Structure

Physi-Chem Properties

Molecular Weight:  123.03
Volume:  121.807
LogP:  0.147
LogD:  -0.181
LogS:  0.222
# Rotatable Bonds:  1
TPSA:  50.19
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.6
Synthetic Accessibility Score:  1.64
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:  -4.938
MDCK Permeability:  1.9600205632741563e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.716
Plasma Protein Binding (PPB):  20.35331153869629%
Volume Distribution (VD):  0.342
Pgp-substrate:  73.00904083251953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.032
CYP1A2-substrate:  0.088
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.134
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.122
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.057

ADMET: Excretion

Clearance (CL):  1.807
Half-life (T1/2):  0.726

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.362
Drug-inuced Liver Injury (DILI):  0.959
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.558
Maximum Recommended Daily Dose:  0.008
Skin Sensitization:  0.289
Carcinogencity:  0.029
Eye Corrosion:  0.076
Eye Irritation:  0.996
Respiratory Toxicity:  0.843

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

  Natural Product: NPC302159

Natural Product ID:  NPC302159
Common Name*:   2-Picolinic Acid
IUPAC Name:   pyridine-2-carboxylic acid
Synonyms:   NSC-89
Standard InCHIKey:  SIOXPEMLGUPBBT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)
SMILES:  OC(=O)c1ccccn1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL72628
PubChem CID:   1018
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
NPT2807 Individual Protein Hypoxia-inducible factor prolyl 4-hydroxylase Homo sapiens IC50 = 100000.0 nM PMID[465712]
NPT2807 Individual Protein Hypoxia-inducible factor prolyl 4-hydroxylase Homo sapiens IC50 = 111500.0 nM PMID[465714]
NPT3581 Individual Protein Dihydrodipicolinate synthase Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145) IC50 = 1000000.0 nM PMID[465715]
NPT3994 Individual Protein Metallo beta-lactamase Pseudomonas aeruginosa Activity = 31.0 % PMID[465716]
NPT3994 Individual Protein Metallo beta-lactamase Pseudomonas aeruginosa Activity = 54.0 % PMID[465716]
NPT3989 Individual Protein Beta-lactamase L1 Stenotrophomonas maltophilia Activity = 29.0 % PMID[465716]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 = 61801.64 nM PMID[465717]
NPT370 Cell Line NCI-H23 Homo sapiens TGI = 73960.53 nM PMID[465717]
NPT370 Cell Line NCI-H23 Homo sapiens LC50 = 88511.56 nM PMID[465717]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 = 693.43 nM PMID[465717]
NPT455 Cell Line NCI-H522 Homo sapiens TGI = 1054.39 nM PMID[465717]
NPT455 Cell Line NCI-H522 Homo sapiens LC50 = 10519.62 nM PMID[465717]
NPT81 Cell Line A549 Homo sapiens GI50 = 65162.84 nM PMID[465717]
NPT81 Cell Line A549 Homo sapiens TGI = 82035.15 nM PMID[465717]
NPT81 Cell Line A549 Homo sapiens LC50 = 100000.0 nM PMID[465717]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 35481.3 nM PMID[465719]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 25118.9 nM PMID[465719]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 50118.7 nM PMID[465720]
NPT569 Individual Protein Matrix metalloproteinase 8 Homo sapiens Inhibition = 30.0 % PMID[465721]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition = 25.0 % PMID[465721]
NPT270 Individual Protein Nitric oxide synthase, inducible Mus musculus Inhibition = 6.0 % PMID[465721]
NPT280 Individual Protein Matrix metalloproteinase 9 Homo sapiens Inhibition = 0.0 % PMID[465721]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 74.0 % PMID[465721]
NPT150 Individual Protein Anthrax lethal factor Bacillus anthracis Inhibition = 49.0 % PMID[465721]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 16.0 % PMID[465721]
NPT567 Individual Protein Matrix metalloproteinase 3 Homo sapiens Inhibition = 99.0 % PMID[465721]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 3981.1 nM PMID[465720]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 562.3 nM PMID[465720]
NPT63 Individual Protein Bromodomain adjacent to zinc finger domain protein 2B Homo sapiens Potency n.a. 2818.4 nM PMID[465720]
NPT1006 Individual Protein Proton-coupled amino acid transporter 1 Homo sapiens Ki = 18000000.0 nM PMID[465723]
NPT1006 Individual Protein Proton-coupled amino acid transporter 1 Homo sapiens pKi = -1.26 mM PMID[465723]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[465724]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2059.6 nM PMID[465720]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 25929.0 nM PMID[465720]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 83.0 % PMID[465734]
NPT2805 Individual Protein Dopamine beta-hydroxylase Bos taurus Inhibition = 55.0 % PMID[465734]
NPT2 Others Unspecified Activity = 95.0 % PMID[465716]
NPT2 Others Unspecified Activity = 80.0 % PMID[465716]
NPT2 Others Unspecified Activity = 59.0 % PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Activity = 8.0 % PMID[465716]
NPT2 Others Unspecified Activity = 62.0 % PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 46000.0 nM PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 76000.0 nM PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 440000.0 nM PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 1100000.0 nM PMID[465716]
NPT24374 SINGLE PROTEIN Beta-lactamase Aeromonas hydrophila Ki = 5700.0 nM PMID[465716]
NPT2 Others Unspecified Ki = 13000.0 nM PMID[465716]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 406000.0 nM PMID[465718]
NPT864 Individual Protein Lethal(3)malignant brain tumor-like protein 1 Homo sapiens Potency = 14125.4 nM PMID[465720]
NPT69 Individual Protein Matrix metalloproteinase-1 Homo sapiens Inhibition = 3.0 % PMID[465721]
NPT2 Others Unspecified Ki = 301995.17 nM PMID[465722]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 9528.3 nM PMID[465719]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[465720]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 14125.4 nM PMID[465720]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 79432.8 nM PMID[465720]
NPT35 Others n.a. pKa n.a. 0.99 n.a. PMID[465725]
NPT22584 SINGLE PROTEIN OXA-48 Klebsiella pneumoniae Kd > 1000000.0 nM PMID[465726]
NPT22584 SINGLE PROTEIN OXA-48 Klebsiella pneumoniae IC50 > 2000000.0 nM PMID[465726]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -4.94 % PMID[465727]
NPT2 Others Unspecified Inhibition = -45.0 % PMID[465728]
NPT22586 SINGLE PROTEIN Nicotinate phosphoribosyltransferase Homo sapiens Ki = 1.16 nM PMID[465730]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.75 % PMID[465731]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.27 % PMID[465732]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[465733]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[465733]
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 625 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 15.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10682.2 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 NPC302159 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
0.9073 High Similarity NPC41717
0.9007 High Similarity NPC85443
0.8929 High Similarity NPC328029
0.8896 High Similarity NPC273532
0.8774 High Similarity NPC253810
0.8667 High Similarity NPC33229
0.8472 Intermediate Similarity NPC114310
0.8405 Intermediate Similarity NPC207851
0.8322 Intermediate Similarity NPC167400
0.8298 Intermediate Similarity NPC313823
0.8235 Intermediate Similarity NPC312860
0.8089 Intermediate Similarity NPC322644
0.8069 Intermediate Similarity NPC322488
0.7949 Intermediate Similarity NPC263455
0.7905 Intermediate Similarity NPC29702
0.7895 Intermediate Similarity NPC230085
0.7895 Intermediate Similarity NPC159630
0.7799 Intermediate Similarity NPC113812
0.7742 Intermediate Similarity NPC112741
0.7707 Intermediate Similarity NPC109158
0.7692 Intermediate Similarity NPC13432
0.7677 Intermediate Similarity NPC220523
0.7654 Intermediate Similarity NPC57398
0.7636 Intermediate Similarity NPC302647
0.7614 Intermediate Similarity NPC77061
0.7547 Intermediate Similarity NPC107287
0.753 Intermediate Similarity NPC249614
0.75 Intermediate Similarity NPC71236
0.75 Intermediate Similarity NPC472288
0.7466 Intermediate Similarity NPC151489
0.7429 Intermediate Similarity NPC469489
0.7416 Intermediate Similarity NPC109922
0.7414 Intermediate Similarity NPC278434
0.74 Intermediate Similarity NPC174421
0.7399 Intermediate Similarity NPC295158
0.7399 Intermediate Similarity NPC311282
0.7386 Intermediate Similarity NPC114974
0.7368 Intermediate Similarity NPC317010
0.7368 Intermediate Similarity NPC291517
0.7365 Intermediate Similarity NPC165370
0.7365 Intermediate Similarity NPC306397
0.7365 Intermediate Similarity NPC212125
0.736 Intermediate Similarity NPC135950
0.733 Intermediate Similarity NPC83111
0.7312 Intermediate Similarity NPC52110
0.7305 Intermediate Similarity NPC470894
0.7294 Intermediate Similarity NPC476419
0.7293 Intermediate Similarity NPC103361
0.7293 Intermediate Similarity NPC123395
0.7278 Intermediate Similarity NPC90229
0.7255 Intermediate Similarity NPC23215
0.7244 Intermediate Similarity NPC318935
0.7238 Intermediate Similarity NPC474916
0.7209 Intermediate Similarity NPC164340
0.72 Intermediate Similarity NPC241025
0.72 Intermediate Similarity NPC471589
0.7195 Intermediate Similarity NPC116573
0.7188 Intermediate Similarity NPC257142
0.7178 Intermediate Similarity NPC209362
0.7178 Intermediate Similarity NPC298288
0.7174 Intermediate Similarity NPC231655
0.7143 Intermediate Similarity NPC248782
0.7135 Intermediate Similarity NPC144381
0.7108 Intermediate Similarity NPC473706
0.7102 Intermediate Similarity NPC282103
0.7091 Intermediate Similarity NPC213914
0.7079 Intermediate Similarity NPC75544
0.7069 Intermediate Similarity NPC325705
0.7069 Intermediate Similarity NPC52831
0.7063 Intermediate Similarity NPC467188
0.7055 Intermediate Similarity NPC472260
0.7055 Intermediate Similarity NPC284348
0.7055 Intermediate Similarity NPC70406
0.7053 Intermediate Similarity NPC82370
0.7048 Intermediate Similarity NPC80681
0.7035 Intermediate Similarity NPC303225
0.7017 Intermediate Similarity NPC230403
0.7017 Intermediate Similarity NPC473821
0.7012 Intermediate Similarity NPC251391
0.7005 Intermediate Similarity NPC472259
0.6994 Remote Similarity NPC313889
0.6993 Remote Similarity NPC315320
0.6984 Remote Similarity NPC266249
0.6978 Remote Similarity NPC146724
0.6978 Remote Similarity NPC93390
0.6977 Remote Similarity NPC477976
0.6975 Remote Similarity NPC105811
0.6954 Remote Similarity NPC219848
0.6948 Remote Similarity NPC256893
0.6935 Remote Similarity NPC98864
0.6931 Remote Similarity NPC193238
0.6927 Remote Similarity NPC118940
0.6919 Remote Similarity NPC229893
0.6914 Remote Similarity NPC256268
0.6911 Remote Similarity NPC123839
0.6906 Remote Similarity NPC138370
0.6905 Remote Similarity NPC25899
0.6903 Remote Similarity NPC330326
0.6902 Remote Similarity NPC74153
0.6902 Remote Similarity NPC473814
0.6902 Remote Similarity NPC78767
0.6902 Remote Similarity NPC141454
0.6901 Remote Similarity NPC70949
0.6898 Remote Similarity NPC328318
0.6898 Remote Similarity NPC328596
0.6897 Remote Similarity NPC286195
0.6889 Remote Similarity NPC44354
0.6872 Remote Similarity NPC118084
0.6864 Remote Similarity NPC48192
0.6861 Remote Similarity NPC83987
0.686 Remote Similarity NPC314940
0.686 Remote Similarity NPC473764
0.6833 Remote Similarity NPC36498
0.6829 Remote Similarity NPC123906
0.6826 Remote Similarity NPC142688
0.6823 Remote Similarity NPC309845
0.6818 Remote Similarity NPC283219
0.6818 Remote Similarity NPC126709
0.6818 Remote Similarity NPC248041
0.6804 Remote Similarity NPC317752
0.6798 Remote Similarity NPC243058
0.6797 Remote Similarity NPC471311
0.6797 Remote Similarity NPC471313
0.6796 Remote Similarity NPC209917
0.6793 Remote Similarity NPC202812
0.679 Remote Similarity NPC471323
0.6789 Remote Similarity NPC317373
0.6786 Remote Similarity NPC212742
0.6774 Remote Similarity NPC472284
0.6768 Remote Similarity NPC54066
0.6766 Remote Similarity NPC229055
0.6766 Remote Similarity NPC63562
0.6761 Remote Similarity NPC157583
0.6761 Remote Similarity NPC111275
0.676 Remote Similarity NPC203635
0.6754 Remote Similarity NPC316403
0.6753 Remote Similarity NPC318299
0.6743 Remote Similarity NPC469938
0.6743 Remote Similarity NPC139763
0.6743 Remote Similarity NPC203468
0.6743 Remote Similarity NPC110500
0.6743 Remote Similarity NPC149155
0.6737 Remote Similarity NPC327592
0.6737 Remote Similarity NPC25442
0.6737 Remote Similarity NPC12944
0.6731 Remote Similarity NPC324611
0.6728 Remote Similarity NPC470403
0.6728 Remote Similarity NPC470404
0.6728 Remote Similarity NPC470394
0.6726 Remote Similarity NPC74357
0.6722 Remote Similarity NPC318020
0.6705 Remote Similarity NPC267885
0.6705 Remote Similarity NPC78020
0.6703 Remote Similarity NPC182814
0.6701 Remote Similarity NPC472285
0.6687 Remote Similarity NPC473878
0.6686 Remote Similarity NPC269919
0.6686 Remote Similarity NPC132680
0.6685 Remote Similarity NPC90415
0.6685 Remote Similarity NPC194040
0.6685 Remote Similarity NPC61011
0.6684 Remote Similarity NPC59033
0.6684 Remote Similarity NPC165599
0.6667 Remote Similarity NPC156044
0.6667 Remote Similarity NPC285923
0.6667 Remote Similarity NPC46895
0.6667 Remote Similarity NPC100726
0.6667 Remote Similarity NPC471944
0.6649 Remote Similarity NPC474767
0.6648 Remote Similarity NPC161887
0.6648 Remote Similarity NPC266551
0.6648 Remote Similarity NPC219963
0.6647 Remote Similarity NPC217021
0.6647 Remote Similarity NPC470679
0.6646 Remote Similarity NPC470395
0.663 Remote Similarity NPC127647
0.6629 Remote Similarity NPC252590
0.6628 Remote Similarity NPC265100
0.6628 Remote Similarity NPC162268
0.6616 Remote Similarity NPC27041
0.6614 Remote Similarity NPC315491
0.6614 Remote Similarity NPC45459
0.6611 Remote Similarity NPC325093
0.661 Remote Similarity NPC150048
0.661 Remote Similarity NPC84347
0.661 Remote Similarity NPC203754
0.6608 Remote Similarity NPC322976
0.6608 Remote Similarity NPC63338
0.6608 Remote Similarity NPC131718
0.6608 Remote Similarity NPC324203
0.6599 Remote Similarity NPC237740
0.6597 Remote Similarity NPC143325
0.6592 Remote Similarity NPC471997
0.6592 Remote Similarity NPC73994
0.659 Remote Similarity NPC474383
0.6588 Remote Similarity NPC138018
0.6587 Remote Similarity NPC471655
0.6582 Remote Similarity NPC194541
0.6582 Remote Similarity NPC111732
0.658 Remote Similarity NPC244741

  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 NPC302159 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
0.8322 Intermediate Similarity NPD9075 Approved
0.8322 Intermediate Similarity NPD9074 Approved
0.8054 Intermediate Similarity NPD107 Approved
0.8 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD3178 Discontinued
0.7919 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1096 Discontinued
0.78 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD9271 Approved
0.7738 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD2896 Discontinued
0.7419 Intermediate Similarity NPD4805 Approved
0.7407 Intermediate Similarity NPD820 Phase 3
0.7365 Intermediate Similarity NPD9284 Approved
0.7365 Intermediate Similarity NPD9080 Approved
0.736 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD158 Discontinued
0.7333 Intermediate Similarity NPD5088 Discontinued
0.729 Intermediate Similarity NPD4804 Approved
0.7289 Intermediate Similarity NPD1568 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD9343 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD3779 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD1631 Approved
0.7174 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD9098 Phase 3
0.7161 Intermediate Similarity NPD9506 Approved
0.716 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1573 Approved
0.716 Intermediate Similarity NPD1575 Approved
0.7152 Intermediate Similarity NPD5255 Approved
0.7152 Intermediate Similarity NPD604 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD9510 Approved
0.7048 Intermediate Similarity NPD1630 Approved
0.7025 Intermediate Similarity NPD1649 Discontinued
0.7017 Intermediate Similarity NPD1173 Approved
0.7 Intermediate Similarity NPD1352 Discontinued
0.6993 Remote Similarity NPD9207 Approved
0.6993 Remote Similarity NPD9206 Approved
0.6966 Remote Similarity NPD3315 Phase 3
0.6961 Remote Similarity NPD6665 Discontinued
0.6951 Remote Similarity NPD510 Phase 1
0.6923 Remote Similarity NPD272 Approved
0.6903 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6903 Remote Similarity NPD9100 Approved
0.6894 Remote Similarity NPD751 Clinical (unspecified phase)
0.6894 Remote Similarity NPD3813 Approved
0.6867 Remote Similarity NPD2809 Approved
0.6862 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6833 Remote Similarity NPD9363 Approved
0.6833 Remote Similarity NPD9364 Phase 2
0.6832 Remote Similarity NPD3717 Discontinued
0.6831 Remote Similarity NPD4529 Approved
0.6831 Remote Similarity NPD4528 Approved
0.6831 Remote Similarity NPD4526 Approved
0.6825 Remote Similarity NPD5901 Discontinued
0.6818 Remote Similarity NPD1587 Approved
0.6818 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6813 Remote Similarity NPD2336 Approved
0.6786 Remote Similarity NPD2581 Approved
0.6786 Remote Similarity NPD2582 Approved
0.6782 Remote Similarity NPD750 Phase 2
0.6782 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6776 Remote Similarity NPD981 Phase 2
0.6776 Remote Similarity NPD4376 Phase 3
0.6774 Remote Similarity NPD772 Phase 3
0.677 Remote Similarity NPD5020 Approved
0.6758 Remote Similarity NPD3321 Discontinued
0.6753 Remote Similarity NPD5352 Clinical (unspecified phase)
0.6743 Remote Similarity NPD4883 Approved
0.6743 Remote Similarity NPD9690 Approved
0.6743 Remote Similarity NPD482 Approved
0.6742 Remote Similarity NPD9362 Approved
0.6738 Remote Similarity NPD6137 Clinical (unspecified phase)
0.6708 Remote Similarity NPD9599 Approved
0.6706 Remote Similarity NPD2511 Approved
0.6706 Remote Similarity NPD112 Approved
0.6706 Remote Similarity NPD9705 Discontinued
0.6705 Remote Similarity NPD749 Clinical (unspecified phase)
0.6704 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6689 Remote Similarity NPD9396 Approved
0.6689 Remote Similarity NPD9392 Approved
0.6686 Remote Similarity NPD926 Approved
0.6686 Remote Similarity NPD9383 Approved
0.6686 Remote Similarity NPD9382 Approved
0.6686 Remote Similarity NPD925 Approved
0.6685 Remote Similarity NPD3288 Approved
0.6667 Remote Similarity NPD4703 Approved
0.6667 Remote Similarity NPD6752 Phase 1
0.6667 Remote Similarity NPD2307 Discontinued
0.6667 Remote Similarity NPD4702 Approved
0.6667 Remote Similarity NPD721 Approved
0.6667 Remote Similarity NPD1270 Approved
0.6667 Remote Similarity NPD2061 Approved
0.6667 Remote Similarity NPD6753 Phase 1
0.6667 Remote Similarity NPD1213 Phase 3
0.6649 Remote Similarity NPD944 Approved
0.6648 Remote Similarity NPD1586 Approved
0.6648 Remote Similarity NPD4948 Discontinued
0.6647 Remote Similarity NPD9595 Approved
0.6647 Remote Similarity NPD9596 Approved
0.6647 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6647 Remote Similarity NPD9706 Clinical (unspecified phase)
0.6646 Remote Similarity NPD175 Clinical (unspecified phase)
0.6633 Remote Similarity NPD3795 Approved
0.6633 Remote Similarity NPD3794 Approved
0.6615 Remote Similarity NPD5475 Discontinued
0.6614 Remote Similarity NPD484 Approved
0.6608 Remote Similarity NPD9398 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6452 Discontinued
0.6592 Remote Similarity NPD1643 Phase 3
0.6579 Remote Similarity NPD5017 Discontinued
0.6562 Remote Similarity NPD4906 Approved
0.6562 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6562 Remote Similarity NPD4903 Approved
0.6562 Remote Similarity NPD4905 Approved
0.6554 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6552 Remote Similarity NPD425 Approved
0.6552 Remote Similarity NPD424 Approved
0.6552 Remote Similarity NPD4554 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5611 Phase 2
0.655 Remote Similarity NPD704 Clinical (unspecified phase)
0.6546 Remote Similarity NPD2510 Approved
0.6546 Remote Similarity NPD2509 Approved
0.6538 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6533 Remote Similarity NPD3326 Clinical (unspecified phase)
0.6531 Remote Similarity NPD7927 Clinical (unspecified phase)
0.6529 Remote Similarity NPD276 Clinical (unspecified phase)
0.6528 Remote Similarity NPD4559 Clinical (unspecified phase)
0.6528 Remote Similarity NPD4904 Approved
0.6522 Remote Similarity NPD201 Phase 2
0.6522 Remote Similarity NPD200 Phase 2
0.6519 Remote Similarity NPD2094 Phase 2
0.6519 Remote Similarity NPD2092 Phase 2
0.6519 Remote Similarity NPD2095 Phase 2
0.6517 Remote Similarity NPD5827 Discontinued
0.6517 Remote Similarity NPD5100 Phase 3
0.6514 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5505 Discontinued
0.6502 Remote Similarity NPD6173 Approved
0.6491 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6489 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6488 Remote Similarity NPD7913 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6485 Remote Similarity NPD8823 Approved
0.6484 Remote Similarity NPD2096 Phase 2
0.6484 Remote Similarity NPD2091 Phase 2
0.6484 Remote Similarity NPD6178 Phase 3
0.6482 Remote Similarity NPD3353 Approved
0.6482 Remote Similarity NPD3394 Approved
0.6482 Remote Similarity NPD3389 Approved
0.6482 Remote Similarity NPD3393 Approved
0.6477 Remote Similarity NPD3947 Discontinued
0.6477 Remote Similarity NPD7396 Approved
0.6474 Remote Similarity NPD5400 Approved
0.6474 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6474 Remote Similarity NPD6999 Discontinued
0.6471 Remote Similarity NPD5257 Clinical (unspecified phase)
0.6465 Remote Similarity NPD3243 Approved
0.6463 Remote Similarity NPD4824 Approved
0.6463 Remote Similarity NPD4823 Approved
0.6461 Remote Similarity NPD5065 Approved
0.6461 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6453 Remote Similarity NPD3433 Clinical (unspecified phase)
0.6453 Remote Similarity NPD8356 Approved
0.6447 Remote Similarity NPD4417 Approved
0.6443 Remote Similarity NPD7010 Phase 3
0.6442 Remote Similarity NPD569 Clinical (unspecified phase)
0.6439 Remote Similarity NPD8289 Discontinued
0.6437 Remote Similarity NPD863 Approved
0.6437 Remote Similarity NPD862 Approved
0.6437 Remote Similarity NPD861 Approved
0.6436 Remote Similarity NPD3280 Approved
0.6433 Remote Similarity NPD1031 Discontinued
0.6433 Remote Similarity NPD1274 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7401 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3576 Approved
0.6429 Remote Similarity NPD3575 Approved
0.6429 Remote Similarity NPD6529 Discontinued
0.6425 Remote Similarity NPD3238 Discontinued
0.6425 Remote Similarity NPD5513 Phase 2
0.6424 Remote Similarity NPD3525 Discontinued
0.6422 Remote Similarity NPD3222 Phase 2
0.6421 Remote Similarity NPD7204 Clinical (unspecified phase)
0.642 Remote Similarity NPD1343 Approved
0.642 Remote Similarity NPD2781 Approved
0.642 Remote Similarity NPD5862 Discovery
0.6418 Remote Similarity NPD1623 Approved
0.6417 Remote Similarity NPD9243 Approved
0.6417 Remote Similarity NPD5317 Clinical (unspecified phase)
0.6413 Remote Similarity NPD706 Phase 1
0.6413 Remote Similarity NPD5809 Phase 3
0.641 Remote Similarity NPD3371 Approved
0.641 Remote Similarity NPD3410 Approved
0.641 Remote Similarity NPD3411 Phase 2
0.6409 Remote Similarity NPD1618 Phase 2

  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