Structure

Physi-Chem Properties

Molecular Weight:  360.14
Volume:  339.382
LogP:  -0.543
LogD:  -0.84
LogS:  -0.845
# Rotatable Bonds:  7
TPSA:  138.07
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.39
Synthetic Accessibility Score:  3.564
Fsp3:  0.625
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:  -5.528
MDCK Permeability:  6.543652125401422e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.196
Human Intestinal Absorption (HIA):  0.556
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.327
Plasma Protein Binding (PPB):  25.06060791015625%
Volume Distribution (VD):  0.498
Pgp-substrate:  41.65796661376953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.034
CYP1A2-substrate:  0.358
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.805
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.316
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.277
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.061

ADMET: Excretion

Clearance (CL):  3.041
Half-life (T1/2):  0.831

ADMET: Toxicity

hERG Blockers:  0.199
Human Hepatotoxicity (H-HT):  0.252
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.089
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.46
Carcinogencity:  0.035
Eye Corrosion:  0.003
Eye Irritation:  0.036
Respiratory Toxicity:  0.011

Download Data

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Structure MOL file  
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  Natural Product: NPC69513

Natural Product ID:  NPC69513
Common Name*:   2,6-Dimethoxy-4-(2-Hydroxyethyl)Phenol 1-O-Beta-D-Glucopyranoside
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[4-(2-hydroxyethyl)-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  PSZXKZGDJMPMIO-SSZWKKLZSA-N
Standard InCHI:  InChI=1S/C16H24O9/c1-22-9-5-8(3-4-17)6-10(23-2)15(9)25-16-14(21)13(20)12(19)11(7-18)24-16/h5-6,11-14,16-21H,3-4,7H2,1-2H3/t11-,12-,13+,14-,16+/m1/s1
SMILES:  COc1cc(CCO)cc(c1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2332680
PubChem CID:   10959332
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:0004165] Phenolic 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
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[10757717]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. aerial part n.a. PMID[12943781]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12951446]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota stems Thailand n.a. PMID[14510595]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. PMID[14738381]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. Argentine n.a. PMID[14738381]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. PMID[21905650]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. PMID[23540981]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[24697288]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[32998509]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota sclerotia n.a. n.a. PMID[9599285]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12416 Quercus mongolica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15961 Sida cordifolia Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23289 Heracleum sphondylium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13375 Palafoxia rosea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15393 Eucalyptus flocktoniae Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24176 Streptomyces fradiae Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO24732 Cereus weberi Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26017 Dalbergia stipulacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16847 Consolida ajacis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15138 Rheum webbianum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14218 Spodoptera littoralis Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4267 Ceratocystis clavigera Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16516 Centaurea seridis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4935 Dinemasporium strigosum Species Chaetosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12977 Solenopsis invicta Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16758 Satureja cuneifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15755 Thymbra spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14555 Porella swartziana Species Porellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13548 Chrozophora obliqua Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5269 Coleus garckeanus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22437 Eurya japonica Species Pentaphylacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8499 Osmerus mordax Species Osmeridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7484 Salacia chinensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11194 Bombus hortorum Species Apidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14034 Salvia coulteri Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9780 Merremia umbellata Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13859 Senecio flavus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11881 Adenopeltis colliguaya Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5552 Solanum sisymbriifolium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14869 Ormosia panamensis Species Limoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16175 Trichia floriformis Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5728 Gerbera piloselloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2353 Bituminaria bituminosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13230 Pedicularis condensata Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13710 Lyophyllum shimeji Species Lyophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16678 Flindersia brayleyana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11599 Elaeagnus commutata Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3391 Jungermannia obovata Species Jungermanniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9420 Aspergillus arenarius Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15858 Phoebe formosana Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14826 Streptomyces mobaraensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12450 Cneorum pulverulentum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15015 Meconopsis napaulensis Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15510 Kummerowia striata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12680 Perityle vaseyi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15272 Mascarenhasia arborescens Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5078 Turraeanthus mannii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12555 Aspergillus quadrilineatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16428 Millettia conraui Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12416 Quercus mongolica Species Fagaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity ED50 > 100.0 uM PMID[533641]

☑ 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 NPC69513 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC215833
0.9921 High Similarity NPC13745
0.9921 High Similarity NPC48863
0.9921 High Similarity NPC251981
0.9764 High Similarity NPC162093
0.9764 High Similarity NPC299144
0.9688 High Similarity NPC49074
0.9612 High Similarity NPC107478
0.9606 High Similarity NPC80600
0.9606 High Similarity NPC472024
0.9538 High Similarity NPC470236
0.9528 High Similarity NPC26653
0.9528 High Similarity NPC270849
0.9466 High Similarity NPC164857
0.9457 High Similarity NPC470270
0.9449 High Similarity NPC302378
0.9403 High Similarity NPC469559
0.9403 High Similarity NPC189115
0.9385 High Similarity NPC132895
0.938 High Similarity NPC9912
0.9375 High Similarity NPC248355
0.9375 High Similarity NPC166040
0.9328 High Similarity NPC469661
0.9323 High Similarity NPC98777
0.9323 High Similarity NPC212770
0.9318 High Similarity NPC25695
0.9318 High Similarity NPC172818
0.9318 High Similarity NPC104167
0.9313 High Similarity NPC187194
0.9265 High Similarity NPC25292
0.9265 High Similarity NPC473045
0.9259 High Similarity NPC475084
0.9254 High Similarity NPC210478
0.9248 High Similarity NPC65530
0.9248 High Similarity NPC59324
0.9237 High Similarity NPC25821
0.9231 High Similarity NPC65942
0.9231 High Similarity NPC248307
0.9197 High Similarity NPC277867
0.9197 High Similarity NPC475096
0.9197 High Similarity NPC161700
0.9191 High Similarity NPC473044
0.9173 High Similarity NPC242028
0.9173 High Similarity NPC203230
0.9167 High Similarity NPC476411
0.9154 High Similarity NPC469612
0.9154 High Similarity NPC262606
0.9154 High Similarity NPC469614
0.913 High Similarity NPC125755
0.913 High Similarity NPC190714
0.913 High Similarity NPC99515
0.9118 High Similarity NPC5262
0.9118 High Similarity NPC472714
0.9111 High Similarity NPC226547
0.9104 High Similarity NPC470413
0.9104 High Similarity NPC138738
0.9104 High Similarity NPC195196
0.9091 High Similarity NPC115022
0.9091 High Similarity NPC294166
0.9084 High Similarity NPC469698
0.9084 High Similarity NPC30043
0.9084 High Similarity NPC469625
0.9084 High Similarity NPC473412
0.9084 High Similarity NPC469613
0.9077 High Similarity NPC470258
0.9077 High Similarity NPC218856
0.9077 High Similarity NPC210623
0.9077 High Similarity NPC190629
0.9077 High Similarity NPC285339
0.9077 High Similarity NPC273295
0.9077 High Similarity NPC3439
0.9077 High Similarity NPC222004
0.9077 High Similarity NPC226788
0.9077 High Similarity NPC202582
0.9077 High Similarity NPC307110
0.907 High Similarity NPC474119
0.9065 High Similarity NPC227902
0.9065 High Similarity NPC39657
0.9062 High Similarity NPC12308
0.9051 High Similarity NPC252169
0.9051 High Similarity NPC37793
0.9023 High Similarity NPC470881
0.9023 High Similarity NPC170694
0.9023 High Similarity NPC35731
0.9015 High Similarity NPC85799
0.9015 High Similarity NPC184447
0.9015 High Similarity NPC303422
0.9015 High Similarity NPC26080
0.9015 High Similarity NPC35932
0.9015 High Similarity NPC7903
0.9015 High Similarity NPC165686
0.9015 High Similarity NPC16208
0.9015 High Similarity NPC160991
0.9 High Similarity NPC248132
0.9 High Similarity NPC270751
0.9 High Similarity NPC93924
0.9 High Similarity NPC175976
0.9 High Similarity NPC130449
0.8992 High Similarity NPC473960
0.8986 High Similarity NPC138227
0.8986 High Similarity NPC472713
0.8986 High Similarity NPC168579
0.8986 High Similarity NPC469313
0.8986 High Similarity NPC76176
0.8986 High Similarity NPC473046
0.8986 High Similarity NPC187774
0.8986 High Similarity NPC472712
0.8986 High Similarity NPC118385
0.8963 High Similarity NPC283949
0.8955 High Similarity NPC236522
0.8955 High Similarity NPC55040
0.8955 High Similarity NPC238243
0.8947 High Similarity NPC6836
0.8947 High Similarity NPC263064
0.8939 High Similarity NPC121376
0.8939 High Similarity NPC472597
0.8939 High Similarity NPC475067
0.8939 High Similarity NPC166168
0.8936 High Similarity NPC51328
0.8936 High Similarity NPC35877
0.8936 High Similarity NPC106138
0.8936 High Similarity NPC55158
0.8936 High Similarity NPC286235
0.8936 High Similarity NPC55715
0.8936 High Similarity NPC95392
0.8929 High Similarity NPC15538
0.8929 High Similarity NPC473480
0.8905 High Similarity NPC76871
0.8905 High Similarity NPC210192
0.8889 High Similarity NPC138350
0.8889 High Similarity NPC165482
0.8889 High Similarity NPC177035
0.8889 High Similarity NPC197723
0.8889 High Similarity NPC37468
0.8889 High Similarity NPC52277
0.8889 High Similarity NPC471719
0.8889 High Similarity NPC199459
0.8889 High Similarity NPC3293
0.8889 High Similarity NPC40664
0.8881 High Similarity NPC188555
0.8881 High Similarity NPC87696
0.8881 High Similarity NPC130496
0.8881 High Similarity NPC310854
0.8873 High Similarity NPC472710
0.8873 High Similarity NPC472709
0.8872 High Similarity NPC252833
0.8865 High Similarity NPC96294
0.8864 High Similarity NPC472338
0.8841 High Similarity NPC60249
0.8841 High Similarity NPC246947
0.8832 High Similarity NPC56091
0.8832 High Similarity NPC106944
0.8832 High Similarity NPC46591
0.8824 High Similarity NPC474039
0.8824 High Similarity NPC124149
0.8824 High Similarity NPC185908
0.8824 High Similarity NPC304152
0.8819 High Similarity NPC198734
0.8819 High Similarity NPC469412
0.8815 High Similarity NPC260898
0.8815 High Similarity NPC234333
0.8815 High Similarity NPC61946
0.8815 High Similarity NPC47398
0.8815 High Similarity NPC150534
0.8806 High Similarity NPC196937
0.8797 High Similarity NPC309787
0.8797 High Similarity NPC470096
0.8797 High Similarity NPC470095
0.8794 High Similarity NPC52740
0.8788 High Similarity NPC218003
0.8777 High Similarity NPC185307
0.8777 High Similarity NPC46092
0.8777 High Similarity NPC470950
0.8777 High Similarity NPC81638
0.876 High Similarity NPC220598
0.876 High Similarity NPC165375
0.8759 High Similarity NPC292487
0.8759 High Similarity NPC100389
0.875 High Similarity NPC215060
0.875 High Similarity NPC302610
0.875 High Similarity NPC21902
0.875 High Similarity NPC16435
0.875 High Similarity NPC306441
0.875 High Similarity NPC476352
0.8741 High Similarity NPC114740
0.8741 High Similarity NPC238140
0.8741 High Similarity NPC309744
0.874 High Similarity NPC469708
0.874 High Similarity NPC60589
0.8732 High Similarity NPC280945
0.8732 High Similarity NPC478237
0.8731 High Similarity NPC201587
0.8731 High Similarity NPC253105
0.8731 High Similarity NPC470752
0.873 High Similarity NPC63083
0.8722 High Similarity NPC474491
0.8714 High Similarity NPC471667
0.8714 High Similarity NPC79429
0.8714 High Similarity NPC217635
0.8714 High Similarity NPC129417

  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 NPC69513 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8647 High Similarity NPD3027 Phase 3
0.8542 High Similarity NPD1653 Approved
0.8462 Intermediate Similarity NPD1091 Approved
0.8456 Intermediate Similarity NPD1613 Approved
0.8456 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8321 Intermediate Similarity NPD3705 Approved
0.8239 Intermediate Similarity NPD6674 Discontinued
0.8222 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8162 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD7054 Approved
0.7972 Intermediate Similarity NPD7266 Discontinued
0.7955 Intermediate Similarity NPD1357 Approved
0.7947 Intermediate Similarity NPD37 Approved
0.7926 Intermediate Similarity NPD2982 Phase 2
0.7926 Intermediate Similarity NPD2983 Phase 2
0.7925 Intermediate Similarity NPD7074 Phase 3
0.7925 Intermediate Similarity NPD7472 Approved
0.7908 Intermediate Similarity NPD4965 Approved
0.7908 Intermediate Similarity NPD4967 Phase 2
0.7908 Intermediate Similarity NPD4966 Approved
0.7852 Intermediate Similarity NPD2981 Phase 2
0.7826 Intermediate Similarity NPD3018 Phase 2
0.7821 Intermediate Similarity NPD7199 Phase 2
0.7806 Intermediate Similarity NPD6234 Discontinued
0.7799 Intermediate Similarity NPD7228 Approved
0.7799 Intermediate Similarity NPD3818 Discontinued
0.7778 Intermediate Similarity NPD7808 Phase 3
0.7764 Intermediate Similarity NPD6797 Phase 2
0.7716 Intermediate Similarity NPD7251 Discontinued
0.7692 Intermediate Similarity NPD7843 Approved
0.7669 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7656 Intermediate Similarity NPD2684 Approved
0.7652 Intermediate Similarity NPD7157 Approved
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7628 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD1652 Phase 2
0.7615 Intermediate Similarity NPD228 Approved
0.761 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD7240 Approved
0.7597 Intermediate Similarity NPD1934 Approved
0.7584 Intermediate Similarity NPD5058 Phase 3
0.7564 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD6842 Approved
0.7545 Intermediate Similarity NPD6841 Approved
0.7545 Intermediate Similarity NPD6843 Phase 3
0.7536 Intermediate Similarity NPD4749 Approved
0.7535 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7535 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1610 Phase 2
0.7516 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3817 Phase 2
0.75 Intermediate Similarity NPD5283 Phase 1
0.7483 Intermediate Similarity NPD1375 Discontinued
0.7481 Intermediate Similarity NPD1548 Phase 1
0.7453 Intermediate Similarity NPD6166 Phase 2
0.7453 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD290 Approved
0.7436 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD4536 Approved
0.7397 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD4538 Approved
0.7394 Intermediate Similarity NPD6559 Discontinued
0.7386 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD4675 Approved
0.7355 Intermediate Similarity NPD4678 Approved
0.7325 Intermediate Similarity NPD2801 Approved
0.7325 Intermediate Similarity NPD8455 Phase 2
0.7324 Intermediate Similarity NPD2861 Phase 2
0.7323 Intermediate Similarity NPD291 Approved
0.7317 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD4237 Approved
0.7267 Intermediate Similarity NPD4236 Phase 3
0.7266 Intermediate Similarity NPD422 Phase 1
0.726 Intermediate Similarity NPD5124 Phase 1
0.726 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD3540 Phase 1
0.7241 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD8651 Approved
0.7233 Intermediate Similarity NPD3882 Suspended
0.723 Intermediate Similarity NPD5588 Approved
0.723 Intermediate Similarity NPD5960 Phase 3
0.7226 Intermediate Similarity NPD3686 Approved
0.7226 Intermediate Similarity NPD3687 Approved
0.7222 Intermediate Similarity NPD3787 Discontinued
0.7222 Intermediate Similarity NPD4625 Phase 3
0.7215 Intermediate Similarity NPD2978 Approved
0.7215 Intermediate Similarity NPD2977 Approved
0.7212 Intermediate Similarity NPD5844 Phase 1
0.7197 Intermediate Similarity NPD556 Approved
0.7192 Intermediate Similarity NPD3620 Phase 2
0.7192 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD1558 Phase 1
0.719 Intermediate Similarity NPD1774 Approved
0.7181 Intermediate Similarity NPD3539 Phase 1
0.7179 Intermediate Similarity NPD4005 Discontinued
0.7171 Intermediate Similarity NPD2677 Approved
0.7171 Intermediate Similarity NPD2219 Phase 1
0.7163 Intermediate Similarity NPD3685 Discontinued
0.7163 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD7097 Phase 1
0.7152 Intermediate Similarity NPD4162 Approved
0.7143 Intermediate Similarity NPD230 Phase 1
0.7132 Intermediate Similarity NPD6671 Approved
0.7126 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD6233 Phase 2
0.7107 Intermediate Similarity NPD5772 Approved
0.7107 Intermediate Similarity NPD5773 Approved
0.7105 Intermediate Similarity NPD4110 Phase 3
0.7105 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6653 Approved
0.7086 Intermediate Similarity NPD2424 Discontinued
0.7083 Intermediate Similarity NPD7685 Pre-registration
0.7078 Intermediate Similarity NPD1511 Approved
0.7075 Intermediate Similarity NPD4060 Phase 1
0.7047 Intermediate Similarity NPD6111 Discontinued
0.7039 Intermediate Similarity NPD3060 Approved
0.7034 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD4123 Phase 3
0.7029 Intermediate Similarity NPD5536 Phase 2
0.7027 Intermediate Similarity NPD5735 Approved
0.7025 Intermediate Similarity NPD4380 Phase 2
0.702 Intermediate Similarity NPD5762 Approved
0.702 Intermediate Similarity NPD5763 Approved
0.7 Intermediate Similarity NPD5126 Approved
0.7 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4108 Discontinued
0.7 Intermediate Similarity NPD5125 Phase 3
0.7 Intermediate Similarity NPD6516 Phase 2
0.7 Intermediate Similarity NPD5846 Approved
0.7 Intermediate Similarity NPD1465 Phase 2
0.6994 Remote Similarity NPD5494 Approved
0.6993 Remote Similarity NPD4628 Phase 3
0.6987 Remote Similarity NPD7526 Approved
0.6987 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1512 Approved
0.6987 Remote Similarity NPD52 Approved
0.6986 Remote Similarity NPD7095 Approved
0.6986 Remote Similarity NPD3180 Approved
0.6986 Remote Similarity NPD3179 Approved
0.6975 Remote Similarity NPD7075 Discontinued
0.6972 Remote Similarity NPD2231 Phase 2
0.6972 Remote Similarity NPD2235 Phase 2
0.6968 Remote Similarity NPD4357 Discontinued
0.6968 Remote Similarity NPD6799 Approved
0.6966 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5353 Approved
0.6957 Remote Similarity NPD5402 Approved
0.6954 Remote Similarity NPD2161 Phase 2
0.695 Remote Similarity NPD3496 Discontinued
0.6948 Remote Similarity NPD6190 Approved
0.6946 Remote Similarity NPD3751 Discontinued
0.6939 Remote Similarity NPD6798 Discontinued
0.6937 Remote Similarity NPD3384 Approved
0.6937 Remote Similarity NPD3382 Approved
0.6937 Remote Similarity NPD3383 Approved
0.6928 Remote Similarity NPD5177 Phase 3
0.6913 Remote Similarity NPD6355 Discontinued
0.6912 Remote Similarity NPD821 Approved
0.6906 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7124 Phase 2
0.6894 Remote Similarity NPD7819 Suspended
0.6892 Remote Similarity NPD4062 Phase 3
0.6883 Remote Similarity NPD3892 Phase 2
0.6883 Remote Similarity NPD6331 Phase 2
0.6883 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6883 Remote Similarity NPD4535 Phase 3
0.6879 Remote Similarity NPD1778 Approved
0.6879 Remote Similarity NPD5261 Clinical (unspecified phase)
0.686 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6859 Remote Similarity NPD7212 Phase 2
0.6859 Remote Similarity NPD7213 Phase 3
0.6852 Remote Similarity NPD2563 Approved
0.6852 Remote Similarity NPD2560 Approved
0.6848 Remote Similarity NPD8127 Discontinued
0.6846 Remote Similarity NPD4140 Approved
0.6846 Remote Similarity NPD2238 Phase 2
0.6842 Remote Similarity NPD6099 Approved
0.6842 Remote Similarity NPD7549 Discontinued
0.6842 Remote Similarity NPD6100 Approved
0.6842 Remote Similarity NPD968 Approved
0.6842 Remote Similarity NPD3454 Phase 3
0.6835 Remote Similarity NPD5403 Approved
0.6835 Remote Similarity NPD2122 Discontinued
0.6832 Remote Similarity NPD6801 Discontinued
0.6821 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6815 Remote Similarity NPD3022 Approved
0.6815 Remote Similarity NPD5401 Approved
0.6815 Remote Similarity NPD7447 Phase 1
0.6815 Remote Similarity NPD4739 Approved
0.6815 Remote Similarity NPD3021 Approved
0.6813 Remote Similarity NPD7680 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