NPASS Compound

Structure

CID26326 OpenBabel06191715352D 31 34 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 2.0000 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 -2.5981 0.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 -4.3301 3.5000 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 3.4641 0.0000 0.0000 C 0 0 2 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 0.0000 0.0000 C 0 0 2 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 0.5000 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 3.4641 -1.0000 0.0000 C 0 0 2 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 -4.3301 4.5000 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 1.7321 2.0000 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 15 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 6 16 2 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 1 1 6 0 0 0 9 21 1 0 0 0 0 9 30 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 20 1 0 0 0 0 12 24 2 0 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 21 1 0 0 0 0 14 26 1 1 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 19 1 1 0 0 0 17 30 1 0 0 0 0 18 20 2 0 0 0 0 18 31 1 0 0 0 0 19 22 2 0 0 0 0 20 22 1 0 0 0 0 21 27 1 6 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.13
Volume:	412.863
LogP:	2.796
LogD:	1.321
LogS:	-4.094
# Rotatable Bonds:	3
TPSA:	149.82
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.021
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.384
MDCK Permeability:	6.234925422177184e-06
Pgp-inhibitor:	0.04
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.419
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.6359634399414%
Volume Distribution (VD):	0.616
Pgp-substrate:	9.315324783325195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.512
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.251
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	4.756
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.428
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.906
Carcinogencity:	0.13
Eye Corrosion:	0.003
Eye Irritation:	0.624
Respiratory Toxicity:	0.598

Download Data

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

Natural Product: NPC26326

Natural Product ID:	NPC26326
*Common Name:**	6-C-Beta-L-Boivinopyranoside
IUPAC Name:	6-[(2R,4R,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	VOXHZFGNVVKUEG-NRGAKEJDSA-N
Standard InCHI:	InChI=1S/C22H22O9/c1-9-21(27)14(26)8-17(30-9)19-13(25)7-18-20(22(19)28)12(24)6-16(31-18)10-3-4-15(29-2)11(23)5-10/h3-7,9,14,17,21,23,25-28H,8H2,1-2H3/t9-,14+,17+,21+/m0/s1
SMILES:	C[C@H]1[C@H]([C@@H](C[C@H](c2c(cc3c(c(=O)cc(c4ccc(c(c4)O)OC)o3)c2O)O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462245
PubChem CID:	44566792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-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
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15810	Zea mays	Species	Poaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Inhibition	=	64.2	%	PMID[506652]

☑ 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 NPC26326 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	433
0.1-0.2	1718
0.2-0.3	3915
0.3-0.4	9818
0.4-0.5	8497
0.5-0.6	3815
0.6-0.7	4884
0.7-0.8	5006
0.8-0.85	2238
0.85-0.9	1621
0.9-0.95	726
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC474038
0.9868	High Similarity	NPC117418
0.9868	High Similarity	NPC53545
0.9804	High Similarity	NPC118256
0.9804	High Similarity	NPC192686
0.9804	High Similarity	NPC119209
0.9804	High Similarity	NPC475784
0.9803	High Similarity	NPC472598
0.9803	High Similarity	NPC474055
0.9742	High Similarity	NPC472625
0.974	High Similarity	NPC142252
0.974	High Similarity	NPC289771
0.974	High Similarity	NPC472634
0.974	High Similarity	NPC472632
0.974	High Similarity	NPC471499
0.9737	High Similarity	NPC35038
0.9737	High Similarity	NPC195796
0.9737	High Similarity	NPC278778
0.9737	High Similarity	NPC291878
0.9677	High Similarity	NPC474033
0.9677	High Similarity	NPC472635
0.9677	High Similarity	NPC474034
0.9677	High Similarity	NPC476247
0.9675	High Similarity	NPC470326
0.9675	High Similarity	NPC282009
0.9675	High Similarity	NPC287328
0.9675	High Similarity	NPC472631
0.9675	High Similarity	NPC472630
0.9675	High Similarity	NPC174953
0.9673	High Similarity	NPC27337
0.9673	High Similarity	NPC284820
0.9673	High Similarity	NPC473272
0.9673	High Similarity	NPC291508
0.9671	High Similarity	NPC200761
0.9671	High Similarity	NPC470327
0.9671	High Similarity	NPC477503
0.9671	High Similarity	NPC45849
0.9671	High Similarity	NPC321779
0.962	High Similarity	NPC475212
0.9618	High Similarity	NPC471213
0.9615	High Similarity	NPC186686
0.9613	High Similarity	NPC471210
0.9613	High Similarity	NPC165970
0.9613	High Similarity	NPC471212
0.9613	High Similarity	NPC305987
0.9613	High Similarity	NPC288131
0.9613	High Similarity	NPC158188
0.9613	High Similarity	NPC84324
0.9613	High Similarity	NPC66618
0.9613	High Similarity	NPC113163
0.9613	High Similarity	NPC471211
0.961	High Similarity	NPC22192
0.961	High Similarity	NPC473990
0.961	High Similarity	NPC284127
0.961	High Similarity	NPC476410
0.961	High Similarity	NPC172202
0.9608	High Similarity	NPC209614
0.9608	High Similarity	NPC470328
0.9608	High Similarity	NPC472626
0.9605	High Similarity	NPC192083
0.9605	High Similarity	NPC213896
0.9605	High Similarity	NPC18727
0.9551	High Similarity	NPC474150
0.9551	High Similarity	NPC474162
0.9548	High Similarity	NPC101731
0.9548	High Similarity	NPC472624
0.9548	High Similarity	NPC36217
0.9545	High Similarity	NPC52889
0.9545	High Similarity	NPC471209
0.9545	High Similarity	NPC223787
0.9545	High Similarity	NPC63454
0.9545	High Similarity	NPC183851
0.9542	High Similarity	NPC226025
0.9539	High Similarity	NPC106976
0.9539	High Similarity	NPC244583
0.9539	High Similarity	NPC56232
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC161881
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC10807
0.9539	High Similarity	NPC150123
0.9539	High Similarity	NPC471982
0.95	High Similarity	NPC256760
0.9494	High Similarity	NPC43319
0.9494	High Similarity	NPC13481
0.9494	High Similarity	NPC207575
0.949	High Similarity	NPC124038
0.9487	High Similarity	NPC134783
0.9487	High Similarity	NPC198829
0.9487	High Similarity	NPC266314
0.9484	High Similarity	NPC74178
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC204879
0.9484	High Similarity	NPC187792
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC184755
0.9481	High Similarity	NPC471985
0.9481	High Similarity	NPC250922
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9477	High Similarity	NPC74924
0.9477	High Similarity	NPC298692
0.9474	High Similarity	NPC209846
0.9474	High Similarity	NPC328740
0.9474	High Similarity	NPC289774
0.9474	High Similarity	NPC477897
0.9441	High Similarity	NPC208668
0.9437	High Similarity	NPC150767
0.9437	High Similarity	NPC78734
0.9437	High Similarity	NPC102277
0.9437	High Similarity	NPC279209
0.9434	High Similarity	NPC474024
0.9434	High Similarity	NPC218226
0.9434	High Similarity	NPC243877
0.9434	High Similarity	NPC260266
0.9434	High Similarity	NPC229729
0.9434	High Similarity	NPC477502
0.943	High Similarity	NPC470457
0.943	High Similarity	NPC311830
0.943	High Similarity	NPC36916
0.943	High Similarity	NPC58223
0.943	High Similarity	NPC36
0.943	High Similarity	NPC293319
0.943	High Similarity	NPC62261
0.943	High Similarity	NPC72787
0.943	High Similarity	NPC7154
0.943	High Similarity	NPC7688
0.943	High Similarity	NPC125039
0.943	High Similarity	NPC50960
0.943	High Similarity	NPC22832
0.9427	High Similarity	NPC219927
0.9427	High Similarity	NPC220912
0.9427	High Similarity	NPC201800
0.9427	High Similarity	NPC83922
0.9427	High Similarity	NPC472448
0.9423	High Similarity	NPC321399
0.9423	High Similarity	NPC328102
0.9423	High Similarity	NPC204290
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC474681
0.9419	High Similarity	NPC218313
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC470402
0.9419	High Similarity	NPC78071
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC117992
0.9416	High Similarity	NPC230149
0.9416	High Similarity	NPC234255
0.9416	High Similarity	NPC304745
0.9416	High Similarity	NPC57674
0.9416	High Similarity	NPC111341
0.9416	High Similarity	NPC168247
0.9416	High Similarity	NPC152951
0.9412	High Similarity	NPC323626
0.9412	High Similarity	NPC472912
0.9412	High Similarity	NPC324233
0.9408	High Similarity	NPC88804
0.9408	High Similarity	NPC338131
0.9408	High Similarity	NPC3825
0.9375	High Similarity	NPC288813
0.9371	High Similarity	NPC236934
0.9371	High Similarity	NPC5778
0.9371	High Similarity	NPC119589
0.9367	High Similarity	NPC284960
0.9367	High Similarity	NPC191306
0.9367	High Similarity	NPC470459
0.9367	High Similarity	NPC270335
0.9367	High Similarity	NPC476295
0.9367	High Similarity	NPC309025
0.9367	High Similarity	NPC222936
0.9367	High Similarity	NPC88023
0.9367	High Similarity	NPC243930
0.9367	High Similarity	NPC19709
0.9363	High Similarity	NPC29876
0.9363	High Similarity	NPC167678
0.9363	High Similarity	NPC228383
0.9359	High Similarity	NPC469658
0.9359	High Similarity	NPC210459
0.9355	High Similarity	NPC133970
0.9355	High Similarity	NPC78492
0.9355	High Similarity	NPC6633
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC5322
0.9355	High Similarity	NPC208152
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC471500
0.9355	High Similarity	NPC282307
0.9355	High Similarity	NPC235165
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC170026
0.9355	High Similarity	NPC472455

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 NPC26326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	912
0.2-0.3	1811
0.3-0.4	2641
0.4-0.5	1852
0.5-0.6	973
0.6-0.7	386
0.7-0.8	128
0.8-0.85	25
0.85-0.9	20
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9605	High Similarity	NPD2393	Clinical (unspecified phase)
0.9539	High Similarity	NPD1934	Approved
0.943	High Similarity	NPD6167	Clinical (unspecified phase)
0.943	High Similarity	NPD6168	Clinical (unspecified phase)
0.943	High Similarity	NPD6166	Phase 2
0.9281	High Similarity	NPD4380	Phase 2
0.9255	High Similarity	NPD7054	Approved
0.9226	High Similarity	NPD2801	Approved
0.9198	High Similarity	NPD7074	Phase 3
0.9198	High Similarity	NPD7472	Approved
0.9074	High Similarity	NPD3818	Discontinued
0.9024	High Similarity	NPD6797	Phase 2
0.9013	High Similarity	NPD1511	Approved
0.897	High Similarity	NPD7251	Discontinued
0.8931	High Similarity	NPD4381	Clinical (unspecified phase)
0.8924	High Similarity	NPD3817	Phase 2
0.8916	High Similarity	NPD7808	Phase 3
0.8916	High Similarity	NPD4338	Clinical (unspecified phase)
0.8896	High Similarity	NPD1512	Approved
0.8868	High Similarity	NPD4868	Clinical (unspecified phase)
0.8868	High Similarity	NPD3882	Suspended
0.8831	High Similarity	NPD4378	Clinical (unspecified phase)
0.882	High Similarity	NPD5494	Approved
0.8812	High Similarity	NPD7075	Discontinued
0.8788	High Similarity	NPD7804	Clinical (unspecified phase)
0.8688	High Similarity	NPD8443	Clinical (unspecified phase)
0.8679	High Similarity	NPD6801	Discontinued
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8563	High Similarity	NPD5844	Phase 1
0.8562	High Similarity	NPD1549	Phase 2
0.8537	High Similarity	NPD6959	Discontinued
0.8509	High Similarity	NPD7819	Suspended
0.85	High Similarity	NPD7411	Suspended
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7473	Discontinued
0.8431	Intermediate Similarity	NPD2796	Approved
0.8412	Intermediate Similarity	NPD6559	Discontinued
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD5402	Approved
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.825	Intermediate Similarity	NPD5403	Approved
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5401	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD919	Approved
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD943	Approved
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3926	Phase 2
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3750	Approved
0.7866	Intermediate Similarity	NPD1653	Approved
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7199	Phase 2
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD7228	Approved
0.774	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7706	Intermediate Similarity	NPD3749	Approved
0.7705	Intermediate Similarity	NPD4360	Phase 2
0.7705	Intermediate Similarity	NPD4363	Phase 3
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7697	Intermediate Similarity	NPD920	Approved
0.7684	Intermediate Similarity	NPD7685	Pre-registration
0.7679	Intermediate Similarity	NPD37	Approved
0.7658	Intermediate Similarity	NPD6651	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7632	Intermediate Similarity	NPD7584	Approved
0.763	Intermediate Similarity	NPD3787	Discontinued
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7607	Intermediate Similarity	NPD6190	Approved
0.7605	Intermediate Similarity	NPD3226	Approved
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD1243	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3748	Approved
0.7561	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6100	Approved
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD6777	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7484	Intermediate Similarity	NPD5124	Phase 1
0.7484	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.747	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7436	Intermediate Similarity	NPD9494	Approved
0.7427	Intermediate Similarity	NPD8455	Phase 2
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7362	Intermediate Similarity	NPD7266	Discontinued
0.7362	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD2424	Discontinued
0.731	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7240	Approved
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD4361	Phase 2
0.7287	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7237	Intermediate Similarity	NPD1548	Phase 1
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7231	Intermediate Similarity	NPD7585	Approved
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7197	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD6798	Discontinued
0.7188	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD2309	Approved
0.7184	Intermediate Similarity	NPD5353	Approved
0.7179	Intermediate Similarity	NPD7583	Approved
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7874	Approved
0.7152	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3823	Discontinued
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7107	Intermediate Similarity	NPD3018	Phase 2
0.7099	Intermediate Similarity	NPD4060	Phase 1
0.7089	Intermediate Similarity	NPD2797	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD4662	Approved
0.7059	Intermediate Similarity	NPD4661	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