NPASS Compound

Structure

NPC472345 OpenBabel07101718232D 33 35 0 0 1 0 0 0 0 0999 V2000 -1.6839 2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4197 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5777 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9722 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 -1.8142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5777 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7358 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7358 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8938 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0518 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8938 3.4028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2098 0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8938 0.4861 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 7 1 0 0 0 0 2 8 1 0 0 0 0 4 12 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 11 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 3 1 1 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 23 2 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 32 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 27 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 33 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.21
Volume:	467.153
LogP:	4.246
LogD:	2.049
LogS:	-3.289
# Rotatable Bonds:	6
TPSA:	137.43
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.481
Synthetic Accessibility Score:	4.219
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.937
MDCK Permeability:	1.5576490113744512e-05
Pgp-inhibitor:	0.46
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.088
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	99.7127456665039%
Volume Distribution (VD):	0.23
Pgp-substrate:	1.083353042602539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.899
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.365
CYP2C9-inhibitor:	0.524
CYP2C9-substrate:	0.798
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.227
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	4.3
Half-life (T1/2):	0.229

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.777
Skin Sensitization:	0.917
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.409

Download Data

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

Natural Product: NPC472345

Natural Product ID:	NPC472345
*Common Name:**	MEDYWYRUBCUSBS-GTNSWQLSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MEDYWYRUBCUSBS-GTNSWQLSSA-N
Standard InCHI:	InChI=1S/C25H32O8/c1-7-11(3)19(27)18-22(30)13(9-15-20(28)12(4)16(8-2)32-24(15)31)21(29)14-10-17(26)25(5,6)33-23(14)18/h11,17,26,28-30H,7-10H2,1-6H3/t11-,17-/m0/s1
SMILES:	CC[C@@H](C(=O)c1c(O)c(Cc2c(=O)oc(c(c2O)C)CC)c(c2c1OC(C)(C)[C@H](C2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359526
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858757]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	aerial parts	Alpa Corral, Cordoba, Argentina	2008-Aug	PMID[25517209]
NPO29471	Achyrocline satureioides	Species	Asteraceae	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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128000.0	nM	PMID[466044]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128000.0	nM	PMID[466044]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	>	128000.0	nM	PMID[466044]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	128000.0	nM	PMID[466044]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128000.0	nM	PMID[466044]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128000.0	nM	PMID[466044]

☑ 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 NPC472345 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	345
0.1-0.2	1609
0.2-0.3	3924
0.3-0.4	8790
0.4-0.5	10519
0.5-0.6	4327
0.6-0.7	6011
0.7-0.8	5505
0.8-0.85	1318
0.85-0.9	310
0.9-0.95	38
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9441	High Similarity	NPC112749
0.9324	High Similarity	NPC256141
0.932	High Similarity	NPC321387
0.932	High Similarity	NPC470908
0.932	High Similarity	NPC327059
0.9306	High Similarity	NPC18886
0.9252	High Similarity	NPC307052
0.9252	High Similarity	NPC139966
0.9247	High Similarity	NPC474108
0.9247	High Similarity	NPC177995
0.9241	High Similarity	NPC118059
0.9241	High Similarity	NPC470554
0.9241	High Similarity	NPC288910
0.9241	High Similarity	NPC133060
0.922	High Similarity	NPC470982
0.922	High Similarity	NPC470983
0.9189	High Similarity	NPC180351
0.9184	High Similarity	NPC10097
0.9178	High Similarity	NPC470910
0.9172	High Similarity	NPC307895
0.9172	High Similarity	NPC470909
0.9172	High Similarity	NPC470553
0.9172	High Similarity	NPC96216
0.9172	High Similarity	NPC33653
0.9172	High Similarity	NPC474939
0.9172	High Similarity	NPC184738
0.9116	High Similarity	NPC47388
0.9116	High Similarity	NPC470670
0.9116	High Similarity	NPC85773
0.9116	High Similarity	NPC473133
0.9116	High Similarity	NPC91902
0.9116	High Similarity	NPC285748
0.9103	High Similarity	NPC276565
0.9103	High Similarity	NPC112829
0.9103	High Similarity	NPC472344
0.9103	High Similarity	NPC294432
0.9103	High Similarity	NPC470556
0.906	High Similarity	NPC38775
0.9048	High Similarity	NPC474302
0.9013	High Similarity	NPC474609
0.9013	High Similarity	NPC129053
0.9013	High Similarity	NPC474738
0.9013	High Similarity	NPC78554
0.9013	High Similarity	NPC109967
0.9013	High Similarity	NPC10754
0.9013	High Similarity	NPC20530
0.9013	High Similarity	NPC469936
0.9013	High Similarity	NPC321372
0.9013	High Similarity	NPC475797
0.9013	High Similarity	NPC215917
0.9	High Similarity	NPC471677
0.898	High Similarity	NPC294365
0.8947	High Similarity	NPC108937
0.8947	High Similarity	NPC470603
0.8947	High Similarity	NPC470604
0.8947	High Similarity	NPC279218
0.8947	High Similarity	NPC470605
0.894	High Similarity	NPC150123
0.894	High Similarity	NPC10807
0.894	High Similarity	NPC161881
0.894	High Similarity	NPC244583
0.894	High Similarity	NPC56232
0.8933	High Similarity	NPC474735
0.8933	High Similarity	NPC476509
0.8904	High Similarity	NPC74397
0.8897	High Similarity	NPC19476
0.8897	High Similarity	NPC241975
0.8897	High Similarity	NPC472343
0.8896	High Similarity	NPC470607
0.8882	High Similarity	NPC223701
0.8882	High Similarity	NPC472583
0.8882	High Similarity	NPC248793
0.8882	High Similarity	NPC180301
0.8882	High Similarity	NPC268950
0.8882	High Similarity	NPC108706
0.8882	High Similarity	NPC469405
0.8882	High Similarity	NPC78021
0.8882	High Similarity	NPC87304
0.8882	High Similarity	NPC7989
0.8882	High Similarity	NPC211158
0.8874	High Similarity	NPC471676
0.8874	High Similarity	NPC472422
0.8874	High Similarity	NPC244577
0.8874	High Similarity	NPC472420
0.8874	High Similarity	NPC474021
0.8874	High Similarity	NPC209846
0.8874	High Similarity	NPC263384
0.8874	High Similarity	NPC250488
0.8874	High Similarity	NPC328740
0.8874	High Similarity	NPC289774
0.8874	High Similarity	NPC474023
0.8874	High Similarity	NPC477897
0.8867	High Similarity	NPC472628
0.8867	High Similarity	NPC104236
0.8867	High Similarity	NPC164205
0.8859	High Similarity	NPC202494
0.8854	High Similarity	NPC294722
0.8851	High Similarity	NPC171656
0.8831	High Similarity	NPC470606
0.8828	High Similarity	NPC183639
0.8828	High Similarity	NPC219584
0.8828	High Similarity	NPC470083
0.8828	High Similarity	NPC199458
0.8824	High Similarity	NPC111341
0.8824	High Similarity	NPC48579
0.8824	High Similarity	NPC304745
0.8824	High Similarity	NPC477958
0.8824	High Similarity	NPC469934
0.8824	High Similarity	NPC304207
0.8824	High Similarity	NPC470681
0.8824	High Similarity	NPC207809
0.8824	High Similarity	NPC217706
0.8824	High Similarity	NPC259710
0.8816	High Similarity	NPC475131
0.8816	High Similarity	NPC473770
0.8816	High Similarity	NPC475790
0.8816	High Similarity	NPC217149
0.8816	High Similarity	NPC473509
0.8816	High Similarity	NPC216035
0.8816	High Similarity	NPC138288
0.8808	High Similarity	NPC105136
0.8805	High Similarity	NPC102810
0.8797	High Similarity	NPC13481
0.8797	High Similarity	NPC207575
0.8782	High Similarity	NPC97812
0.8782	High Similarity	NPC92589
0.8776	High Similarity	NPC470555
0.8776	High Similarity	NPC285659
0.8776	High Similarity	NPC157497
0.8776	High Similarity	NPC81337
0.8767	High Similarity	NPC240305
0.8767	High Similarity	NPC64664
0.8766	High Similarity	NPC471787
0.8766	High Similarity	NPC17521
0.8759	High Similarity	NPC131782
0.8759	High Similarity	NPC474624
0.8759	High Similarity	NPC138047
0.8758	High Similarity	NPC293286
0.8758	High Similarity	NPC112701
0.8758	High Similarity	NPC326592
0.8758	High Similarity	NPC109594
0.8758	High Similarity	NPC268193
0.875	High Similarity	NPC471675
0.875	High Similarity	NPC134819
0.875	High Similarity	NPC290671
0.875	High Similarity	NPC262039
0.875	High Similarity	NPC190217
0.875	High Similarity	NPC319910
0.875	High Similarity	NPC278476
0.875	High Similarity	NPC254412
0.875	High Similarity	NPC472636
0.875	High Similarity	NPC262038
0.8742	High Similarity	NPC89442
0.8742	High Similarity	NPC164299
0.8742	High Similarity	NPC19238
0.8734	High Similarity	NPC473908
0.8734	High Similarity	NPC475979
0.8733	High Similarity	NPC472627
0.8725	High Similarity	NPC470890
0.8725	High Similarity	NPC224714
0.8725	High Similarity	NPC71184
0.8725	High Similarity	NPC297788
0.8725	High Similarity	NPC206212
0.8718	High Similarity	NPC472631
0.8718	High Similarity	NPC472630
0.8707	High Similarity	NPC221173
0.8701	High Similarity	NPC477687
0.8701	High Similarity	NPC477671
0.8699	High Similarity	NPC248995
0.8699	High Similarity	NPC272844
0.8699	High Similarity	NPC254168
0.8693	High Similarity	NPC35567
0.8693	High Similarity	NPC473996
0.8693	High Similarity	NPC171651
0.8693	High Similarity	NPC477957
0.8693	High Similarity	NPC476238
0.8693	High Similarity	NPC31627
0.8693	High Similarity	NPC243171
0.8693	High Similarity	NPC285623
0.8693	High Similarity	NPC327269
0.8684	High Similarity	NPC124478
0.8684	High Similarity	NPC214454
0.8684	High Similarity	NPC177308
0.8684	High Similarity	NPC106025
0.8684	High Similarity	NPC477240
0.8684	High Similarity	NPC191154
0.8675	High Similarity	NPC470359
0.8671	High Similarity	NPC124155
0.8671	High Similarity	NPC183672
0.8671	High Similarity	NPC257566
0.8667	High Similarity	NPC285630
0.8667	High Similarity	NPC472629
0.8667	High Similarity	NPC127059
0.8667	High Similarity	NPC470322
0.8667	High Similarity	NPC181388
0.8662	High Similarity	NPC472634
0.8658	High Similarity	NPC255133
0.8658	High Similarity	NPC242100
0.8649	High Similarity	NPC476508
0.8649	High Similarity	NPC201820

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 NPC472345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1049
0.2-0.3	2180
0.3-0.4	2597
0.4-0.5	1770
0.5-0.6	854
0.6-0.7	277
0.7-0.8	105
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD7075	Discontinued
0.8693	High Similarity	NPD6801	Discontinued
0.8684	High Similarity	NPD4380	Phase 2
0.8636	High Similarity	NPD7096	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD6651	Approved
0.8471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7819	Suspended
0.8269	Intermediate Similarity	NPD7411	Suspended
0.8235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1934	Approved
0.8146	Intermediate Similarity	NPD2800	Approved
0.8133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7054	Approved
0.8117	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD2534	Approved
0.8117	Intermediate Similarity	NPD2533	Approved
0.8113	Intermediate Similarity	NPD3817	Phase 2
0.8079	Intermediate Similarity	NPD1549	Phase 2
0.8072	Intermediate Similarity	NPD7074	Phase 3
0.8072	Intermediate Similarity	NPD7472	Approved
0.8063	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD6799	Approved
0.8049	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6166	Phase 2
0.8041	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5124	Phase 1
0.8013	Intermediate Similarity	NPD5403	Approved
0.7976	Intermediate Similarity	NPD6559	Discontinued
0.7976	Intermediate Similarity	NPD7251	Discontinued
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3818	Discontinued
0.7947	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2801	Approved
0.7929	Intermediate Similarity	NPD7808	Phase 3
0.7929	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6797	Phase 2
0.7892	Intermediate Similarity	NPD7473	Discontinued
0.7888	Intermediate Similarity	NPD5402	Approved
0.7885	Intermediate Similarity	NPD5401	Approved
0.7881	Intermediate Similarity	NPD1510	Phase 2
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.784	Intermediate Similarity	NPD7768	Phase 2
0.7821	Intermediate Similarity	NPD1511	Approved
0.7785	Intermediate Similarity	NPD920	Approved
0.7722	Intermediate Similarity	NPD1512	Approved
0.7711	Intermediate Similarity	NPD6232	Discontinued
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5494	Approved
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD1243	Approved
0.7677	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3750	Approved
0.7628	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD3882	Suspended
0.7616	Intermediate Similarity	NPD1240	Approved
0.7605	Intermediate Similarity	NPD5710	Approved
0.7605	Intermediate Similarity	NPD5711	Approved
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7286	Phase 2
0.7576	Intermediate Similarity	NPD3749	Approved
0.7571	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7425	Intermediate Similarity	NPD919	Approved
0.7419	Intermediate Similarity	NPD7033	Discontinued
0.7419	Intermediate Similarity	NPD7584	Approved
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.7414	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6100	Approved
0.7372	Intermediate Similarity	NPD6099	Approved
0.7345	Intermediate Similarity	NPD8434	Phase 2
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7308	Intermediate Similarity	NPD3748	Approved
0.7293	Intermediate Similarity	NPD4360	Phase 2
0.7293	Intermediate Similarity	NPD4363	Phase 3
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7256	Intermediate Similarity	NPD3226	Approved
0.7255	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD6832	Phase 2
0.7226	Intermediate Similarity	NPD230	Phase 1
0.7219	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2346	Discontinued
0.7196	Intermediate Similarity	NPD7585	Approved
0.7195	Intermediate Similarity	NPD1653	Approved
0.717	Intermediate Similarity	NPD2424	Discontinued
0.7166	Intermediate Similarity	NPD7435	Discontinued
0.7158	Intermediate Similarity	NPD8151	Discontinued
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD7583	Approved
0.7143	Intermediate Similarity	NPD7985	Registered
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD37	Approved
0.7126	Intermediate Similarity	NPD7228	Approved
0.7118	Intermediate Similarity	NPD6234	Discontinued
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7114	Intermediate Similarity	NPD422	Phase 1
0.7107	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6005	Phase 3
0.7107	Intermediate Similarity	NPD6004	Phase 3
0.7107	Intermediate Similarity	NPD6002	Phase 3
0.7101	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD4965	Approved
0.7101	Intermediate Similarity	NPD4967	Phase 2
0.7095	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7783	Phase 2
0.7083	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD9717	Approved
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7051	Intermediate Similarity	NPD1613	Approved
0.7051	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2797	Approved
0.7039	Intermediate Similarity	NPD1203	Approved
0.7032	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.703	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3751	Discontinued
0.7025	Intermediate Similarity	NPD7097	Phase 1
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD2403	Approved
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD447	Suspended
0.7005	Intermediate Similarity	NPD6777	Approved
0.7005	Intermediate Similarity	NPD6779	Approved
0.7005	Intermediate Similarity	NPD6776	Approved
0.7005	Intermediate Similarity	NPD6781	Approved
0.7005	Intermediate Similarity	NPD6782	Approved
0.7005	Intermediate Similarity	NPD6780	Approved
0.7005	Intermediate Similarity	NPD6778	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6994	Remote Similarity	NPD3787	Discontinued
0.6981	Remote Similarity	NPD4308	Phase 3
0.6973	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4361	Phase 2
0.6954	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7390	Discontinued
0.6943	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7874	Approved
0.6941	Remote Similarity	NPD5353	Approved
0.6933	Remote Similarity	NPD6190	Approved
0.6915	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1933	Approved
0.6895	Remote Similarity	NPD7696	Phase 3
0.6895	Remote Similarity	NPD7698	Approved
0.6895	Remote Similarity	NPD7697	Approved
0.6894	Remote Similarity	NPD2344	Approved
0.6894	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1610	Phase 2
0.6883	Remote Similarity	NPD2798	Approved
0.6879	Remote Similarity	NPD6233	Phase 2
0.6875	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5049	Phase 3
0.6864	Remote Similarity	NPD5889	Approved
0.6864	Remote Similarity	NPD5890	Approved
0.6859	Remote Similarity	NPD8320	Phase 1
0.6859	Remote Similarity	NPD8319	Approved
0.6859	Remote Similarity	NPD7870	Phase 2
0.6859	Remote Similarity	NPD7871	Phase 2
0.6857	Remote Similarity	NPD3926	Phase 2
0.6846	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD6823	Phase 2
0.6839	Remote Similarity	NPD7701	Phase 2
0.6839	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4060	Phase 1
0.6835	Remote Similarity	NPD943	Approved
0.6828	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6535	Approved
0.6821	Remote Similarity	NPD7801	Approved
0.6818	Remote Similarity	NPD3266	Approved
0.6818	Remote Similarity	NPD3267	Approved
0.6816	Remote Similarity	NPD3823	Discontinued

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