NPASS Compound

Structure

NPC285108 OpenBabel07101718202D 41 44 0 0 1 0 0 0 0 0999 V2000 8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 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 6.9282 1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 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 2.5981 -0.5000 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 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 7.7942 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 6.0000 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 -1.7321 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 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.0000 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 -2.5981 1.5000 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 8.6603 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 38 1 0 0 0 0 2 3 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 21 1 0 0 0 0 6 14 2 0 0 0 0 6 16 1 0 0 0 0 7 14 1 0 0 0 0 7 17 2 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 20 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 29 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 17 39 1 0 0 0 0 18 21 2 0 0 0 0 18 31 1 0 0 0 0 19 23 2 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 33 1 0 0 0 0 21 38 1 0 0 0 0 22 12 1 6 0 0 0 22 24 1 0 0 0 0 22 40 1 0 0 0 0 23 34 1 0 0 0 0 24 25 1 0 0 0 0 24 35 1 1 0 0 0 25 26 1 0 0 0 0 25 36 1 6 0 0 0 26 28 1 0 0 0 0 26 41 1 1 0 0 0 27 37 2 0 0 0 0 27 41 1 0 0 0 0 28 39 1 6 0 0 0 28 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	572.15
Volume:	543.89
LogP:	1.74
LogD:	1.227
LogS:	-3.497
# Rotatable Bonds:	9
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	4.162
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.336
MDCK Permeability:	7.495797490264522e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.041
Human Intestinal Absorption (HIA):	0.702
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	93.10796356201172%
Volume Distribution (VD):	0.421
Pgp-substrate:	3.211866617202759%

ADMET: Metabolism

CYP1A2-inhibitor:	0.605
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.183
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	9.939
Half-life (T1/2):	0.946

ADMET: Toxicity

hERG Blockers:	0.332
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.35
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.952
Carcinogencity:	0.104
Eye Corrosion:	0.003
Eye Irritation:	0.82
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC285108

Natural Product ID:	NPC285108
*Common Name:**	[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[3-Hydroxy-5-[(E)-2-(3-Hydroxy-4-Methoxyphenyl)Ethenyl]Phenoxy]-6-(Hydroxymethyl)Oxan-3-Yl] 3,4,5-Trihydroxybenzoate
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxan-3-yl] 3,4,5-trihydroxybenzoate
Synonyms:
Standard InCHIKey:	DBHYLGJAFYCFGS-XJVIDBJFSA-N
Standard InCHI:	InChI=1S/C28H28O13/c1-38-21-5-4-13(8-18(21)31)2-3-14-6-16(30)11-17(7-14)39-28-26(25(36)24(35)22(12-29)40-28)41-27(37)15-9-19(32)23(34)20(33)10-15/h2-11,22,24-26,28-36H,12H2,1H3/b3-2+/t22-,24-,25+,26-,28-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)cc(c2)/C=C/c2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL320571
PubChem CID:	10325743
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10714491]
NPO88	Rheum undulatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO88	Rheum undulatum	Species	Polygonaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	13000.0	nM	PMID[463064]

☑ 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 NPC285108 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	363
0.1-0.2	1598
0.2-0.3	4007
0.3-0.4	8729
0.4-0.5	9246
0.5-0.6	4303
0.6-0.7	5406
0.7-0.8	6537
0.8-0.85	1650
0.85-0.9	722
0.9-0.95	108
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33298
0.9869	High Similarity	NPC289346
0.9804	High Similarity	NPC160780
0.9804	High Similarity	NPC289811
0.9742	High Similarity	NPC90905
0.9742	High Similarity	NPC4013
0.974	High Similarity	NPC239966
0.974	High Similarity	NPC203020
0.9739	High Similarity	NPC133984
0.9739	High Similarity	NPC1913
0.9684	High Similarity	NPC658
0.9684	High Similarity	NPC197708
0.9677	High Similarity	NPC311803
0.9677	High Similarity	NPC472859
0.9677	High Similarity	NPC25389
0.9613	High Similarity	NPC166277
0.9613	High Similarity	NPC119125
0.961	High Similarity	NPC472860
0.9563	High Similarity	NPC5786
0.9563	High Similarity	NPC102851
0.9548	High Similarity	NPC287872
0.9548	High Similarity	NPC74319
0.9542	High Similarity	NPC194095
0.9542	High Similarity	NPC191046
0.9542	High Similarity	NPC327032
0.9503	High Similarity	NPC88560
0.9503	High Similarity	NPC172033
0.9503	High Similarity	NPC175230
0.95	High Similarity	NPC149011
0.95	High Similarity	NPC204937
0.9477	High Similarity	NPC310661
0.9477	High Similarity	NPC105827
0.9437	High Similarity	NPC95421
0.9437	High Similarity	NPC198125
0.9419	High Similarity	NPC471405
0.9412	High Similarity	NPC134905
0.9412	High Similarity	NPC36130
0.9387	High Similarity	NPC67629
0.9387	High Similarity	NPC79736
0.9383	High Similarity	NPC472993
0.9375	High Similarity	NPC116745
0.9367	High Similarity	NPC148273
0.9363	High Similarity	NPC53889
0.9355	High Similarity	NPC10205
0.9351	High Similarity	NPC3746
0.9351	High Similarity	NPC205037
0.9351	High Similarity	NPC44260
0.9351	High Similarity	NPC16024
0.9351	High Similarity	NPC61152
0.9329	High Similarity	NPC267549
0.9317	High Similarity	NPC149300
0.9308	High Similarity	NPC121290
0.9299	High Similarity	NPC87317
0.9286	High Similarity	NPC75695
0.9268	High Similarity	NPC472991
0.9268	High Similarity	NPC472992
0.9264	High Similarity	NPC163165
0.9255	High Similarity	NPC473818
0.9245	High Similarity	NPC41009
0.9241	High Similarity	NPC476373
0.9241	High Similarity	NPC24164
0.9236	High Similarity	NPC156818
0.9236	High Similarity	NPC68324
0.9236	High Similarity	NPC289322
0.9236	High Similarity	NPC38779
0.9236	High Similarity	NPC160512
0.9236	High Similarity	NPC114179
0.9226	High Similarity	NPC137813
0.9226	High Similarity	NPC157898
0.9221	High Similarity	NPC140151
0.9216	High Similarity	NPC111785
0.9216	High Similarity	NPC92117
0.9212	High Similarity	NPC217520
0.9212	High Similarity	NPC476620
0.9212	High Similarity	NPC139571
0.9212	High Similarity	NPC476618
0.9212	High Similarity	NPC476623
0.9212	High Similarity	NPC476619
0.9212	High Similarity	NPC476621
0.9212	High Similarity	NPC476622
0.9212	High Similarity	NPC35167
0.9212	High Similarity	NPC472387
0.9207	High Similarity	NPC84482
0.9207	High Similarity	NPC169645
0.9202	High Similarity	NPC47140
0.9202	High Similarity	NPC67134
0.9202	High Similarity	NPC172807
0.9202	High Similarity	NPC211594
0.9202	High Similarity	NPC254540
0.9198	High Similarity	NPC229687
0.9187	High Similarity	NPC88043
0.9172	High Similarity	NPC250436
0.9172	High Similarity	NPC300845
0.9172	High Similarity	NPC88803
0.9172	High Similarity	NPC104983
0.9172	High Similarity	NPC291948
0.9162	High Similarity	NPC36138
0.9157	High Similarity	NPC471030
0.9156	High Similarity	NPC473091
0.9152	High Similarity	NPC61904
0.9152	High Similarity	NPC144097
0.9152	High Similarity	NPC297574
0.915	High Similarity	NPC120621
0.915	High Similarity	NPC248257
0.9146	High Similarity	NPC4390
0.9136	High Similarity	NPC229729
0.9136	High Similarity	NPC45400
0.913	High Similarity	NPC22832
0.913	High Similarity	NPC165720
0.913	High Similarity	NPC311830
0.913	High Similarity	NPC142614
0.9125	High Similarity	NPC476371
0.9125	High Similarity	NPC476372
0.9114	High Similarity	NPC238419
0.9114	High Similarity	NPC226759
0.9114	High Similarity	NPC172419
0.9108	High Similarity	NPC145425
0.9107	High Similarity	NPC470416
0.9096	High Similarity	NPC267680
0.9096	High Similarity	NPC113836
0.9096	High Similarity	NPC37668
0.9096	High Similarity	NPC253521
0.9096	High Similarity	NPC477895
0.9096	High Similarity	NPC293626
0.9096	High Similarity	NPC217387
0.9096	High Similarity	NPC258044
0.9096	High Similarity	NPC196127
0.9091	High Similarity	NPC98809
0.9091	High Similarity	NPC34267
0.9091	High Similarity	NPC477848
0.9091	High Similarity	NPC476394
0.9091	High Similarity	NPC223426
0.9091	High Similarity	NPC214621
0.9091	High Similarity	NPC81042
0.9085	High Similarity	NPC307518
0.9085	High Similarity	NPC175107
0.9085	High Similarity	NPC472386
0.9085	High Similarity	NPC153755
0.9085	High Similarity	NPC48773
0.9085	High Similarity	NPC205076
0.9085	High Similarity	NPC190003
0.908	High Similarity	NPC201292
0.908	High Similarity	NPC226294
0.908	High Similarity	NPC186807
0.908	High Similarity	NPC93337
0.908	High Similarity	NPC45638
0.908	High Similarity	NPC105025
0.908	High Similarity	NPC469931
0.908	High Similarity	NPC58053
0.908	High Similarity	NPC475942
0.9074	High Similarity	NPC236934
0.9074	High Similarity	NPC5778
0.9068	High Similarity	NPC88023
0.9068	High Similarity	NPC243930
0.9068	High Similarity	NPC191306
0.9068	High Similarity	NPC19709
0.9068	High Similarity	NPC270335
0.9068	High Similarity	NPC168822
0.9068	High Similarity	NPC222936
0.9068	High Similarity	NPC284960
0.9068	High Similarity	NPC309025
0.9062	High Similarity	NPC217950
0.9051	High Similarity	NPC318432
0.9051	High Similarity	NPC247629
0.9051	High Similarity	NPC239019
0.9048	High Similarity	NPC35924
0.9048	High Similarity	NPC199172
0.9042	High Similarity	NPC80956
0.9036	High Similarity	NPC472723
0.9036	High Similarity	NPC211532
0.9036	High Similarity	NPC233994
0.9036	High Similarity	NPC472385
0.9036	High Similarity	NPC296018
0.9036	High Similarity	NPC198324
0.9036	High Similarity	NPC154741
0.9032	High Similarity	NPC205054
0.903	High Similarity	NPC34436
0.903	High Similarity	NPC166674
0.903	High Similarity	NPC219600
0.903	High Similarity	NPC46640
0.903	High Similarity	NPC263119
0.903	High Similarity	NPC316539
0.9026	High Similarity	NPC142528
0.9026	High Similarity	NPC472969
0.9024	High Similarity	NPC471416
0.9024	High Similarity	NPC51326
0.9024	High Similarity	NPC183357
0.9024	High Similarity	NPC155763
0.9024	High Similarity	NPC224462
0.9024	High Similarity	NPC34287
0.9024	High Similarity	NPC105511
0.9024	High Similarity	NPC235260
0.9024	High Similarity	NPC21190
0.9024	High Similarity	NPC244776
0.9024	High Similarity	NPC44558
0.9024	High Similarity	NPC474434
0.9024	High Similarity	NPC22195
0.9024	High Similarity	NPC206123
0.9024	High Similarity	NPC20505
0.9024	High Similarity	NPC116864

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 NPC285108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	888
0.2-0.3	1863
0.3-0.4	2642
0.4-0.5	1889
0.5-0.6	966
0.6-0.7	421
0.7-0.8	132
0.8-0.85	23
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD4868	Clinical (unspecified phase)
0.8976	High Similarity	NPD4338	Clinical (unspecified phase)
0.8963	High Similarity	NPD7054	Approved
0.8909	High Similarity	NPD7472	Approved
0.8909	High Similarity	NPD7074	Phase 3
0.8902	High Similarity	NPD3818	Discontinued
0.8743	High Similarity	NPD6797	Phase 2
0.869	High Similarity	NPD7251	Discontinued
0.8667	High Similarity	NPD6166	Phase 2
0.8667	High Similarity	NPD6168	Clinical (unspecified phase)
0.8667	High Similarity	NPD6167	Clinical (unspecified phase)
0.8642	High Similarity	NPD4381	Clinical (unspecified phase)
0.8639	High Similarity	NPD7808	Phase 3
0.8631	High Similarity	NPD7993	Clinical (unspecified phase)
0.858	High Similarity	NPD7685	Pre-registration
0.8544	High Similarity	NPD6980	Clinical (unspecified phase)
0.8512	High Similarity	NPD5844	Phase 1
0.8509	High Similarity	NPD1934	Approved
0.8491	Intermediate Similarity	NPD1653	Approved
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1465	Phase 2
0.8344	Intermediate Similarity	NPD2801	Approved
0.8343	Intermediate Similarity	NPD7228	Approved
0.8293	Intermediate Similarity	NPD3817	Phase 2
0.8263	Intermediate Similarity	NPD7199	Phase 2
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8253	Intermediate Similarity	NPD6234	Discontinued
0.8242	Intermediate Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD230	Phase 1
0.8228	Intermediate Similarity	NPD6190	Approved
0.8205	Intermediate Similarity	NPD7266	Discontinued
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD37	Approved
0.8133	Intermediate Similarity	NPD4967	Phase 2
0.8133	Intermediate Similarity	NPD4966	Approved
0.8133	Intermediate Similarity	NPD4965	Approved
0.8107	Intermediate Similarity	NPD6232	Discontinued
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8068	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.7965	Intermediate Similarity	NPD7473	Discontinued
0.7964	Intermediate Similarity	NPD5402	Approved
0.7937	Intermediate Similarity	NPD4628	Phase 3
0.7914	Intermediate Similarity	NPD1512	Approved
0.7904	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7845	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6801	Discontinued
0.7841	Intermediate Similarity	NPD7240	Approved
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7819	Suspended
0.7798	Intermediate Similarity	NPD8455	Phase 2
0.7791	Intermediate Similarity	NPD6799	Approved
0.7758	Intermediate Similarity	NPD5403	Approved
0.7751	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.7714	Intermediate Similarity	NPD3751	Discontinued
0.7707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD1549	Phase 2
0.7701	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5353	Approved
0.764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5401	Approved
0.7636	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7613	Intermediate Similarity	NPD9494	Approved
0.7607	Intermediate Similarity	NPD3750	Approved
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7602	Intermediate Similarity	NPD7768	Phase 2
0.7586	Intermediate Similarity	NPD3787	Discontinued
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3749	Approved
0.7547	Intermediate Similarity	NPD447	Suspended
0.753	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7680	Approved
0.7516	Intermediate Similarity	NPD9269	Phase 2
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2796	Approved
0.7469	Intermediate Similarity	NPD1551	Phase 2
0.7452	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7038	Approved
0.7444	Intermediate Similarity	NPD7039	Approved
0.7443	Intermediate Similarity	NPD5242	Approved
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7435	Intermediate Similarity	NPD7435	Discontinued
0.7421	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD1510	Phase 2
0.7389	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7585	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6385	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7368	Intermediate Similarity	NPD6386	Approved
0.7355	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD3926	Phase 2
0.733	Intermediate Similarity	NPD8127	Discontinued
0.7322	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7583	Approved
0.7314	Intermediate Similarity	NPD919	Approved
0.7301	Intermediate Similarity	NPD3748	Approved
0.7267	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD943	Approved
0.7256	Intermediate Similarity	NPD2935	Discontinued
0.7255	Intermediate Similarity	NPD9268	Approved
0.725	Intermediate Similarity	NPD6798	Discontinued
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7231	Intermediate Similarity	NPD7584	Approved
0.7229	Intermediate Similarity	NPD6674	Discontinued
0.7226	Intermediate Similarity	NPD1091	Approved
0.7219	Intermediate Similarity	NPD2533	Approved
0.7219	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2534	Approved
0.7216	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD7871	Phase 2
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7874	Approved
0.719	Intermediate Similarity	NPD9545	Approved
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1607	Approved
0.7176	Intermediate Similarity	NPD6273	Approved
0.7165	Intermediate Similarity	NPD7698	Approved
0.7165	Intermediate Similarity	NPD7696	Phase 3
0.7165	Intermediate Similarity	NPD7697	Approved
0.7159	Intermediate Similarity	NPD6971	Discontinued
0.7151	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3764	Approved
0.7135	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7126	Intermediate Similarity	NPD1652	Phase 2
0.712	Intermediate Similarity	NPD7549	Discontinued
0.7113	Intermediate Similarity	NPD6823	Phase 2
0.7107	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7104	Intermediate Similarity	NPD5953	Discontinued
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.707	Intermediate Similarity	NPD1608	Approved
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD8150	Discontinued
0.7052	Intermediate Similarity	NPD3455	Phase 2
0.7044	Intermediate Similarity	NPD1203	Approved
0.7041	Intermediate Similarity	NPD8319	Approved
0.7041	Intermediate Similarity	NPD8320	Phase 1
0.7035	Intermediate Similarity	NPD920	Approved
0.7019	Intermediate Similarity	NPD6832	Phase 2
0.7012	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5124	Phase 1
0.701	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7440	Discontinued
0.7	Intermediate Similarity	NPD7801	Approved
0.6995	Remote Similarity	NPD7699	Phase 2
0.6995	Remote Similarity	NPD7700	Phase 2
0.6995	Remote Similarity	NPD7286	Phase 2
0.6988	Remote Similarity	NPD7033	Discontinued
0.6982	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4110	Phase 3
0.6982	Remote Similarity	NPD8166	Discontinued
0.6981	Remote Similarity	NPD3225	Approved
0.6946	Remote Similarity	NPD6099	Approved
0.6946	Remote Similarity	NPD6100	Approved
0.6942	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2983	Phase 2
0.6918	Remote Similarity	NPD2982	Phase 2
0.6909	Remote Similarity	NPD6355	Discontinued
0.6905	Remote Similarity	NPD2346	Discontinued
0.6903	Remote Similarity	NPD5536	Phase 2
0.6899	Remote Similarity	NPD422	Phase 1
0.689	Remote Similarity	NPD4062	Phase 3
0.6886	Remote Similarity	NPD2799	Discontinued
0.6886	Remote Similarity	NPD4308	Phase 3
0.6886	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD17	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