Structure

Physi-Chem Properties

Molecular Weight:  176.09
Volume:  184.641
LogP:  0.056
LogD:  0.432
LogS:  0.675
# Rotatable Bonds:  1
TPSA:  33.2
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.647
Synthetic Accessibility Score:  2.742
Fsp3:  0.4
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.248
MDCK Permeability:  3.204784297849983e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.426
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.812
Plasma Protein Binding (PPB):  28.013446807861328%
Volume Distribution (VD):  1.166
Pgp-substrate:  70.96936798095703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.777
CYP2C19-inhibitor:  0.086
CYP2C19-substrate:  0.798
CYP2C9-inhibitor:  0.032
CYP2C9-substrate:  0.601
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.439
CYP3A4-inhibitor:  0.132
CYP3A4-substrate:  0.571

ADMET: Excretion

Clearance (CL):  7.662
Half-life (T1/2):  0.392

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.469
Drug-inuced Liver Injury (DILI):  0.896
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.282
Maximum Recommended Daily Dose:  0.944
Skin Sensitization:  0.812
Carcinogencity:  0.274
Eye Corrosion:  0.022
Eye Irritation:  0.676
Respiratory Toxicity:  0.094

Download Data

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

  Natural Product: NPC65408

Natural Product ID:  NPC65408
Common Name*:   Cotinine
IUPAC Name:   (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one
Synonyms:   Cotinine
Standard InCHIKey:  UIKROCXWUNQSPJ-VIFPVBQESA-N
Standard InCHI:  InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
SMILES:  CN1[C@@H](CCC1=O)c1cccnc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL578211
PubChem CID:   854019
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001975] Pyrrolidinylpyridines

*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

☑ 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
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens IC50 = 5400000.0 nM PMID[520043]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens IC50 = 35000000.0 nM PMID[520044]
NPT1420 Individual Protein Cytochrome P450 2A5 Mus musculus IC50 = 1500000.0 nM PMID[520044]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 6510.4 nM PMID[520049]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 28.65 % PMID[520056]
NPT1304 Individual Protein Nicotinic acetylcholine receptor alpha 5 subunit Musca domestica Ki > 1000000.0 nM PMID[520057]
NPT3044 Individual Protein Acetylcholinesterase Musca domestica IC50 = 260000000.0 nM PMID[520057]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens IC50 > 400000.0 nM PMID[520061]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens IC50 >= 400000.0 nM PMID[520063]
NPT182 Individual Protein Protein kinase C alpha Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT273 Individual Protein Phosphodiesterase 5A Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT297 Individual Protein Neurokinin 1 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT247 Individual Protein Endothelin receptor ET-A Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT230 Individual Protein Bradykinin B2 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT4358 Individual Protein Type-1 angiotensin II receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT2769 Individual Protein Thromboxane A2 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT256 Individual Protein Cysteinyl leukotriene receptor 1 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT3068 Individual Protein Leukotriene B4 receptor 1 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT296 Individual Protein Sigma opioid receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT1785 Individual Protein Serotonin 7 (5-HT7) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT4011 Individual Protein Serotonin 4 (5-HT4) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT425 Individual Protein Serotonin 3a (5-HT3a) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT290 Individual Protein Serotonin 2a (5-HT2a) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT292 Individual Protein Serotonin 2c (5-HT2c) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT295 Individual Protein Serotonin transporter Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT266 Individual Protein Muscarinic acetylcholine receptor M5 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT265 Individual Protein Muscarinic acetylcholine receptor M4 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT263 Individual Protein Muscarinic acetylcholine receptor M2 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT264 Individual Protein Muscarinic acetylcholine receptor M3 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT262 Individual Protein Muscarinic acetylcholine receptor M1 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT252 Individual Protein Histamine H2 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT251 Individual Protein Histamine H1 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT1407 Individual Protein GABA-B receptor 1 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT1406 Individual Protein GABA receptor alpha-1 subunit Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT245 Individual Protein Dopamine D4 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT243 Individual Protein Dopamine D2 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT244 Individual Protein Dopamine D3 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT242 Individual Protein Dopamine D1 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT246 Individual Protein Dopamine transporter Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT226 Individual Protein Beta-2 adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT225 Individual Protein Beta-1 adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT224 Individual Protein Alpha-2c adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT223 Individual Protein Alpha-2b adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT216 Individual Protein Adenosine A1 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT222 Individual Protein Alpha-2a adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT1789 Individual Protein Alpha-1b adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT1788 Individual Protein Alpha-1a adrenergic receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT217 Individual Protein Adenosine A2a receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT240 Individual Protein Cytochrome P450 2A6 Homo sapiens IC50 > 400000 nM Patent: US8609708 B2
NPT27 Others Unspecified Ratio = 42.8 n.a. PMID[520044]
NPT605 Organism Homo sapiens Homo sapiens Fg = 1.04 n.a. PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens Vdss = 1.1 L.kg-1 PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens CL_renal = 0.1 mL.min-1.kg-1 PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens CL = 0.8 mL.min-1.kg-1 PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens CL = 0.89 mL.min-1.kg-1 PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens F_fraction = 0.9 n.a. PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens Fa = 0.9 n.a. PMID[520045]
NPT605 Organism Homo sapiens Homo sapiens Fh = 0.97 n.a. PMID[520045]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 12589.25 nM PMID[520047]
NPT27 Others Unspecified CL = 0.89 mL.min-1.kg-1 PMID[520048]
NPT27 Others Unspecified Vdss = 1.1 L.kg-1 PMID[520048]
NPT27 Others Unspecified T1/2 = 17.0 hr PMID[520048]
NPT27 Others Unspecified MRT = 21.0 hr PMID[520048]
NPT27 Others Unspecified logP(lung) = -0.18 n.a. PMID[520050]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 1069.1 nM PMID[520051]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 26679.5 nM PMID[520051]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 6701.6 nM PMID[520049]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 16833.6 nM PMID[520049]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[520052]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[520053]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[520054]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[520051]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[520055]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -0.23 % PMID[520056]
NPT2 Others Unspecified Ki > 1000000.0 nM PMID[520057]
NPT734 Organism Musca domestica Musca domestica FC = 0.03 n.a. PMID[520057]
NPT35 Others n.a. pKa = 4.5 n.a. PMID[520057]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 103.03 % PMID[520058]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 106.54 % PMID[520058]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 76.8 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 78.1 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 76.3 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 82.3 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 66.5 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 61.7 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 60.5 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 61.6 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 63.8 % PMID[520059]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 72.8 % PMID[520059]
NPT21243 SINGLE PROTEIN Galactocerebrosidase Homo sapiens Potency n.a. 562.3 nM PMID[520060]
NPT2 Others Unspecified IC50 n.a. 33330.0 nM PMID[520060]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -6.19 % PMID[520062]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 2.176 % PMID[520064]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.09 % PMID[520065]
NPT20 Organism Candida albicans Candida albicans Inhibition = 4.46 % PMID[520066]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Inhibition = -1.87 % PMID[520066]
NPT19 Organism Escherichia coli Escherichia coli Inhibition = 7.12 % PMID[520066]
NPT173 Organism Klebsiella pneumoniae Klebsiella pneumoniae Inhibition = 5.32 % PMID[520066]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa Inhibition = 2.81 % PMID[520066]
NPT747 Organism Acinetobacter baumannii Acinetobacter baumannii Inhibition = 6.43 % PMID[520066]
NPT2922 Organism Staphylococcus aureus subsp. aureus Staphylococcus aureus subsp. aureus Inhibition = -20.45 % PMID[520066]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[520067]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[520067]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus EC50 = 21000.0 nM PMID[520068]
NPT412 Protein Complex Neuronal acetylcholine receptor; alpha4/beta2 Rattus norvegicus Ki = 3000.0 nM PMID[520068]
NPT27 Others Unspecified T1/2 = 19.0 hr PMID[520068]
NPT2 Others Unspecified Activity >= 20.0 % PMID[520068]
NPT2 Others Unspecified Inhibition < 50.0 % PMID[520068]
NPT20859 SINGLE PROTEIN Neuropeptide Y receptor type 2 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT98 Individual Protein HERG Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT5065 Protein Family Voltage-gated L-type calcium channel Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT24748 SINGLE PROTEIN Sigma intracellular receptor 2 Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT974 Individual Protein Serotonin 1d (5-HT1d) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT92 Individual Protein Serotonin 1a (5-HT1a) receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT987 Individual Protein Histamine H3 receptor Homo sapiens Inhibition < 50.0 % PMID[520068]
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 14960.1 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 NPC65408 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
0.8837 High Similarity NPC265605
0.8837 High Similarity NPC48564
0.8837 High Similarity NPC182570
0.8358 Intermediate Similarity NPC27740
0.8071 Intermediate Similarity NPC324611
0.8065 Intermediate Similarity NPC56233
0.7984 Intermediate Similarity NPC27802
0.797 Intermediate Similarity NPC471402
0.797 Intermediate Similarity NPC297486
0.797 Intermediate Similarity NPC240136
0.7949 Intermediate Similarity NPC114637
0.7914 Intermediate Similarity NPC471313
0.7914 Intermediate Similarity NPC471311
0.7899 Intermediate Similarity NPC166424
0.7899 Intermediate Similarity NPC245244
0.7899 Intermediate Similarity NPC146373
0.7883 Intermediate Similarity NPC290094
0.7881 Intermediate Similarity NPC472260
0.7815 Intermediate Similarity NPC473878
0.7778 Intermediate Similarity NPC91958
0.7778 Intermediate Similarity NPC248462
0.7763 Intermediate Similarity NPC470679
0.7763 Intermediate Similarity NPC217021
0.7762 Intermediate Similarity NPC322488
0.7752 Intermediate Similarity NPC76540
0.773 Intermediate Similarity NPC89490
0.7716 Intermediate Similarity NPC64436
0.7714 Intermediate Similarity NPC202957
0.7714 Intermediate Similarity NPC169625
0.7702 Intermediate Similarity NPC469529
0.7698 Intermediate Similarity NPC476322
0.7676 Intermediate Similarity NPC475105
0.7676 Intermediate Similarity NPC475090
0.7676 Intermediate Similarity NPC329896
0.7669 Intermediate Similarity NPC11126
0.7647 Intermediate Similarity NPC143603
0.7643 Intermediate Similarity NPC194881
0.7639 Intermediate Similarity NPC330326
0.7628 Intermediate Similarity NPC293487
0.7595 Intermediate Similarity NPC478182
0.7595 Intermediate Similarity NPC478184
0.7569 Intermediate Similarity NPC256893
0.7569 Intermediate Similarity NPC471322
0.755 Intermediate Similarity NPC470440
0.7532 Intermediate Similarity NPC242116
0.7532 Intermediate Similarity NPC70406
0.7516 Intermediate Similarity NPC80681
0.75 Intermediate Similarity NPC46358
0.7485 Intermediate Similarity NPC228835
0.7484 Intermediate Similarity NPC200214
0.7484 Intermediate Similarity NPC265100
0.7483 Intermediate Similarity NPC471589
0.7468 Intermediate Similarity NPC470680
0.7468 Intermediate Similarity NPC100104
0.7463 Intermediate Similarity NPC235843
0.7451 Intermediate Similarity NPC105811
0.7451 Intermediate Similarity NPC100726
0.745 Intermediate Similarity NPC110126
0.744 Intermediate Similarity NPC308931
0.744 Intermediate Similarity NPC99939
0.7434 Intermediate Similarity NPC467188
0.7432 Intermediate Similarity NPC471312
0.7432 Intermediate Similarity NPC150259
0.7431 Intermediate Similarity NPC476131
0.7429 Intermediate Similarity NPC329825
0.7427 Intermediate Similarity NPC117244
0.7427 Intermediate Similarity NPC473763
0.7421 Intermediate Similarity NPC478185
0.7417 Intermediate Similarity NPC190296
0.741 Intermediate Similarity NPC73994
0.7407 Intermediate Similarity NPC91895
0.74 Intermediate Similarity NPC238499
0.7394 Intermediate Similarity NPC83774
0.7391 Intermediate Similarity NPC478183
0.7381 Intermediate Similarity NPC477003
0.7379 Intermediate Similarity NPC282398
0.7379 Intermediate Similarity NPC69914
0.7372 Intermediate Similarity NPC251391
0.7355 Intermediate Similarity NPC40070
0.7355 Intermediate Similarity NPC313889
0.7351 Intermediate Similarity NPC476454
0.7348 Intermediate Similarity NPC231655
0.7333 Intermediate Similarity NPC73767
0.7329 Intermediate Similarity NPC101165
0.732 Intermediate Similarity NPC285731
0.732 Intermediate Similarity NPC314372
0.7317 Intermediate Similarity NPC161861
0.7315 Intermediate Similarity NPC314102
0.7315 Intermediate Similarity NPC84911
0.7315 Intermediate Similarity NPC251722
0.7315 Intermediate Similarity NPC105127
0.7305 Intermediate Similarity NPC61011
0.7301 Intermediate Similarity NPC32534
0.7296 Intermediate Similarity NPC474492
0.7292 Intermediate Similarity NPC212125
0.7289 Intermediate Similarity NPC145885
0.7289 Intermediate Similarity NPC14113
0.7289 Intermediate Similarity NPC84827
0.7287 Intermediate Similarity NPC83987
0.7267 Intermediate Similarity NPC21174
0.7267 Intermediate Similarity NPC271797
0.7251 Intermediate Similarity NPC17059
0.7248 Intermediate Similarity NPC96102
0.7248 Intermediate Similarity NPC261195
0.7248 Intermediate Similarity NPC29886
0.7246 Intermediate Similarity NPC476566
0.7241 Intermediate Similarity NPC313823
0.7233 Intermediate Similarity NPC129721
0.7229 Intermediate Similarity NPC267885
0.7226 Intermediate Similarity NPC470111
0.7226 Intermediate Similarity NPC477974
0.7222 Intermediate Similarity NPC233380
0.7222 Intermediate Similarity NPC42372
0.7219 Intermediate Similarity NPC315348
0.7219 Intermediate Similarity NPC316811
0.7219 Intermediate Similarity NPC32002
0.7211 Intermediate Similarity NPC82295
0.7208 Intermediate Similarity NPC159856
0.7193 Intermediate Similarity NPC94752
0.7186 Intermediate Similarity NPC157583
0.7179 Intermediate Similarity NPC123906
0.7178 Intermediate Similarity NPC41717
0.7176 Intermediate Similarity NPC46895
0.7171 Intermediate Similarity NPC469779
0.7171 Intermediate Similarity NPC469784
0.7171 Intermediate Similarity NPC469780
0.7171 Intermediate Similarity NPC469761
0.7171 Intermediate Similarity NPC469783
0.7171 Intermediate Similarity NPC469768
0.7171 Intermediate Similarity NPC469767
0.7169 Intermediate Similarity NPC469938
0.7169 Intermediate Similarity NPC293216
0.7169 Intermediate Similarity NPC203468
0.7169 Intermediate Similarity NPC110500
0.7169 Intermediate Similarity NPC149155
0.716 Intermediate Similarity NPC191415
0.7152 Intermediate Similarity NPC281094
0.7143 Intermediate Similarity NPC126709
0.7143 Intermediate Similarity NPC248041
0.7143 Intermediate Similarity NPC315320
0.7143 Intermediate Similarity NPC12649
0.7134 Intermediate Similarity NPC70949
0.7134 Intermediate Similarity NPC471655
0.7134 Intermediate Similarity NPC24678
0.7134 Intermediate Similarity NPC78020
0.7134 Intermediate Similarity NPC105818
0.7133 Intermediate Similarity NPC29702
0.7124 Intermediate Similarity NPC469766
0.7115 Intermediate Similarity NPC179787
0.7115 Intermediate Similarity NPC471957
0.7115 Intermediate Similarity NPC201380
0.7107 Intermediate Similarity NPC209362
0.7107 Intermediate Similarity NPC229055
0.7105 Intermediate Similarity NPC104483
0.7101 Intermediate Similarity NPC24864
0.7089 Intermediate Similarity NPC470233
0.7086 Intermediate Similarity NPC114310
0.7086 Intermediate Similarity NPC472288
0.7083 Intermediate Similarity NPC237188
0.7075 Intermediate Similarity NPC71236
0.707 Intermediate Similarity NPC321911
0.707 Intermediate Similarity NPC102664
0.7063 Intermediate Similarity NPC74357
0.7063 Intermediate Similarity NPC51054
0.7059 Intermediate Similarity NPC279081
0.7055 Intermediate Similarity NPC306397
0.7051 Intermediate Similarity NPC478186
0.7051 Intermediate Similarity NPC63545
0.7044 Intermediate Similarity NPC469760
0.7044 Intermediate Similarity NPC469763
0.7044 Intermediate Similarity NPC469786
0.7044 Intermediate Similarity NPC73952
0.7044 Intermediate Similarity NPC469765
0.7044 Intermediate Similarity NPC259644
0.7044 Intermediate Similarity NPC25008
0.7041 Intermediate Similarity NPC283219
0.7032 Intermediate Similarity NPC471323
0.7032 Intermediate Similarity NPC159630
0.7032 Intermediate Similarity NPC230085
0.7029 Intermediate Similarity NPC476460
0.7019 Intermediate Similarity NPC213914
0.7018 Intermediate Similarity NPC102755
0.7018 Intermediate Similarity NPC470205
0.7013 Intermediate Similarity NPC277157
0.7011 Intermediate Similarity NPC213629
0.7006 Intermediate Similarity NPC294693
0.7006 Intermediate Similarity NPC469811
0.7006 Intermediate Similarity NPC477976
0.7 Intermediate Similarity NPC70922
0.7 Intermediate Similarity NPC75540
0.7 Intermediate Similarity NPC211572
0.7 Intermediate Similarity NPC80597
0.7 Intermediate Similarity NPC212376
0.6994 Remote Similarity NPC62749
0.6989 Remote Similarity NPC471386
0.6988 Remote Similarity NPC116961
0.6987 Remote Similarity NPC86288
0.6982 Remote Similarity NPC111275
0.6982 Remote Similarity NPC240088
0.6982 Remote Similarity NPC284775

  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 NPC65408 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
1.0 High Similarity NPD200 Phase 2
1.0 High Similarity NPD201 Phase 2
0.8837 High Similarity NPD268 Approved
0.8837 High Similarity NPD271 Approved
0.8837 High Similarity NPD270 Clinical (unspecified phase)
0.8489 Intermediate Similarity NPD206 Clinical (unspecified phase)
0.8417 Intermediate Similarity NPD272 Approved
0.8406 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD748 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD175 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3476 Approved
0.8 Intermediate Similarity NPD3475 Approved
0.8 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD1031 Discontinued
0.7949 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD2511 Approved
0.7877 Intermediate Similarity NPD9599 Approved
0.7871 Intermediate Similarity NPD5400 Approved
0.7862 Intermediate Similarity NPD2896 Discontinued
0.7838 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD3583 Phase 2
0.78 Intermediate Similarity NPD1270 Approved
0.7786 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD991 Phase 2
0.7786 Intermediate Similarity NPD2118 Approved
0.7786 Intermediate Similarity NPD2119 Approved
0.7722 Intermediate Similarity NPD5636 Discontinued
0.7714 Intermediate Similarity NPD9583 Approved
0.7698 Intermediate Similarity NPD9357 Approved
0.7687 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1343 Approved
0.7673 Intermediate Similarity NPD1292 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD6044 Discontinued
0.7643 Intermediate Similarity NPD6771 Discontinued
0.7639 Intermediate Similarity NPD9100 Approved
0.7594 Intermediate Similarity NPD4823 Approved
0.7594 Intermediate Similarity NPD4824 Approved
0.7593 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD4029 Approved
0.7586 Intermediate Similarity NPD4030 Approved
0.7586 Intermediate Similarity NPD4028 Approved
0.7568 Intermediate Similarity NPD4804 Approved
0.7535 Intermediate Similarity NPD1598 Discontinued
0.7485 Intermediate Similarity NPD7564 Discontinued
0.7482 Intermediate Similarity NPD9598 Discontinued
0.7467 Intermediate Similarity NPD4805 Approved
0.7466 Intermediate Similarity NPD3942 Approved
0.7466 Intermediate Similarity NPD3944 Approved
0.7456 Intermediate Similarity NPD4988 Discontinued
0.745 Intermediate Similarity NPD768 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD803 Phase 1
0.7445 Intermediate Similarity NPD9392 Approved
0.7445 Intermediate Similarity NPD9396 Approved
0.7439 Intermediate Similarity NPD4075 Phase 2
0.7423 Intermediate Similarity NPD750 Phase 2
0.7421 Intermediate Similarity NPD4384 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD2006 Phase 2
0.74 Intermediate Similarity NPD2222 Discontinued
0.7399 Intermediate Similarity NPD7619 Phase 3
0.7399 Intermediate Similarity NPD7618 Phase 3
0.7397 Intermediate Similarity NPD1993 Approved
0.7397 Intermediate Similarity NPD1995 Approved
0.7397 Intermediate Similarity NPD1994 Approved
0.7396 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3929 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7469 Discontinued
0.7384 Intermediate Similarity NPD6665 Discontinued
0.7384 Intermediate Similarity NPD5505 Discontinued
0.7384 Intermediate Similarity NPD3430 Approved
0.7384 Intermediate Similarity NPD3431 Approved
0.7383 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD715 Phase 3
0.7348 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD9098 Phase 3
0.7338 Intermediate Similarity NPD4547 Phase 3
0.7338 Intermediate Similarity NPD4702 Approved
0.7338 Intermediate Similarity NPD4703 Approved
0.7333 Intermediate Similarity NPD786 Approved
0.7325 Intermediate Similarity NPD2809 Approved
0.7325 Intermediate Similarity NPD2061 Approved
0.7321 Intermediate Similarity NPD7401 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD6664 Approved
0.7308 Intermediate Similarity NPD510 Phase 1
0.7305 Intermediate Similarity NPD1291 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD3927 Phase 2
0.7303 Intermediate Similarity NPD3717 Discontinued
0.7294 Intermediate Similarity NPD5820 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD9284 Approved
0.7262 Intermediate Similarity NPD4011 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7023 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3813 Approved
0.7248 Intermediate Similarity NPD792 Discontinued
0.7248 Intermediate Similarity NPD198 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD5020 Approved
0.7237 Intermediate Similarity NPD1722 Approved
0.7235 Intermediate Similarity NPD4336 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD3385 Approved
0.7229 Intermediate Similarity NPD6471 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2070 Approved
0.7219 Intermediate Similarity NPD2068 Approved
0.7219 Intermediate Similarity NPD2074 Approved
0.7219 Intermediate Similarity NPD2072 Approved
0.7219 Intermediate Similarity NPD2073 Approved
0.7219 Intermediate Similarity NPD2071 Approved
0.7219 Intermediate Similarity NPD2075 Approved
0.7219 Intermediate Similarity NPD2069 Approved
0.7211 Intermediate Similarity NPD9726 Discontinued
0.7192 Intermediate Similarity NPD3654 Approved
0.7181 Intermediate Similarity NPD2142 Approved
0.7181 Intermediate Similarity NPD2140 Approved
0.7181 Intermediate Similarity NPD2141 Approved
0.7179 Intermediate Similarity NPD2430 Phase 2
0.7175 Intermediate Similarity NPD7204 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1395 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4883 Approved
0.7169 Intermediate Similarity NPD482 Approved
0.7161 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5088 Discontinued
0.7143 Intermediate Similarity NPD9206 Approved
0.7143 Intermediate Similarity NPD9207 Approved
0.7135 Intermediate Similarity NPD5555 Phase 1
0.7134 Intermediate Similarity NPD7913 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD490 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6180 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7402 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD2089 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7175 Phase 1
0.7107 Intermediate Similarity NPD4436 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD5358 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD569 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD7944 Discontinued
0.7101 Intermediate Similarity NPD5508 Phase 1
0.7089 Intermediate Similarity NPD9343 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4364 Phase 1
0.7079 Intermediate Similarity NPD1982 Phase 1
0.7076 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6446 Discontinued
0.7073 Intermediate Similarity NPD5611 Phase 2
0.7069 Intermediate Similarity NPD1905 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD1649 Discontinued
0.7056 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1545 Discontinued
0.7055 Intermediate Similarity NPD9080 Approved
0.7048 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD2837 Discontinued
0.7044 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD4446 Approved
0.7033 Intermediate Similarity NPD7712 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6068 Discontinued
0.7006 Intermediate Similarity NPD1661 Suspended
0.7006 Intermediate Similarity NPD7024 Clinical (unspecified phase)
0.6989 Remote Similarity NPD4922 Phase 2
0.6988 Remote Similarity NPD4973 Approved
0.6982 Remote Similarity NPD2753 Discontinued
0.6977 Remote Similarity NPD2096 Phase 2
0.6977 Remote Similarity NPD7483 Phase 2
0.6977 Remote Similarity NPD2091 Phase 2
0.6977 Remote Similarity NPD7482 Phase 2
0.6975 Remote Similarity NPD5255 Approved
0.6968 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4637 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1851 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3362 Clinical (unspecified phase)
0.6962 Remote Similarity NPD3100 Discontinued
0.6962 Remote Similarity NPD1183 Approved
0.6959 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6957 Remote Similarity NPD5179 Approved
0.6957 Remote Similarity NPD5181 Approved
0.6957 Remote Similarity NPD5180 Approved
0.6957 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6954 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6948 Remote Similarity NPD107 Approved
0.6944 Remote Similarity NPD6999 Discontinued
0.6944 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3077 Approved
0.6941 Remote Similarity NPD2590 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3079 Approved
0.6941 Remote Similarity NPD3076 Approved
0.6941 Remote Similarity NPD3078 Approved
0.694 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6932 Remote Similarity NPD1658 Discontinued
0.6932 Remote Similarity NPD7434 Approved
0.6928 Remote Similarity NPD1380 Discovery
0.6923 Remote Similarity NPD4385 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3238 Discontinued
0.6923 Remote Similarity NPD1352 Discontinued
0.6923 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6919 Remote Similarity NPD2095 Phase 2
0.6919 Remote Similarity NPD2094 Phase 2
0.6919 Remote Similarity NPD2092 Phase 2
0.6918 Remote Similarity NPD2465 Approved
0.6918 Remote Similarity NPD2462 Phase 3
0.6918 Remote Similarity NPD2466 Phase 3
0.6914 Remote Similarity NPD2581 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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