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Showing metabocard for Allopurinol (HMDB0014581)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:13 UTC
HMDB IDHMDB0014581
Secondary Accession Numbers
  • HMDB14581
Metabolite Identification
Common NameAllopurinol
DescriptionAllopurinol is only found in individuals that have used or taken this drug. It is a xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem]Allopurinol and its active metabolite, oxypurinol, inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the serum and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, leading to a feedback inhibition of de novo purin synthesis and a decrease in serum uric acid concentrations as a result of an increase in nucleotide concentration.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014581 (Allopurinol)

437
  Mrv0541 02231214412D          

 10 11  0  0  0  0            999 V2000
    2.3645    1.4001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4 10  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for HMDB0014581 (Allopurinol)

HMDB0014581
     RDKit          3D
Allopurinol
 14 15  0  0  0  0  0  0  0  0999 V2000
   -1.2455    2.4744   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.2489   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3201    0.4681   -0.1263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -0.8575    0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980   -1.5325    0.2176 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502   -0.8253    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -1.1221    0.2081 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -0.0258    0.0512 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2998    1.0431   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058    0.6156   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878   -1.4184    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -2.1013    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   -0.0116    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    2.0443   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  2  1  0
 10  6  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
  9 14  1  0
M  END
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3D SDF for HMDB0014581 (Allopurinol)

437
  Mrv0541 02231214412D          

 10 11  0  0  0  0            999 V2000
    2.3645    1.4001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.9139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -0.2500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597    0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4 10  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014581

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1N=CN=C2NNC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)

> <INCHI_KEY>
OFCNXPDARWKPPY-UHFFFAOYSA-N

> <FORMULA>
C5H4N4O

> <MOLECULAR_WEIGHT>
136.1115

> <EXACT_MASS>
136.03851077

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
11.665587273192898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-1.7583063776666668

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.529859254148572

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.828742070600279

> <JCHEM_PKA_STRONGEST_BASIC>
2.5670119659248782

> <JCHEM_POLAR_SURFACE_AREA>
65.85

> <JCHEM_REFRACTIVITY>
54.24260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ALLO

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014581 (Allopurinol)

HMDB0014581
     RDKit          3D
Allopurinol
 14 15  0  0  0  0  0  0  0  0999 V2000
   -1.2455    2.4744   -0.4193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146    1.2489   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3201    0.4681   -0.1263 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -0.8575    0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980   -1.5325    0.2176 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502   -0.8253    0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -1.1221    0.2081 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0916   -0.0258    0.0512 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2998    1.0431   -0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0058    0.6156   -0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878   -1.4184    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7191   -2.1013    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1240   -0.0116    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    2.0443   -0.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  2  1  0
 10  6  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
  9 14  1  0
M  END
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PDB for HMDB0014581 (Allopurinol)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 437                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       4.414   2.614   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.205  -1.706   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.104  -0.467   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       4.414  -2.007   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       3.080   0.303   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748   0.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -1.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.205   0.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   1.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -1.237   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    7   10                                                       
CONECT    5    9   10                                                       
CONECT    6    7    8    9                                                  
CONECT    7    2    4    6                                                  
CONECT    8    3    6                                                       
CONECT    9    1    5    6                                                  
CONECT   10    4    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0014581 (Allopurinol)

COMPND    HMDB0014581
HETATM    1  O1  UNL     1      -1.245   2.474  -0.419  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.215   1.249  -0.225  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.320   0.468  -0.126  1.00  0.00           N  
HETATM    4  C2  UNL     1      -2.254  -0.857   0.085  1.00  0.00           C  
HETATM    5  N2  UNL     1      -1.098  -1.532   0.218  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.050  -0.825   0.132  1.00  0.00           C  
HETATM    7  N3  UNL     1       1.362  -1.122   0.208  1.00  0.00           N  
HETATM    8  N4  UNL     1       2.092  -0.026   0.051  1.00  0.00           N  
HETATM    9  C4  UNL     1       1.300   1.043  -0.136  1.00  0.00           C  
HETATM   10  C5  UNL     1      -0.006   0.616  -0.097  1.00  0.00           C  
HETATM   11  H1  UNL     1      -3.188  -1.418   0.152  1.00  0.00           H  
HETATM   12  H2  UNL     1       1.719  -2.101   0.371  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.124  -0.012   0.072  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.679   2.044  -0.285  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   10
CONECT    3    4    4
CONECT    4    5   11
CONECT    5    6    6
CONECT    6    7   10
CONECT    7    8   12
CONECT    8    9   13
CONECT    9   10   10   14
END
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SMILES for HMDB0014581 (Allopurinol)

O=C1N=CN=C2NNC=C12
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INCHI for HMDB0014581 (Allopurinol)

InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H4N4O
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
IUPAC Name1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
Traditional NameALLO
CAS Registry Number315-30-0
SMILES
O=C1N=CN=C2NNC=C12
InChI Identifier
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyOFCNXPDARWKPPY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to but and not sharing a nitrogen atom with a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrazolopyrimidines
Sub ClassPyrazolo[3,4-d]pyrimidines
Direct ParentPyrazolo[3,4-d]pyrimidines
Alternative Parents
Substituents
  • Pyrazolo[3,4-d]pyrimidine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Pyrazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point350 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.88 g/LNot Available
LogP-1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00437 details
UrineDetected and Quantified18-23 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00437 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified630 umol/mmol creatinineAdult (>18 years old)BothMolybdenum cofactor deficiency details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Molybdenum cofactor deficiency
  1. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Associated OMIM IDsNone
DrugBank IDDB00437
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2010
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllopurinol
METLIN IDNot Available
PubChem Compound2094
PDB IDNot Available
ChEBI ID40279
Food Biomarker OntologyNot Available
VMH IDALLOP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [PubMed:19584965 ]
  2. George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [PubMed:19436671 ]
  3. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [PubMed:20046204 ]
  4. Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [PubMed:16507884 ]
  5. Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. doi: 10.3810/pgm.2010.03.2133. [PubMed:20203467 ]

Enzymes

Enzyme Details
1. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
References
  1. Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [PubMed:8216357 ]
Enzyme Details
2. Xanthine dehydrogenase/oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [PubMed:19584965 ]
  3. Carro MD, Falkenstein E, Radke WJ, Klandorf H: Effects of allopurinol on uric acid concentrations, xanthine oxidoreductase activity and oxidative stress in broiler chickens. Comp Biochem Physiol C Toxicol Pharmacol. 2010 Jan;151(1):12-7. doi: 10.1016/j.cbpc.2009.07.010. Epub 2009 Aug 3. [PubMed:19654053 ]
  4. George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [PubMed:19436671 ]
  5. Higgins P, Dawson J, Walters M: The potential for xanthine oxidase inhibition in the prevention and treatment of cardiovascular and cerebrovascular disease. Cardiovasc Psychiatry Neurol. 2009;2009:282059. doi: 10.1155/2009/282059. Epub 2009 Nov 4. [PubMed:20029618 ]
  6. Dincer HE, Dincer AP, Levinson DJ: Asymptomatic hyperuricemia: to treat or not to treat. Cleve Clin J Med. 2002 Aug;69(8):594, 597, 600-2 passim. [PubMed:12184468 ]
  7. Kelley WN, Wyngaarden JB: Effects of allopurinol and oxipurinol on purine synthesis in cultured human cells. J Clin Invest. 1970 Mar;49(3):602-9. [PubMed:5415686 ]
  8. Okamoto K: [Inhibitors of xanthine oxidoreductase]. Nihon Rinsho. 2008 Apr;66(4):748-53. [PubMed:18409526 ]
  9. Taha MO, Simoes MJ, Noguerol EC, Mendonca FP, Pascoalick HM, Alves RA, Vivian ME, Morales FP, Campos AC, Magalhaes KG, Venerando PS, Tersariol IL, Monteiro HP, Oliveira-Junior IS, Jurkiewicz A, Caricati-Neto A: Effects of allopurinol on ischemia and reperfusion in rabbit livers. Transplant Proc. 2009 Apr;41(3):820-3. doi: 10.1016/j.transproceed.2009.02.051. [PubMed:19376361 ]
  10. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [PubMed:20046204 ]
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Transporters

Enzyme Details
1. Solute carrier family 22 member 7
General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [PubMed:12065749 ]