Natural Product: NPC321929

Natural Product ID:  NPC321929
Common Name:   Allopurinol
IUPAC Name:   1,2-dihydropyrazolo[3,4-d]pyrimidin-4-one
Synonyms:   Allopurinol; Aloral; Aluline 100; Aluline 300; BW-56-158; BW-56158; Caplenal; Cosuric; Hamarin 100; Hamarin 300; Ledopur; Lopurin; Uricto; Xanthomax-100; Xanthomax-300; Zyloprim; Zyloric; Zyloric-300
Molecular Formula:   C5H4N4O
Standard InCHIKey:  OFCNXPDARWKPPY-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
Canonical SMILES:  Oc1ncnc2c1c[nH]n2
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[21059682]
NPO1797 Homo sapiens Species Hominidae Eukaryota urine PMID[21059682]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 4200 nM 8691450
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Ki = 7000 nM 8691450
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 2.7 min 3351858
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 260 nM 11294382
NPT29 Organism Rattus norvegicus Rattus norvegicus ED20 = 3.5 mg/kg 11294382
NPT29 Organism Rattus norvegicus Rattus norvegicus ED20 > 10 mg/kg 11294382
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 34910 nM 12873513
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 9800 U (mg of protein)-1 11140725
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 1912 U (mg of protein)-1 11140725
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 21 U (mg of protein)-1 11140725
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 >= 150000 nM 17149876
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 7820 nM 17379526
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 93.8 % 17379526
NPT2 Others Unspecified IC50 = 42240 nM 17497807
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 2200 nM 17346963
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Inhibition = 96.3 % 17692432
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 24400 nM 17692432
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 10340 nM 17706325
NPT2 Others Unspecified Inhibition = 42.3 % 18835711
NPT2 Others Unspecified Activity = 84 % 18819730
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 34910 nM 16309309
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 240 nM 9461655
NPT2 Others Unspecified IC50 = 230 nM 9461655
NPT613 Individual Protein Solute carrier family 22 member 1 Homo sapiens Inhibition = 7.7 % 18788725
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 21800 nM 18722771
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 11400 nM 18722771
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 1600 nM 2723668
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 2000 nM 18512985
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 7 % 11975490
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 10.9 11975490
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 24200 nM 10425142
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 9820 nM 16872152
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 7450 nM 15730241
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 2000 nM 18606546
NPT2 Others Unspecified Inhibition = 90 % 18063225
NPT2 Others Unspecified Activity = 77 % 19064319
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Activity = 94 % 19362850
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 23500 nM 19362850
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Activity = 140 nM/s 19388706
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Activity = 120 nM/s 19388706
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Activity = 28 nM/s 19388706
NPT2 Others Unspecified Activity = -77.5 % 19962217
NPT2 Others Unspecified Activity = -66.4 % 19962217
NPT4394 Individual Protein Xanthine dehydrogenase/oxidase Rattus norvegicus IC50 = 21200 nM 19673490
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 2300 nM 19783139
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -3.3 % 19783139
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 35.9 % 19783139
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 180 nM 19476336
NPT2 Others Unspecified Activity = 86 % 20399654
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 3000 nM 20384317
NPT2 Others Unspecified Inhibition = 80 % 20542691
NPT4896 Individual Protein Purine nucleoside phosphorylase Mycobacterium tuberculosis Kd = 1000000 nM 20570524
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 6309.6 nM PubChem BioAssay data set
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 1000 nM PubChem BioAssay data set
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 1000 nM PubChem BioAssay data set
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 5011.9 nM PubChem BioAssay data set
NPT58 Individual Protein Bloom syndrome protein Homo sapiens Potency = 398.1 nM PubChem BioAssay data set
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 15848.9 nM PubChem BioAssay data set
NPT4394 Individual Protein Xanthine dehydrogenase/oxidase Rattus norvegicus IC50 = 753 nM 21163661
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 730 nM 21163661
NPT2 Others Unspecified IC50 = 730 nM 21163661
NPT2 Others Unspecified IC50 = 3000 nM 21174408
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 8300 nM 21353569
NPT2 Others Unspecified Potency 3981.1 nM PubChem BioAssay data set
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency 25.1 nM PubChem BioAssay data set
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 1900 nM 21345544
NPT2 Others Unspecified Inhibition = 42 % 21723119
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 8300 nM 21862335
NPT32 Organism Mus musculus Mus musculus Activity = 3.19 nM 21862335
NPT32 Organism Mus musculus Mus musculus Activity = 2.93 nM 21862335
NPT32 Organism Mus musculus Mus musculus Activity = 2.17 nM 21862335
NPT2 Others Unspecified Potency 20 nM PubChem BioAssay data set
NPT2 Others Unspecified Activity = 69 nmol/min 21930379
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 184 % 22483591
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 5700 nM 22483591
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 100 % 22483591
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 0.53 ug/ml 22677314
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 8500 nM 22901670
NPT10 Individual Protein Geminin Homo sapiens Potency 92 nM PubChem BioAssay data set
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency 31622.8 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency 74978 nM PubChem BioAssay data set
NPT102 Individual Protein Interleukin-8 Homo sapiens Potency 74978 nM PubChem BioAssay data set
NPT1417 Individual Protein Transcriptional regulator ERG Homo sapiens Potency 794.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Inhibition = 41 % 23078966
NPT622 Individual Protein Solute carrier organic anion transporter family member 2B1 Homo sapiens Inhibition = 8.4 % 22541068
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 10.8 % 22541068
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = -35.6 % 22541068
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 130 % 23122864
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 177 % 23122864
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 4190 nM 23122864
NPT2933 Individual Protein Aldehyde oxidase Oryctolagus cuniculus Inhibition = 18 % 21476569
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition = 4 % 21476569
NPT2933 Individual Protein Aldehyde oxidase Oryctolagus cuniculus IC50 > 1000000 nM 21476569
NPT2 Others Unspecified IC50 = 17000 nM 21476569
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 > 1000000 nM 21476569
NPT2 Others Unspecified Inhibition = -77 % 10.1007/s00044-010-9444-9
NPT2 Others Unspecified Inhibition = -83 % 10.1007/s00044-009-9280-y
NPT4394 Individual Protein Xanthine dehydrogenase/oxidase Rattus norvegicus IC50 = 6000 nM 23177727
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 4200 nM 23265878
NPT2 Others Unspecified Potency 5804.8 nM PubChem BioAssay data set
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency 25929 nM PubChem BioAssay data set
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency 35481.3 nM PubChem BioAssay data set
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 1.6 ug/ml 23851116
NPT2 Others Unspecified Inhibition = 51 % 23954239
NPT2 Others Unspecified Activity = 54 % 24090915
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 9620 nM 24090917
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 68.8 % 23571415
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 84.36 % 23571415
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 11100 nM 24388807
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 11230 nM 24556143
NPT614 Tissue Plasma Rattus norvegicus Activity = 94 % 24508129
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 87 % 24508129
NPT2 Others Unspecified Potency 13.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 10.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 6308.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 266 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 37.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 27945.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 1.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 22384.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 44663 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 15 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 5623.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Activity = 49 % 24871900
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 5000 nM 2778
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Inhibition = 100 % 2778
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Ki = 2600 nM 2778
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus Ki = 1000 nM 2778
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 3000 nM 926119
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Ki = 100 nM 25060641
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Ki = 7300 nM 25019478
NPT2 Others Unspecified IC50 = 2000 nM 25245672
NPT2 Others Unspecified AC50 28183.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 56227.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency 15089 nM PubChem BioAssay data set
NPT2 Others Unspecified AC50 1778.3 nM PubChem BioAssay data set
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 2900 nM 26022844
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens Ki = 1550 nM 26712096
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 200 nM 26762836
NPT2 Others Unspecified IC50 = 3740 nM 26774578
NPT1310 Individual Protein Xanthine dehydrogenase Bos taurus IC50 = 44000 nM 27133595
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 950 nM 27162124

  Similar Natural Products 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 NPC321929 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
0.7468 Intermediate Similarity NPC321393
0.746 Intermediate Similarity NPC163105
0.7231 Intermediate Similarity NPC329046
0.7087 Intermediate Similarity NPC75844
0.6947 Remote Similarity NPC27699
0.6853 Remote Similarity NPC14330
0.6806 Remote Similarity NPC287876
0.6458 Remote Similarity NPC248007
0.6429 Remote Similarity NPC68938
0.6376 Remote Similarity NPC57279
0.625 Remote Similarity NPC139776
0.6232 Remote Similarity NPC4837
0.6232 Remote Similarity NPC312187
0.6207 Remote Similarity NPC5707
0.6133 Remote Similarity NPC246193
0.5985 Remote Similarity NPC18335
0.5897 Remote Similarity NPC314646
0.587 Remote Similarity NPC476564
0.586 Remote Similarity NPC62151
0.5771 Remote Similarity NPC222174
0.5769 Remote Similarity NPC326364
0.5769 Remote Similarity NPC327941
0.5766 Remote Similarity NPC87981
0.5766 Remote Similarity NPC174114
0.5714 Remote Similarity NPC222061
0.5613 Remote Similarity NPC104011

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC321929 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD8827 Approved
0.9431 High Similarity NPD8826 Approved
0.8045 Intermediate Similarity NPD8832 Approved
0.7344 Intermediate Similarity NPD9071 Phase 3
0.7087 Intermediate Similarity NPD8566 Approved
0.7055 Intermediate Similarity NPD4089 Clinical (unspecified phase)
0.6947 Remote Similarity NPD8571 Phase 3
0.6835 Remote Similarity NPD420 Discontinued
0.6806 Remote Similarity NPD8829 Clinical (unspecified phase)
0.6781 Remote Similarity NPD9083 Clinical (unspecified phase)
0.6478 Remote Similarity NPD231 Clinical (unspecified phase)
0.6458 Remote Similarity NPD9084 Phase 2
0.6416 Remote Similarity NPD3593 Approved
0.625 Remote Similarity NPD1692 Approved
0.622 Remote Similarity NPD8565 Clinical (unspecified phase)
0.6207 Remote Similarity NPD8830 Phase 3
0.6169 Remote Similarity NPD799 Phase 1
0.6149 Remote Similarity NPD9366 Approved
0.6096 Remote Similarity NPD306 Approved
0.6054 Remote Similarity NPD1734 Clinical (unspecified phase)
0.5985 Remote Similarity NPD8836 Approved
0.5944 Remote Similarity NPD2724 Phase 1
0.5932 Remote Similarity NPD1046 Clinical (unspecified phase)
0.5901 Remote Similarity NPD1730 Discontinued
0.5806 Remote Similarity NPD1264 Phase 2
0.5789 Remote Similarity NPD870 Clinical (unspecified phase)
0.5774 Remote Similarity NPD1017 Clinical (unspecified phase)
0.5738 Remote Similarity NPD1063 Phase 2
0.5735 Remote Similarity NPD9194 Approved
0.5735 Remote Similarity NPD9193 Approved
0.5714 Remote Similarity NPD248 Discontinued
0.5698 Remote Similarity NPD2293 Phase 2
0.5665 Remote Similarity NPD527 Clinical (unspecified phase)
0.5665 Remote Similarity NPD4143 Clinical (unspecified phase)
0.5655 Remote Similarity NPD214 Approved
0.5655 Remote Similarity NPD213 Clinical (unspecified phase)
0.5604 Remote Similarity NPD1675 Phase 1
0.5604 Remote Similarity NPD1674 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   2094
ChEMBL   CHEMBL1467
ZINC  

Physicochemical Properties

Molecular Weight:  136.04
ALogP:  -0.8807
MLogP:  1.46
XLogP:  -0.252
# Rotatable Bonds:  1
Polar Surface Area:  74.69
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  10

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