.75	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6002	Phase 3
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6004	Phase 3
0.7483	Intermediate Similarity	NPD9717	Approved
0.7471	Intermediate Similarity	NPD7549	Discontinued
0.7468	Intermediate Similarity	NPD7003	Approved
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7453	Intermediate Similarity	NPD6273	Approved
0.7453	Intermediate Similarity	NPD5049	Phase 3
0.7438	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4477	Approved
0.7436	Intermediate Similarity	NPD4476	Approved
0.7434	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7685	Pre-registration
0.7412	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1933	Approved
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4340	Discontinued
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7389	Intermediate Similarity	NPD7266	Discontinued
0.7386	Intermediate Similarity	NPD4062	Phase 3
0.738	Intermediate Similarity	NPD7584	Approved
0.7371	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7095	Approved
0.7365	Intermediate Similarity	NPD1608	Approved
0.7365	Intermediate Similarity	NPD1481	Phase 2
0.7321	Intermediate Similarity	NPD6971	Discontinued
0.7318	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7314	Intermediate Similarity	NPD7240	Approved
0.7308	Intermediate Similarity	NPD4536	Approved
0.7308	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4538	Approved
0.7303	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7297	Intermediate Similarity	NPD1535	Discovery
0.7297	Intermediate Similarity	NPD1091	Approved
0.7296	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1247	Approved
0.7284	Intermediate Similarity	NPD7447	Phase 1
0.7267	Intermediate Similarity	NPD5058	Phase 3
0.7267	Intermediate Similarity	NPD8651	Approved
0.7267	Intermediate Similarity	NPD6666	Approved
0.7267	Intermediate Similarity	NPD6667	Approved
0.726	Intermediate Similarity	NPD9545	Approved
0.726	Intermediate Similarity	NPD1894	Discontinued
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7237	Intermediate Similarity	NPD2861	Phase 2
0.7225	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7783	Phase 2
0.7222	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD7213	Phase 3
0.7219	Intermediate Similarity	NPD7435	Discontinued
0.7212	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8150	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