NPASS Compound

Structure

NPC128348 OpenBabel07101719242D 22 23 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 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 0.0000 1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.12
Volume:	310.971
LogP:	2.66
LogD:	2.94
LogS:	-3.522
# Rotatable Bonds:	6
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	2.098
Fsp3:	0.235
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:	-4.695
MDCK Permeability:	1.7216609194292687e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.561
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.313

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.081
Plasma Protein Binding (PPB):	86.4817886352539%
Volume Distribution (VD):	0.595
Pgp-substrate:	8.35632038116455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.75
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	11.71
Half-life (T1/2):	0.914

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.191
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.33
Skin Sensitization:	0.583
Carcinogencity:	0.246
Eye Corrosion:	0.004
Eye Irritation:	0.649
Respiratory Toxicity:	0.29

Download Data

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

Natural Product: NPC128348

Natural Product ID:	NPC128348
*Common Name:**	4,4'-Dihydroxy-2,6-Dimethoxydihydrochalcone
IUPAC Name:	3-(4-hydroxy-2,6-dimethoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	WRSUVSOOJHAIRI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H18O5/c1-21-16-9-13(19)10-17(22-2)14(16)7-8-15(20)11-3-5-12(18)6-4-11/h3-6,9-10,18-19H,7-8H2,1-2H3
SMILES:	COc1cc(O)cc(c1CCC(=O)c1ccc(cc1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400283
PubChem CID:	10424988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003475] Retro-dihydrochalcones

*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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	Myanmar	n.a.	PMID[19689125]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20812	Soymida febrifuga	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	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	5
MIC	1
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	67200.0	nM	PMID[488089]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	69.7	uM	PMID[488089]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	42900.0	nM	PMID[488089]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	49000.0	nM	PMID[488089]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	211900.0	nM	PMID[488088]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40200.0	nM	PMID[488089]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	84400.0	nM	PMID[488089]

☑ 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 NPC128348 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	323
0.1-0.2	1566
0.2-0.3	4141
0.3-0.4	10905
0.4-0.5	7053
0.5-0.6	3700
0.6-0.7	6017
0.7-0.8	6310
0.8-0.85	1707
0.85-0.9	690
0.9-0.95	228
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC309717
1.0	High Similarity	NPC189106
1.0	High Similarity	NPC66384
1.0	High Similarity	NPC112192
1.0	High Similarity	NPC164236
0.9843	High Similarity	NPC27643
0.984	High Similarity	NPC247779
0.9766	High Similarity	NPC286336
0.9688	High Similarity	NPC337373
0.9688	High Similarity	NPC188646
0.9688	High Similarity	NPC242294
0.9688	High Similarity	NPC56031
0.9688	High Similarity	NPC159623
0.9688	High Similarity	NPC144051
0.9688	High Similarity	NPC139813
0.9688	High Similarity	NPC294593
0.9688	High Similarity	NPC28753
0.9688	High Similarity	NPC18877
0.9688	High Similarity	NPC312318
0.9688	High Similarity	NPC263670
0.9688	High Similarity	NPC472365
0.9688	High Similarity	NPC192304
0.9688	High Similarity	NPC20560
0.9688	High Similarity	NPC82225
0.9688	High Similarity	NPC175098
0.9688	High Similarity	NPC204960
0.9615	High Similarity	NPC1486
0.9615	High Similarity	NPC25287
0.9615	High Similarity	NPC186838
0.9615	High Similarity	NPC41461
0.9615	High Similarity	NPC477244
0.9615	High Similarity	NPC477242
0.9615	High Similarity	NPC168105
0.9615	High Similarity	NPC249606
0.9615	High Similarity	NPC150399
0.9615	High Similarity	NPC12165
0.9615	High Similarity	NPC477243
0.9615	High Similarity	NPC98115
0.9615	High Similarity	NPC274109
0.9615	High Similarity	NPC24394
0.9615	High Similarity	NPC66349
0.9609	High Similarity	NPC129132
0.9609	High Similarity	NPC257756
0.9609	High Similarity	NPC205468
0.9609	High Similarity	NPC87231
0.9609	High Similarity	NPC212631
0.9542	High Similarity	NPC317119
0.9542	High Similarity	NPC153979
0.9542	High Similarity	NPC23870
0.9542	High Similarity	NPC472419
0.9538	High Similarity	NPC156092
0.9538	High Similarity	NPC13575
0.9538	High Similarity	NPC131039
0.9531	High Similarity	NPC64359
0.9531	High Similarity	NPC186097
0.9531	High Similarity	NPC475009
0.9531	High Similarity	NPC308037
0.9531	High Similarity	NPC313618
0.9531	High Similarity	NPC262359
0.9531	High Similarity	NPC475008
0.947	High Similarity	NPC21350
0.947	High Similarity	NPC124269
0.947	High Similarity	NPC472368
0.9466	High Similarity	NPC476333
0.9466	High Similarity	NPC213603
0.9466	High Similarity	NPC473391
0.9466	High Similarity	NPC472367
0.9466	High Similarity	NPC472364
0.9462	High Similarity	NPC103842
0.9398	High Similarity	NPC470211
0.9398	High Similarity	NPC472366
0.9398	High Similarity	NPC477956
0.9394	High Similarity	NPC7013
0.9394	High Similarity	NPC303644
0.9394	High Similarity	NPC116632
0.9394	High Similarity	NPC181124
0.9394	High Similarity	NPC209560
0.9394	High Similarity	NPC294409
0.9394	High Similarity	NPC188879
0.9394	High Similarity	NPC162680
0.9328	High Similarity	NPC11056
0.9328	High Similarity	NPC213659
0.9328	High Similarity	NPC204985
0.9328	High Similarity	NPC215311
0.9328	High Similarity	NPC48624
0.9328	High Similarity	NPC172250
0.9328	High Similarity	NPC259166
0.9328	High Similarity	NPC144118
0.9328	High Similarity	NPC80962
0.9328	High Similarity	NPC326109
0.9328	High Similarity	NPC219917
0.9323	High Similarity	NPC12175
0.9323	High Similarity	NPC471620
0.9323	High Similarity	NPC55162
0.9323	High Similarity	NPC309154
0.9323	High Similarity	NPC243528
0.9323	High Similarity	NPC278323
0.9323	High Similarity	NPC279668
0.9323	High Similarity	NPC90665
0.9323	High Similarity	NPC251681
0.9318	High Similarity	NPC240593
0.9297	High Similarity	NPC211120
0.9259	High Similarity	NPC55832
0.9259	High Similarity	NPC268204
0.9259	High Similarity	NPC470087
0.9259	High Similarity	NPC470089
0.9259	High Similarity	NPC49108
0.9259	High Similarity	NPC110969
0.9259	High Similarity	NPC469404
0.9259	High Similarity	NPC26051
0.9259	High Similarity	NPC321980
0.9259	High Similarity	NPC52789
0.9254	High Similarity	NPC283429
0.9254	High Similarity	NPC109232
0.9254	High Similarity	NPC295384
0.9248	High Similarity	NPC250266
0.9248	High Similarity	NPC266597
0.9242	High Similarity	NPC234560
0.9242	High Similarity	NPC39426
0.9225	High Similarity	NPC469929
0.9219	High Similarity	NPC186098
0.9219	High Similarity	NPC80694
0.9191	High Similarity	NPC226636
0.9191	High Similarity	NPC11561
0.9185	High Similarity	NPC6407
0.9185	High Similarity	NPC253822
0.9185	High Similarity	NPC129853
0.9185	High Similarity	NPC110228
0.9185	High Similarity	NPC76445
0.9185	High Similarity	NPC265178
0.9185	High Similarity	NPC69769
0.9185	High Similarity	NPC241100
0.9185	High Similarity	NPC159275
0.9185	High Similarity	NPC188243
0.9185	High Similarity	NPC284550
0.9185	High Similarity	NPC172986
0.9185	High Similarity	NPC101366
0.9185	High Similarity	NPC261227
0.9185	High Similarity	NPC270883
0.9179	High Similarity	NPC99333
0.9179	High Similarity	NPC280284
0.9179	High Similarity	NPC188947
0.9173	High Similarity	NPC47815
0.9173	High Similarity	NPC13408
0.9173	High Similarity	NPC127447
0.9173	High Similarity	NPC29353
0.9173	High Similarity	NPC124784
0.9173	High Similarity	NPC87545
0.9173	High Similarity	NPC473887
0.9173	High Similarity	NPC235428
0.9173	High Similarity	NPC234133
0.9173	High Similarity	NPC194281
0.9173	High Similarity	NPC231772
0.9167	High Similarity	NPC164136
0.916	High Similarity	NPC215875
0.916	High Similarity	NPC15834
0.9147	High Similarity	NPC212379
0.9147	High Similarity	NPC69235
0.9141	High Similarity	NPC128428
0.9141	High Similarity	NPC305518
0.9124	High Similarity	NPC166138
0.9124	High Similarity	NPC68104
0.9124	High Similarity	NPC39329
0.9124	High Similarity	NPC169591
0.9124	High Similarity	NPC257097
0.9124	High Similarity	NPC18585
0.9124	High Similarity	NPC310130
0.9124	High Similarity	NPC117836
0.9124	High Similarity	NPC207732
0.9124	High Similarity	NPC164980
0.9124	High Similarity	NPC149026
0.9124	High Similarity	NPC106985
0.9124	High Similarity	NPC301751
0.9124	High Similarity	NPC143896
0.9124	High Similarity	NPC175504
0.9124	High Similarity	NPC245482
0.9124	High Similarity	NPC105213
0.9124	High Similarity	NPC51887
0.9124	High Similarity	NPC475705
0.9124	High Similarity	NPC91560
0.9124	High Similarity	NPC150408
0.9124	High Similarity	NPC476178
0.9124	High Similarity	NPC75049
0.9124	High Similarity	NPC221432
0.9118	High Similarity	NPC40118
0.9118	High Similarity	NPC147688
0.9118	High Similarity	NPC156590
0.9118	High Similarity	NPC64908
0.9118	High Similarity	NPC118840
0.9118	High Similarity	NPC26238
0.9118	High Similarity	NPC103362
0.9118	High Similarity	NPC3188
0.9118	High Similarity	NPC232021
0.9118	High Similarity	NPC205006
0.9118	High Similarity	NPC126534
0.9118	High Similarity	NPC282300
0.9111	High Similarity	NPC18260
0.9111	High Similarity	NPC78913
0.9111	High Similarity	NPC329203
0.9111	High Similarity	NPC150648

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 NPC128348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	967
0.2-0.3	1415
0.3-0.4	2550
0.4-0.5	1961
0.5-0.6	1263
0.6-0.7	484
0.7-0.8	168
0.8-0.85	32
0.85-0.9	3
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9531	High Similarity	NPD1240	Approved
0.9385	High Similarity	NPD1607	Approved
0.9242	High Similarity	NPD1510	Phase 2
0.9037	High Similarity	NPD1549	Phase 2
0.8963	High Similarity	NPD1552	Clinical (unspecified phase)
0.8963	High Similarity	NPD1550	Clinical (unspecified phase)
0.8921	High Similarity	NPD4378	Clinical (unspecified phase)
0.8786	High Similarity	NPD7410	Clinical (unspecified phase)
0.875	High Similarity	NPD2796	Approved
0.8647	High Similarity	NPD6859	Clinical (unspecified phase)
0.8633	High Similarity	NPD3750	Approved
0.8611	High Similarity	NPD4380	Phase 2
0.8582	High Similarity	NPD6799	Approved
0.8561	High Similarity	NPD7421	Clinical (unspecified phase)
0.8552	High Similarity	NPD7411	Suspended
0.8435	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD6651	Approved
0.8389	Intermediate Similarity	NPD7075	Discontinued
0.8378	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1934	Approved
0.8357	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD6599	Discontinued
0.8345	Intermediate Similarity	NPD2935	Discontinued
0.8322	Intermediate Similarity	NPD1511	Approved
0.8322	Intermediate Similarity	NPD3882	Suspended
0.8321	Intermediate Similarity	NPD3972	Approved
0.8311	Intermediate Similarity	NPD2801	Approved
0.8311	Intermediate Similarity	NPD7819	Suspended
0.8311	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD3748	Approved
0.8267	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD6801	Discontinued
0.8239	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD1551	Phase 2
0.8207	Intermediate Similarity	NPD1512	Approved
0.8116	Intermediate Similarity	NPD943	Approved
0.8112	Intermediate Similarity	NPD4628	Phase 3
0.8079	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7768	Phase 2
0.8077	Intermediate Similarity	NPD9545	Approved
0.8065	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD2800	Approved
0.8028	Intermediate Similarity	NPD2344	Approved
0.8027	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD1203	Approved
0.7971	Intermediate Similarity	NPD3268	Approved
0.797	Intermediate Similarity	NPD422	Phase 1
0.7958	Intermediate Similarity	NPD6099	Approved
0.7958	Intermediate Similarity	NPD6100	Approved
0.7956	Intermediate Similarity	NPD4908	Phase 1
0.7949	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD2798	Approved
0.7939	Intermediate Similarity	NPD1548	Phase 1
0.7935	Intermediate Similarity	NPD6232	Discontinued
0.7917	Intermediate Similarity	NPD1243	Approved
0.7917	Intermediate Similarity	NPD2654	Approved
0.7905	Intermediate Similarity	NPD5403	Approved
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD3817	Phase 2
0.7891	Intermediate Similarity	NPD2532	Approved
0.7891	Intermediate Similarity	NPD2533	Approved
0.7891	Intermediate Similarity	NPD2534	Approved
0.7887	Intermediate Similarity	NPD2799	Discontinued
0.7887	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6959	Discontinued
0.7868	Intermediate Similarity	NPD2797	Approved
0.7848	Intermediate Similarity	NPD3818	Discontinued
0.7842	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1610	Phase 2
0.7826	Intermediate Similarity	NPD6832	Phase 2
0.7812	Intermediate Similarity	NPD5953	Discontinued
0.7808	Intermediate Similarity	NPD2309	Approved
0.7801	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7286	Phase 2
0.7794	Intermediate Similarity	NPD1876	Approved
0.7786	Intermediate Similarity	NPD9493	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7778	Intermediate Similarity	NPD9717	Approved
0.777	Intermediate Similarity	NPD5401	Approved
0.7762	Intermediate Similarity	NPD4308	Phase 3
0.7755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7074	Phase 3
0.774	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3764	Approved
0.7704	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD1241	Discontinued
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7688	Intermediate Similarity	NPD7054	Approved
0.7682	Intermediate Similarity	NPD7458	Discontinued
0.7664	Intermediate Similarity	NPD3225	Approved
0.7651	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1608	Approved
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.764	Intermediate Similarity	NPD7472	Approved
0.7639	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD7003	Approved
0.7612	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3267	Approved
0.7609	Intermediate Similarity	NPD3266	Approved
0.7607	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1465	Phase 2
0.7593	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6797	Phase 2
0.7591	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1296	Phase 2
0.7589	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7390	Discontinued
0.7548	Intermediate Similarity	NPD5402	Approved
0.7548	Intermediate Similarity	NPD4288	Approved
0.7547	Intermediate Similarity	NPD3926	Phase 2
0.7546	Intermediate Similarity	NPD6559	Discontinued
0.7546	Intermediate Similarity	NPD7251	Discontinued
0.752	Intermediate Similarity	NPD846	Approved
0.752	Intermediate Similarity	NPD940	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7468	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6798	Discontinued
0.7451	Intermediate Similarity	NPD3226	Approved
0.745	Intermediate Similarity	NPD2354	Approved
0.7447	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7426	Intermediate Similarity	NPD17	Approved
0.7417	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD919	Approved
0.7397	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1481	Phase 2
0.7376	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3142	Approved
0.7361	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3140	Approved
0.7361	Intermediate Similarity	NPD1613	Approved
0.7357	Intermediate Similarity	NPD1164	Approved
0.7357	Intermediate Similarity	NPD1470	Approved
0.7353	Intermediate Similarity	NPD1651	Approved
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD5536	Phase 2
0.7333	Intermediate Similarity	NPD3887	Approved
0.7319	Intermediate Similarity	NPD1535	Discovery
0.7319	Intermediate Similarity	NPD1201	Approved
0.7317	Intermediate Similarity	NPD1729	Discontinued
0.7312	Intermediate Similarity	NPD1247	Approved
0.731	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD6355	Discontinued
0.7297	Intermediate Similarity	NPD2353	Approved
0.7297	Intermediate Similarity	NPD2346	Discontinued
0.7297	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1283	Approved
0.7279	Intermediate Similarity	NPD1894	Discontinued
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7266	Intermediate Similarity	NPD9269	Phase 2
0.7255	Intermediate Similarity	NPD5049	Phase 3
0.7254	Intermediate Similarity	NPD3018	Phase 2
0.7237	Intermediate Similarity	NPD4357	Discontinued
0.7233	Intermediate Similarity	NPD6971	Discontinued
0.723	Intermediate Similarity	NPD5406	Approved
0.723	Intermediate Similarity	NPD5408	Approved
0.723	Intermediate Similarity	NPD5405	Approved
0.723	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD6104	Discontinued
0.7226	Intermediate Similarity	NPD9268	Approved
0.7226	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD411	Approved
0.7222	Intermediate Similarity	NPD5242	Approved
0.7215	Intermediate Similarity	NPD2296	Approved
0.7214	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7199	Phase 2
0.7203	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD37	Approved
0.7197	Intermediate Similarity	NPD7577	Discontinued
0.7195	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD447	Suspended
0.7184	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1019	Discontinued
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7174	Intermediate Similarity	NPD4626	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD7440	Discontinued
0.7168	Intermediate Similarity	NPD4360	Phase 2
0.7168	Intermediate Similarity	NPD4363	Phase 3
0.716	Intermediate Similarity	NPD7229	Phase 3
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7126	Intermediate Similarity	NPD4362	Clinical (unspecified phase)

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