NPASS Compound

Structure

NPC473818 OpenBabel07101718222D 41 45 0 0 1 0 0 0 0 0999 V2000 6.9282 3.0000 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 6.9282 4.0000 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 6.0622 4.5000 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 1.7321 1.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 1.0000 0.0000 C 0 0 3 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 -5.1962 -2.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 4.3301 4.5000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 16 2 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 24 1 0 0 0 0 8 14 2 0 0 0 0 8 22 1 0 0 0 0 9 14 1 0 0 0 0 9 23 2 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 21 2 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 25 2 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 39 1 0 0 0 0 17 38 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 32 1 0 0 0 0 22 27 2 0 0 0 0 22 33 1 0 0 0 0 23 27 1 0 0 0 0 23 34 1 0 0 0 0 24 40 1 0 0 0 0 25 40 1 0 0 0 0 26 35 1 0 0 0 0 27 41 1 0 0 0 0 28 36 2 0 0 0 0 28 38 1 0 0 0 0 29 37 2 0 0 0 0 29 39 1 0 0 0 0 29 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.11
Volume:	535.93
LogP:	4.028
LogD:	2.928
LogS:	-4.074
# Rotatable Bonds:	8
TPSA:	192.44
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.084
Synthetic Accessibility Score:	3.565
Fsp3:	0.103
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.039
MDCK Permeability:	2.3533573767053895e-05
Pgp-inhibitor:	0.035
Pgp-substrate:	0.1
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.757

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.90081024169922%
Volume Distribution (VD):	0.464
Pgp-substrate:	1.727673053741455%

ADMET: Metabolism

CYP1A2-inhibitor:	0.545
CYP1A2-substrate:	0.062
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.622
CYP2C9-substrate:	0.346
CYP2D6-inhibitor:	0.099
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.122
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	12.032
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.006
Drug-inuced Liver Injury (DILI):	0.473
AMES Toxicity:	0.468
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.974
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.922
Respiratory Toxicity:	0.245

Download Data

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

Natural Product: NPC473818

Natural Product ID:	NPC473818
*Common Name:**	7,4'-Di-O-Galloyltricetifavan
IUPAC Name:	[2-(3,5-dihydroxy-4-phenoxycarbonyloxyphenyl)-5-hydroxy-3,4-dihydro-2H-chromen-7-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	VLAANOKIZGGKIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H22O12/c30-19-12-17(38-28(36)15-10-20(31)26(35)21(32)11-15)13-25-18(19)6-7-24(40-25)14-8-22(33)27(23(34)9-14)41-29(37)39-16-4-2-1-3-5-16/h1-5,8-13,24,30-35H,6-7H2
SMILES:	O=C(Oc1c(O)cc(cc1O)C1CCc2c(O1)cc(cc2O)OC(=O)c1cc(O)c(c(c1)O)O)Oc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452635
PubChem CID:	11706751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002991] Hydroxyflavonoids [CHEMONTID:0002992] 5-hydroxyflavonoids

*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
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	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
Others	10

Activity Type	# Activity
Cell Line	4
Organism	4
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	100.0	ug.mL-1	PMID[493787]
NPT189	Cell Line	Vero	Chlorocebus aethiops	MNCC	=	31.3	ug ml-1	PMID[493787]
NPT616	Cell Line	MDCK	Canis lupus familiaris	CC50	=	60.0	ug.mL-1	PMID[493787]
NPT616	Cell Line	MDCK	Canis lupus familiaris	MNCC	=	31.3	ug ml-1	PMID[493787]
NPT27	Others	Unspecified		CC50	=	62.5	ug.mL-1	PMID[493787]
NPT27	Others	Unspecified		MNCC	=	12.5	ug ml-1	PMID[493787]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	10.0	ug.mL-1	PMID[493787]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.3	n.a.	PMID[493787]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	20.0	ug.mL-1	PMID[493787]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	5.0	n.a.	PMID[493787]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	30.0	ug.mL-1	PMID[493787]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.0	n.a.	PMID[493787]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	25.0	ug.mL-1	PMID[493787]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	2.5	n.a.	PMID[493787]

☑ 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 NPC473818 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	416
0.1-0.2	1786
0.2-0.3	4468
0.3-0.4	9736
0.4-0.5	8214
0.5-0.6	3611
0.6-0.7	5101
0.7-0.8	6455
0.8-0.85	2182
0.85-0.9	658
0.9-0.95	67
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9494	High Similarity	NPC24164
0.9494	High Similarity	NPC53889
0.949	High Similarity	NPC156818
0.949	High Similarity	NPC38779
0.949	High Similarity	NPC160512
0.949	High Similarity	NPC68324
0.949	High Similarity	NPC289322
0.949	High Similarity	NPC114179
0.943	High Similarity	NPC87317
0.9427	High Similarity	NPC318432
0.9427	High Similarity	NPC300845
0.9427	High Similarity	NPC291948
0.9427	High Similarity	NPC104983
0.9427	High Similarity	NPC88803
0.9427	High Similarity	NPC250436
0.9398	High Similarity	NPC80956
0.9379	High Similarity	NPC142614
0.9325	High Similarity	NPC149300
0.9317	High Similarity	NPC121290
0.9277	High Similarity	NPC297574
0.9268	High Similarity	NPC149011
0.9268	High Similarity	NPC204937
0.9268	High Similarity	NPC476365
0.9255	High Similarity	NPC33298
0.9255	High Similarity	NPC285108
0.9255	High Similarity	NPC476372
0.9255	High Similarity	NPC476371
0.925	High Similarity	NPC289346
0.9236	High Similarity	NPC474656
0.9226	High Similarity	NPC8940
0.9222	High Similarity	NPC476623
0.9222	High Similarity	NPC476618
0.9222	High Similarity	NPC476619
0.9222	High Similarity	NPC476622
0.9222	High Similarity	NPC476620
0.9222	High Similarity	NPC476621
0.9212	High Similarity	NPC67134
0.9212	High Similarity	NPC47140
0.9207	High Similarity	NPC198125
0.9207	High Similarity	NPC95421
0.9167	High Similarity	NPC471030
0.9162	High Similarity	NPC472723
0.9162	High Similarity	NPC79736
0.9162	High Similarity	NPC472991
0.9162	High Similarity	NPC472992
0.9162	High Similarity	NPC67629
0.9157	High Similarity	NPC88560
0.9157	High Similarity	NPC98583
0.9157	High Similarity	NPC175230
0.9157	High Similarity	NPC172033
0.9157	High Similarity	NPC472993
0.9136	High Similarity	NPC90905
0.9136	High Similarity	NPC219927
0.9136	High Similarity	NPC4013
0.9136	High Similarity	NPC477841
0.913	High Similarity	NPC239966
0.913	High Similarity	NPC203020
0.913	High Similarity	NPC476373
0.9118	High Similarity	NPC231254
0.9112	High Similarity	NPC208797
0.9112	High Similarity	NPC53680
0.9107	High Similarity	NPC472387
0.9107	High Similarity	NPC267549
0.9096	High Similarity	NPC65333
0.9096	High Similarity	NPC100251
0.9091	High Similarity	NPC658
0.9091	High Similarity	NPC197708
0.907	High Similarity	NPC119094
0.907	High Similarity	NPC142291
0.907	High Similarity	NPC173872
0.907	High Similarity	NPC7839
0.9068	High Similarity	NPC289811
0.9068	High Similarity	NPC160780
0.9064	High Similarity	NPC111490
0.9064	High Similarity	NPC261623
0.9059	High Similarity	NPC97119
0.9059	High Similarity	NPC135831
0.9059	High Similarity	NPC129533
0.9059	High Similarity	NPC297503
0.9059	High Similarity	NPC123259
0.9048	High Similarity	NPC144097
0.9048	High Similarity	NPC61904
0.9042	High Similarity	NPC473550
0.9042	High Similarity	NPC46640
0.9042	High Similarity	NPC219600
0.9042	High Similarity	NPC263119
0.9042	High Similarity	NPC163165
0.9042	High Similarity	NPC34436
0.9042	High Similarity	NPC166674
0.9036	High Similarity	NPC180768
0.9036	High Similarity	NPC181778
0.903	High Similarity	NPC116745
0.903	High Similarity	NPC45400
0.9024	High Similarity	NPC165720
0.9024	High Similarity	NPC477840
0.9012	High Similarity	NPC469649
0.9012	High Similarity	NPC260521
0.9012	High Similarity	NPC65489
0.9006	High Similarity	NPC1913
0.9006	High Similarity	NPC472860
0.9006	High Similarity	NPC133984
0.9	High Similarity	NPC117668
0.8994	High Similarity	NPC35167
0.8994	High Similarity	NPC253521
0.8994	High Similarity	NPC217520
0.8994	High Similarity	NPC113836
0.8994	High Similarity	NPC139571
0.8994	High Similarity	NPC37668
0.8988	High Similarity	NPC81042
0.8988	High Similarity	NPC34267
0.8988	High Similarity	NPC214621
0.8988	High Similarity	NPC223426
0.8982	High Similarity	NPC5786
0.8982	High Similarity	NPC212038
0.8982	High Similarity	NPC271848
0.8982	High Similarity	NPC262580
0.8982	High Similarity	NPC289396
0.8982	High Similarity	NPC102851
0.8982	High Similarity	NPC476370
0.8982	High Similarity	NPC81332
0.8976	High Similarity	NPC476279
0.8976	High Similarity	NPC229687
0.8963	High Similarity	NPC88043
0.8963	High Similarity	NPC67959
0.896	High Similarity	NPC477081
0.896	High Similarity	NPC477083
0.896	High Similarity	NPC223534
0.896	High Similarity	NPC240200
0.896	High Similarity	NPC269046
0.896	High Similarity	NPC290289
0.896	High Similarity	NPC158214
0.8957	High Similarity	NPC25389
0.8957	High Similarity	NPC311803
0.8957	High Similarity	NPC472859
0.8953	High Similarity	NPC104910
0.8953	High Similarity	NPC474093
0.8953	High Similarity	NPC469650
0.8951	High Similarity	NPC287872
0.8951	High Similarity	NPC74319
0.8947	High Similarity	NPC36138
0.8938	High Similarity	NPC469888
0.8935	High Similarity	NPC473713
0.8931	High Similarity	NPC75695
0.8929	High Similarity	NPC476374
0.8922	High Similarity	NPC471416
0.8922	High Similarity	NPC231194
0.8922	High Similarity	NPC34287
0.8922	High Similarity	NPC51326
0.8916	High Similarity	NPC470271
0.8916	High Similarity	NPC243877
0.8916	High Similarity	NPC261411
0.8916	High Similarity	NPC14662
0.8916	High Similarity	NPC190204
0.8916	High Similarity	NPC311389
0.8916	High Similarity	NPC43918
0.8916	High Similarity	NPC229729
0.8909	High Similarity	NPC471788
0.8908	High Similarity	NPC187632
0.8908	High Similarity	NPC472721
0.8908	High Similarity	NPC160543
0.8908	High Similarity	NPC469652
0.8908	High Similarity	NPC31208
0.8908	High Similarity	NPC93065
0.8908	High Similarity	NPC472724
0.8908	High Similarity	NPC201814
0.8908	High Similarity	NPC472720
0.8902	High Similarity	NPC237202
0.8902	High Similarity	NPC148273
0.8902	High Similarity	NPC105591
0.8902	High Similarity	NPC475179
0.8896	High Similarity	NPC119125
0.8896	High Similarity	NPC24627
0.8896	High Similarity	NPC166277
0.8895	High Similarity	NPC470416
0.8889	High Similarity	NPC172419
0.8889	High Similarity	NPC238419
0.8889	High Similarity	NPC125352
0.8889	High Similarity	NPC469371
0.8882	High Similarity	NPC222185
0.8882	High Similarity	NPC258044
0.8882	High Similarity	NPC196127
0.8882	High Similarity	NPC477895
0.8882	High Similarity	NPC293626
0.8882	High Similarity	NPC217387
0.8882	High Similarity	NPC267680
0.8882	High Similarity	NPC476773
0.8876	High Similarity	NPC84482
0.8876	High Similarity	NPC169645
0.8869	High Similarity	NPC307518
0.8869	High Similarity	NPC254540
0.8869	High Similarity	NPC48773
0.8869	High Similarity	NPC205076
0.8869	High Similarity	NPC211594
0.8869	High Similarity	NPC172807
0.8869	High Similarity	NPC472386
0.8862	High Similarity	NPC475212
0.8862	High Similarity	NPC112755
0.8862	High Similarity	NPC170675
0.8862	High Similarity	NPC471457
0.8861	High Similarity	NPC107636

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 NPC473818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	385
0.1-0.2	951
0.2-0.3	1943
0.3-0.4	2595
0.4-0.5	1762
0.5-0.6	931
0.6-0.7	415
0.7-0.8	125
0.8-0.85	31
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9427	High Similarity	NPD4868	Clinical (unspecified phase)
0.9096	High Similarity	NPD7993	Clinical (unspecified phase)
0.881	High Similarity	NPD7074	Phase 3
0.8802	High Similarity	NPD3818	Discontinued
0.8795	High Similarity	NPD6166	Phase 2
0.8795	High Similarity	NPD6167	Clinical (unspecified phase)
0.8795	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD4338	Clinical (unspecified phase)
0.875	High Similarity	NPD7054	Approved
0.8704	High Similarity	NPD1465	Phase 2
0.8698	High Similarity	NPD7472	Approved
0.8642	High Similarity	NPD1934	Approved
0.8639	High Similarity	NPD5844	Phase 1
0.8545	High Similarity	NPD4381	Clinical (unspecified phase)
0.8538	High Similarity	NPD6797	Phase 2
0.8488	Intermediate Similarity	NPD7251	Discontinued
0.8476	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7808	Phase 3
0.8364	Intermediate Similarity	NPD2801	Approved
0.8362	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8282	Intermediate Similarity	NPD1653	Approved
0.8263	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD6232	Discontinued
0.8214	Intermediate Similarity	NPD7075	Discontinued
0.8182	Intermediate Similarity	NPD4380	Phase 2
0.8176	Intermediate Similarity	NPD7199	Phase 2
0.8166	Intermediate Similarity	NPD6234	Discontinued
0.815	Intermediate Similarity	NPD7228	Approved
0.8148	Intermediate Similarity	NPD1511	Approved
0.814	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD7411	Suspended
0.8103	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7473	Discontinued
0.809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8312	Approved
0.8079	Intermediate Similarity	NPD8313	Approved
0.807	Intermediate Similarity	NPD6959	Discontinued
0.8068	Intermediate Similarity	NPD6559	Discontinued
0.8049	Intermediate Similarity	NPD1512	Approved
0.8037	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD8455	Phase 2
0.8012	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD5402	Approved
0.7976	Intermediate Similarity	NPD37	Approved
0.7966	Intermediate Similarity	NPD7685	Pre-registration
0.795	Intermediate Similarity	NPD1549	Phase 2
0.7941	Intermediate Similarity	NPD4965	Approved
0.7941	Intermediate Similarity	NPD4967	Phase 2
0.7941	Intermediate Similarity	NPD7768	Phase 2
0.7941	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD6190	Approved
0.7911	Intermediate Similarity	NPD230	Phase 1
0.7888	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6801	Discontinued
0.7869	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3750	Approved
0.7848	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1613	Approved
0.7841	Intermediate Similarity	NPD3751	Discontinued
0.7818	Intermediate Similarity	NPD6799	Approved
0.7816	Intermediate Similarity	NPD3787	Discontinued
0.7791	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4628	Phase 3
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7266	Discontinued
0.7667	Intermediate Similarity	NPD7240	Approved
0.7665	Intermediate Similarity	NPD5401	Approved
0.7665	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1510	Phase 2
0.7647	Intermediate Similarity	NPD6599	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD8151	Discontinued
0.761	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2796	Approved
0.7588	Intermediate Similarity	NPD7458	Discontinued
0.7578	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD447	Suspended
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD3748	Approved
0.7543	Intermediate Similarity	NPD919	Approved
0.7516	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD3926	Phase 2
0.7462	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7783	Phase 2
0.7461	Intermediate Similarity	NPD7435	Discontinued
0.7458	Intermediate Similarity	NPD8127	Discontinued
0.7432	Intermediate Similarity	NPD7549	Discontinued
0.7425	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1240	Approved
0.7396	Intermediate Similarity	NPD6777	Approved
0.7396	Intermediate Similarity	NPD6780	Approved
0.7396	Intermediate Similarity	NPD6779	Approved
0.7396	Intermediate Similarity	NPD6776	Approved
0.7396	Intermediate Similarity	NPD6781	Approved
0.7396	Intermediate Similarity	NPD6778	Approved
0.7396	Intermediate Similarity	NPD6782	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7384	Intermediate Similarity	NPD3226	Approved
0.7378	Intermediate Similarity	NPD7097	Phase 1
0.7375	Intermediate Similarity	NPD4908	Phase 1
0.7374	Intermediate Similarity	NPD5242	Approved
0.7371	Intermediate Similarity	NPD5353	Approved
0.7371	Intermediate Similarity	NPD7680	Approved
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7344	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD9269	Phase 2
0.7321	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1607	Approved
0.7312	Intermediate Similarity	NPD9494	Approved
0.731	Intermediate Similarity	NPD7585	Approved
0.7284	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7039	Approved
0.7283	Intermediate Similarity	NPD7038	Approved
0.7267	Intermediate Similarity	NPD920	Approved
0.7263	Intermediate Similarity	NPD1247	Approved
0.7259	Intermediate Similarity	NPD7583	Approved
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7870	Phase 2
0.7245	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6233	Phase 2
0.7236	Intermediate Similarity	NPD7874	Approved
0.7236	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD7229	Phase 3
0.7209	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6385	Approved
0.72	Intermediate Similarity	NPD6386	Approved
0.7194	Intermediate Similarity	NPD7698	Approved
0.7194	Intermediate Similarity	NPD7697	Approved
0.7194	Intermediate Similarity	NPD7696	Phase 3
0.7193	Intermediate Similarity	NPD7390	Discontinued
0.7188	Intermediate Similarity	NPD1203	Approved
0.7181	Intermediate Similarity	NPD8150	Discontinued
0.7178	Intermediate Similarity	NPD3764	Approved
0.7166	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD6832	Phase 2
0.7158	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD5124	Phase 1
0.7152	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.7135	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4308	Phase 3
0.7125	Intermediate Similarity	NPD3225	Approved
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7118	Intermediate Similarity	NPD8166	Discontinued
0.7118	Intermediate Similarity	NPD7003	Approved
0.7105	Intermediate Similarity	NPD4287	Approved
0.709	Intermediate Similarity	NPD8434	Phase 2
0.7085	Intermediate Similarity	NPD7584	Approved
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD5405	Approved
0.7083	Intermediate Similarity	NPD5404	Approved
0.7083	Intermediate Similarity	NPD5408	Approved
0.7083	Intermediate Similarity	NPD5406	Approved
0.7081	Intermediate Similarity	NPD2797	Approved
0.7079	Intermediate Similarity	NPD4288	Approved
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7073	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.707	Intermediate Similarity	NPD9268	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1243	Approved
0.7059	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7048	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7044	Intermediate Similarity	NPD422	Phase 1
0.7041	Intermediate Similarity	NPD2346	Discontinued
0.703	Intermediate Similarity	NPD7801	Approved
0.7026	Intermediate Similarity	NPD7699	Phase 2
0.7026	Intermediate Similarity	NPD7700	Phase 2
0.7024	Intermediate Similarity	NPD7033	Discontinued
0.7024	Intermediate Similarity	NPD651	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