NPASS Compound

Structure

NPC156818 OpenBabel07101718232D 31 34 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 1.7321 1.0000 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 -0.5000 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 -0.8660 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 0.8660 2.5000 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 6.0622 -0.5000 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 1.7321 0.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 C 0 0 2 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 0.8660 -4.5000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 10 2 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 2 0 0 0 0 4 12 1 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 18 2 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 0 0 0 0 19 31 1 1 0 0 0 20 28 1 0 0 0 0 21 10 1 1 0 0 0 21 30 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.1
Volume:	407.59
LogP:	2.859
LogD:	1.776
LogS:	-4.005
# Rotatable Bonds:	4
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	3.49
Fsp3:	0.136
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.332
MDCK Permeability:	5.245364718575729e-06
Pgp-inhibitor:	0.018
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.278
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	96.43289184570312%
Volume Distribution (VD):	0.461
Pgp-substrate:	3.1785216331481934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.488
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.731
CYP2D6-inhibitor:	0.306
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.124

ADMET: Excretion

Clearance (CL):	14.356
Half-life (T1/2):	0.926

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.952
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.923
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC156818

Natural Product ID:	NPC156818
*Common Name:**	(-)-Epiafzelechin Gallate
IUPAC Name:	[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:	(-)-Epiafzelechin Gallate
Standard InCHIKey:	SDZPYNMXGUHFMZ-TZIWHRDSSA-N
Standard InCHI:	InChI=1S/C22H18O9/c23-12-3-1-10(2-4-12)21-19(9-14-15(25)7-13(24)8-18(14)30-21)31-22(29)11-5-16(26)20(28)17(27)6-11/h1-8,19,21,23-28H,9H2/t19-,21-/m1/s1
SMILES:	c1cc(ccc1[C@@H]1[C@@H](Cc2c(cc(cc2O1)O)O)OC(=O)c1cc(c(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL159706
PubChem CID:	467295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003012] Flavan-3-ols

*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
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.foodchem.2013.08.121]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[16180814]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	seeds	Shizuoka prefecture, Japan	n.a.	PMID[16499314]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21434603]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	flower	n.a.	PMID[21922925]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[21925888]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22377672]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265489]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaves	Bandung, West Java, Indonesia		PMID[23621359]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8258	Camellia sinensis	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8258	Camellia sinensis	Species	Theaceae	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
NPO8258	NPC156818	Tea Or Coffee	Leaf	3.7	3.7	3.7	mg/100g	Database [DUKE]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	50.0	ug.mL-1	PMID[458849]
NPT2	Others	Unspecified		IC50	=	44300.0	nM	PMID[458850]
NPT1	Others	Radical scavenging activity		IC50	=	2800.0	nM	PMID[458850]

☑ 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 NPC156818 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	386
0.1-0.2	1654
0.2-0.3	4135
0.3-0.4	9104
0.4-0.5	8787
0.5-0.6	3406
0.6-0.7	4850
0.7-0.8	6283
0.8-0.85	2926
0.85-0.9	1067
0.9-0.95	77
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC289322
1.0	High Similarity	NPC68324
1.0	High Similarity	NPC160512
1.0	High Similarity	NPC38779
1.0	High Similarity	NPC114179
0.9933	High Similarity	NPC250436
0.9933	High Similarity	NPC300845
0.9933	High Similarity	NPC291948
0.9933	High Similarity	NPC88803
0.9933	High Similarity	NPC104983
0.9868	High Similarity	NPC24164
0.9868	High Similarity	NPC53889
0.9801	High Similarity	NPC87317
0.98	High Similarity	NPC318432
0.9732	High Similarity	NPC474656
0.949	High Similarity	NPC473818
0.9487	High Similarity	NPC142614
0.9363	High Similarity	NPC471788
0.9359	High Similarity	NPC476372
0.9359	High Similarity	NPC476371
0.9355	High Similarity	NPC289346
0.9313	High Similarity	NPC81332
0.9313	High Similarity	NPC212038
0.9313	High Similarity	NPC271848
0.9313	High Similarity	NPC262580
0.9313	High Similarity	NPC289396
0.9299	High Similarity	NPC121290
0.9276	High Similarity	NPC75695
0.9262	High Similarity	NPC268515
0.9262	High Similarity	NPC40222
0.9255	High Similarity	NPC98583
0.925	High Similarity	NPC476365
0.925	High Similarity	NPC149011
0.925	High Similarity	NPC204937
0.9236	High Similarity	NPC33298
0.9236	High Similarity	NPC285108
0.9236	High Similarity	NPC4013
0.9236	High Similarity	NPC90905
0.9231	High Similarity	NPC476373
0.9231	High Similarity	NPC24627
0.9205	High Similarity	NPC107636
0.9193	High Similarity	NPC67134
0.9193	High Similarity	NPC100251
0.9193	High Similarity	NPC65333
0.9193	High Similarity	NPC47140
0.9182	High Similarity	NPC207575
0.9182	High Similarity	NPC13481
0.9172	High Similarity	NPC142252
0.9172	High Similarity	NPC158188
0.9172	High Similarity	NPC112418
0.9161	High Similarity	NPC165483
0.9145	High Similarity	NPC473091
0.9141	High Similarity	NPC67629
0.9141	High Similarity	NPC79736
0.9139	High Similarity	NPC142528
0.9136	High Similarity	NPC88560
0.9136	High Similarity	NPC175230
0.9136	High Similarity	NPC172033
0.9133	High Similarity	NPC262282
0.913	High Similarity	NPC180768
0.9125	High Similarity	NPC243877
0.9125	High Similarity	NPC14662
0.9125	High Similarity	NPC260266
0.9114	High Similarity	NPC471745
0.9114	High Similarity	NPC476247
0.9114	High Similarity	NPC219927
0.9114	High Similarity	NPC477841
0.9108	High Similarity	NPC203020
0.9108	High Similarity	NPC471744
0.9108	High Similarity	NPC239966
0.9097	High Similarity	NPC203757
0.9097	High Similarity	NPC222185
0.9085	High Similarity	NPC476620
0.9085	High Similarity	NPC476618
0.9085	High Similarity	NPC476621
0.9085	High Similarity	NPC476622
0.9085	High Similarity	NPC476623
0.9085	High Similarity	NPC476619
0.9085	High Similarity	NPC267549
0.9079	High Similarity	NPC476394
0.9079	High Similarity	NPC98809
0.9074	High Similarity	NPC476370
0.9057	High Similarity	NPC67959
0.9051	High Similarity	NPC66618
0.9051	High Similarity	NPC288131
0.9051	High Similarity	NPC165970
0.9051	High Similarity	NPC305987
0.9051	High Similarity	NPC113163
0.9051	High Similarity	NPC84324
0.9045	High Similarity	NPC94220
0.9045	High Similarity	NPC37502
0.9045	High Similarity	NPC287872
0.9045	High Similarity	NPC284127
0.9045	High Similarity	NPC98083
0.9045	High Similarity	NPC117418
0.9045	High Similarity	NPC7543
0.9045	High Similarity	NPC24339
0.9045	High Similarity	NPC74319
0.9045	High Similarity	NPC476410
0.9045	High Similarity	NPC53545
0.9045	High Similarity	NPC166456
0.9045	High Similarity	NPC289811
0.9045	High Similarity	NPC172202
0.9045	High Similarity	NPC267627
0.9045	High Similarity	NPC40702
0.9045	High Similarity	NPC160780
0.9032	High Similarity	NPC18727
0.9032	High Similarity	NPC469888
0.9024	High Similarity	NPC472991
0.9024	High Similarity	NPC61904
0.9024	High Similarity	NPC144097
0.9024	High Similarity	NPC472992
0.9024	High Similarity	NPC297574
0.902	High Similarity	NPC183959
0.902	High Similarity	NPC1612
0.9018	High Similarity	NPC476374
0.9018	High Similarity	NPC472993
0.9013	High Similarity	NPC472969
0.9006	High Similarity	NPC45400
0.9006	High Similarity	NPC116745
0.9	High Similarity	NPC7154
0.9	High Similarity	NPC477840
0.9	High Similarity	NPC22176
0.9	High Similarity	NPC226738
0.9	High Similarity	NPC36916
0.9	High Similarity	NPC72787
0.9	High Similarity	NPC58223
0.9	High Similarity	NPC190587
0.9	High Similarity	NPC125039
0.9	High Similarity	NPC165720
0.9	High Similarity	NPC7688
0.9	High Similarity	NPC36
0.9	High Similarity	NPC121573
0.8987	High Similarity	NPC101731
0.8981	High Similarity	NPC247713
0.8981	High Similarity	NPC63454
0.8981	High Similarity	NPC133984
0.8981	High Similarity	NPC129684
0.8981	High Similarity	NPC472860
0.8981	High Similarity	NPC474836
0.8981	High Similarity	NPC210084
0.8981	High Similarity	NPC474208
0.8981	High Similarity	NPC108456
0.8981	High Similarity	NPC222689
0.8981	High Similarity	NPC475267
0.8981	High Similarity	NPC299520
0.8981	High Similarity	NPC156057
0.8981	High Similarity	NPC291508
0.8981	High Similarity	NPC162869
0.8981	High Similarity	NPC183851
0.8981	High Similarity	NPC99597
0.8981	High Similarity	NPC35598
0.8981	High Similarity	NPC1913
0.8981	High Similarity	NPC48208
0.8976	High Similarity	NPC8940
0.8976	High Similarity	NPC53680
0.8976	High Similarity	NPC208797
0.8974	High Similarity	NPC145425
0.897	High Similarity	NPC253521
0.897	High Similarity	NPC113836
0.897	High Similarity	NPC472387
0.897	High Similarity	NPC37668
0.897	High Similarity	NPC35167
0.8968	High Similarity	NPC257648
0.8968	High Similarity	NPC302950
0.8968	High Similarity	NPC219582
0.8968	High Similarity	NPC236637
0.8968	High Similarity	NPC477231
0.8963	High Similarity	NPC34267
0.8963	High Similarity	NPC223426
0.8963	High Similarity	NPC81042
0.8963	High Similarity	NPC214621
0.8961	High Similarity	NPC243891
0.8954	High Similarity	NPC321011
0.8954	High Similarity	NPC188679
0.8954	High Similarity	NPC294852
0.8951	High Similarity	NPC476279
0.8951	High Similarity	NPC95421
0.8951	High Similarity	NPC658
0.8951	High Similarity	NPC198125
0.8951	High Similarity	NPC197708
0.8951	High Similarity	NPC280493
0.8951	High Similarity	NPC229687
0.8944	High Similarity	NPC224851
0.8944	High Similarity	NPC171985
0.8944	High Similarity	NPC320741
0.8944	High Similarity	NPC471823
0.8944	High Similarity	NPC43065
0.8938	High Similarity	NPC168822
0.8938	High Similarity	NPC29830
0.8938	High Similarity	NPC45943
0.8938	High Similarity	NPC88043
0.8931	High Similarity	NPC155754
0.8931	High Similarity	NPC228383
0.8931	High Similarity	NPC311803
0.8931	High Similarity	NPC109061
0.8931	High Similarity	NPC124747
0.8931	High Similarity	NPC469889
0.8931	High Similarity	NPC25389
0.8931	High Similarity	NPC134783

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 NPC156818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	911
0.2-0.3	1781
0.3-0.4	2552
0.4-0.5	1803
0.5-0.6	1030
0.6-0.7	511
0.7-0.8	140
0.8-0.85	45
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9933	High Similarity	NPD4868	Clinical (unspecified phase)
0.9193	High Similarity	NPD7993	Clinical (unspecified phase)
0.9	High Similarity	NPD6166	Phase 2
0.9	High Similarity	NPD6168	Clinical (unspecified phase)
0.9	High Similarity	NPD6167	Clinical (unspecified phase)
0.8968	High Similarity	NPD1934	Approved
0.891	High Similarity	NPD1465	Phase 2
0.891	High Similarity	NPD2393	Clinical (unspecified phase)
0.8834	High Similarity	NPD5844	Phase 1
0.8773	High Similarity	NPD3818	Discontinued
0.8735	High Similarity	NPD4338	Clinical (unspecified phase)
0.8671	High Similarity	NPD2801	Approved
0.8667	High Similarity	NPD7074	Phase 3
0.8625	High Similarity	NPD4381	Clinical (unspecified phase)
0.8625	High Similarity	NPD7075	Discontinued
0.8616	High Similarity	NPD3817	Phase 2
0.8606	High Similarity	NPD7054	Approved
0.8599	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD1511	Approved
0.8562	High Similarity	NPD3882	Suspended
0.8554	High Similarity	NPD7472	Approved
0.8544	High Similarity	NPD7411	Suspended
0.8528	High Similarity	NPD6232	Discontinued
0.8503	High Similarity	NPD6797	Phase 2
0.8462	Intermediate Similarity	NPD1512	Approved
0.8452	Intermediate Similarity	NPD7251	Discontinued
0.8438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5402	Approved
0.8373	Intermediate Similarity	NPD7473	Discontinued
0.8366	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD230	Phase 1
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD6190	Approved
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7808	Phase 3
0.8293	Intermediate Similarity	NPD5494	Approved
0.8291	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1613	Approved
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD6799	Approved
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5403	Approved
0.8171	Intermediate Similarity	NPD3749	Approved
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD4628	Phase 3
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD7199	Phase 2
0.8129	Intermediate Similarity	NPD6559	Discontinued
0.8125	Intermediate Similarity	NPD1653	Approved
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6234	Discontinued
0.811	Intermediate Similarity	NPD7768	Phase 2
0.8059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1510	Phase 2
0.805	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD5401	Approved
0.8046	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7228	Approved
0.7987	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3748	Approved
0.7927	Intermediate Similarity	NPD37	Approved
0.7919	Intermediate Similarity	NPD7685	Pre-registration
0.791	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD943	Approved
0.7892	Intermediate Similarity	NPD4966	Approved
0.7892	Intermediate Similarity	NPD4965	Approved
0.7892	Intermediate Similarity	NPD4967	Phase 2
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7853	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8312	Approved
0.7829	Intermediate Similarity	NPD3027	Phase 3
0.7829	Intermediate Similarity	NPD8313	Approved
0.7792	Intermediate Similarity	NPD1240	Approved
0.7791	Intermediate Similarity	NPD3751	Discontinued
0.7785	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6798	Discontinued
0.7771	Intermediate Similarity	NPD8455	Phase 2
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7763	Intermediate Similarity	NPD4908	Phase 1
0.7742	Intermediate Similarity	NPD447	Suspended
0.7722	Intermediate Similarity	NPD7266	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7718	Intermediate Similarity	NPD9269	Phase 2
0.7716	Intermediate Similarity	NPD2534	Approved
0.7716	Intermediate Similarity	NPD2533	Approved
0.7716	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7636	Intermediate Similarity	NPD3226	Approved
0.7619	Intermediate Similarity	NPD5353	Approved
0.7616	Intermediate Similarity	NPD5242	Approved
0.7613	Intermediate Similarity	NPD6233	Phase 2
0.7582	Intermediate Similarity	NPD9494	Approved
0.7558	Intermediate Similarity	NPD7229	Phase 3
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3764	Approved
0.7545	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7472	Intermediate Similarity	NPD7549	Discontinued
0.7469	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1203	Approved
0.745	Intermediate Similarity	NPD9268	Approved
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.744	Intermediate Similarity	NPD6386	Approved
0.744	Intermediate Similarity	NPD6385	Approved
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7425	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7416	Intermediate Similarity	NPD7038	Approved
0.7416	Intermediate Similarity	NPD7039	Approved
0.7412	Intermediate Similarity	NPD4288	Approved
0.7407	Intermediate Similarity	NPD1652	Phase 2
0.7405	Intermediate Similarity	NPD5124	Phase 1
0.7405	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7386	Intermediate Similarity	NPD3225	Approved
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7375	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD1608	Approved
0.7349	Intermediate Similarity	NPD6273	Approved
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2797	Approved
0.7326	Intermediate Similarity	NPD6971	Discontinued
0.7325	Intermediate Similarity	NPD3268	Approved
0.732	Intermediate Similarity	NPD7783	Phase 2
0.732	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7312	Intermediate Similarity	NPD7097	Phase 1
0.7303	Intermediate Similarity	NPD422	Phase 1
0.7301	Intermediate Similarity	NPD2800	Approved
0.7301	Intermediate Similarity	NPD1243	Approved
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7177	Discontinued
0.7284	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD7440	Discontinued
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7267	Intermediate Similarity	NPD9545	Approved
0.7257	Intermediate Similarity	NPD5711	Approved
0.7257	Intermediate Similarity	NPD5710	Approved
0.7256	Intermediate Similarity	NPD8166	Discontinued
0.7256	Intermediate Similarity	NPD7003	Approved
0.7254	Intermediate Similarity	NPD7585	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7228	Intermediate Similarity	NPD4287	Approved
0.7225	Intermediate Similarity	NPD7680	Approved
0.7222	Intermediate Similarity	NPD5405	Approved
0.7222	Intermediate Similarity	NPD5404	Approved
0.7222	Intermediate Similarity	NPD5406	Approved
0.7222	Intermediate Similarity	NPD5408	Approved
0.7219	Intermediate Similarity	NPD3455	Phase 2
0.7202	Intermediate Similarity	NPD7583	Approved
0.7196	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD17	Approved
0.716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD4109	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