Showing metabocard for 1-Methylxanthine (MMDBc0000442)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:37:51 UTC
Update Date2024-04-30 19:32:25 UTC
Metabolite IDMMDBc0000442
Metabolite Identification
Common Name1-Methylxanthine
Description1-Methylxanthine is one of the major metabolites of caffeine in humans. The oxidation of 1-methylxanthine to 1-methyluric acid occurs so rapidly that the parent compound could not be detected in plasma, and only low concentrations could be detected in the brain (PMID: 28863020 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fb7e8348530>

  Mrv1652309042000332D          

 12 13  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   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    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fb7e8348530>

HMDB0010738
     RDKit          3D
1-Methylxanthine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.7073   -0.6362   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -0.1314    0.0340 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056    1.1394    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    1.8439    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347    1.6592    0.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100    0.9054    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5423    1.1099    0.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -0.0059   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456   -0.9366   -0.4317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.3914   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684   -0.8801   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -2.0759   -0.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136   -0.2562    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -1.7235    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -0.2338   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    2.6564    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2793   -0.1309   -0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -1.9122   -0.7382 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  2  1  0
 10  6  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007fb7e8348530>

  Mrv1652309042000332D          

 12 13  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   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    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   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    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000442

> <DATABASE_NAME>
MIME

> <SMILES>
CN1C(=O)NC2=C(NC=N2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)

> <INCHI_KEY>
MVOYJPOZRLFTCP-UHFFFAOYSA-N

> <FORMULA>
C6H6N4O2

> <MOLECULAR_WEIGHT>
166.1374

> <EXACT_MASS>
166.049075456

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.919572956844883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-0.40012594174161076

> <ALOGPS_LOGS>
-1.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.732910917910083

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1098722859664147

> <JCHEM_PKA_STRONGEST_BASIC>
1.665090512988736

> <JCHEM_POLAR_SURFACE_AREA>
81.58

> <JCHEM_REFRACTIVITY>
41.264

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methylxanthine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fb7e8348530>

HMDB0010738
     RDKit          3D
1-Methylxanthine
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.7073   -0.6362   -0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3476   -0.1314    0.0340 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056    1.1394    0.4075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327    1.8439    0.6856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347    1.6592    0.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100    0.9054    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5423    1.1099    0.1754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -0.0059   -0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456   -0.9366   -0.4317 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0274   -0.3914   -0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684   -0.8801   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4638   -2.0759   -0.6141 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136   -0.2562    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7635   -1.7235    0.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2715   -0.2338   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627    2.6564    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2793   -0.1309   -0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3816   -1.9122   -0.7382 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
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  2  1  0
 10  6  2  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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PDB for #<Metabolite:0x00007fb7e8348530>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.530   4.383   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END
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3D PDB for #<Metabolite:0x00007fb7e8348530>

COMPND    HMDB0010738
HETATM    1  C1  UNL     1       2.707  -0.636  -0.037  1.00  0.00           C  
HETATM    2  N1  UNL     1       1.348  -0.131   0.034  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.106   1.139   0.408  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.133   1.844   0.686  1.00  0.00           O  
HETATM    5  N2  UNL     1      -0.135   1.659   0.490  1.00  0.00           N  
HETATM    6  C3  UNL     1      -1.210   0.905   0.194  1.00  0.00           C  
HETATM    7  N3  UNL     1      -2.542   1.110   0.175  1.00  0.00           N  
HETATM    8  C4  UNL     1      -3.190  -0.006  -0.205  1.00  0.00           C  
HETATM    9  N4  UNL     1      -2.246  -0.937  -0.432  1.00  0.00           N  
HETATM   10  C5  UNL     1      -1.027  -0.391  -0.191  1.00  0.00           C  
HETATM   11  C6  UNL     1       0.268  -0.880  -0.261  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.464  -2.076  -0.614  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.214  -0.256   0.898  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.763  -1.723   0.011  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.271  -0.234  -0.896  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.263   2.656   0.787  1.00  0.00           H  
HETATM   17  H5  UNL     1      -4.279  -0.131  -0.310  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.382  -1.912  -0.738  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   11
CONECT    3    4    4    5
CONECT    5    6   16
CONECT    6    7   10   10
CONECT    7    8    8
CONECT    8    9   17
CONECT    9   10   18
CONECT   10   11
CONECT   11   12   12
END
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SMILES for #<Metabolite:0x00007fb7e8348530>

CN1C(=O)NC2=C(NC=N2)C1=O
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INCHI for #<Metabolite:0x00007fb7e8348530>

InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
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SynonymsNot Available
Molecular FormulaC6H6N4O2
Average Mass166.1374
Monoisotopic Mass166.049075456
IUPAC Name2-hydroxy-1-methyl-6,9-dihydro-1H-purin-6-one
Traditional Name1-methylxanthine
CAS Registry NumberNot Available
SMILES
CN1C(=O)NC2=C(NC=N2)C1=O
InChI Identifier
InChI=1S/C6H6N4O2/c1-10-5(11)3-4(8-2-7-3)9-6(10)12/h2H,1H3,(H,7,8)(H,9,12)
InChI KeyMVOYJPOZRLFTCP-UHFFFAOYSA-N