NPASS Compound

Structure

CID14875 OpenBabel06191715342D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 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 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 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 1.8171 -0.1910 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 6.1472 1.3090 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 7.8793 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 5.2812 1.8090 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 3 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 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 25 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 23 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	3.527
LogD:	2.878
LogS:	-4.011
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	3.15
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:	-4.626
MDCK Permeability:	1.2478703865781426e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	97.3704605102539%
Volume Distribution (VD):	0.522
Pgp-substrate:	0.8468813896179199%

ADMET: Metabolism

CYP1A2-inhibitor:	0.933
CYP1A2-substrate:	0.467
CYP2C19-inhibitor:	0.875
CYP2C19-substrate:	0.211
CYP2C9-inhibitor:	0.834
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.776
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.487
CYP3A4-substrate:	0.332

ADMET: Excretion

Clearance (CL):	10.288
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.412
Carcinogencity:	0.788
Eye Corrosion:	0.003
Eye Irritation:	0.625
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC14875

Natural Product ID:	NPC14875
*Common Name:**	Licoagrochalcone D
IUPAC Name:	(E)-1-(4-hydroxyphenyl)-3-[2-(2-hydroxypropan-2-yl)-4-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-one
Synonyms:
Standard InCHIKey:	FMKHMNBODOXQLQ-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-21(2,24)19-12-16-18(26-19)11-7-14(20(16)25-3)6-10-17(23)13-4-8-15(22)9-5-13/h4-11,19,22,24H,12H2,1-3H3/b10-6+
SMILES:	CC(C)(C1Cc2c(ccc(/C=C/C(=O)c3ccc(cc3)O)c2OC)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437371
PubChem CID:	5318991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003542] Furanochalcones

*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]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[18181575]
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.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	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]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO26770	Pteris multifida	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26770	Pteris multifida	Species	Pteridaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	50.0	%	PMID[460974]

☑ 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 NPC14875 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	356
0.1-0.2	1332
0.2-0.3	3343
0.3-0.4	8391
0.4-0.5	10128
0.5-0.6	3592
0.6-0.7	5047
0.7-0.8	6468
0.8-0.85	2596
0.85-0.9	1116
0.9-0.95	311
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC472421
0.9722	High Similarity	NPC472423
0.9722	High Similarity	NPC474744
0.9722	High Similarity	NPC474772
0.9655	High Similarity	NPC327269
0.9655	High Similarity	NPC31627
0.9655	High Similarity	NPC473996
0.9655	High Similarity	NPC476238
0.9586	High Similarity	NPC472580
0.9586	High Similarity	NPC471675
0.9586	High Similarity	NPC472636
0.9521	High Similarity	NPC477957
0.9521	High Similarity	NPC285623
0.9452	High Similarity	NPC471676
0.9452	High Similarity	NPC472422
0.9452	High Similarity	NPC472420
0.9452	High Similarity	NPC244577
0.9452	High Similarity	NPC263384
0.9379	High Similarity	NPC168085
0.9375	High Similarity	NPC316769
0.9324	High Similarity	NPC7989
0.9324	High Similarity	NPC472583
0.9324	High Similarity	NPC223701
0.932	High Similarity	NPC471677
0.9315	High Similarity	NPC317492
0.931	High Similarity	NPC202494
0.9272	High Similarity	NPC328102
0.9262	High Similarity	NPC477958
0.9262	High Similarity	NPC108937
0.9262	High Similarity	NPC470681
0.9262	High Similarity	NPC279218
0.9257	High Similarity	NPC475790
0.9257	High Similarity	NPC171651
0.9257	High Similarity	NPC35567
0.9257	High Similarity	NPC243171
0.9231	High Similarity	NPC74397
0.9231	High Similarity	NPC171870
0.9211	High Similarity	NPC92589
0.92	High Similarity	NPC78554
0.92	High Similarity	NPC475797
0.92	High Similarity	NPC109967
0.92	High Similarity	NPC469936
0.92	High Similarity	NPC321372
0.92	High Similarity	NPC474738
0.92	High Similarity	NPC474609
0.92	High Similarity	NPC129053
0.9195	High Similarity	NPC469405
0.9195	High Similarity	NPC293286
0.9189	High Similarity	NPC262038
0.9189	High Similarity	NPC319910
0.9189	High Similarity	NPC254412
0.9189	High Similarity	NPC474021
0.9189	High Similarity	NPC278476
0.9189	High Similarity	NPC474023
0.9189	High Similarity	NPC262039
0.9184	High Similarity	NPC472628
0.9184	High Similarity	NPC89442
0.9178	High Similarity	NPC91902
0.9178	High Similarity	NPC470670
0.9178	High Similarity	NPC51070
0.9178	High Similarity	NPC473133
0.9178	High Similarity	NPC472627
0.9178	High Similarity	NPC222298
0.9178	High Similarity	NPC47388
0.9172	High Similarity	NPC470857
0.9172	High Similarity	NPC297788
0.9172	High Similarity	NPC209040
0.9167	High Similarity	NPC130206
0.9145	High Similarity	NPC304839
0.9145	High Similarity	NPC472624
0.9145	High Similarity	NPC220582
0.9133	High Similarity	NPC48579
0.9133	High Similarity	NPC259710
0.9133	High Similarity	NPC217706
0.9133	High Similarity	NPC207809
0.9133	High Similarity	NPC304207
0.9128	High Similarity	NPC217149
0.9128	High Similarity	NPC216035
0.9128	High Similarity	NPC210597
0.9128	High Similarity	NPC161881
0.9128	High Similarity	NPC244583
0.9128	High Similarity	NPC10807
0.9128	High Similarity	NPC138288
0.9128	High Similarity	NPC56232
0.9128	High Similarity	NPC150123
0.9122	High Similarity	NPC105136
0.9122	High Similarity	NPC321896
0.9122	High Similarity	NPC476509
0.9122	High Similarity	NPC61258
0.9122	High Similarity	NPC476185
0.911	High Similarity	NPC472629
0.9103	High Similarity	NPC310130
0.9103	High Similarity	NPC166138
0.9103	High Similarity	NPC39329
0.9103	High Similarity	NPC169591
0.9103	High Similarity	NPC68104
0.9103	High Similarity	NPC214166
0.9103	High Similarity	NPC221432
0.9103	High Similarity	NPC18585
0.9103	High Similarity	NPC257097
0.9103	High Similarity	NPC478086
0.9103	High Similarity	NPC75049
0.9103	High Similarity	NPC164980
0.9103	High Similarity	NPC149026
0.9103	High Similarity	NPC175504
0.9103	High Similarity	NPC143896
0.9103	High Similarity	NPC106985
0.9103	High Similarity	NPC91560
0.9103	High Similarity	NPC316816
0.9103	High Similarity	NPC150408
0.9097	High Similarity	NPC470089
0.9097	High Similarity	NPC470087
0.9097	High Similarity	NPC321980
0.9091	High Similarity	NPC471286
0.9091	High Similarity	NPC472582
0.9091	High Similarity	NPC137009
0.9091	High Similarity	NPC472581
0.9091	High Similarity	NPC124038
0.9085	High Similarity	NPC45124
0.9085	High Similarity	NPC74854
0.9085	High Similarity	NPC30655
0.9073	High Similarity	NPC20530
0.9073	High Similarity	NPC208152
0.9073	High Similarity	NPC215917
0.9073	High Similarity	NPC78492
0.9073	High Similarity	NPC10754
0.9071	High Similarity	NPC27643
0.9067	High Similarity	NPC209760
0.9067	High Similarity	NPC311579
0.9067	High Similarity	NPC236756
0.9067	High Similarity	NPC100134
0.9067	High Similarity	NPC248793
0.9067	High Similarity	NPC180301
0.906	High Similarity	NPC209846
0.906	High Similarity	NPC477897
0.906	High Similarity	NPC328740
0.906	High Similarity	NPC289774
0.906	High Similarity	NPC318424
0.906	High Similarity	NPC471229
0.9054	High Similarity	NPC5173
0.9054	High Similarity	NPC37226
0.9054	High Similarity	NPC296030
0.9054	High Similarity	NPC39929
0.9054	High Similarity	NPC226644
0.9048	High Similarity	NPC201731
0.9048	High Similarity	NPC79469
0.9048	High Similarity	NPC104406
0.9048	High Similarity	NPC237635
0.9048	High Similarity	NPC12148
0.9048	High Similarity	NPC473077
0.9048	High Similarity	NPC110303
0.9048	High Similarity	NPC130581
0.9048	High Similarity	NPC97716
0.9048	High Similarity	NPC85773
0.9048	High Similarity	NPC23728
0.9048	High Similarity	NPC296998
0.9048	High Similarity	NPC472918
0.9048	High Similarity	NPC24673
0.9041	High Similarity	NPC311741
0.9041	High Similarity	NPC131568
0.9041	High Similarity	NPC470890
0.9041	High Similarity	NPC224714
0.9041	High Similarity	NPC124780
0.9041	High Similarity	NPC473015
0.9041	High Similarity	NPC234629
0.9041	High Similarity	NPC473013
0.9041	High Similarity	NPC197252
0.9041	High Similarity	NPC131579
0.9041	High Similarity	NPC87486
0.9041	High Similarity	NPC236766
0.9034	High Similarity	NPC40833
0.9034	High Similarity	NPC125855
0.9034	High Similarity	NPC166934
0.9034	High Similarity	NPC324134
0.9034	High Similarity	NPC148757
0.9034	High Similarity	NPC161506
0.9034	High Similarity	NPC328164
0.9034	High Similarity	NPC78
0.9034	High Similarity	NPC37496
0.9034	High Similarity	NPC76338
0.9034	High Similarity	NPC167624
0.9034	High Similarity	NPC107572
0.9034	High Similarity	NPC177354
0.9034	High Similarity	NPC1089
0.9034	High Similarity	NPC265040
0.9034	High Similarity	NPC220998
0.9034	High Similarity	NPC76372
0.9034	High Similarity	NPC11561
0.9034	High Similarity	NPC227579
0.9034	High Similarity	NPC166482
0.9034	High Similarity	NPC194432
0.9034	High Similarity	NPC324436
0.9034	High Similarity	NPC32739
0.9034	High Similarity	NPC147145
0.9034	High Similarity	NPC144499
0.9034	High Similarity	NPC226636
0.9034	High Similarity	NPC223500
0.9034	High Similarity	NPC296917
0.9034	High Similarity	NPC10937
0.9034	High Similarity	NPC66515

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 NPC14875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	839
0.2-0.3	1576
0.3-0.4	2517
0.4-0.5	1981
0.5-0.6	1133
0.6-0.7	556
0.7-0.8	184
0.8-0.85	32
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD4380	Phase 2
0.894	High Similarity	NPD2393	Clinical (unspecified phase)
0.8912	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD7075	Discontinued
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8759	High Similarity	NPD1549	Phase 2
0.875	High Similarity	NPD1934	Approved
0.8701	High Similarity	NPD3882	Suspended
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.8658	High Similarity	NPD7410	Clinical (unspecified phase)
0.8645	High Similarity	NPD4381	Clinical (unspecified phase)
0.8627	High Similarity	NPD6801	Discontinued
0.8621	High Similarity	NPD2796	Approved
0.8591	High Similarity	NPD6799	Approved
0.8552	High Similarity	NPD1510	Phase 2
0.8531	High Similarity	NPD1240	Approved
0.8516	High Similarity	NPD8443	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD2801	Approved
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7411	Suspended
0.8418	Intermediate Similarity	NPD5494	Approved
0.8414	Intermediate Similarity	NPD1607	Approved
0.8395	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD4628	Phase 3
0.8377	Intermediate Similarity	NPD6599	Discontinued
0.8354	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8322	Intermediate Similarity	NPD2800	Approved
0.8267	Intermediate Similarity	NPD3750	Approved
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1512	Approved
0.8182	Intermediate Similarity	NPD920	Approved
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8137	Intermediate Similarity	NPD6959	Discontinued
0.8121	Intermediate Similarity	NPD7074	Phase 3
0.8113	Intermediate Similarity	NPD7768	Phase 2
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1243	Approved
0.8065	Intermediate Similarity	NPD5403	Approved
0.8063	Intermediate Similarity	NPD3749	Approved
0.8061	Intermediate Similarity	NPD7054	Approved
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7964	Intermediate Similarity	NPD6797	Phase 2
0.7964	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD2344	Approved
0.7937	Intermediate Similarity	NPD5402	Approved
0.7935	Intermediate Similarity	NPD5401	Approved
0.7933	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD7251	Discontinued
0.7914	Intermediate Similarity	NPD1247	Approved
0.7901	Intermediate Similarity	NPD919	Approved
0.7895	Intermediate Similarity	NPD2424	Discontinued
0.7891	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7808	Phase 3
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD7286	Phase 2
0.7834	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7763	Intermediate Similarity	NPD6100	Approved
0.7763	Intermediate Similarity	NPD6099	Approved
0.7755	Intermediate Similarity	NPD4908	Phase 1
0.7742	Intermediate Similarity	NPD2309	Approved
0.7733	Intermediate Similarity	NPD6355	Discontinued
0.7733	Intermediate Similarity	NPD230	Phase 1
0.7712	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7703	Intermediate Similarity	NPD3027	Phase 3
0.7697	Intermediate Similarity	NPD7033	Discontinued
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD943	Approved
0.7651	Intermediate Similarity	NPD6798	Discontinued
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.764	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1610	Phase 2
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7616	Intermediate Similarity	NPD5124	Phase 1
0.7616	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.759	Intermediate Similarity	NPD7199	Phase 2
0.7586	Intermediate Similarity	NPD8434	Phase 2
0.7582	Intermediate Similarity	NPD4308	Phase 3
0.7576	Intermediate Similarity	NPD6234	Discontinued
0.7568	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1203	Approved
0.7547	Intermediate Similarity	NPD5049	Phase 3
0.7545	Intermediate Similarity	NPD7229	Phase 3
0.7544	Intermediate Similarity	NPD3823	Discontinued
0.7542	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD3268	Approved
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2354	Approved
0.7516	Intermediate Similarity	NPD3887	Approved
0.7516	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.7485	Intermediate Similarity	NPD37	Approved
0.7484	Intermediate Similarity	NPD6005	Phase 3
0.7484	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6002	Phase 3
0.7484	Intermediate Similarity	NPD6004	Phase 3
0.7483	Intermediate Similarity	NPD9545	Approved
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4625	Phase 3
0.7466	Intermediate Similarity	NPD3972	Approved
0.7459	Intermediate Similarity	NPD7584	Approved
0.7456	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4965	Approved
0.744	Intermediate Similarity	NPD5710	Approved
0.744	Intermediate Similarity	NPD5711	Approved
0.7439	Intermediate Similarity	NPD8455	Phase 2
0.7434	Intermediate Similarity	NPD4060	Phase 1
0.7432	Intermediate Similarity	NPD2797	Approved
0.743	Intermediate Similarity	NPD4360	Phase 2
0.743	Intermediate Similarity	NPD4363	Phase 3
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD1652	Phase 2
0.7389	Intermediate Similarity	NPD2654	Approved
0.7389	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4361	Phase 2
0.7376	Intermediate Similarity	NPD1241	Discontinued
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD2403	Approved
0.7347	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD9717	Approved
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD9494	Approved
0.7333	Intermediate Similarity	NPD5761	Phase 2
0.7333	Intermediate Similarity	NPD5760	Phase 2
0.7326	Intermediate Similarity	NPD7585	Approved
0.732	Intermediate Similarity	NPD4307	Phase 2
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4288	Approved
0.7273	Intermediate Similarity	NPD7583	Approved
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.7267	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2353	Approved
0.7255	Intermediate Similarity	NPD4062	Phase 3
0.725	Intermediate Similarity	NPD5058	Phase 3
0.7248	Intermediate Similarity	NPD3225	Approved
0.7248	Intermediate Similarity	NPD1876	Approved
0.7244	Intermediate Similarity	NPD5588	Approved
0.7239	Intermediate Similarity	NPD1653	Approved
0.7233	Intermediate Similarity	NPD7003	Approved
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	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