NPASS Compound

Structure

NPC102028 OpenBabel07101718332D 43 47 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 7.7942 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 6.0622 2.5000 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 2.5000 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 4.3301 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 -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 -4.3301 1.5000 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 4.3301 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 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 -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 -5.1962 0.0000 0.0000 C 0 0 1 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 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 -5.1962 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 -6.0622 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 2.5981 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 -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 6.9282 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 -3.4641 1.0000 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 37 1 0 0 0 0 2 38 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 13 2 0 0 0 0 7 28 1 0 0 0 0 8 39 1 0 0 0 0 9 37 1 0 0 0 0 10 16 2 0 0 0 0 10 29 1 0 0 0 0 11 25 2 0 0 0 0 11 38 1 0 0 0 0 12 17 2 0 0 0 0 12 40 1 0 0 0 0 13 17 1 0 0 0 0 13 41 1 0 0 0 0 14 7 1 1 0 0 0 14 18 1 0 0 0 0 14 42 1 0 0 0 0 15 8 1 1 0 0 0 15 19 1 0 0 0 0 15 43 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 30 1 6 0 0 0 19 22 1 0 0 0 0 19 31 1 6 0 0 0 20 32 2 0 0 0 0 21 23 1 0 0 0 0 21 33 1 1 0 0 0 22 24 1 0 0 0 0 22 34 1 1 0 0 0 23 26 1 0 0 0 0 23 35 1 6 0 0 0 24 27 1 0 0 0 0 24 36 1 6 0 0 0 25 40 1 0 0 0 0 26 39 1 1 0 0 0 26 42 1 0 0 0 0 27 41 1 1 0 0 0 27 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	612.17
Volume:	554.954
LogP:	-0.336
LogD:	-0.343
LogS:	-3.238
# Rotatable Bonds:	8
TPSA:	247.43
# H-Bond Aceptor:	16
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.124
Synthetic Accessibility Score:	4.7
Fsp3:	0.519
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.434
MDCK Permeability:	4.921112849842757e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	66.9910659790039%
Volume Distribution (VD):	0.678
Pgp-substrate:	21.49875831604004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.396
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.785
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.159
Carcinogencity:	0.207
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC102028

Natural Product ID:	NPC102028
*Common Name:**	1-O-[Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl]-8-Hydroxy-3,5-Dimethoxyxanthone
IUPAC Name:	8-hydroxy-3,5-dimethoxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyxanthen-9-one
Synonyms:
Standard InCHIKey:	AHBKLQCFFXMAJT-YUMVGKRXSA-N
Standard InCHI:	InChI=1S/C27H32O16/c1-37-9-5-12-17(20(32)16-10(29)3-4-11(38-2)25(16)40-12)13(6-9)41-27-24(36)22(34)19(31)15(43-27)8-39-26-23(35)21(33)18(30)14(7-28)42-26/h3-6,14-15,18-19,21-24,26-31,33-36H,7-8H2,1-2H3/t14-,15-,18-,19-,21+,22+,23-,24-,26-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(OC)cc4c3c(=O)c3c(o4)c(OC)ccc3O)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409394
PubChem CID:	71745144
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
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23805995]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9824	Swertia kouitchensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	693000.0	nM	PMID[456542]

☑ 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 NPC102028 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	463
0.1-0.2	1858
0.2-0.3	4319
0.3-0.4	9907
0.4-0.5	8224
0.5-0.6	4582
0.6-0.7	5726
0.7-0.8	5007
0.8-0.85	1490
0.85-0.9	578
0.9-0.95	414
0.95-1	129

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC156977
0.9877	High Similarity	NPC267254
0.9877	High Similarity	NPC142996
0.9816	High Similarity	NPC51774
0.9816	High Similarity	NPC239549
0.9816	High Similarity	NPC236191
0.9815	High Similarity	NPC52353
0.9815	High Similarity	NPC293004
0.9815	High Similarity	NPC194483
0.9755	High Similarity	NPC301683
0.9753	High Similarity	NPC293629
0.9753	High Similarity	NPC472383
0.9753	High Similarity	NPC472381
0.9695	High Similarity	NPC204693
0.9693	High Similarity	NPC79056
0.9693	High Similarity	NPC22195
0.9693	High Similarity	NPC105095
0.9693	High Similarity	NPC44328
0.9693	High Similarity	NPC183357
0.9693	High Similarity	NPC44558
0.9693	High Similarity	NPC21190
0.9693	High Similarity	NPC177731
0.9691	High Similarity	NPC93099
0.9639	High Similarity	NPC475261
0.9634	High Similarity	NPC3583
0.9634	High Similarity	NPC259152
0.9634	High Similarity	NPC472386
0.9634	High Similarity	NPC475155
0.9632	High Similarity	NPC210042
0.9632	High Similarity	NPC105283
0.9632	High Similarity	NPC471457
0.9632	High Similarity	NPC61791
0.9632	High Similarity	NPC43587
0.9632	High Similarity	NPC95855
0.9632	High Similarity	NPC170675
0.9632	High Similarity	NPC112755
0.963	High Similarity	NPC70441
0.9581	High Similarity	NPC241423
0.9581	High Similarity	NPC473895
0.9581	High Similarity	NPC473682
0.9581	High Similarity	NPC473571
0.9581	High Similarity	NPC470443
0.9581	High Similarity	NPC126784
0.9581	High Similarity	NPC470444
0.9581	High Similarity	NPC110941
0.9578	High Similarity	NPC169733
0.9573	High Similarity	NPC210808
0.9573	High Similarity	NPC105511
0.9573	High Similarity	NPC34287
0.9573	High Similarity	NPC474434
0.9573	High Similarity	NPC471416
0.9573	High Similarity	NPC199079
0.9527	High Similarity	NPC148710
0.9521	High Similarity	NPC472387
0.9518	High Similarity	NPC198199
0.9515	High Similarity	NPC205076
0.9515	High Similarity	NPC9002
0.9515	High Similarity	NPC137871
0.9515	High Similarity	NPC257011
0.9515	High Similarity	NPC48773
0.9515	High Similarity	NPC307518
0.9515	High Similarity	NPC288152
0.9515	High Similarity	NPC180918
0.9512	High Similarity	NPC186807
0.9512	High Similarity	NPC183036
0.9512	High Similarity	NPC93337
0.9512	High Similarity	NPC195257
0.9512	High Similarity	NPC226294
0.9512	High Similarity	NPC469931
0.9512	High Similarity	NPC86008
0.9512	High Similarity	NPC45638
0.9512	High Similarity	NPC201292
0.9512	High Similarity	NPC58053
0.9512	High Similarity	NPC209296
0.9512	High Similarity	NPC105025
0.9512	High Similarity	NPC475942
0.9512	High Similarity	NPC229687
0.9509	High Similarity	NPC236934
0.9509	High Similarity	NPC5778
0.9467	High Similarity	NPC470449
0.9467	High Similarity	NPC470447
0.9467	High Similarity	NPC470446
0.9467	High Similarity	NPC470445
0.9467	High Similarity	NPC473072
0.9461	High Similarity	NPC8573
0.9461	High Similarity	NPC472384
0.9461	High Similarity	NPC48984
0.9461	High Similarity	NPC65563
0.9461	High Similarity	NPC472382
0.9461	High Similarity	NPC470949
0.9461	High Similarity	NPC472380
0.9461	High Similarity	NPC255799
0.9458	High Similarity	NPC208668
0.9455	High Similarity	NPC224462
0.9455	High Similarity	NPC51326
0.9455	High Similarity	NPC231194
0.9451	High Similarity	NPC45400
0.9451	High Similarity	NPC146792
0.9451	High Similarity	NPC45618
0.9451	High Similarity	NPC135345
0.9451	High Similarity	NPC58716
0.9448	High Similarity	NPC475497
0.9448	High Similarity	NPC15358
0.9448	High Similarity	NPC284277
0.9448	High Similarity	NPC475366
0.9412	High Similarity	NPC470455
0.9412	High Similarity	NPC470451
0.9408	High Similarity	NPC473071
0.9408	High Similarity	NPC473073
0.9405	High Similarity	NPC476619
0.9405	High Similarity	NPC89052
0.9405	High Similarity	NPC476622
0.9405	High Similarity	NPC476621
0.9405	High Similarity	NPC476623
0.9405	High Similarity	NPC120952
0.9405	High Similarity	NPC476620
0.9405	High Similarity	NPC476618
0.9405	High Similarity	NPC251417
0.9401	High Similarity	NPC294815
0.9401	High Similarity	NPC16194
0.9401	High Similarity	NPC476472
0.9401	High Similarity	NPC473327
0.9401	High Similarity	NPC19108
0.9401	High Similarity	NPC220173
0.9398	High Similarity	NPC172807
0.9398	High Similarity	NPC261254
0.9398	High Similarity	NPC256760
0.9398	High Similarity	NPC254540
0.9398	High Similarity	NPC476405
0.9398	High Similarity	NPC211594
0.9398	High Similarity	NPC117260
0.939	High Similarity	NPC115674
0.939	High Similarity	NPC210073
0.939	High Similarity	NPC181616
0.939	High Similarity	NPC8856
0.939	High Similarity	NPC99957
0.9387	High Similarity	NPC127415
0.9387	High Similarity	NPC309025
0.9387	High Similarity	NPC88023
0.9387	High Similarity	NPC243930
0.9387	High Similarity	NPC29830
0.936	High Similarity	NPC473618
0.9353	High Similarity	NPC473883
0.9349	High Similarity	NPC192539
0.9345	High Similarity	NPC219043
0.9345	High Similarity	NPC14187
0.9345	High Similarity	NPC268533
0.9345	High Similarity	NPC202908
0.9345	High Similarity	NPC122467
0.9345	High Similarity	NPC292019
0.9345	High Similarity	NPC257714
0.9341	High Similarity	NPC21666
0.9341	High Similarity	NPC169977
0.9341	High Similarity	NPC45522
0.9341	High Similarity	NPC25724
0.9341	High Similarity	NPC24043
0.9341	High Similarity	NPC42773
0.9341	High Similarity	NPC101026
0.9337	High Similarity	NPC285197
0.9337	High Similarity	NPC150767
0.9337	High Similarity	NPC218488
0.9337	High Similarity	NPC78734
0.9337	High Similarity	NPC245014
0.9337	High Similarity	NPC84265
0.9337	High Similarity	NPC282987
0.9337	High Similarity	NPC67105
0.9333	High Similarity	NPC477502
0.9333	High Similarity	NPC229729
0.9329	High Similarity	NPC311830
0.9329	High Similarity	NPC165720
0.9329	High Similarity	NPC22832
0.9325	High Similarity	NPC148273
0.9325	High Similarity	NPC300537
0.9325	High Similarity	NPC127782
0.9321	High Similarity	NPC97285
0.9321	High Similarity	NPC142860
0.9321	High Similarity	NPC271270
0.9321	High Similarity	NPC246469
0.9302	High Similarity	NPC179947
0.929	High Similarity	NPC168584
0.929	High Similarity	NPC173837
0.929	High Similarity	NPC241196
0.9286	High Similarity	NPC264735
0.9286	High Similarity	NPC477848
0.9286	High Similarity	NPC472607
0.9281	High Similarity	NPC33054
0.9281	High Similarity	NPC155877
0.9281	High Similarity	NPC203259
0.9281	High Similarity	NPC471748
0.9281	High Similarity	NPC134532
0.9281	High Similarity	NPC60735
0.9281	High Similarity	NPC176740
0.9281	High Similarity	NPC26230
0.9281	High Similarity	NPC471725
0.9277	High Similarity	NPC52382
0.9277	High Similarity	NPC227508
0.9277	High Similarity	NPC270578
0.9268	High Similarity	NPC270335
0.9268	High Similarity	NPC88043
0.9268	High Similarity	NPC94777

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 NPC102028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	962
0.2-0.3	2021
0.3-0.4	2741
0.4-0.5	1797
0.5-0.6	824
0.6-0.7	267
0.7-0.8	99
0.8-0.85	17
0.85-0.9	6
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9693	High Similarity	NPD7074	Phase 3
0.9573	High Similarity	NPD7472	Approved
0.9512	High Similarity	NPD7054	Approved
0.9401	High Similarity	NPD7808	Phase 3
0.9341	High Similarity	NPD7251	Discontinued
0.9281	High Similarity	NPD6797	Phase 2
0.9172	High Similarity	NPD4338	Clinical (unspecified phase)
0.9102	High Similarity	NPD3818	Discontinued
0.8982	High Similarity	NPD6166	Phase 2
0.8982	High Similarity	NPD6168	Clinical (unspecified phase)
0.8982	High Similarity	NPD6167	Clinical (unspecified phase)
0.8963	High Similarity	NPD4381	Clinical (unspecified phase)
0.8935	High Similarity	NPD7804	Clinical (unspecified phase)
0.8834	High Similarity	NPD1934	Approved
0.878	High Similarity	NPD2801	Approved
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8521	High Similarity	NPD5494	Approved
0.8452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD3817	Phase 2
0.8373	Intermediate Similarity	NPD4380	Phase 2
0.8352	Intermediate Similarity	NPD6559	Discontinued
0.8343	Intermediate Similarity	NPD3882	Suspended
0.8294	Intermediate Similarity	NPD7075	Discontinued
0.8242	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD1511	Approved
0.8182	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD5402	Approved
0.8156	Intermediate Similarity	NPD8313	Approved
0.8156	Intermediate Similarity	NPD8312	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8125	Intermediate Similarity	NPD7228	Approved
0.8118	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD7473	Discontinued
0.8046	Intermediate Similarity	NPD6959	Discontinued
0.8037	Intermediate Similarity	NPD1549	Phase 2
0.8036	Intermediate Similarity	NPD1653	Approved
0.8033	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7964	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD6801	Discontinued
0.7921	Intermediate Similarity	NPD3751	Discontinued
0.7898	Intermediate Similarity	NPD3787	Discontinued
0.7897	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD7783	Phase 2
0.7895	Intermediate Similarity	NPD7411	Suspended
0.7887	Intermediate Similarity	NPD8151	Discontinued
0.787	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD7685	Pre-registration
0.7845	Intermediate Similarity	NPD7240	Approved
0.7842	Intermediate Similarity	NPD6778	Approved
0.7842	Intermediate Similarity	NPD6781	Approved
0.7842	Intermediate Similarity	NPD6780	Approved
0.7842	Intermediate Similarity	NPD6782	Approved
0.7842	Intermediate Similarity	NPD6779	Approved
0.7842	Intermediate Similarity	NPD6777	Approved
0.7842	Intermediate Similarity	NPD6776	Approved
0.7841	Intermediate Similarity	NPD7199	Phase 2
0.7812	Intermediate Similarity	NPD7696	Phase 3
0.7812	Intermediate Similarity	NPD7435	Discontinued
0.7812	Intermediate Similarity	NPD7698	Approved
0.7812	Intermediate Similarity	NPD7697	Approved
0.7805	Intermediate Similarity	NPD2796	Approved
0.7803	Intermediate Similarity	NPD8455	Phase 2
0.7798	Intermediate Similarity	NPD6799	Approved
0.7772	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5403	Approved
0.7751	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD7701	Phase 2
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7727	Intermediate Similarity	NPD6234	Discontinued
0.7714	Intermediate Similarity	NPD4966	Approved
0.7714	Intermediate Similarity	NPD4967	Phase 2
0.7714	Intermediate Similarity	NPD4965	Approved
0.7709	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7870	Phase 2
0.768	Intermediate Similarity	NPD7871	Phase 2
0.7668	Intermediate Similarity	NPD6823	Phase 2
0.7654	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD5401	Approved
0.7644	Intermediate Similarity	NPD7700	Phase 2
0.7644	Intermediate Similarity	NPD7699	Phase 2
0.764	Intermediate Similarity	NPD1247	Approved
0.763	Intermediate Similarity	NPD6599	Discontinued
0.7607	Intermediate Similarity	NPD1613	Approved
0.7607	Intermediate Similarity	NPD1240	Approved
0.7607	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7584	Approved
0.7588	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6535	Approved
0.7579	Intermediate Similarity	NPD6534	Approved
0.7576	Intermediate Similarity	NPD7874	Approved
0.7576	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD3926	Phase 2
0.7538	Intermediate Similarity	NPD7801	Approved
0.7515	Intermediate Similarity	NPD1607	Approved
0.7515	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD943	Approved
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7472	Intermediate Similarity	NPD3749	Approved
0.7455	Intermediate Similarity	NPD1933	Approved
0.743	Intermediate Similarity	NPD919	Approved
0.7423	Intermediate Similarity	NPD3027	Phase 3
0.7412	Intermediate Similarity	NPD4628	Phase 3
0.7412	Intermediate Similarity	NPD3750	Approved
0.7411	Intermediate Similarity	NPD8319	Approved
0.7411	Intermediate Similarity	NPD8320	Phase 1
0.7396	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6190	Approved
0.7362	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD8434	Phase 2
0.7354	Intermediate Similarity	NPD8150	Discontinued
0.7349	Intermediate Similarity	NPD230	Phase 1
0.7349	Intermediate Similarity	NPD447	Suspended
0.7344	Intermediate Similarity	NPD6212	Phase 3
0.7344	Intermediate Similarity	NPD6213	Phase 3
0.7344	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2534	Approved
0.7341	Intermediate Similarity	NPD2532	Approved
0.7341	Intermediate Similarity	NPD2533	Approved
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1551	Phase 2
0.7273	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD7458	Discontinued
0.7251	Intermediate Similarity	NPD2800	Approved
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6674	Discontinued
0.7247	Intermediate Similarity	NPD6844	Discontinued
0.7231	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7214	Intermediate Similarity	NPD7585	Approved
0.7212	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7286	Phase 2
0.7176	Intermediate Similarity	NPD6100	Approved
0.7176	Intermediate Similarity	NPD6099	Approved
0.7175	Intermediate Similarity	NPD3226	Approved
0.7164	Intermediate Similarity	NPD7583	Approved
0.7159	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD6651	Approved
0.7086	Intermediate Similarity	NPD7390	Discontinued
0.7072	Intermediate Similarity	NPD5353	Approved
0.7053	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6832	Phase 2
0.7048	Intermediate Similarity	NPD4908	Phase 1
0.7045	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD8059	Phase 3
0.7041	Intermediate Similarity	NPD4360	Phase 2
0.7041	Intermediate Similarity	NPD4363	Phase 3
0.7037	Intermediate Similarity	NPD1091	Approved
0.7035	Intermediate Similarity	NPD2346	Discontinued
0.7035	Intermediate Similarity	NPD2344	Approved
0.703	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2799	Discontinued
0.7018	Intermediate Similarity	NPD7033	Discontinued
0.7018	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD9494	Approved
0.6981	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8127	Discontinued
0.6965	Remote Similarity	NPD5005	Approved
0.6965	Remote Similarity	NPD5006	Approved
0.6964	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2313	Discontinued
0.6963	Remote Similarity	NPD7549	Discontinued
0.6959	Remote Similarity	NPD6843	Phase 3
0.6959	Remote Similarity	NPD6842	Approved
0.6959	Remote Similarity	NPD7097	Phase 1
0.6959	Remote Similarity	NPD6841	Approved
0.6954	Remote Similarity	NPD1243	Approved
0.6935	Remote Similarity	NPD5710	Approved
0.6935	Remote Similarity	NPD5711	Approved
0.6933	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD7930	Approved
0.6919	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6385	Approved
0.6906	Remote Similarity	NPD6386	Approved
0.6891	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD2309	Approved
0.6867	Remote Similarity	NPD1203	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