Structure

Physi-Chem Properties

Molecular Weight:  252.0
Volume:  225.177
LogP:  0.382
LogD:  1.278
LogS:  -2.835
# Rotatable Bonds:  3
TPSA:  53.88
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.474
Synthetic Accessibility Score:  3.471
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.849
MDCK Permeability:  0.00013999566726852208
Pgp-inhibitor:  0.001
Pgp-substrate:  0.035
Human Intestinal Absorption (HIA):  0.036
20% Bioavailability (F20%):  0.02
30% Bioavailability (F30%):  0.138

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.074
Plasma Protein Binding (PPB):  46.814048767089844%
Volume Distribution (VD):  0.66
Pgp-substrate:  69.18983459472656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.133
CYP1A2-substrate:  0.781
CYP2C19-inhibitor:  0.727
CYP2C19-substrate:  0.074
CYP2C9-inhibitor:  0.115
CYP2C9-substrate:  0.063
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.035
CYP3A4-inhibitor:  0.002
CYP3A4-substrate:  0.124

ADMET: Excretion

Clearance (CL):  10.304
Half-life (T1/2):  0.561

ADMET: Toxicity

hERG Blockers:  0.529
Human Hepatotoxicity (H-HT):  0.285
Drug-inuced Liver Injury (DILI):  0.714
AMES Toxicity:  0.91
Rat Oral Acute Toxicity:  0.546
Maximum Recommended Daily Dose:  0.044
Skin Sensitization:  0.927
Carcinogencity:  0.49
Eye Corrosion:  0.951
Eye Irritation:  0.972
Respiratory Toxicity:  0.985

Download Data

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

  Natural Product: NPC135488

Natural Product ID:  NPC135488
Common Name*:   Dipyrithione
IUPAC Name:   1-oxido-2-[(1-oxidopyridin-1-ium-2-yl)disulfanyl]pyridin-1-ium
Synonyms:   Dipyrithione; OMDS
Standard InCHIKey:  ZHDBTKPXEJDTTQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H8N2O2S2/c13-11-7-3-1-5-9(11)15-16-10-6-2-4-8-12(10)14/h1-8H
SMILES:  O=n1ccccc1SSc1ccccn1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL549473
PubChem CID:   3109
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines and derivatives
        • [CHEMONTID:0001764] Pyridinium derivatives

*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
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. bulb n.a. PMID[19093848]
NPO13010 Allium stipitatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 112.2 nM PMID[546159]
NPT1197 Individual Protein Huntingtin Homo sapiens Potency = 5011.9 nM PMID[546159]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 891.3 nM PMID[546159]
NPT53 Individual Protein 4'-phosphopantetheinyl transferase ffp Bacillus subtilis Potency = 707.9 nM PMID[546159]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 354.8 nM PMID[546159]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 14125.4 nM PMID[546159]
NPT62 Individual Protein 6-phospho-1-fructokinase Trypanosoma brucei Potency n.a. 25118.9 nM PMID[546159]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 1258.9 nM PMID[546159]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 5623.4 nM PMID[546159]
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency n.a. 1121.2 nM PMID[546159]
NPT445 Individual Protein Peripheral myelin protein 22 Rattus norvegicus Potency n.a. 361.3 nM PMID[546159]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 2557.5 nM PMID[546159]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 6683.8 nM PMID[546159]
NPT100 Individual Protein Glutaminase kidney isoform, mitochondrial Homo sapiens Potency n.a. 22387.2 nM PMID[546159]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 595.7 nM PMID[546159]
NPT1853 Individual Protein Putative uncharacterized protein Trypanosoma brucei brucei (strain 927/4 GUTat10.1) Potency n.a. 11220.2 nM PMID[546159]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 118.9 nM PMID[546160]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 105.9 nM PMID[546160]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 3661.5 nM PMID[21824777]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 3378 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 65.1 nM PMID[15043437]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 535.4 nM PMID[20405844]
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 73.1 nM PMID[1800632]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 1188.3 nM PMID[22545792]
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 207.7 nM PMID[23013356]
NPT1176 Organism Mycobacterium fortuitum Mycobacterium fortuitum MIC = 16.0 ug.mL-1 PMID[546158]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 16.0 ug.mL-1 PMID[546158]
NPT1177 Organism Mycobacterium phlei Mycobacterium phlei MIC = 16.0 ug.mL-1 PMID[546158]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 1.0 ug.mL-1 PMID[546158]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.5 ug.mL-1 PMID[546158]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 477.5 nM PMID[546159]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 849.2 nM PMID[546159]
NPT2 Others Unspecified Potency n.a. 12817.8 nM PMID[546159]
NPT2 Others Unspecified Potency n.a. 3981.1 nM PMID[546160]
NPT2 Others Unspecified Potency n.a. 6309.6 nM PMID[546160]
NPT2 Others Unspecified Potency n.a. 148.2 nM PMID[546160]
NPT2 Others Unspecified IC50 = 991.4 nM PMID[546161]
NPT2 Others Unspecified Ac50 n.a. 1.678 uM PMID[546161]
NPT2 Others Unspecified AC50 n.a. 3981.1 nM PMID[546161]
NPT2 Others Unspecified IC50 n.a. 10000.0 nM PMID[546161]
NPT2 Others Unspecified IC50 = 130.6 nM PMID[546161]
NPT2 Others Unspecified IC50 = 1786.5 nM PMID[546161]
NPT2 Others Unspecified IC50 = 842.5 nM PMID[546161]
NPT2 Others Unspecified Ac50 n.a. 1.259 uM PMID[546161]
NPT2 Others Unspecified Ac50 n.a. 1.882 uM PMID[546161]
NPT2 Others Unspecified Ac50 n.a. 3.981 uM PMID[546161]
NPT2 Others Unspecified IC50 = 719.0 nM PMID[546161]
NPT2 Others Unspecified IC50 = 2231.7 nM PMID[546161]
NPT2 Others Unspecified Ac50 n.a. 0.8408 uM PMID[546161]
NPT2 Others Unspecified AC50 n.a. 1258.9 nM PMID[546161]
NPT2 Others Unspecified Potency n.a. 73.7 nM PMID[21546253]
NPT2 Others Unspecified Potency n.a. 103.2 nM PMID[26836364]
NPT2 Others Unspecified Potency n.a. 5172.1 nM PMID[23219324]
NPT2 Others Unspecified Potency n.a. 2660.3 nM PMID[23398362]
NPT2 Others Unspecified Potency n.a. 668.2 nM PMID[24508307]
NPT2 Others Unspecified Potency n.a. 1496 nM PMID[23102654]
NPT2 Others Unspecified Potency n.a. 1564.2 nM PMID[11473417]
NPT2 Others Unspecified Potency n.a. 82 nM PMID[20163893]
NPT2 Others Unspecified Potency n.a. 92 nM PMID[17417907]
NPT2 Others Unspecified Potency n.a. 163.6 nM DrugMatrix in vitro pharmacology data
NPT2 Others Unspecified Potency n.a. 188.3 nM PMID[19419205]
NPT2 Others Unspecified Potency n.a. 4252.7 nM PMID[23558238]
NPT2 Others Unspecified Potency n.a. 169.3 nM PMID[20624681]
NPT2 Others Unspecified Potency n.a. 211.3 nM PMID[19845338]
NPT2 Others Unspecified Potency n.a. 129.9 nM PMID[26238320]
NPT2 Others Unspecified Potency n.a. 149.6 nM PMID[17869103]
NPT2 Others Unspecified Potency n.a. 6740 nM PMID[15165131]
NPT2 Others Unspecified Potency n.a. 129.9 nM PMID[25856683]
NPT2 Others Unspecified Potency n.a. 3790.2 nM PMID[23398362]
NPT2 Others Unspecified Potency n.a. 46.5 nM PMID[25760525]
NPT2 Others Unspecified Potency n.a. 84.1 nM DrugMatrix in vitro pharmacology data
NPT2 Others Unspecified Potency n.a. 2614.7 nM PMID[17698630]
NPT2 Others Unspecified Potency n.a. 58 nM PMID[19075048]
NPT2 Others Unspecified Potency n.a. 2389.1 nM PMID[19738019]
NPT2 Others Unspecified Potency n.a. 233 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 103.2 nM DrugMatrix in vitro pharmacology data
NPT2 Others Unspecified Potency n.a. 919.6 nM PMID[10869203]
NPT2 Others Unspecified Potency n.a. 2660.3 nM PMID[15217289]
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 656.8 nM PMID[15043423]
NPT2 Others Unspecified Potency n.a. 149.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7497.8 nM PMID[18183025]
NPT2 Others Unspecified Potency n.a. 205.9 nM PMID[22037378]
NPT2 Others Unspecified Potency n.a. 165 nM PMID[23398362]
NPT2 Others Unspecified Potency n.a. 326.3 nM PMID[24387683]
NPT2 Others Unspecified Potency n.a. 674 nM PMID[24931277]
NPT2 Others Unspecified Potency n.a. 5853.6 nM PMID[25136911]
NPT2 Others Unspecified Potency n.a. 4144 nM PMID[25330401]
NPT2 Others Unspecified Potency n.a. 205.9 nM PMID[17959275]
NPT2 Others Unspecified Potency n.a. 59.6 nM PMID[18936188]
NPT2 Others Unspecified Potency n.a. 66.8 nM PMID[20805391]
NPT2 Others Unspecified Potency n.a. 4649.7 nM DrugMatrix in vivo data: Pathology
NPT2 Others Unspecified Potency n.a. 266 nM PMID[20346682]

☑ 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 NPC135488 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
0.9091 High Similarity NPC11863
0.9024 High Similarity NPC56856
0.8595 High Similarity NPC473901
0.7899 Intermediate Similarity NPC83987
0.7612 Intermediate Similarity NPC476322
0.752 Intermediate Similarity NPC76540
0.752 Intermediate Similarity NPC231655
0.748 Intermediate Similarity NPC27802
0.7424 Intermediate Similarity NPC91958
0.7407 Intermediate Similarity NPC290094
0.7364 Intermediate Similarity NPC235843
0.7338 Intermediate Similarity NPC476131
0.7299 Intermediate Similarity NPC146373
0.7299 Intermediate Similarity NPC166424
0.7299 Intermediate Similarity NPC245244
0.7293 Intermediate Similarity NPC143603
0.7286 Intermediate Similarity NPC69914
0.7246 Intermediate Similarity NPC202957
0.7246 Intermediate Similarity NPC169625
0.7218 Intermediate Similarity NPC297486
0.7218 Intermediate Similarity NPC471402
0.7218 Intermediate Similarity NPC240136
0.7197 Intermediate Similarity NPC84268
0.7143 Intermediate Similarity NPC89490
0.7132 Intermediate Similarity NPC48564
0.7132 Intermediate Similarity NPC182570
0.7132 Intermediate Similarity NPC265605
0.7092 Intermediate Similarity NPC329896
0.7092 Intermediate Similarity NPC475105
0.7092 Intermediate Similarity NPC475090
0.708 Intermediate Similarity NPC329825
0.7059 Intermediate Similarity NPC138842
0.7032 Intermediate Similarity NPC469897
0.7029 Intermediate Similarity NPC46358
0.7 Intermediate Similarity NPC476140
0.6978 Remote Similarity NPC27740
0.695 Remote Similarity NPC471313
0.695 Remote Similarity NPC471311
0.6923 Remote Similarity NPC282398
0.6875 Remote Similarity NPC256893
0.6875 Remote Similarity NPC101165
0.6831 Remote Similarity NPC212125
0.6776 Remote Similarity NPC285731
0.6759 Remote Similarity NPC324611
0.6759 Remote Similarity NPC471322
0.6746 Remote Similarity NPC213774
0.6713 Remote Similarity NPC306397
0.6709 Remote Similarity NPC236711
0.669 Remote Similarity NPC315320
0.669 Remote Similarity NPC151489
0.6689 Remote Similarity NPC328029
0.6689 Remote Similarity NPC29702
0.6688 Remote Similarity NPC470111
0.6667 Remote Similarity NPC86288
0.6644 Remote Similarity NPC314102
0.6644 Remote Similarity NPC251722
0.6597 Remote Similarity NPC165370
0.6584 Remote Similarity NPC48192
0.6556 Remote Similarity NPC32002
0.6556 Remote Similarity NPC315348
0.6556 Remote Similarity NPC316811
0.6552 Remote Similarity NPC471589
0.6552 Remote Similarity NPC287895
0.6552 Remote Similarity NPC313823
0.6533 Remote Similarity NPC65408
0.6533 Remote Similarity NPC471312
0.6497 Remote Similarity NPC40070
0.6496 Remote Similarity NPC143156
0.649 Remote Similarity NPC169433
0.6486 Remote Similarity NPC322488
0.6486 Remote Similarity NPC330326
0.6485 Remote Similarity NPC32534
0.6456 Remote Similarity NPC470233
0.642 Remote Similarity NPC25899
0.6419 Remote Similarity NPC174421
0.641 Remote Similarity NPC63545
0.6387 Remote Similarity NPC471323
0.6386 Remote Similarity NPC476518
0.6379 Remote Similarity NPC74382
0.6379 Remote Similarity NPC206251
0.6369 Remote Similarity NPC179787
0.6369 Remote Similarity NPC469811
0.6369 Remote Similarity NPC471957
0.6369 Remote Similarity NPC201380
0.6358 Remote Similarity NPC96102
0.6352 Remote Similarity NPC216713
0.6352 Remote Similarity NPC470823
0.6347 Remote Similarity NPC14651
0.6347 Remote Similarity NPC121658
0.6329 Remote Similarity NPC321911
0.6323 Remote Similarity NPC477977
0.6316 Remote Similarity NPC150259
0.6316 Remote Similarity NPC114310
0.6316 Remote Similarity NPC105127
0.6316 Remote Similarity NPC84911
0.6309 Remote Similarity NPC82295
0.6286 Remote Similarity NPC148140
0.628 Remote Similarity NPC225018
0.628 Remote Similarity NPC71079
0.6266 Remote Similarity NPC477974
0.6266 Remote Similarity NPC105811
0.6258 Remote Similarity NPC476454
0.625 Remote Similarity NPC29886
0.625 Remote Similarity NPC261195
0.625 Remote Similarity NPC472260
0.6242 Remote Similarity NPC467188
0.6242 Remote Similarity NPC474217
0.6242 Remote Similarity NPC97367
0.6241 Remote Similarity NPC81561
0.6234 Remote Similarity NPC110126
0.6234 Remote Similarity NPC73767
0.6233 Remote Similarity NPC273714
0.6218 Remote Similarity NPC320863
0.6218 Remote Similarity NPC190296
0.6211 Remote Similarity NPC325903
0.6209 Remote Similarity NPC472288
0.6205 Remote Similarity NPC471178
0.6205 Remote Similarity NPC85918
0.6203 Remote Similarity NPC288838
0.6197 Remote Similarity NPC162689
0.6197 Remote Similarity NPC54102
0.6194 Remote Similarity NPC469767
0.6194 Remote Similarity NPC469761
0.6194 Remote Similarity NPC469783
0.6194 Remote Similarity NPC469784
0.6194 Remote Similarity NPC469779
0.6194 Remote Similarity NPC318935
0.6194 Remote Similarity NPC279081
0.6194 Remote Similarity NPC469768
0.6194 Remote Similarity NPC469780
0.619 Remote Similarity NPC91895
0.6182 Remote Similarity NPC471177
0.6182 Remote Similarity NPC124542
0.6182 Remote Similarity NPC59779
0.6168 Remote Similarity NPC127730
0.6168 Remote Similarity NPC278366
0.6168 Remote Similarity NPC56233
0.6159 Remote Similarity NPC293487
0.6154 Remote Similarity NPC88121
0.6154 Remote Similarity NPC469766
0.6149 Remote Similarity NPC70406
0.6139 Remote Similarity NPC159856
0.6139 Remote Similarity NPC314372
0.6135 Remote Similarity NPC51054
0.6122 Remote Similarity NPC69277
0.6115 Remote Similarity NPC20144
0.6111 Remote Similarity NPC215519
0.6111 Remote Similarity NPC200214
0.6101 Remote Similarity NPC143872
0.6098 Remote Similarity NPC129721
0.6095 Remote Similarity NPC116961
0.6092 Remote Similarity NPC266551
0.609 Remote Similarity NPC230002
0.6087 Remote Similarity NPC53947
0.6081 Remote Similarity NPC151779
0.608 Remote Similarity NPC14223
0.6076 Remote Similarity NPC159630
0.6076 Remote Similarity NPC230085
0.6074 Remote Similarity NPC209362
0.6067 Remote Similarity NPC71236
0.6067 Remote Similarity NPC224327
0.6065 Remote Similarity NPC104049
0.6061 Remote Similarity NPC477591
0.6048 Remote Similarity NPC478184
0.6048 Remote Similarity NPC478182
0.6038 Remote Similarity NPC469525
0.6038 Remote Similarity NPC167400
0.6037 Remote Similarity NPC476464
0.6034 Remote Similarity NPC164228
0.6034 Remote Similarity NPC134079
0.6026 Remote Similarity NPC104483
0.6026 Remote Similarity NPC88097
0.6024 Remote Similarity NPC44773
0.6024 Remote Similarity NPC122141
0.6024 Remote Similarity NPC470204
0.6024 Remote Similarity NPC215584
0.6023 Remote Similarity NPC111624
0.6012 Remote Similarity NPC157583
0.6012 Remote Similarity NPC251391
0.6012 Remote Similarity NPC107287
0.6 Remote Similarity NPC213914
0.6 Remote Similarity NPC220523
0.6 Remote Similarity NPC302159
0.6 Remote Similarity NPC138018
0.5989 Remote Similarity NPC20249
0.5988 Remote Similarity NPC313889
0.5988 Remote Similarity NPC105818
0.5988 Remote Similarity NPC470203
0.5988 Remote Similarity NPC148592
0.5988 Remote Similarity NPC24678
0.5988 Remote Similarity NPC317054
0.5988 Remote Similarity NPC478185
0.5978 Remote Similarity NPC255909
0.5976 Remote Similarity NPC478183
0.5976 Remote Similarity NPC263455
0.5976 Remote Similarity NPC229055
0.5974 Remote Similarity NPC198988
0.5965 Remote Similarity NPC201634
0.5964 Remote Similarity NPC56765
0.5964 Remote Similarity NPC80681

  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 NPC135488 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
0.9076 High Similarity NPD60 Approved
0.8926 High Similarity NPD8840 Approved
0.752 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD9098 Phase 3
0.75 Intermediate Similarity NPD4824 Approved
0.75 Intermediate Similarity NPD4823 Approved
0.7462 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD792 Discontinued
0.7379 Intermediate Similarity NPD461 Approved
0.7379 Intermediate Similarity NPD1382 Phase 2
0.7379 Intermediate Similarity NPD1383 Phase 3
0.7353 Intermediate Similarity NPD9357 Approved
0.7348 Intermediate Similarity NPD9396 Approved
0.7348 Intermediate Similarity NPD9392 Approved
0.7329 Intermediate Similarity NPD4510 Discontinued
0.7286 Intermediate Similarity NPD715 Phase 3
0.7266 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD9583 Approved
0.7219 Intermediate Similarity NPD4641 Discontinued
0.7172 Intermediate Similarity NPD1380 Discovery
0.7163 Intermediate Similarity NPD235 Discontinued
0.7162 Intermediate Similarity NPD649 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD9598 Discontinued
0.7132 Intermediate Similarity NPD271 Approved
0.7132 Intermediate Similarity NPD268 Approved
0.7113 Intermediate Similarity NPD9726 Discontinued
0.7086 Intermediate Similarity NPD2104 Approved
0.7086 Intermediate Similarity NPD2102 Approved
0.7075 Intermediate Similarity NPD1649 Discontinued
0.7071 Intermediate Similarity NPD2118 Approved
0.7071 Intermediate Similarity NPD2119 Approved
0.7071 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD1598 Discontinued
0.7071 Intermediate Similarity NPD991 Phase 2
0.702 Intermediate Similarity NPD2089 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD3944 Approved
0.7014 Intermediate Similarity NPD3942 Approved
0.7 Intermediate Similarity NPD1365 Approved
0.7 Intermediate Similarity NPD1366 Approved
0.7 Intermediate Similarity NPD1364 Approved
0.6993 Remote Similarity NPD2103 Approved
0.698 Remote Similarity NPD1427 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1395 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3476 Approved
0.6923 Remote Similarity NPD3475 Approved
0.6918 Remote Similarity NPD206 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4436 Clinical (unspecified phase)
0.6903 Remote Similarity NPD1328 Approved
0.6871 Remote Similarity NPD9506 Approved
0.6863 Remote Similarity NPD427 Approved
0.6863 Remote Similarity NPD428 Approved
0.6863 Remote Similarity NPD162 Approved
0.6863 Remote Similarity NPD426 Approved
0.6853 Remote Similarity NPD9305 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2012 Clinical (unspecified phase)
0.6831 Remote Similarity NPD9284 Approved
0.6828 Remote Similarity NPD1627 Clinical (unspecified phase)
0.6828 Remote Similarity NPD1993 Approved
0.6828 Remote Similarity NPD1995 Approved
0.6828 Remote Similarity NPD1994 Approved
0.6821 Remote Similarity NPD1352 Discontinued
0.6818 Remote Similarity NPD971 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1661 Suspended
0.6792 Remote Similarity NPD2385 Clinical (unspecified phase)
0.6781 Remote Similarity NPD4028 Approved
0.6781 Remote Similarity NPD4030 Approved
0.6781 Remote Similarity NPD4029 Approved
0.6735 Remote Similarity NPD2140 Approved
0.6735 Remote Similarity NPD2141 Approved
0.6735 Remote Similarity NPD2142 Approved
0.6733 Remote Similarity NPD2222 Discontinued
0.6731 Remote Similarity NPD491 Approved
0.6713 Remote Similarity NPD9080 Approved
0.6711 Remote Similarity NPD2896 Discontinued
0.669 Remote Similarity NPD9206 Approved
0.669 Remote Similarity NPD9207 Approved
0.6688 Remote Similarity NPD1270 Approved
0.6667 Remote Similarity NPD768 Clinical (unspecified phase)
0.6646 Remote Similarity NPD754 Clinical (unspecified phase)
0.6644 Remote Similarity NPD809 Discontinued
0.6644 Remote Similarity NPD803 Phase 1
0.6627 Remote Similarity NPD2771 Approved
0.6626 Remote Similarity NPD7287 Clinical (unspecified phase)
0.6623 Remote Similarity NPD7469 Discontinued
0.6622 Remote Similarity NPD272 Approved
0.6605 Remote Similarity NPD2719 Clinical (unspecified phase)
0.6605 Remote Similarity NPD2720 Phase 1
0.66 Remote Similarity NPD203 Clinical (unspecified phase)
0.6596 Remote Similarity NPD748 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4547 Phase 3
0.6561 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6556 Remote Similarity NPD4804 Approved
0.6556 Remote Similarity NPD945 Clinical (unspecified phase)
0.6556 Remote Similarity NPD2075 Approved
0.6556 Remote Similarity NPD2070 Approved
0.6556 Remote Similarity NPD2073 Approved
0.6556 Remote Similarity NPD2072 Approved
0.6556 Remote Similarity NPD174 Discontinued
0.6556 Remote Similarity NPD2074 Approved
0.6556 Remote Similarity NPD2069 Approved
0.6556 Remote Similarity NPD2068 Approved
0.6556 Remote Similarity NPD2071 Approved
0.6536 Remote Similarity NPD2006 Phase 2
0.6533 Remote Similarity NPD200 Phase 2
0.6533 Remote Similarity NPD201 Phase 2
0.65 Remote Similarity NPD2145 Clinical (unspecified phase)
0.6494 Remote Similarity NPD751 Clinical (unspecified phase)
0.6494 Remote Similarity NPD3813 Approved
0.6486 Remote Similarity NPD9100 Approved
0.6478 Remote Similarity NPD2809 Approved
0.6471 Remote Similarity NPD4805 Approved
0.6471 Remote Similarity NPD1722 Approved
0.6467 Remote Similarity NPD3859 Clinical (unspecified phase)
0.646 Remote Similarity NPD1679 Approved
0.6454 Remote Similarity NPD4811 Discontinued
0.6438 Remote Similarity NPD1031 Discontinued
0.6429 Remote Similarity NPD2007 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3348 Phase 2
0.6415 Remote Similarity NPD2837 Discontinued
0.6412 Remote Similarity NPD1928 Discontinued
0.6412 Remote Similarity NPD4556 Approved
0.641 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6405 Remote Similarity NPD7135 Phase 2
0.6405 Remote Similarity NPD9599 Approved
0.6392 Remote Similarity NPD2465 Approved
0.6392 Remote Similarity NPD2466 Phase 3
0.6392 Remote Similarity NPD2462 Phase 3
0.6387 Remote Similarity NPD5502 Approved
0.6387 Remote Similarity NPD1918 Clinical (unspecified phase)
0.6387 Remote Similarity NPD3401 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5503 Approved
0.6382 Remote Similarity NPD2059 Approved
0.6382 Remote Similarity NPD2058 Phase 2
0.6382 Remote Similarity NPD2057 Approved
0.6369 Remote Similarity NPD4702 Approved
0.6369 Remote Similarity NPD4703 Approved
0.6364 Remote Similarity NPD5787 Discontinued
0.6358 Remote Similarity NPD704 Clinical (unspecified phase)
0.6358 Remote Similarity NPD198 Clinical (unspecified phase)
0.6341 Remote Similarity NPD1545 Discontinued
0.6337 Remote Similarity NPD952 Approved
0.6329 Remote Similarity NPD1183 Approved
0.6329 Remote Similarity NPD2430 Phase 2
0.6323 Remote Similarity NPD3717 Discontinued
0.6319 Remote Similarity NPD6454 Clinical (unspecified phase)
0.6312 Remote Similarity NPD3339 Approved
0.6296 Remote Similarity NPD6497 Approved
0.6296 Remote Similarity NPD1869 Phase 2
0.6282 Remote Similarity NPD4509 Discontinued
0.6282 Remote Similarity NPD1988 Phase 1
0.628 Remote Similarity NPD418 Approved
0.6273 Remote Similarity NPD2061 Approved
0.6273 Remote Similarity NPD977 Approved
0.6273 Remote Similarity NPD976 Approved
0.6273 Remote Similarity NPD975 Approved
0.6273 Remote Similarity NPD5358 Clinical (unspecified phase)
0.6266 Remote Similarity NPD2110 Approved
0.6265 Remote Similarity NPD5636 Discontinued
0.6258 Remote Similarity NPD5418 Discontinued
0.6258 Remote Similarity NPD5255 Approved
0.6257 Remote Similarity NPD2084 Discontinued
0.625 Remote Similarity NPD490 Clinical (unspecified phase)
0.625 Remote Similarity NPD3262 Approved
0.6242 Remote Similarity NPD175 Clinical (unspecified phase)
0.6242 Remote Similarity NPD264 Clinical (unspecified phase)
0.6242 Remote Similarity NPD5925 Phase 1
0.6234 Remote Similarity NPD786 Approved
0.6229 Remote Similarity NPD3039 Clinical (unspecified phase)
0.6228 Remote Similarity NPD2640 Approved
0.6228 Remote Similarity NPD2641 Approved
0.6215 Remote Similarity NPD3474 Discovery
0.6205 Remote Similarity NPD925 Approved
0.6205 Remote Similarity NPD926 Approved
0.6199 Remote Similarity NPD2753 Discontinued
0.6194 Remote Similarity NPD107 Approved
0.619 Remote Similarity NPD5320 Approved
0.619 Remote Similarity NPD5319 Approved
0.6188 Remote Similarity NPD7913 Clinical (unspecified phase)
0.6188 Remote Similarity NPD2959 Phase 3
0.6188 Remote Similarity NPD4899 Clinical (unspecified phase)
0.6185 Remote Similarity NPD1570 Approved
0.6182 Remote Similarity NPD1015 Phase 2
0.6182 Remote Similarity NPD4384 Clinical (unspecified phase)
0.6182 Remote Similarity NPD1853 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5315 Discontinued
0.6182 Remote Similarity NPD6771 Discontinued
0.6182 Remote Similarity NPD1016 Phase 2
0.6169 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6168 Remote Similarity NPD424 Approved
0.6168 Remote Similarity NPD425 Approved
0.6168 Remote Similarity NPD6446 Discontinued
0.6167 Remote Similarity NPD953 Approved
0.6149 Remote Similarity NPD9595 Approved
0.6149 Remote Similarity NPD5092 Clinical (unspecified phase)
0.6149 Remote Similarity NPD6194 Discontinued
0.6149 Remote Similarity NPD5213 Clinical (unspecified phase)
0.6149 Remote Similarity NPD510 Phase 1
0.6149 Remote Similarity NPD9596 Approved
0.614 Remote Similarity NPD6044 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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