Structure

Physi-Chem Properties

Molecular Weight:  167.02
Volume:  154.047
LogP:  0.275
LogD:  0.842
LogS:  -1.078
# Rotatable Bonds:  2
TPSA:  87.49
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.668
Synthetic Accessibility Score:  1.878
Fsp3:  0.0
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:  -5.907
MDCK Permeability:  9.868133929558098e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.037
20% Bioavailability (F20%):  0.022
30% Bioavailability (F30%):  0.831

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.312
Plasma Protein Binding (PPB):  26.47614288330078%
Volume Distribution (VD):  0.229
Pgp-substrate:  61.7640266418457%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.044
CYP2C19-inhibitor:  0.035
CYP2C19-substrate:  0.036
CYP2C9-inhibitor:  0.03
CYP2C9-substrate:  0.08
CYP2D6-inhibitor:  0.022
CYP2D6-substrate:  0.067
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.016

ADMET: Excretion

Clearance (CL):  1.385
Half-life (T1/2):  0.705

ADMET: Toxicity

hERG Blockers:  0.092
Human Hepatotoxicity (H-HT):  0.338
Drug-inuced Liver Injury (DILI):  0.944
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.188
Maximum Recommended Daily Dose:  0.003
Skin Sensitization:  0.414
Carcinogencity:  0.014
Eye Corrosion:  0.01
Eye Irritation:  0.995
Respiratory Toxicity:  0.81

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

  Natural Product: NPC273532

Natural Product ID:  NPC273532
Common Name*:   Quinolinic Acid
IUPAC Name:   pyridine-2,3-dicarboxylic acid
Synonyms:   Pyridine-2,3-Dicarboxylic Acid; Quinolinic Acid
Standard InCHIKey:  GJAWHXHKYYXBSV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H5NO4/c9-6(10)4-2-1-3-8-5(4)7(11)12/h1-3H,(H,9,10)(H,11,12)
SMILES:  c1cc(c(C(=O)O)nc1)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL286204
PubChem CID:   1066
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

*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
NPT4202 Individual Protein Glutamate [NMDA] receptor subunit epsilon 3 Rattus norvegicus pKa <= 2.0 n.a. PMID[487452]
NPT3994 Individual Protein Metallo beta-lactamase Pseudomonas aeruginosa Activity = 89.0 % PMID[487455]
NPT3994 Individual Protein Metallo beta-lactamase Pseudomonas aeruginosa Activity = 67.0 % PMID[487455]
NPT3989 Individual Protein Beta-lactamase L1 Stenotrophomonas maltophilia Activity = 93.0 % PMID[487455]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 891.3 nM PMID[487459]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 1778.3 nM PMID[487460]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 1995.3 nM PMID[487461]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 5011.9 nM PMID[487462]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 89125.1 nM PMID[487460]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 1122.0 nM PMID[487460]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 15848.9 nM PMID[487459]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 1412.5 nM PMID[487461]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 15811.4 nM PMID[487459]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 629.5 nM PMID[487461]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Potency = 12589.3 nM PMID[487460]
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 100000.0 nM PMID[487459]
NPT1416 Individual Protein Neuropeptide S receptor Homo sapiens Potency = 1000.0 nM PMID[487459]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 1584.9 nM PMID[487460]
NPT270 Individual Protein Nitric oxide synthase, inducible Mus musculus Inhibition = 5.0 % PMID[487464]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 30.0 % PMID[487464]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = 14.0 % PMID[487464]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = -16.0 % PMID[487464]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 49.0 % PMID[487464]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = -8.0 % PMID[487464]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 82.0 % PMID[487464]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 98.0 % PMID[487464]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 891.3 nM PMID[487463]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 19952.6 nM PMID[487459]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 1584.9 nM PMID[487463]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 3548.1 nM PMID[487465]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 2818.4 nM PMID[487465]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 6309.6 nM PMID[487463]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 84.1 nM PMID[487466]
NPT104 Individual Protein Cerebroside-sulfatase Homo sapiens Potency n.a. 849.2 nM PMID[487465]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 84367.9 nM PMID[487463]
NPT1496 Protein Complex Glutamate NMDA receptor Rattus norvegicus IC50 > 100000.0 nM PMID[487452]
NPT3739 Protein Complex Glutamate receptor ionotropic, AMPA Rattus norvegicus IC50 > 100000.0 nM PMID[487452]
NPT29 Organism Rattus norvegicus Rattus norvegicus EC50 = 1500000.0 nM PMID[487452]
NPT29 Organism Rattus norvegicus Rattus norvegicus Enzyme activity = 61.0 % PMID[487453]
NPT29 Organism Rattus norvegicus Rattus norvegicus Enzyme activity = 53.0 % PMID[487453]
NPT1496 Protein Complex Glutamate NMDA receptor Rattus norvegicus IC50 = 100000.0 nM PMID[487454]
NPT2 Others Unspecified Activity = 98.0 % PMID[487455]
NPT2 Others Unspecified Activity = 106.0 % PMID[487455]
NPT2 Others Unspecified Activity = 73.0 % PMID[487455]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Activity = 130.0 % PMID[487455]
NPT2 Others Unspecified Activity = 62.0 % PMID[487455]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 200000.0 nM PMID[487455]
NPT2 Others Unspecified Activity = 11.3 ng/ml PMID[487456]
NPT2 Others Unspecified Activity = 4.19 ng/ml PMID[487456]
NPT2 Others Unspecified Activity = 15.4 ng/ml PMID[487456]
NPT2 Others Unspecified Activity = 8.36 ng/ml PMID[487456]
NPT32 Organism Mus musculus Mus musculus Activity = 335000.0 n.a. PMID[487456]
NPT32 Organism Mus musculus Mus musculus Activity = 312.0 pg/ml PMID[487456]
NPT32 Organism Mus musculus Mus musculus Activity = 263.0 pg/ml PMID[487456]
NPT2 Others Unspecified IC50 > 10000000.0 nM PMID[487457]
NPT2 Others Unspecified IC50 > 5000000.0 nM PMID[487457]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 14988.9 nM PMID[487460]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 39810.7 nM PMID[487460]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 22387.2 nM PMID[487463]
NPT2 Others Unspecified Potency = 8912.5 nM PMID[487459]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 4.0 % PMID[487464]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 14125.4 nM PMID[487459]
NPT2 Others Unspecified Potency n.a. 4109.5 nM PMID[487463]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 446.7 nM PMID[487465]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 39810.7 nM PMID[487463]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 4744.4 nM PMID[487465]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 89125.1 nM PMID[487463]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 9466.2 nM PMID[487465]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[487463]
NPT2 Others Unspecified Potency n.a. 20.0 nM PMID[487459]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 316.2 nM PMID[487465]
NPT533 Protein-Protein Interaction Runt-related transcription factor 1/Core-binding factor subunit beta Homo sapiens Potency n.a. 35481.3 nM PMID[487459]
NPT2 Others Unspecified Potency n.a. 707.9 nM PMID[487463]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 103.91 % PMID[487467]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 104.17 % PMID[487467]
NPT25909 SINGLE PROTEIN Advanced glycosylation end product-specific receptor Rattus norvegicus Kd = 43.0 nM PMID[487468]
NPT25910 SINGLE PROTEIN Advanced glycosylation end product-specific receptor Homo sapiens Kd = 43.0 nM PMID[487468]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -15.45 % PMID[487469]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.0 % PMID[487470]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.27 % PMID[487471]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.16 % PMID[487472]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.07 % PMID[487473]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[487474]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[487474]
NPT2 Others Unspecified Potency n.a. 549.4 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 NPC273532 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
0.8896 High Similarity NPC302159
0.8854 High Similarity NPC312860
0.8831 High Similarity NPC167400
0.8827 High Similarity NPC41717
0.8538 High Similarity NPC207851
0.8447 Intermediate Similarity NPC263455
0.8408 Intermediate Similarity NPC159630
0.8408 Intermediate Similarity NPC230085
0.8293 Intermediate Similarity NPC113812
0.825 Intermediate Similarity NPC112741
0.8153 Intermediate Similarity NPC85443
0.8141 Intermediate Similarity NPC114310
0.8118 Intermediate Similarity NPC249614
0.8049 Intermediate Similarity NPC107287
0.8046 Intermediate Similarity NPC317010
0.8033 Intermediate Similarity NPC103361
0.8012 Intermediate Similarity NPC302647
0.8011 Intermediate Similarity NPC135950
0.8 Intermediate Similarity NPC33229
0.7967 Intermediate Similarity NPC109922
0.7966 Intermediate Similarity NPC311282
0.7962 Intermediate Similarity NPC29702
0.7962 Intermediate Similarity NPC328029
0.7944 Intermediate Similarity NPC114974
0.7917 Intermediate Similarity NPC322644
0.7907 Intermediate Similarity NPC253810
0.7889 Intermediate Similarity NPC469489
0.7885 Intermediate Similarity NPC322488
0.7807 Intermediate Similarity NPC57398
0.7791 Intermediate Similarity NPC470894
0.7784 Intermediate Similarity NPC164340
0.7771 Intermediate Similarity NPC476419
0.773 Intermediate Similarity NPC90229
0.768 Intermediate Similarity NPC278434
0.7637 Intermediate Similarity NPC75544
0.7594 Intermediate Similarity NPC248782
0.7553 Intermediate Similarity NPC123395
0.75 Intermediate Similarity NPC474916
0.75 Intermediate Similarity NPC83111
0.7487 Intermediate Similarity NPC77061
0.7485 Intermediate Similarity NPC213914
0.7473 Intermediate Similarity NPC295158
0.7471 Intermediate Similarity NPC209362
0.7456 Intermediate Similarity NPC70406
0.7452 Intermediate Similarity NPC306397
0.7452 Intermediate Similarity NPC165370
0.7452 Intermediate Similarity NPC212125
0.7448 Intermediate Similarity NPC25442
0.7448 Intermediate Similarity NPC12944
0.7446 Intermediate Similarity NPC44354
0.7444 Intermediate Similarity NPC52831
0.7444 Intermediate Similarity NPC325705
0.7436 Intermediate Similarity NPC309845
0.7433 Intermediate Similarity NPC146724
0.7412 Intermediate Similarity NPC251391
0.7407 Intermediate Similarity NPC59033
0.7405 Intermediate Similarity NPC471589
0.7405 Intermediate Similarity NPC144381
0.7405 Intermediate Similarity NPC313823
0.7396 Intermediate Similarity NPC313889
0.7382 Intermediate Similarity NPC98864
0.7381 Intermediate Similarity NPC105811
0.7377 Intermediate Similarity NPC282103
0.7377 Intermediate Similarity NPC241025
0.7371 Intermediate Similarity NPC156044
0.7365 Intermediate Similarity NPC467188
0.7358 Intermediate Similarity NPC472259
0.734 Intermediate Similarity NPC229893
0.731 Intermediate Similarity NPC82370
0.7297 Intermediate Similarity NPC36498
0.7293 Intermediate Similarity NPC256268
0.7288 Intermediate Similarity NPC70949
0.7273 Intermediate Similarity NPC111732
0.7263 Intermediate Similarity NPC329024
0.7251 Intermediate Similarity NPC109158
0.7249 Intermediate Similarity NPC202812
0.7245 Intermediate Similarity NPC266249
0.724 Intermediate Similarity NPC79223
0.7238 Intermediate Similarity NPC219848
0.7235 Intermediate Similarity NPC123906
0.7225 Intermediate Similarity NPC317672
0.7222 Intermediate Similarity NPC303225
0.7181 Intermediate Similarity NPC138370
0.7172 Intermediate Similarity NPC123839
0.7168 Intermediate Similarity NPC229055
0.7143 Intermediate Similarity NPC309498
0.7135 Intermediate Similarity NPC285923
0.7135 Intermediate Similarity NPC13432
0.7135 Intermediate Similarity NPC324245
0.7135 Intermediate Similarity NPC472284
0.7135 Intermediate Similarity NPC320748
0.7126 Intermediate Similarity NPC74357
0.7121 Intermediate Similarity NPC472752
0.7113 Intermediate Similarity NPC328559
0.7104 Intermediate Similarity NPC283219
0.71 Intermediate Similarity NPC118940
0.7098 Intermediate Similarity NPC474767
0.7083 Intermediate Similarity NPC141454
0.7081 Intermediate Similarity NPC243058
0.7077 Intermediate Similarity NPC328318
0.7077 Intermediate Similarity NPC328596
0.7069 Intermediate Similarity NPC63562
0.7065 Intermediate Similarity NPC317752
0.7059 Intermediate Similarity NPC118084
0.7045 Intermediate Similarity NPC80681
0.7044 Intermediate Similarity NPC472285
0.7043 Intermediate Similarity NPC203635
0.7026 Intermediate Similarity NPC32451
0.7026 Intermediate Similarity NPC471944
0.7024 Intermediate Similarity NPC54066
0.7021 Intermediate Similarity NPC206186
0.7016 Intermediate Similarity NPC473821
0.7015 Intermediate Similarity NPC318299
0.7015 Intermediate Similarity NPC476467
0.7011 Intermediate Similarity NPC126709
0.7011 Intermediate Similarity NPC248041
0.7005 Intermediate Similarity NPC76565
0.7005 Intermediate Similarity NPC250807
0.7005 Intermediate Similarity NPC57797
0.6994 Remote Similarity NPC315320
0.6989 Remote Similarity NPC269919
0.6989 Remote Similarity NPC132680
0.6985 Remote Similarity NPC470190
0.6985 Remote Similarity NPC63041
0.6979 Remote Similarity NPC93390
0.6978 Remote Similarity NPC191310
0.6978 Remote Similarity NPC477976
0.6971 Remote Similarity NPC473850
0.6971 Remote Similarity NPC475137
0.6971 Remote Similarity NPC475498
0.697 Remote Similarity NPC317373
0.6968 Remote Similarity NPC90415
0.6964 Remote Similarity NPC43477
0.6963 Remote Similarity NPC56170
0.6957 Remote Similarity NPC111275
0.6954 Remote Similarity NPC317572
0.6954 Remote Similarity NPC472260
0.6954 Remote Similarity NPC165599
0.6952 Remote Similarity NPC46895
0.695 Remote Similarity NPC48042
0.695 Remote Similarity NPC304179
0.695 Remote Similarity NPC472550
0.6947 Remote Similarity NPC154339
0.694 Remote Similarity NPC110500
0.694 Remote Similarity NPC149155
0.694 Remote Similarity NPC203468
0.6938 Remote Similarity NPC473506
0.6935 Remote Similarity NPC183777
0.6935 Remote Similarity NPC244741
0.6931 Remote Similarity NPC472553
0.6927 Remote Similarity NPC211187
0.6927 Remote Similarity NPC265100
0.6927 Remote Similarity NPC230403
0.6919 Remote Similarity NPC327592
0.6919 Remote Similarity NPC220523
0.6919 Remote Similarity NPC473239
0.6912 Remote Similarity NPC470306
0.691 Remote Similarity NPC322976
0.691 Remote Similarity NPC63338
0.691 Remote Similarity NPC324203
0.6907 Remote Similarity NPC78767
0.6907 Remote Similarity NPC473814
0.6907 Remote Similarity NPC74153
0.6906 Remote Similarity NPC78020
0.6905 Remote Similarity NPC475600
0.6905 Remote Similarity NPC122968
0.6905 Remote Similarity NPC476110
0.6905 Remote Similarity NPC146824
0.6905 Remote Similarity NPC477787
0.6905 Remote Similarity NPC228377
0.6905 Remote Similarity NPC87152
0.6905 Remote Similarity NPC475631
0.6905 Remote Similarity NPC328186
0.6902 Remote Similarity NPC267885
0.6901 Remote Similarity NPC471323
0.6895 Remote Similarity NPC221873
0.6893 Remote Similarity NPC216428
0.6893 Remote Similarity NPC138018
0.6889 Remote Similarity NPC233380
0.6884 Remote Similarity NPC472287
0.6884 Remote Similarity NPC472286
0.6882 Remote Similarity NPC61011
0.6881 Remote Similarity NPC470189
0.6881 Remote Similarity NPC40919
0.6878 Remote Similarity NPC475408
0.6878 Remote Similarity NPC471016
0.6878 Remote Similarity NPC471014
0.6878 Remote Similarity NPC194040
0.6872 Remote Similarity NPC471190
0.6872 Remote Similarity NPC475362
0.6872 Remote Similarity NPC475644
0.6872 Remote Similarity NPC471977
0.6872 Remote Similarity NPC470486
0.6869 Remote Similarity NPC475426
0.6864 Remote Similarity NPC161801
0.6863 Remote Similarity NPC237740
0.6857 Remote Similarity NPC217021
0.6857 Remote Similarity NPC470679
0.685 Remote Similarity NPC193238
0.685 Remote Similarity NPC316403

  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 NPC273532 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
0.8831 High Similarity NPD9074 Approved
0.8831 High Similarity NPD9075 Approved
0.8571 High Similarity NPD107 Approved
0.825 Intermediate Similarity NPD9271 Approved
0.8011 Intermediate Similarity NPD1096 Discontinued
0.8 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3178 Discontinued
0.7912 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD820 Phase 3
0.7862 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD1173 Approved
0.7452 Intermediate Similarity NPD9080 Approved
0.7452 Intermediate Similarity NPD9284 Approved
0.7444 Intermediate Similarity NPD9510 Approved
0.7444 Intermediate Similarity NPD1643 Phase 3
0.7414 Intermediate Similarity NPD1631 Approved
0.7362 Intermediate Similarity NPD9506 Approved
0.7345 Intermediate Similarity NPD1575 Approved
0.7345 Intermediate Similarity NPD1573 Approved
0.7326 Intermediate Similarity NPD6665 Discontinued
0.7317 Intermediate Similarity NPD2896 Discontinued
0.7314 Intermediate Similarity NPD5088 Discontinued
0.7297 Intermediate Similarity NPD9363 Approved
0.7297 Intermediate Similarity NPD9364 Phase 2
0.7273 Intermediate Similarity NPD2336 Approved
0.7241 Intermediate Similarity NPD1630 Approved
0.7213 Intermediate Similarity NPD9362 Approved
0.7209 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD1352 Discontinued
0.7179 Intermediate Similarity NPD944 Approved
0.7136 Intermediate Similarity NPD3779 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD721 Approved
0.7134 Intermediate Similarity NPD272 Approved
0.7128 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1649 Discontinued
0.712 Intermediate Similarity NPD2307 Discontinued
0.7112 Intermediate Similarity NPD4948 Discontinued
0.7108 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3813 Approved
0.7092 Intermediate Similarity NPD7396 Approved
0.7052 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5255 Approved
0.7011 Intermediate Similarity NPD1587 Approved
0.7005 Intermediate Similarity NPD5901 Discontinued
0.7005 Intermediate Similarity NPD3947 Discontinued
0.7005 Intermediate Similarity NPD6753 Phase 1
0.7005 Intermediate Similarity NPD6752 Phase 1
0.7 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.6994 Remote Similarity NPD9207 Approved
0.6994 Remote Similarity NPD9206 Approved
0.6989 Remote Similarity NPD9383 Approved
0.6989 Remote Similarity NPD9382 Approved
0.6983 Remote Similarity NPD1568 Clinical (unspecified phase)
0.698 Remote Similarity NPD3794 Approved
0.698 Remote Similarity NPD3795 Approved
0.6978 Remote Similarity NPD750 Phase 2
0.6977 Remote Similarity NPD1270 Approved
0.6965 Remote Similarity NPD4417 Approved
0.6963 Remote Similarity NPD981 Phase 2
0.6963 Remote Similarity NPD4376 Phase 3
0.6954 Remote Similarity NPD510 Phase 1
0.6944 Remote Similarity NPD4174 Clinical (unspecified phase)
0.694 Remote Similarity NPD482 Approved
0.694 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6935 Remote Similarity NPD3371 Approved
0.6927 Remote Similarity NPD1623 Approved
0.6923 Remote Similarity NPD6173 Approved
0.691 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6909 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6902 Remote Similarity NPD749 Clinical (unspecified phase)
0.6881 Remote Similarity NPD5475 Discontinued
0.6878 Remote Similarity NPD3315 Phase 3
0.686 Remote Similarity NPD175 Clinical (unspecified phase)
0.6859 Remote Similarity NPD3321 Discontinued
0.6848 Remote Similarity NPD1586 Approved
0.6845 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4529 Approved
0.6839 Remote Similarity NPD4528 Approved
0.6839 Remote Similarity NPD4526 Approved
0.6836 Remote Similarity NPD276 Clinical (unspecified phase)
0.6834 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6834 Remote Similarity NPD6987 Phase 1
0.6816 Remote Similarity NPD2510 Approved
0.6816 Remote Similarity NPD2509 Approved
0.6809 Remote Similarity NPD2094 Phase 2
0.6809 Remote Similarity NPD2092 Phase 2
0.6809 Remote Similarity NPD2095 Phase 2
0.6804 Remote Similarity NPD4427 Phase 2
0.6802 Remote Similarity NPD484 Approved
0.6791 Remote Similarity NPD6452 Discontinued
0.6788 Remote Similarity NPD5317 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6782 Remote Similarity NPD6529 Discontinued
0.678 Remote Similarity NPD2809 Approved
0.6779 Remote Similarity NPD3280 Approved
0.6772 Remote Similarity NPD2091 Phase 2
0.6772 Remote Similarity NPD2096 Phase 2
0.6769 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2290 Phase 3
0.6769 Remote Similarity NPD2289 Phase 3
0.6768 Remote Similarity NPD5017 Discontinued
0.6757 Remote Similarity NPD158 Discontinued
0.6757 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6751 Remote Similarity NPD6137 Clinical (unspecified phase)
0.675 Remote Similarity NPD2831 Approved
0.6748 Remote Similarity NPD3394 Approved
0.6748 Remote Similarity NPD3393 Approved
0.6748 Remote Similarity NPD3389 Approved
0.6746 Remote Similarity NPD4301 Approved
0.6738 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6722 Remote Similarity NPD2511 Approved
0.672 Remote Similarity NPD5728 Clinical (unspecified phase)
0.672 Remote Similarity NPD5100 Phase 3
0.6714 Remote Similarity NPD8356 Approved
0.6707 Remote Similarity NPD9100 Approved
0.6704 Remote Similarity NPD2581 Approved
0.6704 Remote Similarity NPD2582 Approved
0.6703 Remote Similarity NPD925 Approved
0.6703 Remote Similarity NPD926 Approved
0.6699 Remote Similarity NPD1996 Discontinued
0.6686 Remote Similarity NPD5020 Approved
0.6686 Remote Similarity NPD4702 Approved
0.6686 Remote Similarity NPD4703 Approved
0.6686 Remote Similarity NPD4805 Approved
0.6685 Remote Similarity NPD2061 Approved
0.6684 Remote Similarity NPD1213 Phase 3
0.6684 Remote Similarity NPD8063 Discontinued
0.6683 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6683 Remote Similarity NPD8097 Phase 3
0.6683 Remote Similarity NPD8096 Phase 3
0.6667 Remote Similarity NPD569 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5490 Discontinued
0.6667 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4906 Approved
0.6667 Remote Similarity NPD6999 Discontinued
0.6667 Remote Similarity NPD3353 Approved
0.6667 Remote Similarity NPD4905 Approved
0.6667 Remote Similarity NPD4883 Approved
0.6667 Remote Similarity NPD9690 Approved
0.6667 Remote Similarity NPD4903 Approved
0.6651 Remote Similarity NPD7404 Approved
0.665 Remote Similarity NPD3243 Approved
0.6649 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6647 Remote Similarity NPD3717 Discontinued
0.6635 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6634 Remote Similarity NPD4904 Approved
0.663 Remote Similarity NPD1343 Approved
0.663 Remote Similarity NPD9705 Discontinued
0.663 Remote Similarity NPD112 Approved
0.662 Remote Similarity NPD8289 Discontinued
0.6615 Remote Similarity NPD5505 Discontinued
0.6614 Remote Similarity NPD1618 Phase 2
0.6606 Remote Similarity NPD1483 Discontinued
0.6589 Remote Similarity NPD8430 Approved
0.6585 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6584 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6576 Remote Similarity NPD4554 Clinical (unspecified phase)
0.6576 Remote Similarity NPD425 Approved
0.6576 Remote Similarity NPD424 Approved
0.6575 Remote Similarity NPD704 Clinical (unspecified phase)
0.6573 Remote Similarity NPD9343 Clinical (unspecified phase)
0.6573 Remote Similarity NPD9706 Clinical (unspecified phase)
0.657 Remote Similarity NPD4804 Approved
0.6554 Remote Similarity NPD3576 Approved
0.6554 Remote Similarity NPD3575 Approved
0.6553 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6553 Remote Similarity NPD7470 Discontinued
0.6552 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7001 Phase 3
0.655 Remote Similarity NPD4396 Clinical (unspecified phase)
0.655 Remote Similarity NPD4491 Clinical (unspecified phase)
0.6542 Remote Similarity NPD5640 Discontinued
0.6541 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5417 Clinical (unspecified phase)
0.6532 Remote Similarity NPD9599 Approved
0.6531 Remote Similarity NPD3406 Suspended
0.6528 Remote Similarity NPD5801 Clinical (unspecified phase)
0.6528 Remote Similarity NPD706 Phase 1
0.6526 Remote Similarity NPD1291 Clinical (unspecified phase)
0.6522 Remote Similarity NPD5866 Approved
0.652 Remote Similarity NPD3410 Approved
0.652 Remote Similarity NPD3411 Phase 2
0.6519 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6519 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6519 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6515 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6513 Remote Similarity NPD5316 Approved
0.6505 Remote Similarity NPD648 Clinical (unspecified phase)
0.65 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6497 Remote Similarity NPD460 Discontinued
0.6492 Remote Similarity NPD4011 Clinical (unspecified phase)
0.6486 Remote Similarity NPD5611 Phase 2
0.6484 Remote Similarity NPD604 Clinical (unspecified phase)
0.6481 Remote Similarity NPD1571 Phase 2
0.6476 Remote Similarity NPD3805 Clinical (unspecified phase)
0.6473 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6473 Remote Similarity NPD5416 Discontinued
0.6471 Remote Similarity NPD6732 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