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Showing NP-Card for 9-Methyluric acid (NP0001261)

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Record Information
Version1.0
Created at2006-05-22 14:17:30 UTC
Updated at2020-11-24 22:22:03 UTC
NP-MRD IDNP0001261
Secondary Accession NumbersNone
Natural Product Identification
Common Name9-Methyluric acid
Description9-Methyluric acid is a methyl derivative of uric acid, found occasionally in human urine. 9-Methyluracil is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine). Methyluric acids are indistinguishable from uric acid by simple methods routinely used in clinical laboratories, requiring the use of high-performance liquid chromatography (HPLC). Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316 , 15833286 , 3506820 , 15013152 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001261 (9-Methyluric acid)


  Mrv1652305271900012D          

 13 14  0  0  0  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
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3D MOL for NP0001261 (9-Methyluric acid)

HMDB0001973
     RDKit          3D
9-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.2920   -1.3726   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069   -0.2051    0.0060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    1.0914    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.5540    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6684    1.8667    0.0411 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279    1.0645    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7936    1.3330    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    2.5076    0.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    0.3054    0.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -0.9433   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860   -1.8957   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456   -1.2217   -0.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654   -0.2220    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361   -1.1700   -0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137   -1.7294    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -2.1519   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900    2.9126    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    0.4649    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -2.1882   -0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13  2  1  0
 13  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  9 18  1  0
 12 19  1  0
M  END
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3D SDF for NP0001261 (9-Methyluric acid)


  Mrv1652305271900012D          

 13 14  0  0  0  0            999 V2000
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)NC2=C1NC(=O)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)

> <INCHI_KEY>
XJEJWDFDVPDMAS-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O3

> <MOLECULAR_WEIGHT>
182.1368

> <EXACT_MASS>
182.043990078

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.6735958640445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-1.32051687

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.170273572362209

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.253180751274491

> <JCHEM_PKA_STRONGEST_BASIC>
-6.233892959187559

> <JCHEM_POLAR_SURFACE_AREA>
90.53999999999999

> <JCHEM_REFRACTIVITY>
50.525299999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-methyl uric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0001261 (9-Methyluric acid)

HMDB0001973
     RDKit          3D
9-Methyluric acid
 19 20  0  0  0  0  0  0  0  0999 V2000
   -2.2920   -1.3726   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069   -0.2051    0.0060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7633    1.0914    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9356    1.5540    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6684    1.8667    0.0411 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279    1.0645    0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7936    1.3330    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1866    2.5076    0.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6598    0.3054    0.0014 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -0.9433   -0.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9860   -1.8957   -0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8456   -1.2217   -0.0201 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654   -0.2220    0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2361   -1.1700   -0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5137   -1.7294    1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -2.1519   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5900    2.9126    0.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    0.4649    0.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4581   -2.1882   -0.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13  2  1  0
 13  6  2  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  9 18  1  0
 12 19  1  0
M  END
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PDB for NP0001261 (9-Methyluric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       3.864  -2.073   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END
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3D PDB for NP0001261 (9-Methyluric acid)

COMPND    HMDB0001973
HETATM    1  C1  UNL     1      -2.292  -1.373  -0.012  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.407  -0.205   0.006  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.763   1.091   0.031  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.936   1.554   0.043  1.00  0.00           O  
HETATM    5  N2  UNL     1      -0.668   1.867   0.041  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.428   1.064   0.023  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.794   1.333   0.023  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.187   2.508   0.043  1.00  0.00           O  
HETATM    9  N3  UNL     1       2.660   0.305   0.001  1.00  0.00           N  
HETATM   10  C5  UNL     1       2.162  -0.943  -0.020  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.986  -1.896  -0.040  1.00  0.00           O  
HETATM   12  N4  UNL     1       0.846  -1.222  -0.020  1.00  0.00           N  
HETATM   13  C6  UNL     1      -0.065  -0.222   0.001  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.236  -1.170  -0.534  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.514  -1.729   1.011  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.757  -2.152  -0.622  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.590   2.913   0.060  1.00  0.00           H  
HETATM   18  H5  UNL     1       3.709   0.465   0.001  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.458  -2.188  -0.036  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   13
CONECT    3    4    4    5
CONECT    5    6   17
CONECT    6    7   13   13
CONECT    7    8    8    9
CONECT    9   10   18
CONECT   10   11   11   12
CONECT   12   13   19
END
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SMILES for NP0001261 (9-Methyluric acid)

CN1C(=O)NC2=C1NC(=O)NC2=O
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INCHI for NP0001261 (9-Methyluric acid)

InChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)
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View in JSmol
Synonyms
ValueSource
9-MethylateGenerator
9-Methylic acidGenerator
7,9-Dihydro-9-methyl-1H-purine-2,6,8(3H)-trioneHMDB
9-Methyl-2,6,8-trihydroxypurineHMDB
MUAHMDB
9-Methyl urateHMDB
9-Methyluric acidMeSH
Chemical FormulaC6H6N4O3
Average Mass182.1368 Da
Monoisotopic Mass182.04399 Da
IUPAC Name9-methyl-2,3,6,7,8,9-hexahydro-1H-purine-2,6,8-trione
Traditional Name9-methyl uric acid
CAS Registry Number55441-71-9
SMILES
CN1C(=O)NC2=C1NC(=O)NC2=O
InChI Identifier
InChI=1S/C6H6N4O3/c1-10-3-2(7-6(10)13)4(11)9-5(12)8-3/h1H3,(H,7,13)(H2,8,9,11,12)
InChI KeyXJEJWDFDVPDMAS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentXanthines
Alternative Parents
Substituents
  • Xanthine
  • 6-oxopurine
  • Purinone
  • Alkaloid or derivatives
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Urea
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.021 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP-1ALOGPS
logP-1.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)7.25ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area90.54 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.53 m³·mol⁻¹ChemAxon
Polarizability15.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001973
DrugBank IDDB03293
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022772
KNApSAcK IDNot Available
Chemspider ID97755
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound108714
PDB IDMUA
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Morris GS, Simmonds HA, Davies PM: Use of biological fluids for the rapid diagnosis of potentially lethal inherited disorders of human purine and pyrimidine metabolism. Biomed Chromatogr. 1986 Jun;1(3):109-18. [PubMed:3506820 ]
  2. Safranow K, Machoy Z: Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 May 25;819(2):229-35. [PubMed:15833286 ]
  3. Safranow K: [Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)]. Ann Acad Med Stetin. 2000;46:35-49. [PubMed:11712316 ]
  4. Caubet MS, Comte B, Brazier JL: Determination of urinary 13C-caffeine metabolites by liquid chromatography-mass spectrometry: the use of metabolic ratios to assess CYP1A2 activity. J Pharm Biomed Anal. 2004 Feb 4;34(2):379-89. [PubMed:15013152 ]
  5. Asami H, Saigusa H: Multiple hydrogen-bonding interactions of uric acid/9-methyluric acid with melamine identified by infrared spectroscopy. J Phys Chem B. 2014 May 8;118(18):4851-7. doi: 10.1021/jp502635w. Epub 2014 Apr 23. [PubMed:24731134 ]