Structure

Physi-Chem Properties

Molecular Weight:  179.09
Volume:  190.991
LogP:  2.404
LogD:  1.073
LogS:  -2.446
# Rotatable Bonds:  4
TPSA:  50.19
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.77
Synthetic Accessibility Score:  1.828
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.638
MDCK Permeability:  2.2023989004082978e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.333

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.293
Plasma Protein Binding (PPB):  79.25231170654297%
Volume Distribution (VD):  0.35
Pgp-substrate:  19.732969284057617%

ADMET: Metabolism

CYP1A2-inhibitor:  0.162
CYP1A2-substrate:  0.136
CYP2C19-inhibitor:  0.079
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.088
CYP2C9-substrate:  0.315
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.124
CYP3A4-inhibitor:  0.02
CYP3A4-substrate:  0.06

ADMET: Excretion

Clearance (CL):  1.581
Half-life (T1/2):  0.702

ADMET: Toxicity

hERG Blockers:  0.126
Human Hepatotoxicity (H-HT):  0.427
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.925
Maximum Recommended Daily Dose:  0.027
Skin Sensitization:  0.156
Carcinogencity:  0.055
Eye Corrosion:  0.013
Eye Irritation:  0.966
Respiratory Toxicity:  0.839

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General Info & Identifiers & Properties  
Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC41717

Natural Product ID:  NPC41717
Common Name*:   Fusaric Acid
IUPAC Name:   5-butylpyridine-2-carboxylic acid
Synonyms:   5-Butylpicolinic Acid; Fusaric Acid
Standard InCHIKey:  DGMPVYSXXIOGJY-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H13NO2/c1-2-3-4-8-5-6-9(10(12)13)11-7-8/h5-7H,2-4H2,1H3,(H,12,13)
SMILES:  CCCCc1ccc(C(=O)O)nc1
Synthetic Gene Cluster:   BGC0001190;
ChEMBL Identifier:   CHEMBL24510
PubChem CID:   3442
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001322] Pyridinecarboxylic acids and derivatives
          • [CHEMONTID:0002414] Pyridinecarboxylic acids
            • [CHEMONTID:0004624] Pyridine-2-carboxylic acids
              • [CHEMONTID:0004627] 5-alkyl-2-carboxypyrimidines

*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
NPO24024 Fusarium semitectum Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[10978211]
NPO24024 Fusarium semitectum Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[22439674]
NPO41421 Fusarium oxysporum + Sarocladium strictum Species n.a. n.a. n.a. n.a. n.a. PMID[26999098]
NPO24024 Fusarium semitectum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11278 Scheffleropsis angkae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12206 Pterocaulon sphacelatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8558 Pseudognaphalium robustum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3889 Streptomyces humidus Species Streptomycetaceae Bacteria 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
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Ki = 149.0 nM PMID[521190]
NPT2806 Individual Protein Dopamine beta-hydroxylase Rattus norvegicus IC50 = 700.0 nM PMID[521191]
NPT2807 Individual Protein Hypoxia-inducible factor prolyl 4-hydroxylase Homo sapiens IC50 = 149000.0 nM PMID[521192]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Ki = 149.0 nM PMID[521193]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 7079.5 nM PMID[521198]
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency = 3162.3 nM PMID[521199]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 3981.1 nM PMID[521198]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 10000.0 nM PMID[521200]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 44668.4 nM PMID[521197]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 25118.9 nM PMID[521199]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 44668.4 nM PMID[521200]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 8912.5 nM PMID[521197]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 17782.8 nM PMID[521198]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 7943.3 nM PMID[521200]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 8912.5 nM PMID[521198]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 25118.9 nM PMID[521200]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 7079.5 nM PMID[521197]
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 2511.9 nM PMID[521198]
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens Potency = 15848.9 nM PMID[521199]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 39810.7 nM PMID[521198]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 28183.8 nM PMID[521200]
NPT52 Individual Protein Pyruvate kinase isozymes M1/M2 Homo sapiens Potency = 251.2 nM PMID[521199]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 44668.4 nM PMID[521197]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 22387.2 nM PMID[521200]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 9976.3 nM PMID[521198]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 8891.4 nM PMID[521197]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 15811.4 nM PMID[521200]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 10000.0 nM PMID[521202]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 3.2 nM PMID[521200]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 7943.3 nM PMID[521198]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 17782.8 nM PMID[521200]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 25118.9 nM PMID[521199]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = 43.0 % PMID[521203]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = 18.0 % PMID[521203]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = 47.0 % PMID[521203]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 29.0 % PMID[521203]
NPT270 Individual Protein Nitric oxide synthase, inducible Mus musculus Inhibition = 10.0 % PMID[521203]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 23.0 % PMID[521203]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 75.0 % PMID[521203]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 80.0 % PMID[521203]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 20596.2 nM PMID[521204]
NPT62 Individual Protein 6-phospho-1-fructokinase Trypanosoma brucei Potency n.a. 28183.8 nM PMID[521201]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 22.4 nM PMID[521200]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 5972.8 nM PMID[521204]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 1122.0 nM PMID[521202]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 3981.1 nM PMID[521202]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens Potency n.a. 19952.6 nM PMID[521199]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens AC50 = 31622.78 nM PMID[521199]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens AC50 = 25118.86 nM PMID[521199]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 33498.3 nM PMID[521201]
NPT2808 Individual Protein Kelch-like ECH-associated protein 1 Homo sapiens Max_Activity_Concent n.a. 0.38 uM PMID[521202]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2818.4 nM PMID[521202]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 33498.3 nM PMID[521205]
NPT71 Cell Line HEK293 Homo sapiens CC50 > 20000.0 nM PMID[521208]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus IC50 = 50.0 nM PMID[521209]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 89.0 % PMID[521209]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 92.0 % PMID[521209]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 58.0 % PMID[521209]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 20.0 % PMID[521209]
NPT29 Organism Rattus norvegicus Rattus norvegicus BP > 60.0 mmHg PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris MBP = -50.0 n.a. PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris HR = 32.0 n.a. PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris MBP = -45.0 n.a. PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris HR = 35.0 n.a. PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris MBP = -30.0 n.a. PMID[521189]
NPT1016 Organism Canis familiaris Canis lupus familiaris HR = 33.0 n.a. PMID[521189]
NPT29 Organism Rattus norvegicus Rattus norvegicus Level = 0.702 ug of tissue PMID[521190]
NPT29 Organism Rattus norvegicus Rattus norvegicus Level = 6.55 ug of tissue PMID[521190]
NPT2 Others Unspecified Ratio = 0.109 n.a. PMID[521190]
NPT29 Organism Rattus norvegicus Rattus norvegicus Increase = 80.0 % PMID[521191]
NPT29 Organism Rattus norvegicus Rattus norvegicus Decrease in blood pressure = 54.0 mmHg PMID[521191]
NPT746 Organism Pasteurella multocida Pasteurella multocida MIC = 100.0 ug.mL-1 PMID[521196]
NPT746 Organism Pasteurella multocida Pasteurella multocida MIC = 50.0 ug.mL-1 PMID[521196]
NPT746 Organism Pasteurella multocida Pasteurella multocida Ratio = 2.0 n.a. PMID[521196]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[521197]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 11220.2 nM PMID[521200]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 8912.5 nM PMID[521200]
NPT794 Individual Protein Endonuclease 4 Escherichia coli K-12 Potency = 10000.0 nM PMID[521200]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 501.2 nM PMID[521198]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 3548.1 nM PMID[521200]
NPT796 Individual Protein Peripheral myelin protein 22 Homo sapiens Potency = 60119.8 nM PMID[521201]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 6309.6 nM PMID[521198]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 15848.9 nM PMID[521199]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 8912.5 nM PMID[521202]
NPT95 Individual Protein Muscarinic acetylcholine receptor M1 Rattus norvegicus Potency = 141.3 nM PMID[521199]
NPT96 Individual Protein Thrombopoietin Homo sapiens Potency = 1995.3 nM PMID[521199]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Potency = 14125.4 nM PMID[521200]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 58.0 % PMID[521203]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 6309.6 nM PMID[521200]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 35481.3 nM PMID[521200]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 4775.5 nM PMID[521201]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 5221.3 nM PMID[521202]
NPT98 Individual Protein HERG Homo sapiens Potency n.a. 5623.4 nM PMID[521200]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[521202]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 18356.4 nM PMID[521202]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity > 60.0 mmHg PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = -50.0 mmHg PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = -45.0 mmHg PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = -30.0 mmHg PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = 32.0 bpm PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = 35.0 bpm PMID[521206]
NPT1016 Organism Canis familiaris Canis lupus familiaris Activity = 33.0 bpm PMID[521206]
NPT2809 Organism Squirrel monkey Saimiri sciureus Activity = -28.0 mmHg PMID[521206]
NPT2809 Organism Squirrel monkey Saimiri sciureus Activity = -53.0 mmHg PMID[521206]
NPT2809 Organism Squirrel monkey Saimiri sciureus Activity = -20.0 bpm PMID[521206]
NPT2809 Organism Squirrel monkey Saimiri sciureus Activity = 10.0 bpm PMID[521206]
NPT20 Organism Candida albicans Candida albicans MIC > 20000.0 nM PMID[521208]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC > 20000.0 nM PMID[521208]
NPT19 Organism Escherichia coli Escherichia coli MIC > 20000.0 nM PMID[521208]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae MIC > 20000.0 nM PMID[521208]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 20000.0 nM PMID[521208]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii MIC > 20000.0 nM PMID[521208]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus MIC > 20000.0 nM PMID[521208]
NPT20950 CELL-LINE Erythrocyte n.a. HC10 > 20.0 uM PMID[521208]
NPT2 Others Unspecified Inhibition = 25.0 % PMID[521209]
NPT2 Others Unspecified IC50 = 0.4 ug/g PMID[521209]
NPT2 Others Unspecified IC50 = 0.1 ug/g PMID[521209]
NPT2 Others Unspecified Potency n.a. 5353.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10682.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23710.1 nM PubChem BioAssay data set

☑ 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 NPC41717 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
0.9146 High Similarity NPC207851
0.9073 High Similarity NPC302159
0.8827 High Similarity NPC273532
0.8742 High Similarity NPC322644
0.8553 High Similarity NPC85443
0.8436 Intermediate Similarity NPC57398
0.8355 Intermediate Similarity NPC328029
0.8301 Intermediate Similarity NPC114310
0.8199 Intermediate Similarity NPC312860
0.8165 Intermediate Similarity NPC167400
0.8125 Intermediate Similarity NPC469489
0.8066 Intermediate Similarity NPC123395
0.8047 Intermediate Similarity NPC253810
0.8039 Intermediate Similarity NPC322488
0.8037 Intermediate Similarity NPC263455
0.8036 Intermediate Similarity NPC470894
0.8 Intermediate Similarity NPC29702
0.7927 Intermediate Similarity NPC33229
0.791 Intermediate Similarity NPC278434
0.7901 Intermediate Similarity NPC109922
0.7877 Intermediate Similarity NPC114974
0.7875 Intermediate Similarity NPC159630
0.7875 Intermediate Similarity NPC230085
0.7857 Intermediate Similarity NPC90229
0.7845 Intermediate Similarity NPC135950
0.7836 Intermediate Similarity NPC302647
0.7836 Intermediate Similarity NPC249614
0.7821 Intermediate Similarity NPC83111
0.7814 Intermediate Similarity NPC474916
0.7797 Intermediate Similarity NPC282103
0.7797 Intermediate Similarity NPC295158
0.779 Intermediate Similarity NPC230403
0.7772 Intermediate Similarity NPC103361
0.7758 Intermediate Similarity NPC107287
0.773 Intermediate Similarity NPC112741
0.7725 Intermediate Similarity NPC266249
0.7722 Intermediate Similarity NPC144381
0.7717 Intermediate Similarity NPC248782
0.7714 Intermediate Similarity NPC164340
0.7697 Intermediate Similarity NPC311282
0.7696 Intermediate Similarity NPC82370
0.7688 Intermediate Similarity NPC477976
0.7679 Intermediate Similarity NPC113812
0.7679 Intermediate Similarity NPC80681
0.7672 Intermediate Similarity NPC193238
0.7663 Intermediate Similarity NPC141454
0.7656 Intermediate Similarity NPC118940
0.7647 Intermediate Similarity NPC328596
0.7647 Intermediate Similarity NPC328318
0.7644 Intermediate Similarity NPC123839
0.7614 Intermediate Similarity NPC126709
0.7614 Intermediate Similarity NPC248041
0.7598 Intermediate Similarity NPC241025
0.7594 Intermediate Similarity NPC98864
0.7582 Intermediate Similarity NPC138370
0.7569 Intermediate Similarity NPC44354
0.7566 Intermediate Similarity NPC472259
0.7554 Intermediate Similarity NPC146724
0.7548 Intermediate Similarity NPC313823
0.7543 Intermediate Similarity NPC139763
0.7543 Intermediate Similarity NPC303225
0.7538 Intermediate Similarity NPC229893
0.7526 Intermediate Similarity NPC317373
0.7526 Intermediate Similarity NPC317752
0.7514 Intermediate Similarity NPC70949
0.7514 Intermediate Similarity NPC283219
0.75 Intermediate Similarity NPC267885
0.75 Intermediate Similarity NPC209362
0.7486 Intermediate Similarity NPC243058
0.7485 Intermediate Similarity NPC70406
0.7484 Intermediate Similarity NPC212125
0.7474 Intermediate Similarity NPC318299
0.7474 Intermediate Similarity NPC327592
0.7472 Intermediate Similarity NPC317010
0.7461 Intermediate Similarity NPC309845
0.7459 Intermediate Similarity NPC118084
0.7458 Intermediate Similarity NPC219848
0.7443 Intermediate Similarity NPC149155
0.7443 Intermediate Similarity NPC110500
0.7443 Intermediate Similarity NPC203468
0.744 Intermediate Similarity NPC251391
0.7421 Intermediate Similarity NPC165599
0.7416 Intermediate Similarity NPC256268
0.7414 Intermediate Similarity NPC78020
0.7405 Intermediate Similarity NPC324611
0.7405 Intermediate Similarity NPC256893
0.7401 Intermediate Similarity NPC476419
0.7401 Intermediate Similarity NPC84347
0.7394 Intermediate Similarity NPC467188
0.7387 Intermediate Similarity NPC54066
0.738 Intermediate Similarity NPC473814
0.738 Intermediate Similarity NPC78767
0.7377 Intermediate Similarity NPC209917
0.7374 Intermediate Similarity NPC471997
0.7374 Intermediate Similarity NPC325705
0.7374 Intermediate Similarity NPC52831
0.7372 Intermediate Similarity NPC471313
0.7372 Intermediate Similarity NPC471311
0.7371 Intermediate Similarity NPC473764
0.7371 Intermediate Similarity NPC314940
0.7366 Intermediate Similarity NPC93390
0.7366 Intermediate Similarity NPC202812
0.7363 Intermediate Similarity NPC194040
0.7363 Intermediate Similarity NPC90415
0.736 Intermediate Similarity NPC157583
0.736 Intermediate Similarity NPC14113
0.736 Intermediate Similarity NPC84827
0.736 Intermediate Similarity NPC111275
0.736 Intermediate Similarity NPC145885
0.7348 Intermediate Similarity NPC203635
0.7348 Intermediate Similarity NPC285923
0.7348 Intermediate Similarity NPC46895
0.7345 Intermediate Similarity NPC469938
0.734 Intermediate Similarity NPC472284
0.7321 Intermediate Similarity NPC313889
0.7312 Intermediate Similarity NPC473821
0.731 Intermediate Similarity NPC116573
0.731 Intermediate Similarity NPC213914
0.7305 Intermediate Similarity NPC257142
0.7305 Intermediate Similarity NPC105811
0.7287 Intermediate Similarity NPC74153
0.7283 Intermediate Similarity NPC183805
0.7283 Intermediate Similarity NPC75544
0.7278 Intermediate Similarity NPC472260
0.7278 Intermediate Similarity NPC217021
0.7278 Intermediate Similarity NPC61011
0.7278 Intermediate Similarity NPC470679
0.7273 Intermediate Similarity NPC36405
0.7263 Intermediate Similarity NPC45459
0.7263 Intermediate Similarity NPC315491
0.7262 Intermediate Similarity NPC123906
0.7261 Intermediate Similarity NPC165370
0.7261 Intermediate Similarity NPC306397
0.7241 Intermediate Similarity NPC265100
0.7236 Intermediate Similarity NPC472285
0.7234 Intermediate Similarity NPC77061
0.7229 Intermediate Similarity NPC471323
0.7228 Intermediate Similarity NPC206186
0.7225 Intermediate Similarity NPC471944
0.7222 Intermediate Similarity NPC55772
0.7222 Intermediate Similarity NPC237740
0.7222 Intermediate Similarity NPC213468
0.7219 Intermediate Similarity NPC473878
0.7216 Intermediate Similarity NPC244741
0.7212 Intermediate Similarity NPC182222
0.7211 Intermediate Similarity NPC81535
0.7207 Intermediate Similarity NPC150048
0.7207 Intermediate Similarity NPC203754
0.7202 Intermediate Similarity NPC473239
0.72 Intermediate Similarity NPC477975
0.7198 Intermediate Similarity NPC159125
0.7184 Intermediate Similarity NPC242116
0.7182 Intermediate Similarity NPC73994
0.7178 Intermediate Similarity NPC472288
0.7178 Intermediate Similarity NPC65408
0.7176 Intermediate Similarity NPC109158
0.7176 Intermediate Similarity NPC284348
0.7174 Intermediate Similarity NPC235684
0.7173 Intermediate Similarity NPC470279
0.7173 Intermediate Similarity NPC213308
0.7167 Intermediate Similarity NPC83774
0.7166 Intermediate Similarity NPC56170
0.7165 Intermediate Similarity NPC472287
0.7165 Intermediate Similarity NPC472286
0.7164 Intermediate Similarity NPC313804
0.7164 Intermediate Similarity NPC315804
0.7158 Intermediate Similarity NPC212213
0.7151 Intermediate Similarity NPC154339
0.715 Intermediate Similarity NPC27041
0.7143 Intermediate Similarity NPC472752
0.7135 Intermediate Similarity NPC36498
0.7135 Intermediate Similarity NPC252590
0.7128 Intermediate Similarity NPC267343
0.7128 Intermediate Similarity NPC45850
0.7128 Intermediate Similarity NPC321428
0.7127 Intermediate Similarity NPC219336
0.7126 Intermediate Similarity NPC131718
0.7125 Intermediate Similarity NPC315320
0.7121 Intermediate Similarity NPC111732
0.712 Intermediate Similarity NPC160127
0.712 Intermediate Similarity NPC50997
0.7114 Intermediate Similarity NPC314270
0.7107 Intermediate Similarity NPC471589
0.7105 Intermediate Similarity NPC106824
0.7104 Intermediate Similarity NPC48938
0.7101 Intermediate Similarity NPC100726
0.7093 Intermediate Similarity NPC63562
0.7091 Intermediate Similarity NPC43477
0.7085 Intermediate Similarity NPC236668
0.7085 Intermediate Similarity NPC89508
0.7081 Intermediate Similarity NPC315555
0.7079 Intermediate Similarity NPC74360
0.7077 Intermediate Similarity NPC82053
0.7076 Intermediate Similarity NPC153769
0.7072 Intermediate Similarity NPC183662
0.7072 Intermediate Similarity NPC217372
0.7072 Intermediate Similarity NPC15573
0.7072 Intermediate Similarity NPC237188
0.7062 Intermediate Similarity NPC114637
0.7059 Intermediate Similarity NPC13432

  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 NPC41717 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
0.8683 High Similarity NPD3178 Discontinued
0.8165 Intermediate Similarity NPD9074 Approved
0.8165 Intermediate Similarity NPD9075 Approved
0.815 Intermediate Similarity NPD1096 Discontinued
0.8086 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD5088 Discontinued
0.8045 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD1631 Approved
0.7911 Intermediate Similarity NPD107 Approved
0.7898 Intermediate Similarity NPD2896 Discontinued
0.7898 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7784 Intermediate Similarity NPD5255 Approved
0.7784 Intermediate Similarity NPD1630 Approved
0.7778 Intermediate Similarity NPD1573 Approved
0.7778 Intermediate Similarity NPD1575 Approved
0.773 Intermediate Similarity NPD9271 Approved
0.7714 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD820 Phase 3
0.7614 Intermediate Similarity NPD1587 Approved
0.7614 Intermediate Similarity NPD5398 Clinical (unspecified phase)
0.7604 Intermediate Similarity NPD3779 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD750 Phase 2
0.758 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD3315 Phase 3
0.7546 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD6665 Discontinued
0.7531 Intermediate Similarity NPD4805 Approved
0.75 Intermediate Similarity NPD1568 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD2336 Approved
0.7484 Intermediate Similarity NPD9284 Approved
0.7474 Intermediate Similarity NPD5901 Discontinued
0.7443 Intermediate Similarity NPD482 Approved
0.7443 Intermediate Similarity NPD1586 Approved
0.7432 Intermediate Similarity NPD3321 Discontinued
0.7429 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD2511 Approved
0.7421 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7412 Intermediate Similarity NPD2581 Approved
0.7412 Intermediate Similarity NPD2582 Approved
0.7407 Intermediate Similarity NPD4804 Approved
0.7389 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD9510 Approved
0.7348 Intermediate Similarity NPD721 Approved
0.7333 Intermediate Similarity NPD3813 Approved
0.7326 Intermediate Similarity NPD2307 Discontinued
0.7322 Intermediate Similarity NPD4948 Discontinued
0.7317 Intermediate Similarity NPD5020 Approved
0.7312 Intermediate Similarity NPD4528 Approved
0.7312 Intermediate Similarity NPD4526 Approved
0.7312 Intermediate Similarity NPD1173 Approved
0.7312 Intermediate Similarity NPD4529 Approved
0.7305 Intermediate Similarity NPD4703 Approved
0.7305 Intermediate Similarity NPD4702 Approved
0.7299 Intermediate Similarity NPD926 Approved
0.7299 Intermediate Similarity NPD925 Approved
0.7294 Intermediate Similarity NPD5257 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD2809 Approved
0.7284 Intermediate Similarity NPD9506 Approved
0.7273 Intermediate Similarity NPD3717 Discontinued
0.7263 Intermediate Similarity NPD484 Approved
0.7261 Intermediate Similarity NPD9080 Approved
0.7257 Intermediate Similarity NPD4554 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD1649 Discontinued
0.7247 Intermediate Similarity NPD4736 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD9690 Approved
0.7245 Intermediate Similarity NPD7927 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD1213 Phase 3
0.7239 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD1352 Discontinued
0.7225 Intermediate Similarity NPD112 Approved
0.7225 Intermediate Similarity NPD9705 Discontinued
0.7211 Intermediate Similarity NPD6137 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD5100 Phase 3
0.7202 Intermediate Similarity NPD1270 Approved
0.7202 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD2092 Phase 2
0.7198 Intermediate Similarity NPD2095 Phase 2
0.7198 Intermediate Similarity NPD2094 Phase 2
0.7192 Intermediate Similarity NPD6753 Phase 1
0.7192 Intermediate Similarity NPD6752 Phase 1
0.7179 Intermediate Similarity NPD2509 Approved
0.7179 Intermediate Similarity NPD2510 Approved
0.7178 Intermediate Similarity NPD201 Phase 2
0.7178 Intermediate Similarity NPD200 Phase 2
0.7172 Intermediate Similarity NPD3794 Approved
0.7172 Intermediate Similarity NPD3795 Approved
0.7169 Intermediate Similarity NPD3525 Discontinued
0.7168 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4376 Phase 3
0.7165 Intermediate Similarity NPD7010 Phase 3
0.716 Intermediate Similarity NPD272 Approved
0.7159 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD2096 Phase 2
0.7158 Intermediate Similarity NPD2091 Phase 2
0.7157 Intermediate Similarity NPD5475 Discontinued
0.7151 Intermediate Similarity NPD158 Discontinued
0.7151 Intermediate Similarity NPD4883 Approved
0.7151 Intermediate Similarity NPD276 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD3326 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7061 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6791 Phase 2
0.7135 Intermediate Similarity NPD9364 Phase 2
0.7135 Intermediate Similarity NPD9363 Approved
0.7129 Intermediate Similarity NPD5827 Discontinued
0.7125 Intermediate Similarity NPD9207 Approved
0.7125 Intermediate Similarity NPD9206 Approved
0.712 Intermediate Similarity NPD6999 Discontinued
0.712 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD3947 Discontinued
0.711 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD3394 Approved
0.71 Intermediate Similarity NPD3389 Approved
0.71 Intermediate Similarity NPD3393 Approved
0.7088 Intermediate Similarity NPD6452 Discontinued
0.7085 Intermediate Similarity NPD3243 Approved
0.7076 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5505 Discontinued
0.7065 Intermediate Similarity NPD6178 Phase 3
0.7062 Intermediate Similarity NPD425 Approved
0.7062 Intermediate Similarity NPD424 Approved
0.7062 Intermediate Similarity NPD5611 Phase 2
0.7059 Intermediate Similarity NPD8356 Approved
0.7059 Intermediate Similarity NPD3575 Approved
0.7059 Intermediate Similarity NPD3576 Approved
0.7059 Intermediate Similarity NPD8063 Discontinued
0.7056 Intermediate Similarity NPD6529 Discontinued
0.7053 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD1274 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD9362 Approved
0.7041 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD8289 Discontinued
0.7027 Intermediate Similarity NPD4889 Approved
0.7026 Intermediate Similarity NPD4903 Approved
0.7026 Intermediate Similarity NPD944 Approved
0.7026 Intermediate Similarity NPD6987 Phase 1
0.7026 Intermediate Similarity NPD4905 Approved
0.7026 Intermediate Similarity NPD4906 Approved
0.7024 Intermediate Similarity NPD3222 Phase 2
0.7024 Intermediate Similarity NPD6173 Approved
0.7022 Intermediate Similarity NPD1343 Approved
0.7022 Intermediate Similarity NPD2781 Approved
0.702 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD3238 Discontinued
0.7011 Intermediate Similarity NPD9383 Approved
0.7011 Intermediate Similarity NPD9382 Approved
0.7011 Intermediate Similarity NPD7401 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD2782 Approved
0.7006 Intermediate Similarity NPD2780 Approved
0.7005 Intermediate Similarity NPD7234 Approved
0.7005 Intermediate Similarity NPD7233 Approved
0.7 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2077 Approved
0.7 Intermediate Similarity NPD2076 Approved
0.6995 Remote Similarity NPD1643 Phase 3
0.6994 Remote Similarity NPD2061 Approved
0.699 Remote Similarity NPD4904 Approved
0.699 Remote Similarity NPD4862 Clinical (unspecified phase)
0.699 Remote Similarity NPD2317 Clinical (unspecified phase)
0.6989 Remote Similarity NPD5400 Approved
0.6985 Remote Similarity NPD7470 Discontinued
0.6984 Remote Similarity NPD981 Phase 2
0.6978 Remote Similarity NPD2753 Discontinued
0.6977 Remote Similarity NPD6158 Phase 2
0.6977 Remote Similarity NPD2882 Phase 1
0.6977 Remote Similarity NPD6476 Clinical (unspecified phase)
0.6974 Remote Similarity NPD5513 Phase 2
0.6965 Remote Similarity NPD7538 Clinical (unspecified phase)
0.6961 Remote Similarity NPD1996 Discontinued
0.6961 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5065 Approved
0.6961 Remote Similarity NPD3280 Approved
0.6959 Remote Similarity NPD5017 Discontinued
0.695 Remote Similarity NPD5866 Approved
0.6946 Remote Similarity NPD9599 Approved
0.6941 Remote Similarity NPD7469 Discontinued
0.6941 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6932 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6927 Remote Similarity NPD5862 Discovery
0.6927 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6927 Remote Similarity NPD2844 Phase 3
0.6923 Remote Similarity NPD7187 Phase 2
0.6923 Remote Similarity NPD8430 Approved
0.6912 Remote Similarity NPD7404 Approved
0.6911 Remote Similarity NPD4427 Phase 2
0.6907 Remote Similarity NPD5043 Discontinued
0.6904 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6904 Remote Similarity NPD7001 Phase 3
0.69 Remote Similarity NPD4417 Approved
0.6898 Remote Similarity NPD5809 Phase 3
0.6898 Remote Similarity NPD706 Phase 1
0.6891 Remote Similarity NPD7204 Clinical (unspecified phase)
0.6891 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6882 Remote Similarity NPD175 Clinical (unspecified phase)
0.6879 Remote Similarity NPD9343 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