NPASS Compound

Structure

NPC236191 OpenBabel07101718312D 41 45 0 0 1 0 0 0 0 0999 V2000 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 6.0622 2.5000 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 4.3301 -1.5000 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 -4.3301 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 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 2.5981 -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 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 1 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 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 5.1962 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 -6.0622 -0.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 1.7321 -2.0000 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 35 1 0 0 0 0 2 36 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 11 1 0 0 0 0 7 37 1 0 0 0 0 8 38 1 0 0 0 0 9 35 1 0 0 0 0 10 24 2 0 0 0 0 10 27 1 0 0 0 0 11 18 1 0 0 0 0 11 28 1 6 0 0 0 12 17 2 0 0 0 0 12 39 1 0 0 0 0 13 16 2 0 0 0 0 13 39 1 0 0 0 0 14 16 1 0 0 0 0 14 40 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 41 1 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 0 0 0 0 18 29 1 1 0 0 0 19 21 1 0 0 0 0 19 30 1 6 0 0 0 20 31 2 0 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 25 1 0 0 0 0 22 33 1 6 0 0 0 23 26 1 0 0 0 0 23 34 1 6 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 25 38 1 1 0 0 0 26 40 1 1 0 0 0 26 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.16
Volume:	528.868
LogP:	-0.113
LogD:	-0.235
LogS:	-4.067
# Rotatable Bonds:	7
TPSA:	227.2
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	4.694
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.369
MDCK Permeability:	3.311169348307885e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.791
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	71.1044692993164%
Volume Distribution (VD):	0.639
Pgp-substrate:	23.32355499267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.287
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.214
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.583
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.727
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.727
Carcinogencity:	0.142
Eye Corrosion:	0.003
Eye Irritation:	0.12
Respiratory Toxicity:	0.021

Download Data

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

Natural Product: NPC236191

Natural Product ID:	NPC236191
*Common Name:**	Gentiabavaroside
IUPAC Name:	2-hydroxy-1,6-dimethoxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
Synonyms:	Gentiabavaroside
Standard InCHIKey:	UKMQUWHBRDHCSO-PVSYHSAYSA-N
Standard InCHI:	InChI=1S/C26H30O15/c1-35-9-5-13-16(20(31)17-12(39-13)4-3-10(27)24(17)36-2)14(6-9)40-26-23(34)21(32)19(30)15(41-26)8-38-25-22(33)18(29)11(28)7-37-25/h3-6,11,15,18-19,21-23,25-30,32-34H,7-8H2,1-2H3/t11-,15-,18+,19-,21+,22-,23-,25+,26-/m1/s1
SMILES:	COc1cc2c(c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O)O1)O)O)O)c(=O)c1c(ccc(c1OC)O)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501591
PubChem CID:	44577325
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18406151]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22057	Gentiana kochiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22057	Gentiana kochiana	Species	Gentianaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	IC50	>	100000.0	nM	PMID[460975]
NPT380	Cell Line	U-251	Homo sapiens	IC50	>	100000.0	nM	PMID[460975]

☑ 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 NPC236191 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	450
0.1-0.2	1859
0.2-0.3	4220
0.3-0.4	9919
0.4-0.5	8345
0.5-0.6	4423
0.6-0.7	5469
0.7-0.8	5212
0.8-0.85	1625
0.85-0.9	670
0.9-0.95	390
0.95-1	115

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC239549
1.0	High Similarity	NPC51774
0.9938	High Similarity	NPC301683
0.9938	High Similarity	NPC267254
0.9876	High Similarity	NPC21190
0.9876	High Similarity	NPC22195
0.9876	High Similarity	NPC183357
0.9816	High Similarity	NPC142996
0.9816	High Similarity	NPC102028
0.9815	High Similarity	NPC156977
0.9814	High Similarity	NPC472383
0.9814	High Similarity	NPC471457
0.9814	High Similarity	NPC112755
0.9814	High Similarity	NPC170675
0.9814	High Similarity	NPC95855
0.9814	High Similarity	NPC472381
0.9814	High Similarity	NPC210042
0.9755	High Similarity	NPC204693
0.9753	High Similarity	NPC79056
0.9753	High Similarity	NPC177731
0.9753	High Similarity	NPC471416
0.9753	High Similarity	NPC293004
0.9753	High Similarity	NPC34287
0.9753	High Similarity	NPC105095
0.9753	High Similarity	NPC44328
0.9753	High Similarity	NPC44558
0.9753	High Similarity	NPC474434
0.9752	High Similarity	NPC93099
0.9693	High Similarity	NPC3583
0.9693	High Similarity	NPC205076
0.9693	High Similarity	NPC472386
0.9693	High Similarity	NPC307518
0.9693	High Similarity	NPC48773
0.9693	High Similarity	NPC259152
0.9691	High Similarity	NPC201292
0.9691	High Similarity	NPC475942
0.9691	High Similarity	NPC469931
0.9691	High Similarity	NPC186807
0.9691	High Similarity	NPC45638
0.9691	High Similarity	NPC93337
0.9691	High Similarity	NPC43587
0.9691	High Similarity	NPC226294
0.9691	High Similarity	NPC293629
0.9691	High Similarity	NPC105025
0.9691	High Similarity	NPC183036
0.9691	High Similarity	NPC229687
0.9691	High Similarity	NPC58053
0.9689	High Similarity	NPC5778
0.9689	High Similarity	NPC236934
0.9636	High Similarity	NPC169733
0.9632	High Similarity	NPC105511
0.9632	High Similarity	NPC231194
0.9632	High Similarity	NPC194483
0.9632	High Similarity	NPC51326
0.9632	High Similarity	NPC52353
0.9632	High Similarity	NPC224462
0.963	High Similarity	NPC45400
0.963	High Similarity	NPC146792
0.963	High Similarity	NPC45618
0.963	High Similarity	NPC58716
0.9578	High Similarity	NPC476623
0.9578	High Similarity	NPC476621
0.9578	High Similarity	NPC476620
0.9578	High Similarity	NPC472387
0.9578	High Similarity	NPC476618
0.9578	High Similarity	NPC476619
0.9578	High Similarity	NPC476622
0.9573	High Similarity	NPC172807
0.9573	High Similarity	NPC476405
0.9573	High Similarity	NPC211594
0.9573	High Similarity	NPC117260
0.9573	High Similarity	NPC475155
0.9573	High Similarity	NPC254540
0.9573	High Similarity	NPC256760
0.9571	High Similarity	NPC105283
0.9571	High Similarity	NPC195257
0.9571	High Similarity	NPC209296
0.9571	High Similarity	NPC61791
0.9568	High Similarity	NPC210073
0.9568	High Similarity	NPC115674
0.9568	High Similarity	NPC70441
0.9568	High Similarity	NPC99957
0.9568	High Similarity	NPC181616
0.9565	High Similarity	NPC29830
0.9521	High Similarity	NPC110941
0.9521	High Similarity	NPC241423
0.9521	High Similarity	NPC473682
0.9521	High Similarity	NPC126784
0.9521	High Similarity	NPC473571
0.9521	High Similarity	NPC470444
0.9521	High Similarity	NPC470443
0.9518	High Similarity	NPC65563
0.9518	High Similarity	NPC472382
0.9518	High Similarity	NPC268533
0.9518	High Similarity	NPC472380
0.9518	High Similarity	NPC8573
0.9518	High Similarity	NPC472384
0.9518	High Similarity	NPC470949
0.9515	High Similarity	NPC42773
0.9515	High Similarity	NPC21666
0.9515	High Similarity	NPC45522
0.9515	High Similarity	NPC24043
0.9515	High Similarity	NPC101026
0.9515	High Similarity	NPC169977
0.9515	High Similarity	NPC208668
0.9512	High Similarity	NPC78734
0.9512	High Similarity	NPC282987
0.9512	High Similarity	NPC245014
0.9512	High Similarity	NPC84265
0.9512	High Similarity	NPC150767
0.9509	High Similarity	NPC135345
0.9509	High Similarity	NPC477502
0.9509	High Similarity	NPC229729
0.9506	High Similarity	NPC22832
0.9506	High Similarity	NPC311830
0.9506	High Similarity	NPC165720
0.9503	High Similarity	NPC127782
0.9503	High Similarity	NPC300537
0.9467	High Similarity	NPC148710
0.9464	High Similarity	NPC473071
0.9464	High Similarity	NPC473073
0.9461	High Similarity	NPC168584
0.9461	High Similarity	NPC475261
0.9458	High Similarity	NPC477848
0.9458	High Similarity	NPC198199
0.9458	High Similarity	NPC472607
0.9455	High Similarity	NPC261254
0.9455	High Similarity	NPC180918
0.9451	High Similarity	NPC270578
0.9451	High Similarity	NPC86008
0.9451	High Similarity	NPC52382
0.9448	High Similarity	NPC8856
0.9444	High Similarity	NPC191306
0.9444	High Similarity	NPC270335
0.9444	High Similarity	NPC222936
0.9444	High Similarity	NPC88023
0.9444	High Similarity	NPC127415
0.9444	High Similarity	NPC88043
0.9444	High Similarity	NPC243930
0.9444	High Similarity	NPC284960
0.9444	High Similarity	NPC94777
0.9444	High Similarity	NPC19709
0.9444	High Similarity	NPC309025
0.9415	High Similarity	NPC473618
0.9408	High Similarity	NPC473072
0.9408	High Similarity	NPC470446
0.9408	High Similarity	NPC470449
0.9408	High Similarity	NPC470447
0.9408	High Similarity	NPC470445
0.9405	High Similarity	NPC473895
0.9401	High Similarity	NPC255799
0.9401	High Similarity	NPC472385
0.9401	High Similarity	NPC198324
0.9401	High Similarity	NPC472991
0.9401	High Similarity	NPC233994
0.9401	High Similarity	NPC211532
0.9401	High Similarity	NPC472992
0.9394	High Similarity	NPC210808
0.9394	High Similarity	NPC95866
0.9394	High Similarity	NPC285197
0.9394	High Similarity	NPC212748
0.9394	High Similarity	NPC67105
0.9394	High Similarity	NPC218488
0.9394	High Similarity	NPC199079
0.939	High Similarity	NPC160156
0.939	High Similarity	NPC92565
0.939	High Similarity	NPC116745
0.939	High Similarity	NPC14662
0.9387	High Similarity	NPC475366
0.9387	High Similarity	NPC475497
0.9387	High Similarity	NPC284277
0.9383	High Similarity	NPC473043
0.9383	High Similarity	NPC77660
0.9383	High Similarity	NPC189142
0.9357	High Similarity	NPC179947
0.9353	High Similarity	NPC470455
0.9353	High Similarity	NPC470451
0.9345	High Similarity	NPC89052
0.9345	High Similarity	NPC251417
0.9345	High Similarity	NPC120952
0.9341	High Similarity	NPC237435
0.9341	High Similarity	NPC115760
0.9341	High Similarity	NPC101191
0.9341	High Similarity	NPC108202
0.9341	High Similarity	NPC49344
0.9341	High Similarity	NPC473327
0.9341	High Similarity	NPC476472
0.9341	High Similarity	NPC294629
0.9341	High Similarity	NPC16194
0.9341	High Similarity	NPC19108
0.9341	High Similarity	NPC135277
0.9341	High Similarity	NPC210094
0.9341	High Similarity	NPC264735
0.9341	High Similarity	NPC220173
0.9341	High Similarity	NPC294815
0.9341	High Similarity	NPC43211
0.9337	High Similarity	NPC137871
0.9337	High Similarity	NPC67134
0.9337	High Similarity	NPC176740
0.9337	High Similarity	NPC235575

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 NPC236191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	947
0.2-0.3	1984
0.3-0.4	2769
0.4-0.5	1784
0.5-0.6	845
0.6-0.7	279
0.7-0.8	107
0.8-0.85	15
0.85-0.9	6
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9753	High Similarity	NPD7074	Phase 3
0.9571	High Similarity	NPD7054	Approved
0.9512	High Similarity	NPD7472	Approved
0.9341	High Similarity	NPD4338	Clinical (unspecified phase)
0.9337	High Similarity	NPD6797	Phase 2
0.9281	High Similarity	NPD7251	Discontinued
0.9273	High Similarity	NPD3818	Discontinued
0.9226	High Similarity	NPD7808	Phase 3
0.9152	High Similarity	NPD6167	Clinical (unspecified phase)
0.9152	High Similarity	NPD6168	Clinical (unspecified phase)
0.9152	High Similarity	NPD6166	Phase 2
0.9018	High Similarity	NPD4381	Clinical (unspecified phase)
0.9006	High Similarity	NPD1934	Approved
0.8951	High Similarity	NPD2801	Approved
0.8876	High Similarity	NPD7804	Clinical (unspecified phase)
0.8834	High Similarity	NPD2393	Clinical (unspecified phase)
0.8614	High Similarity	NPD4868	Clinical (unspecified phase)
0.8571	High Similarity	NPD5494	Approved
0.8503	High Similarity	NPD3882	Suspended
0.8448	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD3817	Phase 2
0.8424	Intermediate Similarity	NPD4380	Phase 2
0.84	Intermediate Similarity	NPD6559	Discontinued
0.8395	Intermediate Similarity	NPD1511	Approved
0.8293	Intermediate Similarity	NPD1512	Approved
0.8235	Intermediate Similarity	NPD7075	Discontinued
0.8229	Intermediate Similarity	NPD5844	Phase 1
0.8225	Intermediate Similarity	NPD5402	Approved
0.8193	Intermediate Similarity	NPD1653	Approved
0.8187	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7228	Approved
0.8166	Intermediate Similarity	NPD1465	Phase 2
0.8137	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6959	Discontinued
0.8086	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD8312	Approved
0.8	Intermediate Similarity	NPD8313	Approved
0.7966	Intermediate Similarity	NPD3751	Discontinued
0.7953	Intermediate Similarity	NPD7819	Suspended
0.7943	Intermediate Similarity	NPD3787	Discontinued
0.7941	Intermediate Similarity	NPD7411	Suspended
0.7917	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7685	Pre-registration
0.7886	Intermediate Similarity	NPD7199	Phase 2
0.7884	Intermediate Similarity	NPD6776	Approved
0.7884	Intermediate Similarity	NPD6780	Approved
0.7884	Intermediate Similarity	NPD6778	Approved
0.7884	Intermediate Similarity	NPD6781	Approved
0.7884	Intermediate Similarity	NPD6777	Approved
0.7884	Intermediate Similarity	NPD6782	Approved
0.7884	Intermediate Similarity	NPD6779	Approved
0.7874	Intermediate Similarity	NPD6234	Discontinued
0.7853	Intermediate Similarity	NPD2796	Approved
0.7846	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7783	Phase 2
0.7844	Intermediate Similarity	NPD6799	Approved
0.7814	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5403	Approved
0.7798	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD37	Approved
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.7764	Intermediate Similarity	NPD1613	Approved
0.7764	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7435	Discontinued
0.776	Intermediate Similarity	NPD7696	Phase 3
0.776	Intermediate Similarity	NPD7697	Approved
0.776	Intermediate Similarity	NPD7698	Approved
0.7759	Intermediate Similarity	NPD4965	Approved
0.7759	Intermediate Similarity	NPD4967	Phase 2
0.7759	Intermediate Similarity	NPD4966	Approved
0.7753	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8151	Discontinued
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7266	Discontinued
0.7692	Intermediate Similarity	NPD7701	Phase 2
0.7692	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD7240	Approved
0.7684	Intermediate Similarity	NPD1247	Approved
0.7674	Intermediate Similarity	NPD6599	Discontinued
0.7654	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD943	Approved
0.7644	Intermediate Similarity	NPD8455	Phase 2
0.7633	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7871	Phase 2
0.7629	Intermediate Similarity	NPD7870	Phase 2
0.7619	Intermediate Similarity	NPD6534	Approved
0.7619	Intermediate Similarity	NPD6535	Approved
0.7617	Intermediate Similarity	NPD6823	Phase 2
0.7598	Intermediate Similarity	NPD3926	Phase 2
0.7592	Intermediate Similarity	NPD7700	Phase 2
0.7592	Intermediate Similarity	NPD7699	Phase 2
0.7578	Intermediate Similarity	NPD3027	Phase 3
0.7561	Intermediate Similarity	NPD1607	Approved
0.756	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7584	Approved
0.753	Intermediate Similarity	NPD2935	Discontinued
0.7525	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7874	Approved
0.7516	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6190	Approved
0.7514	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7487	Intermediate Similarity	NPD7801	Approved
0.7472	Intermediate Similarity	NPD919	Approved
0.7458	Intermediate Similarity	NPD7768	Phase 2
0.7456	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD3750	Approved
0.7453	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD447	Suspended
0.7384	Intermediate Similarity	NPD2534	Approved
0.7384	Intermediate Similarity	NPD2533	Approved
0.7384	Intermediate Similarity	NPD2532	Approved
0.7382	Intermediate Similarity	NPD6213	Phase 3
0.7382	Intermediate Similarity	NPD6212	Phase 3
0.7382	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8319	Approved
0.736	Intermediate Similarity	NPD8320	Phase 1
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7317	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7680	Approved
0.7302	Intermediate Similarity	NPD8150	Discontinued
0.7294	Intermediate Similarity	NPD2800	Approved
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5953	Discontinued
0.7216	Intermediate Similarity	NPD7458	Discontinued
0.7216	Intermediate Similarity	NPD3226	Approved
0.7211	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD920	Approved
0.7193	Intermediate Similarity	NPD6674	Discontinued
0.7191	Intermediate Similarity	NPD6844	Discontinued
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD7585	Approved
0.7163	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3748	Approved
0.7151	Intermediate Similarity	NPD7286	Phase 2
0.7134	Intermediate Similarity	NPD9494	Approved
0.7126	Intermediate Similarity	NPD7390	Discontinued
0.7118	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD6099	Approved
0.7114	Intermediate Similarity	NPD7583	Approved
0.7095	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4908	Phase 1
0.709	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1091	Approved
0.7077	Intermediate Similarity	NPD4360	Phase 2
0.7077	Intermediate Similarity	NPD4363	Phase 3
0.7076	Intermediate Similarity	NPD2344	Approved
0.7076	Intermediate Similarity	NPD2346	Discontinued
0.7065	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7041	Intermediate Similarity	NPD6651	Approved
0.7027	Intermediate Similarity	NPD5242	Approved
0.7017	Intermediate Similarity	NPD5353	Approved
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD5006	Approved
0.7	Intermediate Similarity	NPD7549	Discontinued
0.6995	Remote Similarity	NPD8059	Phase 3
0.6995	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6832	Phase 2
0.6975	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5711	Approved
0.6973	Remote Similarity	NPD5710	Approved
0.6971	Remote Similarity	NPD643	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2798	Approved
0.6964	Remote Similarity	NPD6233	Phase 2
0.6959	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2861	Phase 2
0.6927	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD2309	Approved
0.6909	Remote Similarity	NPD1203	Approved
0.6907	Remote Similarity	NPD6842	Approved
0.6907	Remote Similarity	NPD6841	Approved
0.6907	Remote Similarity	NPD6843	Phase 3
0.6905	Remote Similarity	NPD6798	Discontinued
0.6901	Remote Similarity	NPD7097	Phase 1

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