NPASS Compound

Structure

CID11056 OpenBabel06191715342D 26 27 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 -1.7321 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 5.1962 1.0000 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 2.5000 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 6.0622 2.5000 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 1.0000 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 4.3301 2.5000 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 3.4641 3.0000 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 -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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 26 1 0 0 0 0 5 21 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 20 2 0 0 0 0 14 22 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 19 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	374.882
LogP:	4.393
LogD:	3.645
LogS:	-3.956
# Rotatable Bonds:	6
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	2.771
Fsp3:	0.19
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:	-4.951
MDCK Permeability:	1.8278677089256234e-05
Pgp-inhibitor:	0.43
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.30521392822266%
Volume Distribution (VD):	0.48
Pgp-substrate:	0.6737911701202393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.778
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.82
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	3.949
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.393
AMES Toxicity:	0.497
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.942
Carcinogencity:	0.556
Eye Corrosion:	0.013
Eye Irritation:	0.94
Respiratory Toxicity:	0.505

Download Data

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

Natural Product: NPC11056

Natural Product ID:	NPC11056
*Common Name:**	Licochalcone G
IUPAC Name:	(E)-1-(2,4-dihydroxyphenyl)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]prop-2-en-1-one
Synonyms:	Licochalcone G
Standard InCHIKey:	UYRRMZSSCNIGNC-RMKNXTFCSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-5-21(2,3)16-10-13(20(26-4)12-19(16)25)6-9-17(23)15-8-7-14(22)11-18(15)24/h5-12,22,24-25H,1H2,2-4H3/b9-6+
SMILES:	C=CC(c1cc(/C=C/C(=O)c2ccc(cc2O)O)c(cc1O)OC)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644931
PubChem CID:	49856081
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
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]
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]
NPO1698	Glycyrrhiza inflata	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]
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
IC50	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT344	Individual Protein	Sialidase	Clostridium perfringens	IC50	=	0.84	ug.mL-1	PMID[489811]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	37.68	ug.mL-1	PMID[489811]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	41.53	ug.mL-1	PMID[489811]
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	=	42.11	ug.mL-1	PMID[489811]

☑ 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 NPC11056 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	1539
0.2-0.3	3497
0.3-0.4	9093
0.4-0.5	9509
0.5-0.6	3490
0.6-0.7	6085
0.7-0.8	5672
0.8-0.85	1996
0.85-0.9	1052
0.9-0.95	358
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9776	High Similarity	NPC23870
0.971	High Similarity	NPC476055
0.9704	High Similarity	NPC21350
0.9701	High Similarity	NPC66349
0.9701	High Similarity	NPC168105
0.9701	High Similarity	NPC41461
0.9701	High Similarity	NPC12165
0.9701	High Similarity	NPC477243
0.9701	High Similarity	NPC98115
0.9701	High Similarity	NPC249606
0.9701	High Similarity	NPC150399
0.9701	High Similarity	NPC186838
0.9701	High Similarity	NPC274109
0.9701	High Similarity	NPC477244
0.9701	High Similarity	NPC25287
0.9701	High Similarity	NPC1486
0.9701	High Similarity	NPC477242
0.9632	High Similarity	NPC477956
0.9632	High Similarity	NPC472366
0.963	High Similarity	NPC317119
0.963	High Similarity	NPC472419
0.963	High Similarity	NPC153979
0.9627	High Similarity	NPC13575
0.9627	High Similarity	NPC156092
0.9627	High Similarity	NPC131039
0.9562	High Similarity	NPC259166
0.9562	High Similarity	NPC219917
0.9562	High Similarity	NPC215311
0.9562	High Similarity	NPC213659
0.9562	High Similarity	NPC144118
0.9562	High Similarity	NPC204985
0.9562	High Similarity	NPC48624
0.9562	High Similarity	NPC326109
0.9562	High Similarity	NPC80962
0.9562	High Similarity	NPC172250
0.9556	High Similarity	NPC24394
0.9556	High Similarity	NPC213603
0.9552	High Similarity	NPC103842
0.9552	High Similarity	NPC286336
0.9496	High Similarity	NPC11700
0.9493	High Similarity	NPC26051
0.9493	High Similarity	NPC321980
0.9493	High Similarity	NPC55832
0.9493	High Similarity	NPC470089
0.9493	High Similarity	NPC268204
0.9493	High Similarity	NPC469404
0.9493	High Similarity	NPC52789
0.9493	High Similarity	NPC470087
0.9489	High Similarity	NPC283429
0.9489	High Similarity	NPC470211
0.9489	High Similarity	NPC295384
0.9478	High Similarity	NPC472365
0.9478	High Similarity	NPC188646
0.9478	High Similarity	NPC139813
0.9478	High Similarity	NPC242294
0.9478	High Similarity	NPC28753
0.9478	High Similarity	NPC192304
0.9478	High Similarity	NPC20560
0.9478	High Similarity	NPC82225
0.9478	High Similarity	NPC144051
0.9478	High Similarity	NPC27643
0.9478	High Similarity	NPC294593
0.9478	High Similarity	NPC159623
0.9478	High Similarity	NPC337373
0.9478	High Similarity	NPC312318
0.9478	High Similarity	NPC175098
0.9478	High Similarity	NPC263670
0.9478	High Similarity	NPC56031
0.9478	High Similarity	NPC204960
0.9478	High Similarity	NPC18877
0.9433	High Similarity	NPC300988
0.9433	High Similarity	NPC10990
0.9424	High Similarity	NPC297600
0.942	High Similarity	NPC253822
0.942	High Similarity	NPC101366
0.942	High Similarity	NPC265178
0.9416	High Similarity	NPC471620
0.9416	High Similarity	NPC251681
0.9416	High Similarity	NPC472368
0.9416	High Similarity	NPC243528
0.9412	High Similarity	NPC472367
0.9412	High Similarity	NPC473391
0.9412	High Similarity	NPC472364
0.9412	High Similarity	NPC476333
0.9403	High Similarity	NPC212631
0.9403	High Similarity	NPC205468
0.9403	High Similarity	NPC129132
0.9403	High Similarity	NPC257756
0.9403	High Similarity	NPC87231
0.9362	High Similarity	NPC25844
0.9362	High Similarity	NPC477955
0.9357	High Similarity	NPC106985
0.9357	High Similarity	NPC475705
0.9357	High Similarity	NPC476178
0.9357	High Similarity	NPC166138
0.9357	High Similarity	NPC301751
0.9357	High Similarity	NPC51887
0.9357	High Similarity	NPC18585
0.9357	High Similarity	NPC117836
0.9357	High Similarity	NPC245482
0.9353	High Similarity	NPC232021
0.9353	High Similarity	NPC49108
0.9353	High Similarity	NPC126534
0.9353	High Similarity	NPC40118
0.9353	High Similarity	NPC110969
0.9343	High Similarity	NPC116632
0.9343	High Similarity	NPC303644
0.9343	High Similarity	NPC7013
0.9343	High Similarity	NPC209560
0.9343	High Similarity	NPC294409
0.9343	High Similarity	NPC162680
0.9343	High Similarity	NPC181124
0.9328	High Similarity	NPC309717
0.9328	High Similarity	NPC128348
0.9328	High Similarity	NPC112192
0.9328	High Similarity	NPC313618
0.9328	High Similarity	NPC262359
0.9328	High Similarity	NPC66384
0.9328	High Similarity	NPC164236
0.9328	High Similarity	NPC475008
0.9328	High Similarity	NPC64359
0.9328	High Similarity	NPC186097
0.9328	High Similarity	NPC189106
0.9328	High Similarity	NPC308037
0.9328	High Similarity	NPC475009
0.9301	High Similarity	NPC471114
0.9291	High Similarity	NPC234629
0.9291	High Similarity	NPC328623
0.9291	High Similarity	NPC271288
0.9291	High Similarity	NPC311741
0.9286	High Similarity	NPC148545
0.9286	High Similarity	NPC11561
0.9286	High Similarity	NPC144499
0.9286	High Similarity	NPC226636
0.9281	High Similarity	NPC159275
0.9281	High Similarity	NPC241100
0.9281	High Similarity	NPC261227
0.9281	High Similarity	NPC172986
0.9281	High Similarity	NPC270883
0.9281	High Similarity	NPC69769
0.9275	High Similarity	NPC55162
0.9275	High Similarity	NPC278323
0.9275	High Similarity	NPC279668
0.9275	High Similarity	NPC124269
0.9275	High Similarity	NPC477055
0.9275	High Similarity	NPC90665
0.9275	High Similarity	NPC309154
0.9275	High Similarity	NPC12175
0.9275	High Similarity	NPC477056
0.9265	High Similarity	NPC164136
0.9259	High Similarity	NPC15834
0.9259	High Similarity	NPC215875
0.9236	High Similarity	NPC321896
0.9236	High Similarity	NPC188403
0.9236	High Similarity	NPC476185
0.9231	High Similarity	NPC39195
0.9231	High Similarity	NPC135325
0.9231	High Similarity	NPC152233
0.9225	High Similarity	NPC316769
0.922	High Similarity	NPC175504
0.922	High Similarity	NPC91560
0.922	High Similarity	NPC75049
0.922	High Similarity	NPC164980
0.922	High Similarity	NPC39329
0.922	High Similarity	NPC143896
0.922	High Similarity	NPC68104
0.922	High Similarity	NPC257097
0.922	High Similarity	NPC150408
0.922	High Similarity	NPC169591
0.922	High Similarity	NPC310130
0.922	High Similarity	NPC149026
0.922	High Similarity	NPC221432
0.9214	High Similarity	NPC64908
0.9214	High Similarity	NPC282300
0.9214	High Similarity	NPC147688
0.9214	High Similarity	NPC26238
0.9214	High Similarity	NPC103362
0.9214	High Similarity	NPC205006
0.9214	High Similarity	NPC156590
0.9214	High Similarity	NPC118840
0.9214	High Similarity	NPC3188
0.9209	High Similarity	NPC55018
0.9209	High Similarity	NPC18260
0.9209	High Similarity	NPC220062
0.9209	High Similarity	NPC301217
0.9209	High Similarity	NPC303633
0.9209	High Similarity	NPC53181
0.9209	High Similarity	NPC96565
0.9209	High Similarity	NPC217186
0.9209	High Similarity	NPC216978
0.9209	High Similarity	NPC109232
0.9209	High Similarity	NPC78913
0.9203	High Similarity	NPC322301
0.9203	High Similarity	NPC188879
0.9203	High Similarity	NPC255801
0.9197	High Similarity	NPC39426
0.9197	High Similarity	NPC234560
0.9191	High Similarity	NPC16197
0.9185	High Similarity	NPC27490
0.9179	High Similarity	NPC247779

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 NPC11056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	954
0.2-0.3	1450
0.3-0.4	2552
0.4-0.5	2002
0.5-0.6	1199
0.6-0.7	466
0.7-0.8	140
0.8-0.85	35
0.85-0.9	14
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9328	High Similarity	NPD1240	Approved
0.9197	High Similarity	NPD1510	Phase 2
0.9191	High Similarity	NPD1607	Approved
0.9155	High Similarity	NPD4378	Clinical (unspecified phase)
0.8889	High Similarity	NPD7410	Clinical (unspecified phase)
0.8865	High Similarity	NPD1549	Phase 2
0.8844	High Similarity	NPD4380	Phase 2
0.8794	High Similarity	NPD1552	Clinical (unspecified phase)
0.8794	High Similarity	NPD1550	Clinical (unspecified phase)
0.8777	High Similarity	NPD6651	Approved
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8723	High Similarity	NPD2796	Approved
0.8671	High Similarity	NPD2800	Approved
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8658	High Similarity	NPD7411	Suspended
0.8618	High Similarity	NPD7075	Discontinued
0.8592	High Similarity	NPD2935	Discontinued
0.8591	High Similarity	NPD6599	Discontinued
0.8543	High Similarity	NPD7096	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD6799	Approved
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8408	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD3750	Approved
0.8355	Intermediate Similarity	NPD1934	Approved
0.8355	Intermediate Similarity	NPD6801	Discontinued
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8311	Intermediate Similarity	NPD1511	Approved
0.8301	Intermediate Similarity	NPD2801	Approved
0.8288	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8264	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD2799	Discontinued
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD2533	Approved
0.8255	Intermediate Similarity	NPD2534	Approved
0.8255	Intermediate Similarity	NPD2532	Approved
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.82	Intermediate Similarity	NPD1512	Approved
0.8175	Intermediate Similarity	NPD3972	Approved
0.8163	Intermediate Similarity	NPD1243	Approved
0.8151	Intermediate Similarity	NPD2344	Approved
0.8141	Intermediate Similarity	NPD3749	Approved
0.8112	Intermediate Similarity	NPD943	Approved
0.8108	Intermediate Similarity	NPD4628	Phase 3
0.8099	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2798	Approved
0.8038	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD5953	Discontinued
0.8026	Intermediate Similarity	NPD920	Approved
0.8025	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD6099	Approved
0.7959	Intermediate Similarity	NPD6100	Approved
0.795	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6166	Phase 2
0.795	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7390	Discontinued
0.7939	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2309	Approved
0.7922	Intermediate Similarity	NPD7458	Discontinued
0.7914	Intermediate Similarity	NPD7286	Phase 2
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1203	Approved
0.7867	Intermediate Similarity	NPD7003	Approved
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2313	Discontinued
0.7806	Intermediate Similarity	NPD3226	Approved
0.78	Intermediate Similarity	NPD2654	Approved
0.7792	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7758	Intermediate Similarity	NPD7074	Phase 3
0.7754	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1164	Approved
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7697	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7664	Intermediate Similarity	NPD9493	Approved
0.7662	Intermediate Similarity	NPD5401	Approved
0.766	Intermediate Similarity	NPD9717	Approved
0.7651	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD919	Approved
0.7622	Intermediate Similarity	NPD1470	Approved
0.7607	Intermediate Similarity	NPD5710	Approved
0.7607	Intermediate Similarity	NPD5711	Approved
0.7605	Intermediate Similarity	NPD6797	Phase 2
0.7603	Intermediate Similarity	NPD3268	Approved
0.76	Intermediate Similarity	NPD5404	Approved
0.76	Intermediate Similarity	NPD5408	Approved
0.76	Intermediate Similarity	NPD5406	Approved
0.76	Intermediate Similarity	NPD5405	Approved
0.7589	Intermediate Similarity	NPD1201	Approved
0.7589	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1610	Phase 2
0.7562	Intermediate Similarity	NPD5402	Approved
0.756	Intermediate Similarity	NPD7251	Discontinued
0.7554	Intermediate Similarity	NPD9545	Approved
0.7552	Intermediate Similarity	NPD1876	Approved
0.7546	Intermediate Similarity	NPD1247	Approved
0.7533	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD2797	Approved
0.7486	Intermediate Similarity	NPD4363	Phase 3
0.7486	Intermediate Similarity	NPD4360	Phase 2
0.7483	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD422	Phase 1
0.745	Intermediate Similarity	NPD230	Phase 1
0.7443	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD4361	Phase 2
0.744	Intermediate Similarity	NPD1729	Discontinued
0.7436	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.7417	Intermediate Similarity	NPD7033	Discontinued
0.7417	Intermediate Similarity	NPD4308	Phase 3
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7413	Intermediate Similarity	NPD1608	Approved
0.7412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7376	Intermediate Similarity	NPD1651	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6104	Discontinued
0.7346	Intermediate Similarity	NPD4288	Approved
0.7346	Intermediate Similarity	NPD2296	Approved
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1471	Phase 3
0.731	Intermediate Similarity	NPD1283	Approved
0.7303	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3267	Approved
0.726	Intermediate Similarity	NPD3266	Approved
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD411	Approved
0.7241	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1933	Approved
0.7219	Intermediate Similarity	NPD447	Suspended
0.7203	Intermediate Similarity	NPD17	Approved
0.7203	Intermediate Similarity	NPD4626	Approved
0.7194	Intermediate Similarity	NPD1241	Discontinued
0.7192	Intermediate Similarity	NPD3225	Approved
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7178	Intermediate Similarity	NPD5761	Phase 2
0.7178	Intermediate Similarity	NPD5760	Phase 2
0.717	Intermediate Similarity	NPD6273	Approved
0.7163	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD9494	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD4307	Phase 2
0.7151	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7133	Intermediate Similarity	NPD1296	Phase 2
0.7123	Intermediate Similarity	NPD4749	Approved
0.7117	Intermediate Similarity	NPD37	Approved
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD1281	Approved
0.7101	Intermediate Similarity	NPD2403	Approved
0.7095	Intermediate Similarity	NPD1019	Discontinued
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6782	Approved
0.7088	Intermediate Similarity	NPD6779	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.708	Intermediate Similarity	NPD74	Approved
0.708	Intermediate Similarity	NPD9266	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7063	Intermediate Similarity	NPD5049	Phase 3
0.7055	Intermediate Similarity	NPD5889	Approved
0.7055	Intermediate Similarity	NPD5890	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