NPASS Compound

Structure

NPC289396 OpenBabel07101719512D 42 46 0 0 1 0 0 0 0 0999 V2000 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -2.5981 2.5000 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -3.4641 3.0000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 20 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 14 2 0 0 0 0 7 15 2 0 0 0 0 7 17 1 0 0 0 0 8 16 2 0 0 0 0 8 18 1 0 0 0 0 9 29 1 0 0 0 0 11 17 2 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 16 34 1 0 0 0 0 17 40 1 0 0 0 0 18 22 2 0 0 0 0 18 40 1 0 0 0 0 19 9 1 1 0 0 0 19 24 1 0 0 0 0 19 41 1 0 0 0 0 20 35 2 0 0 0 0 20 42 1 0 0 0 0 21 25 2 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 36 2 0 0 0 0 24 26 1 0 0 0 0 24 37 1 6 0 0 0 25 38 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 1 0 0 0 27 21 1 1 0 0 0 27 28 1 0 0 0 0 27 41 1 0 0 0 0 28 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.12
Volume:	541.487
LogP:	1.618
LogD:	0.59
LogS:	-4.087
# Rotatable Bonds:	6
TPSA:	247.81
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	4.41
Fsp3:	0.214
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.481
MDCK Permeability:	5.920701823924901e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.712
Human Intestinal Absorption (HIA):	0.924
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	92.9721450805664%
Volume Distribution (VD):	0.544
Pgp-substrate:	15.98216724395752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.298
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.485
CYP2C9-substrate:	0.195
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	6.628
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.689
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.962
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.878
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC289396

Natural Product ID:	NPC289396
*Common Name:**	2-(2'-O-Trans-Caffeoyl)-C-Beta-D-Glucopyranosyl-1,3,6,7-Tetrahydroxyxanthone
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(1,3,6,7-tetrahydroxy-9-oxoxanthen-2-yl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	KJGSFWHQWXCZRH-GIPHEDKVSA-N
Standard InCHI:	InChI=1S/C28H24O14/c29-9-19-24(37)26(39)28(42-20(35)4-2-10-1-3-12(30)13(31)5-10)27(41-19)21-16(34)8-18-22(25(21)38)23(36)11-6-14(32)15(33)7-17(11)40-18/h1-8,19,24,26-34,37-39H,9H2/b4-2+/t19-,24-,26+,27+,28-/m1/s1
SMILES:	c1cc(c(cc1/C=C/C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1c1c(cc2c(c(=O)c3cc(c(cc3o2)O)O)c1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504852
PubChem CID:	11365276
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
NPO1372	Arrabidaea samydoides	Species	Bignoniaceae	Eukaryota	stems	n.a.	n.a.	PMID[14575443]
NPO1372	Arrabidaea samydoides	Species	Bignoniaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	17810.0	nM	PMID[493622]

☑ 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 NPC289396 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	429
0.1-0.2	1745
0.2-0.3	4015
0.3-0.4	9247
0.4-0.5	9025
0.5-0.6	4150
0.6-0.7	5228
0.7-0.8	4962
0.8-0.85	2197
0.85-0.9	1477
0.9-0.95	209
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271848
1.0	High Similarity	NPC262580
1.0	High Similarity	NPC81332
1.0	High Similarity	NPC212038
0.9568	High Similarity	NPC14662
0.9565	High Similarity	NPC471788
0.9518	High Similarity	NPC476621
0.9518	High Similarity	NPC476623
0.9518	High Similarity	NPC476620
0.9518	High Similarity	NPC476618
0.9518	High Similarity	NPC476619
0.9518	High Similarity	NPC476622
0.95	High Similarity	NPC228383
0.9448	High Similarity	NPC243877
0.9448	High Similarity	NPC260266
0.9441	High Similarity	NPC220912
0.9401	High Similarity	NPC472387
0.9394	High Similarity	NPC67134
0.9394	High Similarity	NPC47140
0.9387	High Similarity	NPC207575
0.9387	High Similarity	NPC13481
0.9379	High Similarity	NPC142252
0.9341	High Similarity	NPC472991
0.9341	High Similarity	NPC472992
0.9321	High Similarity	NPC476247
0.9317	High Similarity	NPC24164
0.9313	High Similarity	NPC289322
0.9313	High Similarity	NPC68324
0.9313	High Similarity	NPC160512
0.9313	High Similarity	NPC38779
0.9313	High Similarity	NPC114179
0.9313	High Similarity	NPC156818
0.9286	High Similarity	NPC265380
0.9277	High Similarity	NPC257667
0.9277	High Similarity	NPC186847
0.9277	High Similarity	NPC472454
0.9268	High Similarity	NPC224851
0.9255	High Similarity	NPC53545
0.9255	High Similarity	NPC117418
0.925	High Similarity	NPC250436
0.925	High Similarity	NPC291948
0.925	High Similarity	NPC300845
0.925	High Similarity	NPC104983
0.925	High Similarity	NPC88803
0.9231	High Similarity	NPC324742
0.9231	High Similarity	NPC185275
0.9217	High Similarity	NPC103307
0.9217	High Similarity	NPC476365
0.9217	High Similarity	NPC204937
0.9217	High Similarity	NPC149011
0.9217	High Similarity	NPC34287
0.9217	High Similarity	NPC471416
0.9212	High Similarity	NPC295082
0.9207	High Similarity	NPC7154
0.9207	High Similarity	NPC36916
0.9207	High Similarity	NPC36
0.9207	High Similarity	NPC125039
0.9207	High Similarity	NPC142614
0.9207	High Similarity	NPC7688
0.9207	High Similarity	NPC72787
0.9207	High Similarity	NPC58223
0.9202	High Similarity	NPC474033
0.9202	High Similarity	NPC477841
0.9202	High Similarity	NPC474034
0.9198	High Similarity	NPC471976
0.9198	High Similarity	NPC53889
0.9176	High Similarity	NPC117668
0.9172	High Similarity	NPC471789
0.9162	High Similarity	NPC472386
0.9162	High Similarity	NPC301683
0.9162	High Similarity	NPC65333
0.9157	High Similarity	NPC112755
0.9157	High Similarity	NPC475212
0.9157	High Similarity	NPC471457
0.9157	High Similarity	NPC170675
0.9152	High Similarity	NPC171985
0.9152	High Similarity	NPC272560
0.9152	High Similarity	NPC320741
0.9141	High Similarity	NPC165970
0.9141	High Similarity	NPC124747
0.9141	High Similarity	NPC66618
0.9141	High Similarity	NPC158188
0.9141	High Similarity	NPC266314
0.9141	High Similarity	NPC289771
0.9141	High Similarity	NPC472632
0.9141	High Similarity	NPC113163
0.9141	High Similarity	NPC84324
0.9141	High Similarity	NPC288131
0.9141	High Similarity	NPC3629
0.9141	High Similarity	NPC305987
0.9141	High Similarity	NPC155754
0.9141	High Similarity	NPC97812
0.9141	High Similarity	NPC26326
0.9141	High Similarity	NPC134783
0.9136	High Similarity	NPC95936
0.9136	High Similarity	NPC250214
0.9136	High Similarity	NPC87317
0.913	High Similarity	NPC318432
0.913	High Similarity	NPC471787
0.913	High Similarity	NPC78492
0.913	High Similarity	NPC208152
0.9123	High Similarity	NPC36138
0.9118	High Similarity	NPC473785
0.9112	High Similarity	NPC61904
0.9112	High Similarity	NPC268533
0.9112	High Similarity	NPC144097
0.9107	High Similarity	NPC98583
0.9107	High Similarity	NPC239549
0.9107	High Similarity	NPC172033
0.9107	High Similarity	NPC51774
0.9107	High Similarity	NPC472993
0.9107	High Similarity	NPC236191
0.9107	High Similarity	NPC88560
0.9107	High Similarity	NPC175230
0.9102	High Similarity	NPC21190
0.9102	High Similarity	NPC22195
0.9102	High Similarity	NPC150767
0.9102	High Similarity	NPC218488
0.9102	High Similarity	NPC44558
0.9102	High Similarity	NPC183357
0.9102	High Similarity	NPC474434
0.9102	High Similarity	NPC78734
0.9102	High Similarity	NPC74559
0.9096	High Similarity	NPC6588
0.9096	High Similarity	NPC45400
0.9096	High Similarity	NPC477154
0.9096	High Similarity	NPC117854
0.9091	High Similarity	NPC477840
0.9091	High Similarity	NPC50960
0.9085	High Similarity	NPC219927
0.9085	High Similarity	NPC472448
0.9085	High Similarity	NPC83922
0.908	High Similarity	NPC101731
0.908	High Similarity	NPC174953
0.9075	High Similarity	NPC179947
0.9075	High Similarity	NPC105591
0.9074	High Similarity	NPC35598
0.9074	High Similarity	NPC474208
0.9074	High Similarity	NPC162869
0.9074	High Similarity	NPC210084
0.9074	High Similarity	NPC474055
0.9074	High Similarity	NPC223787
0.9074	High Similarity	NPC78225
0.9074	High Similarity	NPC262286
0.9074	High Similarity	NPC36852
0.9074	High Similarity	NPC222689
0.9074	High Similarity	NPC474836
0.9074	High Similarity	NPC471209
0.9074	High Similarity	NPC48208
0.9074	High Similarity	NPC475267
0.9074	High Similarity	NPC99597
0.9074	High Similarity	NPC156057
0.9074	High Similarity	NPC291508
0.9074	High Similarity	NPC472598
0.907	High Similarity	NPC49690
0.907	High Similarity	NPC470416
0.9068	High Similarity	NPC321779
0.9068	High Similarity	NPC113906
0.9064	High Similarity	NPC469371
0.9062	High Similarity	NPC474656
0.9059	High Similarity	NPC37668
0.9059	High Similarity	NPC207467
0.9059	High Similarity	NPC113836
0.9059	High Similarity	NPC35167
0.9059	High Similarity	NPC253521
0.9053	High Similarity	NPC214621
0.9053	High Similarity	NPC34267
0.9053	High Similarity	NPC472607
0.9053	High Similarity	NPC223426
0.9053	High Similarity	NPC81042
0.9048	High Similarity	NPC100251
0.9048	High Similarity	NPC267254
0.9048	High Similarity	NPC259152
0.9048	High Similarity	NPC48773
0.9048	High Similarity	NPC3583
0.9048	High Similarity	NPC205076
0.9048	High Similarity	NPC121333
0.9048	High Similarity	NPC254540
0.9048	High Similarity	NPC172807
0.9048	High Similarity	NPC211594
0.9048	High Similarity	NPC307518
0.9048	High Similarity	NPC256760
0.9042	High Similarity	NPC229687
0.9042	High Similarity	NPC95855
0.9042	High Similarity	NPC472383
0.9042	High Similarity	NPC472381
0.9042	High Similarity	NPC326877
0.9042	High Similarity	NPC177480
0.9042	High Similarity	NPC183036
0.9042	High Similarity	NPC210042
0.9042	High Similarity	NPC107627
0.9042	High Similarity	NPC280493
0.9036	High Similarity	NPC471213
0.9036	High Similarity	NPC120593
0.9036	High Similarity	NPC128293
0.903	High Similarity	NPC29830
0.903	High Similarity	NPC121290
0.903	High Similarity	NPC124038
0.9029	High Similarity	NPC264302
0.9024	High Similarity	NPC308992

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 NPC289396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	934
0.2-0.3	1928
0.3-0.4	2598
0.4-0.5	1863
0.5-0.6	928
0.6-0.7	329
0.7-0.8	130
0.8-0.85	26
0.85-0.9	25
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.925	High Similarity	NPD4868	Clinical (unspecified phase)
0.9207	High Similarity	NPD6166	Phase 2
0.9207	High Similarity	NPD6168	Clinical (unspecified phase)
0.9207	High Similarity	NPD6167	Clinical (unspecified phase)
0.9048	High Similarity	NPD7993	Clinical (unspecified phase)
0.9006	High Similarity	NPD2393	Clinical (unspecified phase)
0.8941	High Similarity	NPD4338	Clinical (unspecified phase)
0.8876	High Similarity	NPD7074	Phase 3
0.8827	High Similarity	NPD1934	Approved
0.882	High Similarity	NPD4380	Phase 2
0.8817	High Similarity	NPD7054	Approved
0.8817	High Similarity	NPD5844	Phase 1
0.8773	High Similarity	NPD2801	Approved
0.8765	High Similarity	NPD7472	Approved
0.8757	High Similarity	NPD3818	Discontinued
0.8735	High Similarity	NPD5494	Approved
0.8727	High Similarity	NPD7075	Discontinued
0.8713	High Similarity	NPD6797	Phase 2
0.8663	High Similarity	NPD7251	Discontinued
0.865	High Similarity	NPD7411	Suspended
0.8614	High Similarity	NPD4381	Clinical (unspecified phase)
0.8606	High Similarity	NPD5402	Approved
0.8545	High Similarity	NPD7096	Clinical (unspecified phase)
0.8521	High Similarity	NPD6232	Discontinued
0.8506	High Similarity	NPD7808	Phase 3
0.8494	Intermediate Similarity	NPD3817	Phase 2
0.8488	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD6801	Discontinued
0.848	Intermediate Similarity	NPD7473	Discontinued
0.8462	Intermediate Similarity	NPD6959	Discontinued
0.8447	Intermediate Similarity	NPD1511	Approved
0.8443	Intermediate Similarity	NPD3882	Suspended
0.8434	Intermediate Similarity	NPD7819	Suspended
0.8434	Intermediate Similarity	NPD1465	Phase 2
0.8421	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1512	Approved
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8324	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8249	Intermediate Similarity	NPD8312	Approved
0.8249	Intermediate Similarity	NPD8313	Approved
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5403	Approved
0.8171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7768	Phase 2
0.811	Intermediate Similarity	NPD6799	Approved
0.807	Intermediate Similarity	NPD3749	Approved
0.8061	Intermediate Similarity	NPD5401	Approved
0.8012	Intermediate Similarity	NPD2935	Discontinued
0.7988	Intermediate Similarity	NPD6190	Approved
0.7975	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7929	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD1653	Approved
0.791	Intermediate Similarity	NPD3751	Discontinued
0.791	Intermediate Similarity	NPD7228	Approved
0.7901	Intermediate Similarity	NPD2796	Approved
0.7876	Intermediate Similarity	NPD8151	Discontinued
0.7857	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1247	Approved
0.7818	Intermediate Similarity	NPD3750	Approved
0.7816	Intermediate Similarity	NPD919	Approved
0.7814	Intermediate Similarity	NPD8150	Discontinued
0.7812	Intermediate Similarity	NPD943	Approved
0.7812	Intermediate Similarity	NPD1613	Approved
0.7812	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7435	Discontinued
0.7795	Intermediate Similarity	NPD7783	Phase 2
0.7795	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.7766	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD230	Phase 1
0.7738	Intermediate Similarity	NPD2533	Approved
0.7738	Intermediate Similarity	NPD2532	Approved
0.7738	Intermediate Similarity	NPD2534	Approved
0.7737	Intermediate Similarity	NPD6777	Approved
0.7737	Intermediate Similarity	NPD6782	Approved
0.7737	Intermediate Similarity	NPD6778	Approved
0.7737	Intermediate Similarity	NPD6776	Approved
0.7737	Intermediate Similarity	NPD6780	Approved
0.7737	Intermediate Similarity	NPD6781	Approved
0.7737	Intermediate Similarity	NPD6779	Approved
0.7727	Intermediate Similarity	NPD7199	Phase 2
0.7714	Intermediate Similarity	NPD6234	Discontinued
0.7711	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD1240	Approved
0.7683	Intermediate Similarity	NPD1551	Phase 2
0.768	Intermediate Similarity	NPD5953	Discontinued
0.7661	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD920	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7633	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD37	Approved
0.7617	Intermediate Similarity	NPD7697	Approved
0.7617	Intermediate Similarity	NPD7698	Approved
0.7617	Intermediate Similarity	NPD7696	Phase 3
0.7607	Intermediate Similarity	NPD1607	Approved
0.76	Intermediate Similarity	NPD4965	Approved
0.76	Intermediate Similarity	NPD4967	Phase 2
0.76	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2313	Discontinued
0.7577	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD7870	Phase 2
0.7569	Intermediate Similarity	NPD7286	Phase 2
0.7563	Intermediate Similarity	NPD7874	Approved
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7701	Phase 2
0.7546	Intermediate Similarity	NPD447	Suspended
0.7542	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7685	Pre-registration
0.753	Intermediate Similarity	NPD2346	Discontinued
0.7527	Intermediate Similarity	NPD8434	Phase 2
0.7515	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6535	Approved
0.7474	Intermediate Similarity	NPD6534	Approved
0.7474	Intermediate Similarity	NPD6823	Phase 2
0.7471	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7390	Discontinued
0.7469	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD7700	Phase 2
0.7448	Intermediate Similarity	NPD7699	Phase 2
0.7446	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD2800	Approved
0.7425	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7362	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7458	Discontinued
0.735	Intermediate Similarity	NPD7801	Approved
0.7333	Intermediate Similarity	NPD1933	Approved
0.7326	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7584	Approved
0.7317	Intermediate Similarity	NPD6233	Phase 2
0.7312	Intermediate Similarity	NPD7549	Discontinued
0.731	Intermediate Similarity	NPD8319	Approved
0.731	Intermediate Similarity	NPD8320	Phase 1
0.7305	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5711	Approved
0.7293	Intermediate Similarity	NPD5710	Approved
0.7293	Intermediate Similarity	NPD7229	Phase 3
0.7282	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1203	Approved
0.7262	Intermediate Similarity	NPD5405	Approved
0.7262	Intermediate Similarity	NPD5406	Approved
0.7262	Intermediate Similarity	NPD5404	Approved
0.7262	Intermediate Similarity	NPD5408	Approved
0.7256	Intermediate Similarity	NPD6798	Discontinued
0.724	Intermediate Similarity	NPD6212	Phase 3
0.724	Intermediate Similarity	NPD6213	Phase 3
0.724	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7239	Intermediate Similarity	NPD4908	Phase 1
0.7238	Intermediate Similarity	NPD8127	Discontinued
0.7232	Intermediate Similarity	NPD6844	Discontinued
0.7229	Intermediate Similarity	NPD5124	Phase 1
0.7229	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2344	Approved
0.7202	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD4363	Phase 3
0.7202	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD9269	Phase 2
0.7186	Intermediate Similarity	NPD6651	Approved
0.7173	Intermediate Similarity	NPD4287	Approved
0.7172	Intermediate Similarity	NPD7680	Approved
0.7158	Intermediate Similarity	NPD5242	Approved
0.7151	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7585	Approved
0.7093	Intermediate Similarity	NPD8166	Discontinued
0.7093	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD6273	Approved
0.7074	Intermediate Similarity	NPD7038	Approved
0.7074	Intermediate Similarity	NPD7039	Approved
0.7073	Intermediate Similarity	NPD9494	Approved
0.7065	Intermediate Similarity	NPD7583	Approved
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7056	Intermediate Similarity	NPD8285	Discontinued
0.7052	Intermediate Similarity	NPD2309	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