NPASS Compound

Structure

NPC163165 OpenBabel07101719252D 46 50 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 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 -4.3301 1.5000 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 2.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 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 -3.4641 2.0000 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 3.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 4.3301 4.5000 0.0000 C 0 0 2 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 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 6.0622 4.5000 0.0000 C 0 0 1 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 6.0622 3.5000 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 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 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 5.0000 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 3.0000 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 0.8660 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 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 4.3301 3.5000 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 1 40 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 14 1 0 0 0 0 5 20 1 0 0 0 0 6 11 2 0 0 0 0 6 16 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 30 1 0 0 0 0 10 41 1 0 0 0 0 11 15 1 0 0 0 0 12 27 1 0 0 0 0 13 16 2 0 0 0 0 13 31 1 0 0 0 0 14 17 2 0 0 0 0 14 43 1 0 0 0 0 15 42 1 0 0 0 0 16 44 1 0 0 0 0 17 40 1 0 0 0 0 18 9 1 6 0 0 0 18 21 1 0 0 0 0 18 45 1 0 0 0 0 19 10 1 6 0 0 0 19 22 1 0 0 0 0 19 46 1 0 0 0 0 20 32 2 0 0 0 0 20 42 1 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 25 1 0 0 0 0 23 35 1 6 0 0 0 24 26 1 0 0 0 0 24 36 1 6 0 0 0 25 28 1 0 0 0 0 25 37 1 1 0 0 0 26 29 1 0 0 0 0 26 38 1 1 0 0 0 27 39 2 0 0 0 0 27 41 1 0 0 0 0 28 43 1 6 0 0 0 28 45 1 0 0 0 0 29 44 1 6 0 0 0 29 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.16
Volume:	593.063
LogP:	-0.24
LogD:	-0.318
LogS:	-3.002
# Rotatable Bonds:	10
TPSA:	264.5
# H-Bond Aceptor:	17
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.089
Synthetic Accessibility Score:	4.647
Fsp3:	0.448
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.585
MDCK Permeability:	5.242261249804869e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.89
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.196
Plasma Protein Binding (PPB):	68.07852935791016%
Volume Distribution (VD):	0.616
Pgp-substrate:	14.620062828063965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.053
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.011

ADMET: Excretion

Clearance (CL):	1.682
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.727
Human Hepatotoxicity (H-HT):	0.093
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.138
Carcinogencity:	0.197
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC163165

Natural Product ID:	NPC163165
*Common Name:**	6-[6-(4-O-Beta-D-Glucopyranosyloxy-3-Methoxybenzoyl)]-O-Beta-D-Glucopyranosyloxy-7-Hydroxycoumarin
IUPAC Name:	[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(7-hydroxy-2-oxochromen-6-yl)oxyoxan-2-yl]methyl 3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Synonyms:
Standard InCHIKey:	GLBGTIVKNQKHLD-BTXJZROQSA-N
Standard InCHI:	InChI=1S/C29H32O17/c1-40-17-7-12(2-4-14(17)43-28-25(37)23(35)21(33)18(9-30)45-28)27(39)41-10-19-22(34)24(36)26(38)29(46-19)44-16-6-11-3-5-20(32)42-15(11)8-13(16)31/h2-8,18-19,21-26,28-31,33-38H,9-10H2,1H3/t18-,19-,21-,22-,23+,24+,25-,26-,28-,29-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2OC)C(=O)OC[C@H]2O[C@@H](Oc3cc4ccc(=O)oc4cc3O)[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:	CHEMBL389851
PubChem CID:	16681193
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	3
Others	3
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	5000.0	nM	PMID[520788]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	5000.0	nM	PMID[520788]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5000.0	nM	PMID[520788]
NPT2	Others	Unspecified		Inhibition	=	30.8	%	PMID[520788]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	>	10000.0	nM	PMID[520788]
NPT27	Others	Unspecified		IC50	>	5000.0	nM	PMID[520788]

☑ 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 NPC163165 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	430
0.1-0.2	1920
0.2-0.3	4618
0.3-0.4	9919
0.4-0.5	8199
0.5-0.6	4571
0.6-0.7	5679
0.7-0.8	5253
0.8-0.85	1219
0.85-0.9	627
0.9-0.95	245
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9695	High Similarity	NPC84482
0.9695	High Similarity	NPC169645
0.9573	High Similarity	NPC5786
0.9573	High Similarity	NPC102851
0.9451	High Similarity	NPC197708
0.9451	High Similarity	NPC658
0.9441	High Similarity	NPC311803
0.9441	High Similarity	NPC472859
0.9441	High Similarity	NPC25389
0.9408	High Similarity	NPC470446
0.9408	High Similarity	NPC470449
0.9408	High Similarity	NPC470447
0.9408	High Similarity	NPC470445
0.9398	High Similarity	NPC204693
0.9379	High Similarity	NPC166277
0.9379	High Similarity	NPC119125
0.9353	High Similarity	NPC470455
0.9353	High Similarity	NPC470451
0.9337	High Similarity	NPC211594
0.9337	High Similarity	NPC172807
0.9337	High Similarity	NPC254540
0.9337	High Similarity	NPC3583
0.9337	High Similarity	NPC259152
0.9317	High Similarity	NPC74319
0.9317	High Similarity	NPC160780
0.9317	High Similarity	NPC287872
0.9317	High Similarity	NPC289811
0.929	High Similarity	NPC470444
0.929	High Similarity	NPC110941
0.929	High Similarity	NPC473571
0.929	High Similarity	NPC470443
0.929	High Similarity	NPC473682
0.929	High Similarity	NPC126784
0.929	High Similarity	NPC241423
0.9286	High Similarity	NPC472991
0.9286	High Similarity	NPC169733
0.9286	High Similarity	NPC472992
0.9268	High Similarity	NPC142614
0.9264	High Similarity	NPC90905
0.9264	High Similarity	NPC33298
0.9264	High Similarity	NPC285108
0.9264	High Similarity	NPC4013
0.9259	High Similarity	NPC203020
0.9259	High Similarity	NPC239966
0.9255	High Similarity	NPC1913
0.9231	High Similarity	NPC472387
0.9231	High Similarity	NPC476620
0.9231	High Similarity	NPC173837
0.9231	High Similarity	NPC476621
0.9231	High Similarity	NPC120952
0.9231	High Similarity	NPC476623
0.9231	High Similarity	NPC476618
0.9231	High Similarity	NPC476619
0.9231	High Similarity	NPC476622
0.9226	High Similarity	NPC102028
0.9226	High Similarity	NPC477848
0.9226	High Similarity	NPC142996
0.9222	High Similarity	NPC307518
0.9222	High Similarity	NPC472386
0.9222	High Similarity	NPC475155
0.9222	High Similarity	NPC205076
0.9222	High Similarity	NPC48773
0.9217	High Similarity	NPC86008
0.9217	High Similarity	NPC93337
0.9217	High Similarity	NPC475942
0.9217	High Similarity	NPC201292
0.9217	High Similarity	NPC198125
0.9217	High Similarity	NPC95421
0.9217	High Similarity	NPC209296
0.9217	High Similarity	NPC105025
0.9217	High Similarity	NPC469931
0.9217	High Similarity	NPC58053
0.9217	High Similarity	NPC45638
0.9217	High Similarity	NPC195257
0.9217	High Similarity	NPC186807
0.9217	High Similarity	NPC226294
0.9181	High Similarity	NPC473072
0.9181	High Similarity	NPC36138
0.9172	High Similarity	NPC8573
0.9172	High Similarity	NPC211532
0.9172	High Similarity	NPC89127
0.9172	High Similarity	NPC472385
0.9172	High Similarity	NPC198324
0.9172	High Similarity	NPC470949
0.9172	High Similarity	NPC297574
0.9172	High Similarity	NPC233994
0.9172	High Similarity	NPC471669
0.9172	High Similarity	NPC65563
0.9167	High Similarity	NPC239549
0.9167	High Similarity	NPC219600
0.9167	High Similarity	NPC51774
0.9167	High Similarity	NPC473550
0.9167	High Similarity	NPC472993
0.9167	High Similarity	NPC46640
0.9167	High Similarity	NPC263119
0.9167	High Similarity	NPC236191
0.9167	High Similarity	NPC166674
0.9167	High Similarity	NPC34436
0.9162	High Similarity	NPC105511
0.9162	High Similarity	NPC21190
0.9162	High Similarity	NPC224462
0.9162	High Similarity	NPC34287
0.9162	High Similarity	NPC22195
0.9162	High Similarity	NPC183357
0.9162	High Similarity	NPC51326
0.9162	High Similarity	NPC231194
0.9162	High Similarity	NPC44558
0.9162	High Similarity	NPC471416
0.9162	High Similarity	NPC474434
0.9157	High Similarity	NPC45618
0.9157	High Similarity	NPC58716
0.9157	High Similarity	NPC116745
0.9157	High Similarity	NPC146792
0.9146	High Similarity	NPC148273
0.9141	High Similarity	NPC289346
0.9136	High Similarity	NPC472860
0.9128	High Similarity	NPC21359
0.9128	High Similarity	NPC470717
0.9128	High Similarity	NPC25946
0.9128	High Similarity	NPC470416
0.9128	High Similarity	NPC470720
0.9128	High Similarity	NPC148710
0.9128	High Similarity	NPC470713
0.9128	High Similarity	NPC460984
0.9123	High Similarity	NPC473071
0.9123	High Similarity	NPC473073
0.9118	High Similarity	NPC475261
0.9112	High Similarity	NPC294815
0.9112	High Similarity	NPC473327
0.9112	High Similarity	NPC43211
0.9112	High Similarity	NPC210094
0.9112	High Similarity	NPC49344
0.9112	High Similarity	NPC101191
0.9112	High Similarity	NPC237435
0.9112	High Similarity	NPC253685
0.9112	High Similarity	NPC198199
0.9112	High Similarity	NPC16194
0.9112	High Similarity	NPC19108
0.9112	High Similarity	NPC264735
0.9112	High Similarity	NPC115760
0.9112	High Similarity	NPC220173
0.9112	High Similarity	NPC476472
0.9112	High Similarity	NPC135277
0.9107	High Similarity	NPC301683
0.9107	High Similarity	NPC156977
0.9107	High Similarity	NPC180918
0.9107	High Similarity	NPC476405
0.9107	High Similarity	NPC267254
0.9107	High Similarity	NPC117260
0.9102	High Similarity	NPC95855
0.9102	High Similarity	NPC472381
0.9102	High Similarity	NPC183036
0.9102	High Similarity	NPC472383
0.9102	High Similarity	NPC210042
0.9102	High Similarity	NPC229687
0.9102	High Similarity	NPC149300
0.9102	High Similarity	NPC112755
0.9102	High Similarity	NPC471457
0.9102	High Similarity	NPC170675
0.9096	High Similarity	NPC99957
0.9096	High Similarity	NPC181616
0.9096	High Similarity	NPC115674
0.9096	High Similarity	NPC8856
0.9096	High Similarity	NPC210073
0.9091	High Similarity	NPC121290
0.9085	High Similarity	NPC217950
0.9075	High Similarity	NPC473554
0.9075	High Similarity	NPC470719
0.9075	High Similarity	NPC295625
0.907	High Similarity	NPC162394
0.907	High Similarity	NPC470718
0.907	High Similarity	NPC35924
0.907	High Similarity	NPC199172
0.907	High Similarity	NPC241781
0.907	High Similarity	NPC156785
0.9068	High Similarity	NPC327032
0.9068	High Similarity	NPC194095
0.9068	High Similarity	NPC191046
0.9064	High Similarity	NPC471030
0.9064	High Similarity	NPC473895
0.9059	High Similarity	NPC472382
0.9059	High Similarity	NPC67629
0.9059	High Similarity	NPC472384
0.9059	High Similarity	NPC79736
0.9059	High Similarity	NPC472380
0.9059	High Similarity	NPC473862
0.9059	High Similarity	NPC268533
0.9059	High Similarity	NPC257714
0.9053	High Similarity	NPC208668
0.9053	High Similarity	NPC175230
0.9053	High Similarity	NPC4390
0.9053	High Similarity	NPC172033
0.9053	High Similarity	NPC21666
0.9053	High Similarity	NPC42773
0.9053	High Similarity	NPC169977
0.9053	High Similarity	NPC101026
0.9053	High Similarity	NPC88560
0.9053	High Similarity	NPC24043
0.9053	High Similarity	NPC45522
0.9048	High Similarity	NPC204937

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 NPC163165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	981
0.2-0.3	2115
0.3-0.4	2724
0.4-0.5	1767
0.5-0.6	810
0.6-0.7	226
0.7-0.8	110
0.8-0.85	17
0.85-0.9	3
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9277	High Similarity	NPD7472	Approved
0.9217	High Similarity	NPD7054	Approved
0.9112	High Similarity	NPD4338	Clinical (unspecified phase)
0.9053	High Similarity	NPD7251	Discontinued
0.9048	High Similarity	NPD7074	Phase 3
0.9	High Similarity	NPD7808	Phase 3
0.8994	High Similarity	NPD6797	Phase 2
0.8817	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD1653	Approved
0.8727	High Similarity	NPD4868	Clinical (unspecified phase)
0.8563	High Similarity	NPD4381	Clinical (unspecified phase)
0.8555	High Similarity	NPD7993	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD2801	Approved
0.848	Intermediate Similarity	NPD6166	Phase 2
0.848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD5844	Phase 1
0.8439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7685	Pre-registration
0.8383	Intermediate Similarity	NPD1465	Phase 2
0.8323	Intermediate Similarity	NPD1934	Approved
0.8276	Intermediate Similarity	NPD7228	Approved
0.8225	Intermediate Similarity	NPD3817	Phase 2
0.8166	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD5402	Approved
0.807	Intermediate Similarity	NPD3882	Suspended
0.8035	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD7266	Discontinued
0.8023	Intermediate Similarity	NPD7075	Discontinued
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD1511	Approved
0.7917	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD8313	Approved
0.7901	Intermediate Similarity	NPD8312	Approved
0.7889	Intermediate Similarity	NPD7240	Approved
0.7886	Intermediate Similarity	NPD7199	Phase 2
0.7874	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD1512	Approved
0.7849	Intermediate Similarity	NPD8455	Phase 2
0.7849	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6190	Approved
0.7826	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD37	Approved
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7759	Intermediate Similarity	NPD4965	Approved
0.7759	Intermediate Similarity	NPD4967	Phase 2
0.7759	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD7819	Suspended
0.774	Intermediate Similarity	NPD6232	Discontinued
0.7709	Intermediate Similarity	NPD7473	Discontinued
0.7706	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7665	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7783	Phase 2
0.7653	Intermediate Similarity	NPD8151	Discontinued
0.7633	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6799	Approved
0.763	Intermediate Similarity	NPD7411	Suspended
0.7588	Intermediate Similarity	NPD5401	Approved
0.7577	Intermediate Similarity	NPD7435	Discontinued
0.756	Intermediate Similarity	NPD3750	Approved
0.756	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD1613	Approved
0.7546	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.7531	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7585	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD447	Suspended
0.7486	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7583	Approved
0.7461	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2796	Approved
0.7423	Intermediate Similarity	NPD6781	Approved
0.7423	Intermediate Similarity	NPD6777	Approved
0.7423	Intermediate Similarity	NPD6776	Approved
0.7423	Intermediate Similarity	NPD6780	Approved
0.7423	Intermediate Similarity	NPD6778	Approved
0.7423	Intermediate Similarity	NPD6779	Approved
0.7423	Intermediate Similarity	NPD6782	Approved
0.7401	Intermediate Similarity	NPD5353	Approved
0.7398	Intermediate Similarity	NPD7698	Approved
0.7398	Intermediate Similarity	NPD7680	Approved
0.7398	Intermediate Similarity	NPD7696	Phase 3
0.7398	Intermediate Similarity	NPD7697	Approved
0.7384	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD919	Approved
0.7371	Intermediate Similarity	NPD6599	Discontinued
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7362	Intermediate Similarity	NPD3027	Phase 3
0.736	Intermediate Similarity	NPD7768	Phase 2
0.735	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7701	Phase 2
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7318	Intermediate Similarity	NPD3749	Approved
0.7314	Intermediate Similarity	NPD7458	Discontinued
0.7301	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1247	Approved
0.7286	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7262	Intermediate Similarity	NPD3748	Approved
0.7259	Intermediate Similarity	NPD6823	Phase 2
0.7239	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD9494	Approved
0.7231	Intermediate Similarity	NPD7700	Phase 2
0.7231	Intermediate Similarity	NPD7699	Phase 2
0.7211	Intermediate Similarity	NPD8434	Phase 2
0.7198	Intermediate Similarity	NPD8127	Discontinued
0.7193	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6534	Approved
0.7165	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7126	Intermediate Similarity	NPD943	Approved
0.7126	Intermediate Similarity	NPD1240	Approved
0.712	Intermediate Similarity	NPD3926	Phase 2
0.712	Intermediate Similarity	NPD8150	Discontinued
0.712	Intermediate Similarity	NPD5242	Approved
0.7102	Intermediate Similarity	NPD920	Approved
0.71	Intermediate Similarity	NPD8320	Phase 1
0.71	Intermediate Similarity	NPD8319	Approved
0.7093	Intermediate Similarity	NPD6674	Discontinued
0.7092	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6832	Phase 2
0.7086	Intermediate Similarity	NPD2532	Approved
0.7086	Intermediate Similarity	NPD2534	Approved
0.7086	Intermediate Similarity	NPD2533	Approved
0.7083	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5124	Phase 1
0.7081	Intermediate Similarity	NPD1091	Approved
0.7066	Intermediate Similarity	NPD6233	Phase 2
0.7055	Intermediate Similarity	NPD3225	Approved
0.7041	Intermediate Similarity	NPD1607	Approved
0.7039	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7038	Approved
0.7037	Intermediate Similarity	NPD7039	Approved
0.7022	Intermediate Similarity	NPD3226	Approved
0.7022	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1203	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.7	Intermediate Similarity	NPD7097	Phase 1
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5953	Discontinued
0.6982	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD422	Phase 1
0.6968	Remote Similarity	NPD7286	Phase 2
0.6959	Remote Similarity	NPD4308	Phase 3
0.6959	Remote Similarity	NPD7033	Discontinued
0.6939	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6213	Phase 3
0.6939	Remote Similarity	NPD6212	Phase 3
0.6934	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6100	Approved
0.6919	Remote Similarity	NPD6099	Approved
0.6909	Remote Similarity	NPD2797	Approved
0.6905	Remote Similarity	NPD6798	Discontinued
0.6905	Remote Similarity	NPD3268	Approved
0.6897	Remote Similarity	NPD1243	Approved
0.6894	Remote Similarity	NPD9268	Approved
0.6886	Remote Similarity	NPD4908	Phase 1
0.6882	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6273	Approved
0.6832	Remote Similarity	NPD9545	Approved
0.6831	Remote Similarity	NPD4288	Approved
0.6829	Remote Similarity	NPD9717	Approved
0.6821	Remote Similarity	NPD6842	Approved
0.6821	Remote Similarity	NPD6841	Approved
0.6821	Remote Similarity	NPD6843	Phase 3
0.6809	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2313	Discontinued
0.6782	Remote Similarity	NPD2346	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data