Structure

Physi-Chem Properties

Molecular Weight:  270.09
Volume:  282.249
LogP:  2.77
LogD:  2.869
LogS:  -3.317
# Rotatable Bonds:  4
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.662
Synthetic Accessibility Score:  2.002
Fsp3:  0.062
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:  -4.712
MDCK Permeability:  1.411413904861547e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.031
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.137
Plasma Protein Binding (PPB):  98.58489990234375%
Volume Distribution (VD):  0.554
Pgp-substrate:  1.240850567817688%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.851
CYP2C19-inhibitor:  0.88
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.742
CYP2C9-substrate:  0.965
CYP2D6-inhibitor:  0.646
CYP2D6-substrate:  0.913
CYP3A4-inhibitor:  0.842
CYP3A4-substrate:  0.293

ADMET: Excretion

Clearance (CL):  12.0
Half-life (T1/2):  0.928

ADMET: Toxicity

hERG Blockers:  0.064
Human Hepatotoxicity (H-HT):  0.115
Drug-inuced Liver Injury (DILI):  0.509
AMES Toxicity:  0.463
Rat Oral Acute Toxicity:  0.794
Maximum Recommended Daily Dose:  0.566
Skin Sensitization:  0.936
Carcinogencity:  0.781
Eye Corrosion:  0.058
Eye Irritation:  0.978
Respiratory Toxicity:  0.745

Download Data

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

  Natural Product: NPC247779

Natural Product ID:  NPC247779
Common Name*:   Echinatin
IUPAC Name:   (E)-3-(4-hydroxy-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms:   Echinantin
Standard InCHIKey:  QJKMIJNRNRLQSS-WEVVVXLNSA-N
Standard InCHI:  InChI=1S/C16H14O4/c1-20-16-10-14(18)8-4-12(16)5-9-15(19)11-2-6-13(17)7-3-11/h2-10,17-18H,1H3/b9-5+
SMILES:  COc1cc(ccc1/C=C/C(=O)c1ccc(cc1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL141530
PubChem CID:   6442675
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003474] Retrochalcones

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20984 Glycyrrhiza echinata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20984 Glycyrrhiza echinata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20984 Glycyrrhiza echinata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 > 50000.0 nM PMID[538885]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 2.19 ug.mL-1 PMID[538887]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 2.49 ug.mL-1 PMID[538887]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 5.7 ug.mL-1 PMID[538887]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 5.8 ug.mL-1 PMID[538887]
NPT344 Individual Protein Sialidase Clostridium perfringens IC50 = 8.13 ug.mL-1 PMID[538887]
NPT493 Individual Protein Neuraminidase Influenza A virus IC50 = 8.23 ug.mL-1 PMID[538887]
NPT2548 Cell Line SNU-638 Homo sapiens IC50 = 10410.0 nM PMID[538888]
NPT396 Cell Line T47D Homo sapiens IC50 = 12110.0 nM PMID[538888]
NPT469 Individual Protein Cathepsin L Homo sapiens IC50 = 30340.0 nM PMID[538888]
NPT214 Individual Protein Cathepsin B Homo sapiens IC50 = 57680.0 nM PMID[538888]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Inhibition = 1.6 % PMID[538888]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens Inhibition = 2.1 % PMID[538888]
NPT143 Individual Protein DNA topoisomerase I Homo sapiens Inhibition = 88.9 % PMID[538888]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition < 50.0 % PMID[538889]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 5.46 n.a. PMID[538891]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 6.8 n.a. PMID[538891]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 4.3 n.a. PMID[538891]
NPT83 Cell Line MCF7 Homo sapiens GI = 0.0 % PMID[538892]
NPT660 Cell Line SW480 Homo sapiens GI = 24.0 % PMID[538892]
NPT65 Cell Line HepG2 Homo sapiens GI = 6.0 % PMID[538892]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 26.0 % PMID[538892]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 75.0 % PMID[538892]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 4.09 n.a. PMID[538893]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Activity > 60.0 % PMID[538893]
NPT1166 Individual Protein Angiotensin-converting enzyme Homo sapiens Inhibition = 72.52 % PMID[538894]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition > 60.0 % PMID[538896]
NPT65 Cell Line HepG2 Homo sapiens Activity = 80.0 % PMID[538896]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens IC50 = 45000.0 nM PMID[538897]
NPT393 Cell Line HCT-116 Homo sapiens GI50 = 64000.0 nM PMID[538897]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Inhibition = 20.0 % PMID[538897]
NPT83 Cell Line MCF7 Homo sapiens CI < 0.3 n.a. PMID[538897]
NPT81 Cell Line A549 Homo sapiens GI50 = 36000.0 nM PMID[538897]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 43000.0 nM PMID[538897]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 68000.0 nM PMID[538883]
NPT27 Others Unspecified IC50 = 94000.0 nM PMID[538883]
NPT841 Organism Leishmania major Leishmania major Inhibition = 86.8 % PMID[538884]
NPT841 Organism Leishmania major Leishmania major Inhibition = 69.3 % PMID[538884]
NPT841 Organism Leishmania major Leishmania major Inhibition = 50.3 % PMID[538884]
NPT841 Organism Leishmania major Leishmania major Inhibition = 30.0 % PMID[538884]
NPT841 Organism Leishmania major Leishmania major Inhibition = 16.4 % PMID[538884]
NPT27 Others Unspecified Inhibition = 26.4 % PMID[538884]
NPT27 Others Unspecified Inhibition = 18.0 % PMID[538884]
NPT27 Others Unspecified Inhibition = 10.4 % PMID[538884]
NPT27 Others Unspecified Inhibition = 9.2 % PMID[538884]
NPT27 Others Unspecified Inhibition = 7.8 % PMID[538884]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 94.0 % PMID[538884]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 92.0 % PMID[538884]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 62.0 % PMID[538884]
NPT633 Organism Leishmania donovani Leishmania donovani Inhibition = 57.0 % PMID[538884]
NPT2 Others Unspecified Ratio IC50 = 240.0 n.a. PMID[538887]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 30000.0 nM PMID[538890]
NPT742 Organism Influenza A virus Influenza A virus Activity > 30.0 % PMID[538891]
NPT32 Organism Mus musculus Mus musculus Activity = 2.42 nmol PMID[538891]
NPT32 Organism Mus musculus Mus musculus Activity = 2.58 nmol PMID[538891]
NPT2 Others Unspecified Inhibition = 0.0 % PMID[538892]
NPT2 Others Unspecified Inhibition = 16.0 % PMID[538892]
NPT32 Organism Mus musculus Mus musculus Activity = 70.0 U/L PMID[538893]
NPT32 Organism Mus musculus Mus musculus Activity = 150.0 U/L PMID[538893]
NPT32 Organism Mus musculus Mus musculus Activity = 800.0 U/L PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus Cmax = 0.2283 ug.mL-1 PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus Tmax = 0.5 hr PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus T1/2 = 7.32 hr PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus AUC = 685.92 ng.hr.mL-1 PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus AUC = 1154.92 ng.hr.mL-1 PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus MRT(t) = 3.98 hr PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus MRT = 3.98 hr PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus CLz/F = 20.97 L/hr/kg PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus Vd/F = 154.13 L.kg-1 PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus VRT(t) = 9.97 hr2 PMID[538893]
NPT29 Organism Rattus norvegicus Rattus norvegicus VRT = 217.15 hr2 PMID[538893]
NPT2 Others Unspecified Inhibition > 40.0 % PMID[538896]
NPT21657 SINGLE PROTEIN DNA topoisomerase I Bos taurus Inhibition = 30.0 % PMID[538897]

☑ 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 NPC247779 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
0.984 High Similarity NPC128348
0.984 High Similarity NPC112192
0.984 High Similarity NPC309717
0.984 High Similarity NPC189106
0.984 High Similarity NPC164236
0.984 High Similarity NPC66384
0.9762 High Similarity NPC212631
0.9762 High Similarity NPC87231
0.9762 High Similarity NPC205468
0.9762 High Similarity NPC129132
0.9762 High Similarity NPC257756
0.9685 High Similarity NPC337373
0.9685 High Similarity NPC188646
0.9685 High Similarity NPC242294
0.9685 High Similarity NPC56031
0.9685 High Similarity NPC27643
0.9685 High Similarity NPC139813
0.9685 High Similarity NPC175098
0.9685 High Similarity NPC192304
0.9685 High Similarity NPC312318
0.9685 High Similarity NPC263670
0.9685 High Similarity NPC472365
0.9683 High Similarity NPC308037
0.9683 High Similarity NPC262359
0.9683 High Similarity NPC64359
0.9609 High Similarity NPC286336
0.9531 High Similarity NPC144051
0.9531 High Similarity NPC28753
0.9531 High Similarity NPC294593
0.9531 High Similarity NPC159623
0.9531 High Similarity NPC82225
0.9531 High Similarity NPC18877
0.9531 High Similarity NPC20560
0.9531 High Similarity NPC204960
0.9528 High Similarity NPC313618
0.9462 High Similarity NPC41461
0.9462 High Similarity NPC25287
0.9462 High Similarity NPC477244
0.9462 High Similarity NPC477243
0.9462 High Similarity NPC150399
0.9462 High Similarity NPC476333
0.9462 High Similarity NPC98115
0.9462 High Similarity NPC12165
0.9462 High Similarity NPC477242
0.9462 High Similarity NPC186838
0.9462 High Similarity NPC24394
0.9462 High Similarity NPC274109
0.9462 High Similarity NPC1486
0.9462 High Similarity NPC473391
0.9462 High Similarity NPC66349
0.9462 High Similarity NPC472367
0.9462 High Similarity NPC472364
0.9462 High Similarity NPC168105
0.9462 High Similarity NPC249606
0.9389 High Similarity NPC153979
0.9389 High Similarity NPC23870
0.9389 High Similarity NPC209560
0.9389 High Similarity NPC266597
0.9389 High Similarity NPC294409
0.9389 High Similarity NPC303644
0.9389 High Similarity NPC188879
0.9389 High Similarity NPC162680
0.9389 High Similarity NPC250266
0.9389 High Similarity NPC7013
0.9389 High Similarity NPC472419
0.9389 High Similarity NPC317119
0.9389 High Similarity NPC116632
0.9389 High Similarity NPC181124
0.9385 High Similarity NPC156092
0.9385 High Similarity NPC131039
0.9385 High Similarity NPC13575
0.9375 High Similarity NPC475008
0.9375 High Similarity NPC186097
0.9375 High Similarity NPC475009
0.9365 High Similarity NPC186098
0.9365 High Similarity NPC80694
0.9318 High Similarity NPC21350
0.9318 High Similarity NPC472368
0.9318 High Similarity NPC279668
0.9318 High Similarity NPC188947
0.9318 High Similarity NPC278323
0.9318 High Similarity NPC124269
0.9318 High Similarity NPC280284
0.9318 High Similarity NPC12175
0.9318 High Similarity NPC90665
0.9318 High Similarity NPC99333
0.9318 High Similarity NPC55162
0.9318 High Similarity NPC309154
0.9313 High Similarity NPC213603
0.9313 High Similarity NPC194281
0.9313 High Similarity NPC124784
0.9313 High Similarity NPC127447
0.9313 High Similarity NPC231772
0.9313 High Similarity NPC473887
0.9313 High Similarity NPC234133
0.9313 High Similarity NPC29353
0.9313 High Similarity NPC47815
0.9313 High Similarity NPC240593
0.9308 High Similarity NPC103842
0.9291 High Similarity NPC211120
0.9286 High Similarity NPC128428
0.9286 High Similarity NPC305518
0.9248 High Similarity NPC477956
0.9248 High Similarity NPC295384
0.9248 High Similarity NPC470211
0.9248 High Similarity NPC472366
0.9242 High Similarity NPC275055
0.9242 High Similarity NPC290291
0.9237 High Similarity NPC39426
0.9237 High Similarity NPC234560
0.9219 High Similarity NPC185497
0.9219 High Similarity NPC469929
0.9179 High Similarity NPC80962
0.9179 High Similarity NPC172250
0.9179 High Similarity NPC326109
0.9179 High Similarity NPC101366
0.9179 High Similarity NPC48624
0.9179 High Similarity NPC219917
0.9179 High Similarity NPC213659
0.9179 High Similarity NPC204985
0.9179 High Similarity NPC269652
0.9179 High Similarity NPC259166
0.9179 High Similarity NPC11056
0.9179 High Similarity NPC110419
0.9179 High Similarity NPC215311
0.9179 High Similarity NPC281207
0.9179 High Similarity NPC144118
0.9173 High Similarity NPC243528
0.9173 High Similarity NPC471620
0.9173 High Similarity NPC251681
0.9167 High Similarity NPC87545
0.9167 High Similarity NPC235428
0.9167 High Similarity NPC13408
0.916 High Similarity NPC172262
0.9141 High Similarity NPC212379
0.9141 High Similarity NPC69235
0.9141 High Similarity NPC60558
0.9111 High Similarity NPC136840
0.9111 High Similarity NPC268204
0.9111 High Similarity NPC3188
0.9111 High Similarity NPC49108
0.9111 High Similarity NPC52789
0.9111 High Similarity NPC301178
0.9111 High Similarity NPC470089
0.9111 High Similarity NPC26051
0.9111 High Similarity NPC284556
0.9111 High Similarity NPC110969
0.9111 High Similarity NPC469404
0.9111 High Similarity NPC321980
0.9111 High Similarity NPC55832
0.9111 High Similarity NPC470087
0.9111 High Similarity NPC312256
0.9104 High Similarity NPC310135
0.9104 High Similarity NPC274784
0.9104 High Similarity NPC222342
0.9104 High Similarity NPC109232
0.9104 High Similarity NPC20709
0.9104 High Similarity NPC265871
0.9104 High Similarity NPC18260
0.9104 High Similarity NPC261234
0.9104 High Similarity NPC283429
0.9104 High Similarity NPC241838
0.9104 High Similarity NPC329203
0.9104 High Similarity NPC78913
0.9104 High Similarity NPC150648
0.9104 High Similarity NPC143799
0.9104 High Similarity NPC225153
0.9104 High Similarity NPC152042
0.9098 High Similarity NPC212767
0.9098 High Similarity NPC228661
0.9091 High Similarity NPC9985
0.9091 High Similarity NPC239495
0.9084 High Similarity NPC274121
0.9084 High Similarity NPC78540
0.9084 High Similarity NPC50898
0.9084 High Similarity NPC213216
0.9084 High Similarity NPC57601
0.9077 High Similarity NPC31872
0.9077 High Similarity NPC473584
0.9077 High Similarity NPC475589
0.907 High Similarity NPC42292
0.907 High Similarity NPC307732
0.9044 High Similarity NPC202981
0.9044 High Similarity NPC119663
0.9044 High Similarity NPC11561
0.9044 High Similarity NPC471417
0.9044 High Similarity NPC226636
0.9037 High Similarity NPC59951
0.9037 High Similarity NPC146679
0.9037 High Similarity NPC265178
0.9037 High Similarity NPC270883
0.9037 High Similarity NPC76445
0.9037 High Similarity NPC284550
0.9037 High Similarity NPC6407
0.9037 High Similarity NPC103342
0.9037 High Similarity NPC261227
0.9037 High Similarity NPC103904
0.9037 High Similarity NPC69769
0.9037 High Similarity NPC253822
0.9037 High Similarity NPC110228

  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 NPC247779 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
0.9528 High Similarity NPD1240 Approved
0.938 High Similarity NPD1607 Approved
0.9237 High Similarity NPD1510 Phase 2
0.903 High Similarity NPD1549 Phase 2
0.8955 High Similarity NPD1552 Clinical (unspecified phase)
0.8955 High Similarity NPD1550 Clinical (unspecified phase)
0.8777 High Similarity NPD4378 Clinical (unspecified phase)
0.8643 High Similarity NPD7410 Clinical (unspecified phase)
0.8636 High Similarity NPD6859 Clinical (unspecified phase)
0.8623 High Similarity NPD3750 Approved
0.8603 High Similarity NPD2796 Approved
0.8571 High Similarity NPD6799 Approved
0.8478 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8472 Intermediate Similarity NPD4380 Phase 2
0.844 Intermediate Similarity NPD1511 Approved
0.8417 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8414 Intermediate Similarity NPD7411 Suspended
0.8357 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD1934 Approved
0.8333 Intermediate Similarity NPD1551 Phase 2
0.8322 Intermediate Similarity NPD1512 Approved
0.8311 Intermediate Similarity NPD3882 Suspended
0.8299 Intermediate Similarity NPD2801 Approved
0.8299 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD3748 Approved
0.8255 Intermediate Similarity NPD7075 Discontinued
0.8248 Intermediate Similarity NPD6651 Approved
0.8243 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD6599 Discontinued
0.8203 Intermediate Similarity NPD9545 Approved
0.8201 Intermediate Similarity NPD2935 Discontinued
0.8176 Intermediate Similarity NPD7819 Suspended
0.8176 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD3972 Approved
0.8133 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD1203 Approved
0.8108 Intermediate Similarity NPD6801 Discontinued
0.8102 Intermediate Similarity NPD943 Approved
0.8092 Intermediate Similarity NPD422 Phase 1
0.8062 Intermediate Similarity NPD1548 Phase 1
0.8028 Intermediate Similarity NPD2800 Approved
0.8014 Intermediate Similarity NPD2344 Approved
0.8013 Intermediate Similarity NPD3749 Approved
0.7972 Intermediate Similarity NPD4628 Phase 3
0.7947 Intermediate Similarity NPD7768 Phase 2
0.7947 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD230 Phase 1
0.7907 Intermediate Similarity NPD9493 Approved
0.7902 Intermediate Similarity NPD1243 Approved
0.7902 Intermediate Similarity NPD2654 Approved
0.7895 Intermediate Similarity NPD9717 Approved
0.7891 Intermediate Similarity NPD5403 Approved
0.7891 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD3817 Phase 2
0.7877 Intermediate Similarity NPD5401 Approved
0.7872 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD3268 Approved
0.7821 Intermediate Similarity NPD6166 Phase 2
0.7821 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.782 Intermediate Similarity NPD1610 Phase 2
0.7817 Intermediate Similarity NPD6100 Approved
0.7817 Intermediate Similarity NPD6099 Approved
0.7812 Intermediate Similarity NPD1241 Discontinued
0.781 Intermediate Similarity NPD4908 Phase 1
0.781 Intermediate Similarity NPD6832 Phase 2
0.7806 Intermediate Similarity NPD6232 Discontinued
0.7794 Intermediate Similarity NPD2798 Approved
0.7793 Intermediate Similarity NPD2309 Approved
0.7778 Intermediate Similarity NPD1876 Approved
0.7778 Intermediate Similarity NPD3225 Approved
0.7771 Intermediate Similarity NPD7473 Discontinued
0.777 Intermediate Similarity NPD920 Approved
0.7755 Intermediate Similarity NPD2532 Approved
0.7755 Intermediate Similarity NPD2534 Approved
0.7755 Intermediate Similarity NPD2533 Approved
0.7746 Intermediate Similarity NPD4308 Phase 3
0.7746 Intermediate Similarity NPD2799 Discontinued
0.7742 Intermediate Similarity NPD6959 Discontinued
0.774 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD3818 Discontinued
0.7721 Intermediate Similarity NPD2797 Approved
0.7698 Intermediate Similarity NPD3764 Approved
0.7698 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD5953 Discontinued
0.7687 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD7286 Phase 2
0.7673 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD7054 Approved
0.7635 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD1608 Approved
0.7625 Intermediate Similarity NPD7074 Phase 3
0.7625 Intermediate Similarity NPD7472 Approved
0.7619 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD9494 Approved
0.7603 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7591 Intermediate Similarity NPD3267 Approved
0.7591 Intermediate Similarity NPD3266 Approved
0.7582 Intermediate Similarity NPD1465 Phase 2
0.7578 Intermediate Similarity NPD6797 Phase 2
0.7574 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD1296 Phase 2
0.7571 Intermediate Similarity NPD2313 Discontinued
0.7564 Intermediate Similarity NPD5494 Approved
0.7562 Intermediate Similarity NPD5844 Phase 1
0.755 Intermediate Similarity NPD7458 Discontinued
0.7532 Intermediate Similarity NPD5402 Approved
0.7532 Intermediate Similarity NPD4288 Approved
0.7531 Intermediate Similarity NPD7251 Discontinued
0.75 Intermediate Similarity NPD3027 Phase 3
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1481 Phase 2
0.75 Intermediate Similarity NPD7033 Discontinued
0.7485 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7808 Phase 3
0.7483 Intermediate Similarity NPD7003 Approved
0.7469 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4307 Phase 2
0.7463 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD7390 Discontinued
0.7434 Intermediate Similarity NPD3226 Approved
0.7432 Intermediate Similarity NPD2354 Approved
0.7429 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD1535 Discovery
0.7423 Intermediate Similarity NPD6559 Discontinued
0.7421 Intermediate Similarity NPD3926 Phase 2
0.7413 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1933 Approved
0.7407 Intermediate Similarity NPD17 Approved
0.7389 Intermediate Similarity NPD919 Approved
0.7388 Intermediate Similarity NPD1894 Discontinued
0.7378 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD9269 Phase 2
0.736 Intermediate Similarity NPD940 Approved
0.736 Intermediate Similarity NPD846 Approved
0.7357 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD3847 Discontinued
0.7343 Intermediate Similarity NPD3140 Approved
0.7343 Intermediate Similarity NPD1613 Approved
0.7343 Intermediate Similarity NPD3142 Approved
0.7343 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1164 Approved
0.7338 Intermediate Similarity NPD1470 Approved
0.7333 Intermediate Similarity NPD9268 Approved
0.7324 Intermediate Similarity NPD6798 Discontinued
0.7324 Intermediate Similarity NPD411 Approved
0.7313 Intermediate Similarity NPD5536 Phase 2
0.7305 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1201 Approved
0.7296 Intermediate Similarity NPD1247 Approved
0.7292 Intermediate Similarity NPD447 Suspended
0.7292 Intermediate Similarity NPD5124 Phase 1
0.7292 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD74 Approved
0.7287 Intermediate Similarity NPD9266 Approved
0.7286 Intermediate Similarity NPD1019 Discontinued
0.7285 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2346 Discontinued
0.7279 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD2353 Approved
0.7279 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7266 Intermediate Similarity NPD1283 Approved
0.7254 Intermediate Similarity NPD4625 Phase 3
0.7234 Intermediate Similarity NPD3018 Phase 2
0.7219 Intermediate Similarity NPD4357 Discontinued
0.7215 Intermediate Similarity NPD6971 Discontinued
0.7209 Intermediate Similarity NPD9267 Approved
0.7209 Intermediate Similarity NPD9263 Approved
0.7209 Intermediate Similarity NPD9264 Approved
0.7206 Intermediate Similarity NPD1651 Approved
0.72 Intermediate Similarity NPD3887 Approved
0.7197 Intermediate Similarity NPD2296 Approved
0.7195 Intermediate Similarity NPD1729 Discontinued
0.7194 Intermediate Similarity NPD4749 Approved
0.7172 Intermediate Similarity NPD6355 Discontinued
0.716 Intermediate Similarity NPD1898 Discontinued
0.7153 Intermediate Similarity NPD6233 Phase 2
0.7152 Intermediate Similarity NPD7440 Discontinued
0.7143 Intermediate Similarity NPD5711 Approved
0.7143 Intermediate Similarity NPD1242 Phase 1
0.7143 Intermediate Similarity NPD5710 Approved
0.7124 Intermediate Similarity NPD5049 Phase 3
0.7111 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6104 Discontinued
0.7099 Intermediate Similarity NPD5242 Approved
0.7097 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD5405 Approved
0.7095 Intermediate Similarity NPD5404 Approved
0.7095 Intermediate Similarity NPD5408 Approved
0.7095 Intermediate Similarity NPD5406 Approved
0.7086 Intermediate Similarity NPD6190 Approved
0.7081 Intermediate Similarity NPD7199 Phase 2
0.7073 Intermediate Similarity NPD3751 Discontinued
0.7073 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD2982 Phase 2
0.7071 Intermediate Similarity NPD2983 Phase 2
0.7071 Intermediate Similarity NPD3600 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