Structure

Physi-Chem Properties

Molecular Weight:  310.12
Volume:  325.58
LogP:  5.436
LogD:  3.393
LogS:  -3.161
# Rotatable Bonds:  3
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.612
Synthetic Accessibility Score:  2.657
Fsp3:  0.158
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.96
MDCK Permeability:  1.5484290997846983e-05
Pgp-inhibitor:  0.065
Pgp-substrate:  0.788
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.997
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.014
Plasma Protein Binding (PPB):  99.0132827758789%
Volume Distribution (VD):  1.405
Pgp-substrate:  2.084280252456665%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.364
CYP2C19-inhibitor:  0.934
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.69
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.919
CYP2D6-substrate:  0.873
CYP3A4-inhibitor:  0.602
CYP3A4-substrate:  0.134

ADMET: Excretion

Clearance (CL):  11.318
Half-life (T1/2):  0.594

ADMET: Toxicity

hERG Blockers:  0.073
Human Hepatotoxicity (H-HT):  0.296
Drug-inuced Liver Injury (DILI):  0.487
AMES Toxicity:  0.031
Rat Oral Acute Toxicity:  0.148
Maximum Recommended Daily Dose:  0.843
Skin Sensitization:  0.943
Carcinogencity:  0.066
Eye Corrosion:  0.003
Eye Irritation:  0.891
Respiratory Toxicity:  0.593

Download Data

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

  Natural Product: NPC167576

Natural Product ID:  NPC167576
Common Name*:   Moracin C
IUPAC Name:   5-(6-hydroxy-1-benzofuran-2-yl)-2-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:   Moracin C
Standard InCHIKey:  ZTGHWUWBQNCCOH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C19H18O4/c1-11(2)3-6-15-16(21)7-13(8-17(15)22)18-9-12-4-5-14(20)10-19(12)23-18/h3-5,7-10,20-22H,6H2,1-2H3
SMILES:  CC(=CCc1c(O)cc(cc1O)c1cc2c(o1)cc(cc2)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2018876
PubChem CID:   155248
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO28803 Artocarpus chama Species Moraceae Eukaryota n.a. root n.a. PMID[15165133]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO27320 Morus notabilis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[21737271]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28803 Artocarpus chama Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27368 Sinularia mayi Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27589 Artemisia lehmanniana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27280 Stachys spectabilis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27147 Habenaria repens Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27320 Morus notabilis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27071 Spirastrella coccinea Species Spirastrellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29149 Zexmenia phyllocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27478 Geodia japonica Species Geodiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27089 Nectandra glabrescens Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28584 Euphorbia indica Species Euphorbiaceae 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
NPT1464 Individual Protein Phosphodiesterase 4D Homo sapiens IC50 = 26000.0 nM PMID[506954]
NPT4735 Individual Protein Phosphodiesterase 4B Homo sapiens IC50 = 18100.0 nM PMID[506954]
NPT273 Individual Protein Phosphodiesterase 5A Homo sapiens IC50 > 50000.0 nM PMID[506954]
NPT4736 Individual Protein Phosphodiesterase 9A Homo sapiens IC50 > 100000.0 nM PMID[506954]
NPT1970 Cell Line THP-1 Homo sapiens IC50 = 3200.0 nM PMID[506955]
NPT5154 Individual Protein Enoyl-[acyl-carrier-protein] reductase Staphylococcus aureus subsp. aureus MRSA252 IC50 = 83800.0 nM PMID[506956]
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 = 2270.0 nM PMID[506956]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 8000.0 nM PMID[506956]
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa Inhibition = 64.8 % PMID[506957]
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa IC50 = 32000.0 nM PMID[506957]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 2350.0 nM PMID[506958]
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 = 210.0 nM PMID[506958]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 16800.0 nM PMID[506959]
NPT2788 Cell Line 3T3 Mus musculus Inhibition = 13.8 % PMID[25461329]
NPT2954 Individual Protein Glycerol-3-phosphate dehydrogenase [NAD+], cytoplasmic Mus musculus Inhibition = 8.2 % PMID[25461329]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC > 100.0 ug.mL-1 PMID[506956]
NPT19 Organism Escherichia coli Escherichia coli MIC > 100.0 ug.mL-1 PMID[506956]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 3.13 ug.mL-1 PMID[506956]
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 12.5 ug.mL-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 12.5 ug.mL-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 6.25 ug.mL-1 PMID[506956]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 100.0 ug.mL-1 PMID[506956]
NPT1101 Organism Staphylococcus aureus subsp. aureus RN4220 Staphylococcus aureus subsp. aureus RN4220 MIC = 32.0 ug.mL-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 32.0 ug.mL-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 74800.0 nM PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 188400.0 nM PMID[506956]
NPT2897 Organism Citrobacter freundii Citrobacter freundii MIC = 156.0 ug.mL-1 PMID[506956]
NPT19 Organism Escherichia coli Escherichia coli MIC = 39.0 ug.mL-1 PMID[506956]
NPT3152 Organism Shigella dysenteriae Shigella dysenteriae MIC = 5.0 ug.mL-1 PMID[506956]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 10.0 ug.mL-1 PMID[506956]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC = 312.0 ug.mL-1 PMID[506956]
NPT1242 Organism Salmonella typhi Salmonella enterica subsp. enterica serovar Typhi MIC = 10.0 ug.mL-1 PMID[506956]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 78.0 ug.mL-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 78.0 ug.mL-1 PMID[506956]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 39.0 ug.mL-1 PMID[506956]
NPT20 Organism Candida albicans Candida albicans MIC = 68.0 ug.mL-1 PMID[506956]
NPT4737 Organism Microsporum audouinii Microsporum audouinii MIC = 78.0 ug.mL-1 PMID[506956]
NPT2897 Organism Citrobacter freundii Citrobacter freundii MBC = 625.0 ug ml-1 PMID[506956]
NPT19 Organism Escherichia coli Escherichia coli MBC = 78.0 ug ml-1 PMID[506956]
NPT3152 Organism Shigella dysenteriae Shigella dysenteriae MBC = 39.0 ug ml-1 PMID[506956]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MBC = 39.0 ug ml-1 PMID[506956]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MBC = 625.0 ug ml-1 PMID[506956]
NPT1242 Organism Salmonella typhi Salmonella enterica subsp. enterica serovar Typhi MBC = 39.0 ug ml-1 PMID[506956]
NPT314 Organism Bacillus cereus Bacillus cereus MBC = 156.0 ug ml-1 PMID[506956]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 156.0 ug ml-1 PMID[506956]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MBC = 78.0 ug ml-1 PMID[506956]
NPT20 Organism Candida albicans Candida albicans MFC = 156.0 ug ml-1 PMID[506956]
NPT4737 Organism Microsporum audouinii Microsporum audouinii MFC = 312.0 ug ml-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 3.5 ug.mL-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 7.0 ug.mL-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 224.0 ug.mL-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 14.0 ug.mL-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 112.0 ug.mL-1 PMID[506956]
NPT2955 Organism Rosellinia necatrix Rosellinia necatrix MIC = 3.5 ug.mL-1 PMID[506956]
NPT610 Others Molecular identity unknown MIC = 28.0 ug.mL-1 PMID[506956]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 73.0 % PMID[506956]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 64.0 % PMID[506956]
NPT2 Others Unspecified IC50 = 4040.0 nM PMID[506956]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 100.0 % PMID[506956]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens IC50 = 1210.0 nM PMID[506958]

☑ 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 NPC167576 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
0.9795 High Similarity NPC72370
0.9724 High Similarity NPC230713
0.9724 High Similarity NPC78335
0.9658 High Similarity NPC170169
0.9658 High Similarity NPC23668
0.9658 High Similarity NPC193976
0.9655 High Similarity NPC178202
0.9653 High Similarity NPC17816
0.965 High Similarity NPC155144
0.9597 High Similarity NPC164110
0.9597 High Similarity NPC96342
0.9597 High Similarity NPC246647
0.9597 High Similarity NPC212967
0.9592 High Similarity NPC142308
0.9592 High Similarity NPC207624
0.953 High Similarity NPC137100
0.953 High Similarity NPC180924
0.9527 High Similarity NPC235333
0.9527 High Similarity NPC472462
0.9524 High Similarity NPC115324
0.9524 High Similarity NPC106372
0.9524 High Similarity NPC58668
0.9521 High Similarity NPC226644
0.9521 High Similarity NPC37226
0.9514 High Similarity NPC98926
0.9463 High Similarity NPC198490
0.9463 High Similarity NPC99199
0.9463 High Similarity NPC213936
0.9463 High Similarity NPC148938
0.9463 High Similarity NPC297531
0.9448 High Similarity NPC210826
0.9444 High Similarity NPC302181
0.9396 High Similarity NPC183874
0.9384 High Similarity NPC130581
0.9384 High Similarity NPC12148
0.9379 High Similarity NPC230943
0.9375 High Similarity NPC53192
0.9338 High Similarity NPC268360
0.932 High Similarity NPC135325
0.9315 High Similarity NPC51641
0.9315 High Similarity NPC300267
0.931 High Similarity NPC225884
0.9286 High Similarity NPC159508
0.9276 High Similarity NPC472877
0.9267 High Similarity NPC213608
0.9267 High Similarity NPC1477
0.9257 High Similarity NPC296030
0.9257 High Similarity NPC221868
0.9257 High Similarity NPC37208
0.9257 High Similarity NPC39929
0.9231 High Similarity NPC112757
0.9226 High Similarity NPC169471
0.92 High Similarity NPC67654
0.92 High Similarity NPC5871
0.9195 High Similarity NPC13282
0.9189 High Similarity NPC272194
0.9184 High Similarity NPC130176
0.9184 High Similarity NPC99454
0.9184 High Similarity NPC196114
0.9145 High Similarity NPC160015
0.9145 High Similarity NPC247677
0.9145 High Similarity NPC45131
0.9133 High Similarity NPC156244
0.911 High Similarity NPC1534
0.9108 High Similarity NPC253730
0.9108 High Similarity NPC286230
0.9097 High Similarity NPC272722
0.9097 High Similarity NPC312056
0.9097 High Similarity NPC84515
0.9091 High Similarity NPC304839
0.9091 High Similarity NPC220582
0.9085 High Similarity NPC65504
0.9085 High Similarity NPC260902
0.9085 High Similarity NPC296957
0.9073 High Similarity NPC263676
0.9073 High Similarity NPC125300
0.9073 High Similarity NPC253872
0.906 High Similarity NPC37135
0.906 High Similarity NPC186397
0.9054 High Similarity NPC469758
0.9034 High Similarity NPC109232
0.9032 High Similarity NPC30655
0.9032 High Similarity NPC74854
0.9032 High Similarity NPC188486
0.9032 High Similarity NPC45124
0.9026 High Similarity NPC40583
0.9026 High Similarity NPC196879
0.9026 High Similarity NPC16935
0.9026 High Similarity NPC244750
0.9026 High Similarity NPC476349
0.9026 High Similarity NPC476350
0.902 High Similarity NPC472461
0.9013 High Similarity NPC122365
0.9007 High Similarity NPC116604
0.9007 High Similarity NPC258249
0.9 High Similarity NPC266499
0.9 High Similarity NPC317492
0.9 High Similarity NPC474052
0.9 High Similarity NPC223988
0.9 High Similarity NPC269420
0.8994 High Similarity NPC476641
0.8993 High Similarity NPC150215
0.8986 High Similarity NPC469764
0.8981 High Similarity NPC36320
0.898 High Similarity NPC159855
0.898 High Similarity NPC169479
0.8974 High Similarity NPC193998
0.8968 High Similarity NPC115432
0.8968 High Similarity NPC260296
0.8966 High Similarity NPC124269
0.8958 High Similarity NPC472364
0.8958 High Similarity NPC473391
0.8947 High Similarity NPC41326
0.8933 High Similarity NPC168085
0.8926 High Similarity NPC299011
0.8924 High Similarity NPC277480
0.8924 High Similarity NPC53640
0.8917 High Similarity NPC133065
0.8912 High Similarity NPC49108
0.891 High Similarity NPC304387
0.8897 High Similarity NPC228661
0.8897 High Similarity NPC188879
0.8882 High Similarity NPC65885
0.8882 High Similarity NPC149085
0.8882 High Similarity NPC24748
0.8882 High Similarity NPC216842
0.8882 High Similarity NPC59491
0.8882 High Similarity NPC476640
0.8882 High Similarity NPC82217
0.8874 High Similarity NPC100985
0.8874 High Similarity NPC10027
0.8874 High Similarity NPC158338
0.8874 High Similarity NPC65775
0.8874 High Similarity NPC97028
0.8874 High Similarity NPC65589
0.8874 High Similarity NPC288036
0.8874 High Similarity NPC97029
0.8868 High Similarity NPC247973
0.8868 High Similarity NPC470704
0.8868 High Similarity NPC50394
0.8861 High Similarity NPC45449
0.8861 High Similarity NPC39306
0.8861 High Similarity NPC474591
0.8861 High Similarity NPC37183
0.8861 High Similarity NPC291110
0.8859 High Similarity NPC311144
0.8859 High Similarity NPC311741
0.8859 High Similarity NPC303185
0.8859 High Similarity NPC234629
0.8859 High Similarity NPC184649
0.8854 High Similarity NPC3448
0.8854 High Similarity NPC477239
0.8854 High Similarity NPC219861
0.8851 High Similarity NPC96791
0.8851 High Similarity NPC470636
0.8851 High Similarity NPC144499
0.8851 High Similarity NPC226942
0.8851 High Similarity NPC73028
0.8844 High Similarity NPC171094
0.8844 High Similarity NPC69769
0.8844 High Similarity NPC270883
0.8844 High Similarity NPC172986
0.8844 High Similarity NPC261227
0.8844 High Similarity NPC28337
0.8828 High Similarity NPC240593
0.8828 High Similarity NPC13408
0.8827 High Similarity NPC287243
0.8824 High Similarity NPC142527
0.8824 High Similarity NPC154683
0.8824 High Similarity NPC45934
0.8824 High Similarity NPC130015
0.8824 High Similarity NPC40356
0.8824 High Similarity NPC38361
0.882 High Similarity NPC230619
0.882 High Similarity NPC54098
0.8819 High Similarity NPC286336
0.8816 High Similarity NPC227122
0.8816 High Similarity NPC472421
0.8816 High Similarity NPC101957
0.8816 High Similarity NPC120105
0.8808 High Similarity NPC2569
0.8808 High Similarity NPC27221
0.8808 High Similarity NPC256672
0.8808 High Similarity NPC7025
0.8808 High Similarity NPC172329
0.8808 High Similarity NPC39195
0.88 High Similarity NPC290133
0.88 High Similarity NPC187282
0.88 High Similarity NPC24136
0.8797 High Similarity NPC1755
0.8797 High Similarity NPC263092
0.8797 High Similarity NPC1706
0.8797 High Similarity NPC39305
0.8797 High Similarity NPC472581
0.8797 High Similarity NPC59295
0.8797 High Similarity NPC155640
0.8792 High Similarity NPC262935
0.8792 High Similarity NPC17262
0.8792 High Similarity NPC18585
0.8792 High Similarity NPC172182

  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 NPC167576 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
0.8767 High Similarity NPD2344 Approved
0.875 High Similarity NPD1607 Approved
0.8733 High Similarity NPD4378 Clinical (unspecified phase)
0.8718 High Similarity NPD3749 Approved
0.8654 High Similarity NPD3882 Suspended
0.8611 High Similarity NPD1240 Approved
0.8609 High Similarity NPD7410 Clinical (unspecified phase)
0.8581 High Similarity NPD1549 Phase 2
0.8543 High Similarity NPD1511 Approved
0.8537 High Similarity NPD6559 Discontinued
0.8533 High Similarity NPD2309 Approved
0.8526 High Similarity NPD2801 Approved
0.8526 High Similarity NPD2393 Clinical (unspecified phase)
0.8514 High Similarity NPD1550 Clinical (unspecified phase)
0.8514 High Similarity NPD1552 Clinical (unspecified phase)
0.8503 High Similarity NPD1510 Phase 2
0.8462 Intermediate Similarity NPD1934 Approved
0.8446 Intermediate Similarity NPD2796 Approved
0.8438 Intermediate Similarity NPD6959 Discontinued
0.8431 Intermediate Similarity NPD1512 Approved
0.84 Intermediate Similarity NPD1243 Approved
0.84 Intermediate Similarity NPD2800 Approved
0.8377 Intermediate Similarity NPD920 Approved
0.8366 Intermediate Similarity NPD2533 Approved
0.8366 Intermediate Similarity NPD2532 Approved
0.8366 Intermediate Similarity NPD2534 Approved
0.8333 Intermediate Similarity NPD3926 Phase 2
0.8293 Intermediate Similarity NPD3818 Discontinued
0.8291 Intermediate Similarity NPD7819 Suspended
0.828 Intermediate Similarity NPD7411 Suspended
0.8272 Intermediate Similarity NPD6232 Discontinued
0.8247 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD7473 Discontinued
0.8217 Intermediate Similarity NPD6599 Discontinued
0.8217 Intermediate Similarity NPD4380 Phase 2
0.82 Intermediate Similarity NPD1551 Phase 2
0.8182 Intermediate Similarity NPD6799 Approved
0.8171 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8171 Intermediate Similarity NPD6166 Phase 2
0.8171 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8148 Intermediate Similarity NPD5494 Approved
0.8137 Intermediate Similarity NPD7075 Discontinued
0.8137 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD3750 Approved
0.8098 Intermediate Similarity NPD1247 Approved
0.8092 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD2935 Discontinued
0.8075 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD7768 Phase 2
0.8063 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8061 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD3226 Approved
0.8013 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD3817 Phase 2
0.7987 Intermediate Similarity NPD943 Approved
0.7975 Intermediate Similarity NPD919 Approved
0.7961 Intermediate Similarity NPD6100 Approved
0.7961 Intermediate Similarity NPD6099 Approved
0.7949 Intermediate Similarity NPD7390 Discontinued
0.7922 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD5844 Phase 1
0.7908 Intermediate Similarity NPD2346 Discontinued
0.7901 Intermediate Similarity NPD2296 Approved
0.7895 Intermediate Similarity NPD2799 Discontinued
0.7888 Intermediate Similarity NPD6801 Discontinued
0.787 Intermediate Similarity NPD7074 Phase 3
0.7852 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7054 Approved
0.7792 Intermediate Similarity NPD1471 Phase 3
0.7791 Intermediate Similarity NPD5402 Approved
0.7778 Intermediate Similarity NPD3748 Approved
0.7765 Intermediate Similarity NPD7472 Approved
0.7756 Intermediate Similarity NPD4628 Phase 3
0.7756 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7755 Intermediate Similarity NPD1203 Approved
0.7733 Intermediate Similarity NPD2313 Discontinued
0.773 Intermediate Similarity NPD1465 Phase 2
0.7725 Intermediate Similarity NPD5710 Approved
0.7725 Intermediate Similarity NPD5711 Approved
0.7719 Intermediate Similarity NPD5953 Discontinued
0.7719 Intermediate Similarity NPD6797 Phase 2
0.7706 Intermediate Similarity NPD7286 Phase 2
0.7706 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7251 Discontinued
0.7673 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD4287 Approved
0.7647 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD6651 Approved
0.763 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD7808 Phase 3
0.763 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD411 Approved
0.7582 Intermediate Similarity NPD447 Suspended
0.7578 Intermediate Similarity NPD5403 Approved
0.7561 Intermediate Similarity NPD6280 Approved
0.7561 Intermediate Similarity NPD6279 Approved
0.7551 Intermediate Similarity NPD9717 Approved
0.755 Intermediate Similarity NPD4625 Phase 3
0.7548 Intermediate Similarity NPD4308 Phase 3
0.7515 Intermediate Similarity NPD7229 Phase 3
0.75 Intermediate Similarity NPD3764 Approved
0.75 Intermediate Similarity NPD5404 Approved
0.75 Intermediate Similarity NPD5408 Approved
0.75 Intermediate Similarity NPD5406 Approved
0.75 Intermediate Similarity NPD5405 Approved
0.7483 Intermediate Similarity NPD4908 Phase 1
0.7483 Intermediate Similarity NPD6832 Phase 2
0.7468 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD230 Phase 1
0.7468 Intermediate Similarity NPD2654 Approved
0.7467 Intermediate Similarity NPD2798 Approved
0.7453 Intermediate Similarity NPD5401 Approved
0.7436 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD1608 Approved
0.7432 Intermediate Similarity NPD3972 Approved
0.7412 Intermediate Similarity NPD6808 Phase 2
0.741 Intermediate Similarity NPD5760 Phase 2
0.741 Intermediate Similarity NPD5761 Phase 2
0.74 Intermediate Similarity NPD1470 Approved
0.7391 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD3268 Approved
0.7383 Intermediate Similarity NPD4749 Approved
0.7378 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD422 Phase 1
0.7365 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD8434 Phase 2
0.7356 Intermediate Similarity NPD1729 Discontinued
0.7325 Intermediate Similarity NPD7033 Discontinued
0.7303 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD4307 Phase 2
0.7288 Intermediate Similarity NPD8312 Approved
0.7288 Intermediate Similarity NPD8313 Approved
0.7285 Intermediate Similarity NPD2797 Approved
0.7278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD7199 Phase 2
0.7248 Intermediate Similarity NPD1201 Approved
0.7248 Intermediate Similarity NPD1610 Phase 2
0.7241 Intermediate Similarity NPD3751 Discontinued
0.723 Intermediate Similarity NPD17 Approved
0.7225 Intermediate Similarity NPD2403 Approved
0.7211 Intermediate Similarity NPD1548 Phase 1
0.7205 Intermediate Similarity NPD7003 Approved
0.7179 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1613 Approved
0.7176 Intermediate Similarity NPD6971 Discontinued
0.7174 Intermediate Similarity NPD4361 Phase 2
0.7174 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4288 Approved
0.7143 Intermediate Similarity NPD6844 Discontinued
0.7143 Intermediate Similarity NPD7177 Discontinued
0.7143 Intermediate Similarity NPD37 Approved
0.7135 Intermediate Similarity NPD6234 Discontinued
0.7126 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4363 Phase 3
0.712 Intermediate Similarity NPD4360 Phase 2
0.7119 Intermediate Similarity NPD1252 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD4967 Phase 2
0.7118 Intermediate Similarity NPD4966 Approved
0.7118 Intermediate Similarity NPD4965 Approved
0.7112 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD3787 Discontinued
0.7105 Intermediate Similarity NPD3225 Approved
0.7104 Intermediate Similarity NPD3269 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3027 Phase 3
0.7095 Intermediate Similarity NPD9545 Approved
0.7083 Intermediate Similarity NPD8151 Discontinued
0.7083 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD2861 Phase 2
0.7075 Intermediate Similarity NPD9493 Approved
0.7066 Intermediate Similarity NPD7458 Discontinued
0.7059 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3266 Approved
0.7059 Intermediate Similarity NPD3267 Approved
0.7059 Intermediate Similarity NPD1164 Approved
0.7051 Intermediate Similarity NPD1296 Phase 2
0.7051 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD1651 Approved
0.7043 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1933 Approved
0.7021 Intermediate Similarity NPD6779 Approved
0.7021 Intermediate Similarity NPD6782 Approved
0.7021 Intermediate Similarity NPD6781 Approved
0.7021 Intermediate Similarity NPD6780 Approved
0.7021 Intermediate Similarity NPD6778 Approved
0.7021 Intermediate Similarity NPD6776 Approved
0.7021 Intermediate Similarity NPD6777 Approved
0.7017 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD1019 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data