NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	284.13
Volume:	278.419
LogP:	0.065
LogD:	0.202
LogS:	-0.707
# Rotatable Bonds:	5
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	3.243
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.278
MDCK Permeability:	7.432374695781618e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.918
20% Bioavailability (F20%):	0.788
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.302
Plasma Protein Binding (PPB):	54.07495880126953%
Volume Distribution (VD):	0.732
Pgp-substrate:	34.166412353515625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.157
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	2.25
Half-life (T1/2):	0.816

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.303
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.717
Carcinogencity:	0.077
Eye Corrosion:	0.006
Eye Irritation:	0.841
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: NPC262826

Natural Product ID:	NPC262826
*Common Name:**	2-Phenylethyl-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-phenylethoxy)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	MLRIJUWUQTVDQE-RKQHYHRCSA-N
Standard InCHI:	InChI=1S/C14H20O6/c15-8-10-11(16)12(17)13(18)14(20-10)19-7-6-9-4-2-1-3-5-9/h1-5,10-18H,6-8H2/t10-,11-,12+,13-,14-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510617
PubChem CID:	11289099
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.indcrop.2012.04.060]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2007.07.001]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(02)00288-1]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	bought from a drugstore in Beijing	n.a.	PMID[10514305]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[14738377]
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844940]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
NPO3784	Saccharopolyspora spinosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18345667]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	Tubers	n.a.	n.a.	PMID[20684540]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21524582]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3882	Asclepias incarnata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6861	Galium dasypodum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9385	Glycosmis ovoidea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1889	Panorpa japonica	Species	Panorpidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO218	Acer carpinifolium	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4698	Polymnia uvedalia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8829	Baccharis obtusifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4384	Cetraria aculeata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12620	Carum carvi	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14305	Moricandia arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26095	Hypericum revolutum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2090	Baccharis thesioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14084	Roccella fucoides	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6594	Hypericum sikokumontanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO969	Streptomyces setonensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2509	Strombus gigas	Species	Strombidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO368	Dendroaspis angusticeps	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12602	Leuzea centauroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5406	Veronica chamaedrys	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5633	Osyris abyssinica	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO940	Vernonia anisochaetoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1590	Sinningia aggregata	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18458	Raukaua simplex	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4759	Helleborus multifidus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19067	Symphyotrichum subspicatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14730	Bonnetia dinizii	Species	Bonnetiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3784	Saccharopolyspora spinosa	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3882	Asclepias incarnata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11577	Buddleja officinalis	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7084	Montezuma speciosissima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO40	Ostryopsis davidiana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4322	Scabiosa succisa	Species	Caprifoliaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	13.02	%	PMID[536424]

☑ 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 NPC262826 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	206
0.1-0.2	1006
0.2-0.3	2778
0.3-0.4	9466
0.4-0.5	15627
0.5-0.6	11124
0.6-0.7	2215
0.7-0.8	244
0.8-0.85	17
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC47286
0.9184	High Similarity	NPC37714
0.9184	High Similarity	NPC152384
0.8824	High Similarity	NPC474148
0.8824	High Similarity	NPC276061
0.8788	High Similarity	NPC469527
0.8738	High Similarity	NPC264784
0.8738	High Similarity	NPC30563
0.87	High Similarity	NPC148060
0.8667	High Similarity	NPC120217
0.8585	High Similarity	NPC157338
0.8426	Intermediate Similarity	NPC148055
0.8365	Intermediate Similarity	NPC184633
0.8349	Intermediate Similarity	NPC266389
0.8349	Intermediate Similarity	NPC216605
0.8349	Intermediate Similarity	NPC122245
0.8257	Intermediate Similarity	NPC175771
0.8241	Intermediate Similarity	NPC313193
0.8131	Intermediate Similarity	NPC470825
0.8125	Intermediate Similarity	NPC469702
0.8125	Intermediate Similarity	NPC282409
0.8053	Intermediate Similarity	NPC469548
0.8053	Intermediate Similarity	NPC476445
0.8053	Intermediate Similarity	NPC469703
0.8053	Intermediate Similarity	NPC476448
0.8053	Intermediate Similarity	NPC469704
0.8053	Intermediate Similarity	NPC201402
0.8053	Intermediate Similarity	NPC160854
0.8037	Intermediate Similarity	NPC43584
0.8036	Intermediate Similarity	NPC14950
0.7982	Intermediate Similarity	NPC55608
0.7982	Intermediate Similarity	NPC474641
0.7982	Intermediate Similarity	NPC266045
0.7982	Intermediate Similarity	NPC469686
0.7965	Intermediate Similarity	NPC469708
0.7965	Intermediate Similarity	NPC60589
0.7913	Intermediate Similarity	NPC471067
0.7913	Intermediate Similarity	NPC476142
0.7909	Intermediate Similarity	NPC29607
0.7895	Intermediate Similarity	NPC229600
0.7895	Intermediate Similarity	NPC469412
0.7895	Intermediate Similarity	NPC269242
0.7895	Intermediate Similarity	NPC198734
0.7845	Intermediate Similarity	NPC232454
0.7845	Intermediate Similarity	NPC470907
0.7845	Intermediate Similarity	NPC212176
0.7845	Intermediate Similarity	NPC178449
0.7826	Intermediate Similarity	NPC226712
0.7778	Intermediate Similarity	NPC57607
0.7778	Intermediate Similarity	NPC317163
0.7778	Intermediate Similarity	NPC244454
0.7712	Intermediate Similarity	NPC123704
0.7712	Intermediate Similarity	NPC90318
0.7692	Intermediate Similarity	NPC266343
0.7672	Intermediate Similarity	NPC11724
0.7627	Intermediate Similarity	NPC287429
0.7607	Intermediate Similarity	NPC140561
0.7607	Intermediate Similarity	NPC141970
0.7607	Intermediate Similarity	NPC52097
0.7586	Intermediate Similarity	NPC476872
0.7583	Intermediate Similarity	NPC79715
0.7583	Intermediate Similarity	NPC108659
0.7583	Intermediate Similarity	NPC264900
0.7583	Intermediate Similarity	NPC288416
0.7583	Intermediate Similarity	NPC469687
0.7583	Intermediate Similarity	NPC231607
0.7579	Intermediate Similarity	NPC121478
0.7579	Intermediate Similarity	NPC73637
0.7563	Intermediate Similarity	NPC470510
0.7521	Intermediate Similarity	NPC301857
0.7521	Intermediate Similarity	NPC148982
0.75	Intermediate Similarity	NPC475203
0.75	Intermediate Similarity	NPC472316
0.75	Intermediate Similarity	NPC136962
0.75	Intermediate Similarity	NPC114096
0.75	Intermediate Similarity	NPC472315
0.75	Intermediate Similarity	NPC94179
0.75	Intermediate Similarity	NPC474376
0.75	Intermediate Similarity	NPC37115
0.7479	Intermediate Similarity	NPC162925
0.7479	Intermediate Similarity	NPC145287
0.7479	Intermediate Similarity	NPC87153
0.7477	Intermediate Similarity	NPC185840
0.7477	Intermediate Similarity	NPC280616
0.7477	Intermediate Similarity	NPC242913
0.7477	Intermediate Similarity	NPC171831
0.7473	Intermediate Similarity	NPC108218
0.7459	Intermediate Similarity	NPC97326
0.7459	Intermediate Similarity	NPC469549
0.7459	Intermediate Similarity	NPC270849
0.7459	Intermediate Similarity	NPC11025
0.7459	Intermediate Similarity	NPC184092
0.7459	Intermediate Similarity	NPC26653
0.7459	Intermediate Similarity	NPC27712
0.7456	Intermediate Similarity	NPC473556
0.7456	Intermediate Similarity	NPC301651
0.7438	Intermediate Similarity	NPC198798
0.7438	Intermediate Similarity	NPC148026
0.7417	Intermediate Similarity	NPC83218
0.7417	Intermediate Similarity	NPC28069
0.7417	Intermediate Similarity	NPC77651
0.7417	Intermediate Similarity	NPC126991
0.7398	Intermediate Similarity	NPC17567
0.7398	Intermediate Similarity	NPC470122
0.7398	Intermediate Similarity	NPC469705
0.7398	Intermediate Similarity	NPC319995
0.7398	Intermediate Similarity	NPC17968
0.7398	Intermediate Similarity	NPC472024
0.7398	Intermediate Similarity	NPC80600
0.7398	Intermediate Similarity	NPC289415
0.7395	Intermediate Similarity	NPC138798
0.7377	Intermediate Similarity	NPC40377
0.7377	Intermediate Similarity	NPC158673
0.7377	Intermediate Similarity	NPC146540
0.7368	Intermediate Similarity	NPC164449
0.7368	Intermediate Similarity	NPC184030
0.7355	Intermediate Similarity	NPC290276
0.7355	Intermediate Similarity	NPC10883
0.7355	Intermediate Similarity	NPC35338
0.7355	Intermediate Similarity	NPC276047
0.7355	Intermediate Similarity	NPC198918
0.7355	Intermediate Similarity	NPC267733
0.7355	Intermediate Similarity	NPC204214
0.7355	Intermediate Similarity	NPC124878
0.7355	Intermediate Similarity	NPC471157
0.7355	Intermediate Similarity	NPC10121
0.7355	Intermediate Similarity	NPC471026
0.7355	Intermediate Similarity	NPC231888
0.7355	Intermediate Similarity	NPC252114
0.7355	Intermediate Similarity	NPC63404
0.7355	Intermediate Similarity	NPC92283
0.735	Intermediate Similarity	NPC146673
0.735	Intermediate Similarity	NPC233923
0.7347	Intermediate Similarity	NPC99482
0.7339	Intermediate Similarity	NPC478255
0.7339	Intermediate Similarity	NPC65942
0.7339	Intermediate Similarity	NPC9912
0.7339	Intermediate Similarity	NPC248307
0.7339	Intermediate Similarity	NPC46137
0.7339	Intermediate Similarity	NPC475067
0.7339	Intermediate Similarity	NPC235294
0.7321	Intermediate Similarity	NPC234376
0.7317	Intermediate Similarity	NPC166040
0.7295	Intermediate Similarity	NPC471025
0.7295	Intermediate Similarity	NPC471882
0.7295	Intermediate Similarity	NPC471881
0.7295	Intermediate Similarity	NPC35288
0.7295	Intermediate Similarity	NPC156692
0.7295	Intermediate Similarity	NPC106677
0.7295	Intermediate Similarity	NPC173150
0.7295	Intermediate Similarity	NPC231627
0.7295	Intermediate Similarity	NPC45224
0.7295	Intermediate Similarity	NPC175333
0.7292	Intermediate Similarity	NPC117180
0.729	Intermediate Similarity	NPC154905
0.729	Intermediate Similarity	NPC60373
0.728	Intermediate Similarity	NPC471095
0.728	Intermediate Similarity	NPC269421
0.728	Intermediate Similarity	NPC254275
0.728	Intermediate Similarity	NPC471066
0.7273	Intermediate Similarity	NPC12308
0.7273	Intermediate Similarity	NPC277788
0.7265	Intermediate Similarity	NPC238582
0.7265	Intermediate Similarity	NPC477803
0.7258	Intermediate Similarity	NPC262606
0.7257	Intermediate Similarity	NPC265002
0.7255	Intermediate Similarity	NPC317645
0.7253	Intermediate Similarity	NPC208302
0.7245	Intermediate Similarity	NPC304538
0.7236	Intermediate Similarity	NPC302378
0.7236	Intermediate Similarity	NPC471024
0.7236	Intermediate Similarity	NPC237182
0.7236	Intermediate Similarity	NPC226101
0.7236	Intermediate Similarity	NPC225307
0.7236	Intermediate Similarity	NPC232880
0.7222	Intermediate Similarity	NPC164172
0.7216	Intermediate Similarity	NPC103326
0.7216	Intermediate Similarity	NPC283012
0.7216	Intermediate Similarity	NPC329319
0.7216	Intermediate Similarity	NPC475199
0.7216	Intermediate Similarity	NPC99394
0.7216	Intermediate Similarity	NPC87299
0.7213	Intermediate Similarity	NPC61181
0.72	Intermediate Similarity	NPC475824
0.72	Intermediate Similarity	NPC476407
0.72	Intermediate Similarity	NPC225384
0.72	Intermediate Similarity	NPC166168
0.72	Intermediate Similarity	NPC138777
0.72	Intermediate Similarity	NPC246869
0.7193	Intermediate Similarity	NPC172525
0.7188	Intermediate Similarity	NPC309279
0.7177	Intermediate Similarity	NPC218003
0.7177	Intermediate Similarity	NPC248355
0.7177	Intermediate Similarity	NPC477294
0.7177	Intermediate Similarity	NPC307110
0.7177	Intermediate Similarity	NPC477293
0.7177	Intermediate Similarity	NPC253595
0.7177	Intermediate Similarity	NPC295970
0.7177	Intermediate Similarity	NPC229784
0.7165	Intermediate Similarity	NPC476411

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 NPC262826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	737
0.2-0.3	1517
0.3-0.4	3389
0.4-0.5	2226
0.5-0.6	975
0.6-0.7	122
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7826	Intermediate Similarity	NPD1091	Approved
0.7807	Intermediate Similarity	NPD5126	Approved
0.7807	Intermediate Similarity	NPD5125	Phase 3
0.7477	Intermediate Similarity	NPD969	Suspended
0.73	Intermediate Similarity	NPD531	Approved
0.7027	Intermediate Similarity	NPD6685	Approved
0.6964	Remote Similarity	NPD9532	Phase 3
0.6947	Remote Similarity	NPD7266	Discontinued
0.6937	Remote Similarity	NPD5048	Discontinued
0.6909	Remote Similarity	NPD5765	Approved
0.6875	Remote Similarity	NPD9294	Approved
0.6852	Remote Similarity	NPD9495	Approved
0.6789	Remote Similarity	NPD7798	Approved
0.6757	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD689	Discontinued
0.6724	Remote Similarity	NPD6912	Phase 3
0.6695	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD290	Approved
0.6634	Remote Similarity	NPD9491	Approved
0.6612	Remote Similarity	NPD7741	Discontinued
0.6607	Remote Similarity	NPD6647	Phase 2
0.6594	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD694	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4198	Discontinued
0.6466	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD2684	Approved
0.6449	Remote Similarity	NPD5058	Phase 3
0.6436	Remote Similarity	NPD226	Approved
0.6434	Remote Similarity	NPD2613	Approved
0.6429	Remote Similarity	NPD7876	Discontinued
0.6415	Remote Similarity	NPD800	Approved
0.6412	Remote Similarity	NPD4404	Approved
0.641	Remote Similarity	NPD2067	Discontinued
0.6406	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3705	Approved
0.6387	Remote Similarity	NPD7843	Approved
0.6385	Remote Similarity	NPD3027	Phase 3
0.6381	Remote Similarity	NPD1282	Approved
0.6379	Remote Similarity	NPD6406	Approved
0.6372	Remote Similarity	NPD4719	Phase 2
0.6364	Remote Similarity	NPD1613	Approved
0.6364	Remote Similarity	NPD1989	Approved
0.6364	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD1089	Approved
0.6355	Remote Similarity	NPD1090	Approved
0.6355	Remote Similarity	NPD1086	Approved
0.635	Remote Similarity	NPD6674	Discontinued
0.6338	Remote Similarity	NPD1653	Approved
0.6333	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3719	Approved
0.633	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3718	Approved
0.6321	Remote Similarity	NPD1101	Approved
0.6316	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1239	Approved
0.629	Remote Similarity	NPD1357	Approved
0.6288	Remote Similarity	NPD2570	Approved
0.6288	Remote Similarity	NPD3090	Approved
0.6288	Remote Similarity	NPD3616	Approved
0.6288	Remote Similarity	NPD3088	Approved
0.6288	Remote Similarity	NPD2571	Approved
0.6288	Remote Similarity	NPD4746	Phase 3
0.6288	Remote Similarity	NPD3089	Approved
0.6288	Remote Similarity	NPD4745	Approved
0.6288	Remote Similarity	NPD3615	Approved
0.6288	Remote Similarity	NPD2573	Approved
0.6288	Remote Similarity	NPD3087	Approved
0.6288	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD2566	Approved
0.6288	Remote Similarity	NPD2574	Discontinued
0.6288	Remote Similarity	NPD3614	Approved
0.6273	Remote Similarity	NPD1693	Approved
0.6273	Remote Similarity	NPD2933	Approved
0.6273	Remote Similarity	NPD2934	Approved
0.6271	Remote Similarity	NPD9713	Approved
0.6261	Remote Similarity	NPD1237	Approved
0.625	Remote Similarity	NPD9611	Approved
0.625	Remote Similarity	NPD9609	Approved
0.625	Remote Similarity	NPD9612	Approved
0.624	Remote Similarity	NPD5723	Approved
0.6239	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD752	Approved
0.6239	Remote Similarity	NPD1088	Approved
0.6238	Remote Similarity	NPD9490	Approved
0.6233	Remote Similarity	NPD8455	Phase 2
0.6232	Remote Similarity	NPD1652	Phase 2
0.623	Remote Similarity	NPD7157	Approved
0.623	Remote Similarity	NPD7508	Discontinued
0.6228	Remote Similarity	NPD854	Approved
0.6228	Remote Similarity	NPD846	Approved
0.6228	Remote Similarity	NPD940	Approved
0.6228	Remote Similarity	NPD855	Approved
0.6226	Remote Similarity	NPD9538	Approved
0.6226	Remote Similarity	NPD4793	Discontinued
0.6222	Remote Similarity	NPD4536	Approved
0.6222	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5886	Approved
0.6222	Remote Similarity	NPD4538	Approved
0.6222	Remote Similarity	NPD41	Approved
0.6218	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD2860	Approved
0.6216	Remote Similarity	NPD2859	Approved
0.6204	Remote Similarity	NPD3673	Approved
0.6204	Remote Similarity	NPD3672	Approved
0.6202	Remote Similarity	NPD2160	Approved
0.6202	Remote Similarity	NPD2626	Approved
0.6202	Remote Similarity	NPD2159	Approved
0.6202	Remote Similarity	NPD2627	Approved
0.6202	Remote Similarity	NPD2628	Approved
0.6202	Remote Similarity	NPD2625	Approved
0.6198	Remote Similarity	NPD6010	Discontinued
0.6195	Remote Similarity	NPD2066	Phase 3
0.6194	Remote Similarity	NPD4684	Phase 3
0.6194	Remote Similarity	NPD4685	Phase 3
0.6194	Remote Similarity	NPD4686	Approved
0.6187	Remote Similarity	NPD2575	Approved
0.6182	Remote Similarity	NPD720	Approved
0.6182	Remote Similarity	NPD1066	Discontinued
0.6182	Remote Similarity	NPD719	Approved
0.6176	Remote Similarity	NPD5588	Approved
0.6176	Remote Similarity	NPD5960	Phase 3
0.6154	Remote Similarity	NPD5704	Approved
0.6154	Remote Similarity	NPD968	Approved
0.6154	Remote Similarity	NPD5705	Approved
0.6154	Remote Similarity	NPD5706	Approved
0.6142	Remote Similarity	NPD2611	Approved
0.6142	Remote Similarity	NPD2612	Approved
0.6142	Remote Similarity	NPD2609	Approved
0.6142	Remote Similarity	NPD3132	Approved
0.6142	Remote Similarity	NPD4217	Approved
0.6142	Remote Similarity	NPD2608	Approved
0.6142	Remote Similarity	NPD4215	Approved
0.6142	Remote Similarity	NPD2610	Approved
0.6142	Remote Similarity	NPD4216	Approved
0.6142	Remote Similarity	NPD3131	Approved
0.6142	Remote Similarity	NPD4218	Approved
0.614	Remote Similarity	NPD2558	Approved
0.614	Remote Similarity	NPD2555	Approved
0.614	Remote Similarity	NPD2552	Approved
0.614	Remote Similarity	NPD2553	Approved
0.614	Remote Similarity	NPD2550	Approved
0.614	Remote Similarity	NPD2549	Approved
0.6139	Remote Similarity	NPD225	Approved
0.6139	Remote Similarity	NPD227	Approved
0.6134	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4814	Discontinued
0.6126	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD9250	Approved
0.6111	Remote Similarity	NPD5346	Phase 2
0.6111	Remote Similarity	NPD5306	Approved
0.6111	Remote Similarity	NPD5347	Phase 2
0.6111	Remote Similarity	NPD5305	Approved
0.6107	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4189	Approved
0.6087	Remote Similarity	NPD4188	Approved
0.6083	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.608	Remote Similarity	NPD1548	Phase 1
0.6077	Remote Similarity	NPD3094	Phase 2
0.6075	Remote Similarity	NPD1087	Approved
0.6068	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2652	Approved
0.6066	Remote Similarity	NPD2650	Approved
0.6063	Remote Similarity	NPD4136	Approved
0.6063	Remote Similarity	NPD4106	Approved
0.6063	Remote Similarity	NPD4135	Approved
0.6061	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3020	Approved
0.6047	Remote Similarity	NPD3685	Discontinued
0.6045	Remote Similarity	NPD6233	Phase 2
0.6036	Remote Similarity	NPD1409	Phase 3
0.6036	Remote Similarity	NPD845	Approved
0.6034	Remote Similarity	NPD744	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD1875	Phase 1
0.6018	Remote Similarity	NPD1564	Approved
0.6018	Remote Similarity	NPD1565	Approved
0.6018	Remote Similarity	NPD1566	Phase 3
0.6017	Remote Similarity	NPD3526	Approved
0.6017	Remote Similarity	NPD812	Approved
0.6017	Remote Similarity	NPD810	Approved
0.6017	Remote Similarity	NPD811	Approved
0.6017	Remote Similarity	NPD3524	Approved
0.6016	Remote Similarity	NPD4806	Approved
0.6016	Remote Similarity	NPD1610	Phase 2
0.6016	Remote Similarity	NPD4807	Approved
0.6015	Remote Similarity	NPD4738	Phase 2
0.6015	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1242	Phase 1
0.6	Remote Similarity	NPD530	Approved
0.6	Remote Similarity	NPD3021	Approved
0.6	Remote Similarity	NPD3022	Approved
0.6	Remote Similarity	NPD8651	Approved
0.5985	Remote Similarity	NPD2861	Phase 2
0.5985	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7097	Phase 1
0.5984	Remote Similarity	NPD6516	Phase 2
0.5984	Remote Similarity	NPD9384	Approved
0.5984	Remote Similarity	NPD1138	Approved
0.5984	Remote Similarity	NPD5238	Clinical (unspecified phase)

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