NPASS Compound

Structure

CID67134 OpenBabel06191715402D 42 46 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 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 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 3.4641 -0.0000 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 -6.9282 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 -6.9282 -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 -2.5981 -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 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 -6.0622 -1.5000 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 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 2 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 -3.4641 -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 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -2.0000 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 -4.3301 -4.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 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 15 2 0 0 0 0 5 15 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 25 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 17 1 0 0 0 0 12 23 2 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 39 1 0 0 0 0 17 40 1 0 0 0 0 18 19 2 0 0 0 0 18 31 1 0 0 0 0 19 32 1 0 0 0 0 20 26 2 0 0 0 0 20 33 1 0 0 0 0 21 26 1 0 0 0 0 21 34 2 0 0 0 0 22 16 1 1 0 0 0 22 41 1 0 0 0 0 23 26 1 0 0 0 0 23 41 1 0 0 0 0 24 14 1 1 0 0 0 24 27 1 0 0 0 0 24 42 1 0 0 0 0 25 35 2 0 0 0 0 25 39 1 0 0 0 0 27 28 1 0 0 0 0 27 36 1 6 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 40 1 1 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.16
Volume:	558.499
LogP:	2.778
LogD:	2.556
LogS:	-4.999
# 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:	0.135
Synthetic Accessibility Score:	4.267
Fsp3:	0.267
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:	-6.176
MDCK Permeability:	1.5336765500251204e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.706
Human Intestinal Absorption (HIA):	0.531
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	98.09938049316406%
Volume Distribution (VD):	0.422
Pgp-substrate:	1.8902357816696167%

ADMET: Metabolism

CYP1A2-inhibitor:	0.214
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.428
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.54
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	6.725
Half-life (T1/2):	0.556

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.603
Rat Oral Acute Toxicity:	0.217
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.946
Carcinogencity:	0.715
Eye Corrosion:	0.003
Eye Irritation:	0.908
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC67134

Natural Product ID:	NPC67134
*Common Name:**	Visartiside B
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[[(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-2,3-dihydrochromen-7-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-phenylprop-2-enoate
Synonyms:	Visartiside B
Standard InCHIKey:	XJWKDASPAHTQCB-SJNSNYLYSA-N
Standard InCHI:	InChI=1S/C30H28O12/c31-18-8-7-16(10-19(18)32)22-13-21(34)26-20(33)11-17(12-23(26)41-22)40-30-29(38)28(37)27(36)24(42-30)14-39-25(35)9-6-15-4-2-1-3-5-15/h1-12,22,24,27-33,36-38H,13-14H2/b9-6+/t22-,24+,27+,28-,29+,30+/m0/s1
SMILES:	O=C(/C=C/c1ccccc1)OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077013
PubChem CID:	46184560
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

*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
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00231-5]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12377236]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121165]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16561	Viscum articulatum	Species	Viscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15592	Swertia punctata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO539	Picea vulgaris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14062	Oophaga speciosa	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16561	Viscum articulatum	Species	Viscaceae	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
ED50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	25100.0	nM	PMID[557138]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	100.0	%	PMID[557138]
NPT1	Others	Radical scavenging activity		ED50	=	34.1	uM	PMID[557138]

☑ 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 NPC67134 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	398
0.1-0.2	1680
0.2-0.3	3884
0.3-0.4	8605
0.4-0.5	9288
0.5-0.6	4344
0.6-0.7	5016
0.7-0.8	5723
0.8-0.85	2347
0.85-0.9	952
0.9-0.95	435
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC47140
0.9756	High Similarity	NPC476620
0.9756	High Similarity	NPC476622
0.9756	High Similarity	NPC476621
0.9756	High Similarity	NPC476619
0.9756	High Similarity	NPC476618
0.9756	High Similarity	NPC476623
0.9693	High Similarity	NPC472993
0.9691	High Similarity	NPC204937
0.9691	High Similarity	NPC149011
0.9639	High Similarity	NPC469371
0.9636	High Similarity	NPC472387
0.9634	High Similarity	NPC214621
0.9634	High Similarity	NPC34267
0.9634	High Similarity	NPC223426
0.9634	High Similarity	NPC81042
0.9625	High Similarity	NPC29830
0.9625	High Similarity	NPC121290
0.9576	High Similarity	NPC472991
0.9576	High Similarity	NPC472992
0.9576	High Similarity	NPC144097
0.9576	High Similarity	NPC61904
0.9573	High Similarity	NPC172033
0.9573	High Similarity	NPC175230
0.9573	High Similarity	NPC88560
0.9571	High Similarity	NPC51326
0.9571	High Similarity	NPC231194
0.9568	High Similarity	NPC45400
0.9563	High Similarity	NPC472876
0.9518	High Similarity	NPC35167
0.9518	High Similarity	NPC37668
0.9518	High Similarity	NPC217520
0.9518	High Similarity	NPC113836
0.9518	High Similarity	NPC139571
0.9518	High Similarity	NPC253521
0.9509	High Similarity	NPC229687
0.9509	High Similarity	NPC43587
0.9509	High Similarity	NPC105283
0.9506	High Similarity	NPC115674
0.9506	High Similarity	NPC236934
0.9506	High Similarity	NPC5778
0.9506	High Similarity	NPC210073
0.9506	High Similarity	NPC8856
0.9503	High Similarity	NPC168822
0.9464	High Similarity	NPC241781
0.9464	High Similarity	NPC470718
0.9464	High Similarity	NPC162394
0.9464	High Similarity	NPC156785
0.9461	High Similarity	NPC471030
0.9451	High Similarity	NPC105095
0.9451	High Similarity	NPC79056
0.9451	High Similarity	NPC150767
0.9451	High Similarity	NPC78734
0.9451	High Similarity	NPC218488
0.9451	High Similarity	NPC34287
0.9451	High Similarity	NPC44328
0.9451	High Similarity	NPC177731
0.9451	High Similarity	NPC471416
0.9448	High Similarity	NPC116745
0.9448	High Similarity	NPC160156
0.9448	High Similarity	NPC92565
0.9448	High Similarity	NPC229729
0.9444	High Similarity	NPC165720
0.9441	High Similarity	NPC127782
0.9441	High Similarity	NPC300537
0.9441	High Similarity	NPC77660
0.9441	High Similarity	NPC189142
0.9408	High Similarity	NPC25946
0.9408	High Similarity	NPC460984
0.9408	High Similarity	NPC470720
0.9408	High Similarity	NPC470717
0.9408	High Similarity	NPC21359
0.9408	High Similarity	NPC231254
0.9408	High Similarity	NPC223860
0.9408	High Similarity	NPC275977
0.9408	High Similarity	NPC470713
0.9408	High Similarity	NPC249560
0.9401	High Similarity	NPC293626
0.9401	High Similarity	NPC267680
0.9401	High Similarity	NPC477895
0.9401	High Similarity	NPC217387
0.9401	High Similarity	NPC196127
0.9401	High Similarity	NPC258044
0.9398	High Similarity	NPC253685
0.9394	High Similarity	NPC81332
0.9394	High Similarity	NPC262580
0.9394	High Similarity	NPC289396
0.9394	High Similarity	NPC212038
0.9394	High Similarity	NPC256760
0.9394	High Similarity	NPC301683
0.9394	High Similarity	NPC271848
0.9394	High Similarity	NPC472386
0.939	High Similarity	NPC86008
0.939	High Similarity	NPC195257
0.939	High Similarity	NPC270578
0.939	High Similarity	NPC209296
0.939	High Similarity	NPC471457
0.939	High Similarity	NPC52382
0.939	High Similarity	NPC293629
0.939	High Similarity	NPC170675
0.939	High Similarity	NPC112755
0.9383	High Similarity	NPC270335
0.9383	High Similarity	NPC191306
0.9383	High Similarity	NPC19709
0.9383	High Similarity	NPC88043
0.9379	High Similarity	NPC477628
0.9379	High Similarity	NPC270675
0.9379	High Similarity	NPC472994
0.9379	High Similarity	NPC210961
0.9379	High Similarity	NPC195685
0.9379	High Similarity	NPC477629
0.9353	High Similarity	NPC33083
0.9353	High Similarity	NPC295625
0.9353	High Similarity	NPC470719
0.9353	High Similarity	NPC473554
0.9349	High Similarity	NPC135831
0.9349	High Similarity	NPC297503
0.9349	High Similarity	NPC199172
0.9349	High Similarity	NPC35924
0.9349	High Similarity	NPC97119
0.9349	High Similarity	NPC36138
0.9341	High Similarity	NPC89127
0.9341	High Similarity	NPC296018
0.9341	High Similarity	NPC268533
0.9341	High Similarity	NPC154741
0.9341	High Similarity	NPC471669
0.9337	High Similarity	NPC51774
0.9337	High Similarity	NPC239549
0.9337	High Similarity	NPC236191
0.9337	High Similarity	NPC208668
0.9333	High Similarity	NPC67105
0.9333	High Similarity	NPC116864
0.9333	High Similarity	NPC95866
0.9333	High Similarity	NPC156869
0.9333	High Similarity	NPC235260
0.9333	High Similarity	NPC29958
0.9333	High Similarity	NPC259896
0.9333	High Similarity	NPC255157
0.9333	High Similarity	NPC254855
0.9333	High Similarity	NPC21190
0.9333	High Similarity	NPC285197
0.9333	High Similarity	NPC44558
0.9333	High Similarity	NPC474434
0.9333	High Similarity	NPC136042
0.9333	High Similarity	NPC20505
0.9333	High Similarity	NPC183357
0.9333	High Similarity	NPC67326
0.9333	High Similarity	NPC22195
0.9333	High Similarity	NPC155763
0.9333	High Similarity	NPC244776
0.9329	High Similarity	NPC275454
0.9329	High Similarity	NPC477502
0.9325	High Similarity	NPC311830
0.9325	High Similarity	NPC277205
0.9325	High Similarity	NPC22832
0.9321	High Similarity	NPC473043
0.9317	High Similarity	NPC289346
0.9298	High Similarity	NPC105591
0.9298	High Similarity	NPC30011
0.9298	High Similarity	NPC65489
0.9298	High Similarity	NPC97817
0.9298	High Similarity	NPC72554
0.9294	High Similarity	NPC470416
0.9286	High Similarity	NPC173837
0.9286	High Similarity	NPC476773
0.9286	High Similarity	NPC120952
0.9281	High Similarity	NPC294629
0.9277	High Similarity	NPC471748
0.9277	High Similarity	NPC134532
0.9277	High Similarity	NPC60735
0.9277	High Similarity	NPC261254
0.9277	High Similarity	NPC175107
0.9277	High Similarity	NPC235575
0.9277	High Similarity	NPC205076
0.9277	High Similarity	NPC48773
0.9277	High Similarity	NPC3583
0.9277	High Similarity	NPC26230
0.9277	High Similarity	NPC267254
0.9277	High Similarity	NPC155877
0.9277	High Similarity	NPC33054
0.9277	High Similarity	NPC190003
0.9277	High Similarity	NPC471725
0.9277	High Similarity	NPC254540
0.9277	High Similarity	NPC153755
0.9277	High Similarity	NPC307518
0.9277	High Similarity	NPC172807
0.9277	High Similarity	NPC259152
0.9277	High Similarity	NPC211594
0.9277	High Similarity	NPC180918
0.9277	High Similarity	NPC176740
0.9277	High Similarity	NPC203259
0.9273	High Similarity	NPC183036
0.9273	High Similarity	NPC210042
0.9273	High Similarity	NPC138927
0.9273	High Similarity	NPC227508
0.9273	High Similarity	NPC472383
0.9273	High Similarity	NPC472381
0.9273	High Similarity	NPC95855
0.9273	High Similarity	NPC61791
0.9268	High Similarity	NPC56077

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 NPC67134 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	924
0.2-0.3	1881
0.3-0.4	2618
0.4-0.5	1845
0.5-0.6	945
0.6-0.7	377
0.7-0.8	134
0.8-0.85	41
0.85-0.9	13
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9451	High Similarity	NPD7074	Phase 3
0.939	High Similarity	NPD7054	Approved
0.9333	High Similarity	NPD7472	Approved
0.9277	High Similarity	NPD6797	Phase 2
0.9222	High Similarity	NPD7251	Discontinued
0.9212	High Similarity	NPD3818	Discontinued
0.9207	High Similarity	NPD6168	Clinical (unspecified phase)
0.9207	High Similarity	NPD6166	Phase 2
0.9207	High Similarity	NPD6167	Clinical (unspecified phase)
0.9193	High Similarity	NPD4381	Clinical (unspecified phase)
0.9167	High Similarity	NPD4338	Clinical (unspecified phase)
0.913	High Similarity	NPD4868	Clinical (unspecified phase)
0.9053	High Similarity	NPD7808	Phase 3
0.8935	High Similarity	NPD7993	Clinical (unspecified phase)
0.8827	High Similarity	NPD1934	Approved
0.8817	High Similarity	NPD7804	Clinical (unspecified phase)
0.8773	High Similarity	NPD2393	Clinical (unspecified phase)
0.8663	High Similarity	NPD6559	Discontinued
0.8589	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD7075	Discontinued
0.8494	Intermediate Similarity	NPD3817	Phase 2
0.8457	Intermediate Similarity	NPD8312	Approved
0.8457	Intermediate Similarity	NPD8313	Approved
0.8447	Intermediate Similarity	NPD1511	Approved
0.8434	Intermediate Similarity	NPD2801	Approved
0.8424	Intermediate Similarity	NPD7411	Suspended
0.8382	Intermediate Similarity	NPD5844	Phase 1
0.8344	Intermediate Similarity	NPD1512	Approved
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5402	Approved
0.8263	Intermediate Similarity	NPD6801	Discontinued
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8246	Intermediate Similarity	NPD6959	Discontinued
0.8242	Intermediate Similarity	NPD1653	Approved
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7228	Approved
0.8214	Intermediate Similarity	NPD7819	Suspended
0.8208	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5494	Approved
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5403	Approved
0.8166	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7473	Discontinued
0.814	Intermediate Similarity	NPD7199	Phase 2
0.8122	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6799	Approved
0.8107	Intermediate Similarity	NPD8455	Phase 2
0.8063	Intermediate Similarity	NPD8151	Discontinued
0.8061	Intermediate Similarity	NPD5401	Approved
0.8061	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD3751	Discontinued
0.7965	Intermediate Similarity	NPD3749	Approved
0.7963	Intermediate Similarity	NPD7266	Discontinued
0.7952	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7943	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7685	Pre-registration
0.7929	Intermediate Similarity	NPD6599	Discontinued
0.7919	Intermediate Similarity	NPD6234	Discontinued
0.7907	Intermediate Similarity	NPD7768	Phase 2
0.7901	Intermediate Similarity	NPD2796	Approved
0.7892	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3787	Discontinued
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD37	Approved
0.7818	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD4965	Approved
0.7803	Intermediate Similarity	NPD4966	Approved
0.7803	Intermediate Similarity	NPD4967	Phase 2
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7795	Intermediate Similarity	NPD7783	Phase 2
0.7795	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6190	Approved
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7735	Intermediate Similarity	NPD7240	Approved
0.7711	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD943	Approved
0.7702	Intermediate Similarity	NPD1240	Approved
0.7683	Intermediate Similarity	NPD1551	Phase 2
0.7654	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD1933	Approved
0.7633	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7698	Approved
0.7617	Intermediate Similarity	NPD7697	Approved
0.7617	Intermediate Similarity	NPD7696	Phase 3
0.7614	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD1607	Approved
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7584	Approved
0.7579	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7576	Intermediate Similarity	NPD2935	Discontinued
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7458	Discontinued
0.7551	Intermediate Similarity	NPD7701	Phase 2
0.7542	Intermediate Similarity	NPD3926	Phase 2
0.7515	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7469	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3226	Approved
0.7457	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7699	Phase 2
0.7448	Intermediate Similarity	NPD7700	Phase 2
0.7439	Intermediate Similarity	NPD447	Suspended
0.7436	Intermediate Similarity	NPD7680	Approved
0.7433	Intermediate Similarity	NPD8150	Discontinued
0.7427	Intermediate Similarity	NPD2532	Approved
0.7427	Intermediate Similarity	NPD2534	Approved
0.7427	Intermediate Similarity	NPD2533	Approved
0.7409	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7374	Intermediate Similarity	NPD7585	Approved
0.735	Intermediate Similarity	NPD7801	Approved
0.7341	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD1247	Approved
0.7326	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7583	Approved
0.731	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7286	Phase 2
0.7282	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD1203	Approved
0.7256	Intermediate Similarity	NPD6798	Discontinued
0.7256	Intermediate Similarity	NPD2313	Discontinued
0.7249	Intermediate Similarity	NPD8434	Phase 2
0.724	Intermediate Similarity	NPD6213	Phase 3
0.724	Intermediate Similarity	NPD6212	Phase 3
0.724	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7239	Intermediate Similarity	NPD4908	Phase 1
0.7235	Intermediate Similarity	NPD1243	Approved
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7202	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD2799	Discontinued
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD2800	Approved
0.7135	Intermediate Similarity	NPD6674	Discontinued
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7549	Discontinued
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1091	Approved
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2344	Approved
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD4287	Approved
0.7081	Intermediate Similarity	NPD9269	Phase 2
0.7074	Intermediate Similarity	NPD7038	Approved
0.7074	Intermediate Similarity	NPD7039	Approved
0.7065	Intermediate Similarity	NPD5242	Approved
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7056	Intermediate Similarity	NPD5353	Approved
0.7041	Intermediate Similarity	NPD7097	Phase 1
0.7037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1652	Phase 2
0.7029	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD4360	Phase 2
0.7026	Intermediate Similarity	NPD4363	Phase 3
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2798	Approved
0.7011	Intermediate Similarity	NPD5710	Approved
0.7011	Intermediate Similarity	NPD5711	Approved
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8166	Discontinued
0.699	Remote Similarity	NPD7930	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