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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:57:36 UTC

Update Date

2022-09-22 17:44:19 UTC

HMDB ID

HMDB0245912

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Isobutyl-1-methylxanthine

Description

3-Isobutyl-1-methylxanthine, also known as 1-methyl-3-isobutylxanthine or IBMX, 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. Based on a literature review a significant number of articles have been published on 3-Isobutyl-1-methylxanthine. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-isobutyl-1-methylxanthine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-Isobutyl-1-methylxanthine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0245912
     RDKit          3D
3-Isobutyl-1-methylxanthine
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1965   -0.7911    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0951    0.5379    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.7463   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.5751   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908    0.3230   -0.4181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097    1.2770    0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    2.4899    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760    0.9978    0.4171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2193    2.0821    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464   -0.2609    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.4593    0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -1.2577   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -2.5840   -0.1454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -3.1257   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1162   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -0.9455   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9369   -0.6728    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -1.5151    0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.1088    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    1.3390    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006    1.1729   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    1.4460    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.2344   -0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -0.1425   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109    1.5824   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.3024    1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    2.9986    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    1.7758    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.1952   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788   -2.2368   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16  5  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
M  END

IBM
  Mrv0541 02241213452D          

 16 17  0  0  0  0            999 V2000
   -1.7156   -0.1296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2005   -0.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156   -1.4644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310   -1.2095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310   -0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    0.0280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -0.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -1.2095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165   -2.4470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125    0.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2165    0.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980    1.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980    2.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2125    0.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0245912

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)

> <INCHI_KEY>
APIXJSLKIYYUKG-UHFFFAOYSA-N

> <FORMULA>
C10H14N4O2

> <MOLECULAR_WEIGHT>
222.2438

> <EXACT_MASS>
222.111675712

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.519912244431342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.4356641993333336

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.40813956980946

> <JCHEM_PKA_STRONGEST_BASIC>
2.4238107803722104

> <JCHEM_POLAR_SURFACE_AREA>
69.30000000000001

> <JCHEM_REFRACTIVITY>
57.369

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-isobutyl-1-methylxanthine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245912
     RDKit          3D
3-Isobutyl-1-methylxanthine
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1965   -0.7911    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0951    0.5379    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.7463   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.5751   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908    0.3230   -0.4181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097    1.2770    0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    2.4899    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760    0.9978    0.4171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2193    2.0821    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464   -0.2609    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.4593    0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -1.2577   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -2.5840   -0.1454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -3.1257   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1162   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -0.9455   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9369   -0.6728    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -1.5151    0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.1088    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    1.3390    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006    1.1729   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    1.4460    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.2344   -0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -0.1425   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109    1.5824   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.3024    1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    2.9986    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    1.7758    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.1952   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788   -2.2368   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16  5  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: IBM                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -3.202  -0.242   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -4.108  -1.488   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.202  -2.734   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.738  -2.258   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.738  -0.718   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.404   0.052   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.930  -0.718   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.930  -2.258   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.404  -3.028   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.404  -4.568   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.263   0.052   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.263  -3.028   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.404   1.592   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.930   2.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.930   3.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.263   1.592   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    1    4    6                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9   12                                                  
CONECT    9    4    8   10                                                  
CONECT   10    9                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0245912
HETATM    1  C1  UNL     1       2.197  -0.791   0.914  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.095   0.538   0.198  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.442   0.746  -0.499  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.048   0.575  -0.865  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.291   0.323  -0.418  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.110   1.277   0.005  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.738   2.490   0.040  1.00  0.00           O  
HETATM    8  N2  UNL     1      -2.376   0.998   0.417  1.00  0.00           N  
HETATM    9  C6  UNL     1      -3.219   2.082   0.867  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.846  -0.261   0.411  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.022  -0.459   0.802  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.034  -1.258  -0.016  1.00  0.00           C  
HETATM   13  N3  UNL     1      -2.190  -2.584  -0.145  1.00  0.00           N  
HETATM   14  C9  UNL     1      -1.060  -3.126  -0.624  1.00  0.00           C  
HETATM   15  N4  UNL     1      -0.193  -2.116  -0.792  1.00  0.00           N  
HETATM   16  C10 UNL     1      -0.746  -0.946  -0.431  1.00  0.00           C  
HETATM   17  H1  UNL     1       2.937  -0.673   1.758  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.620  -1.515   0.193  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.248  -1.109   1.378  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.950   1.339   0.951  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.301   1.173  -1.513  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.086   1.446   0.062  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.965  -0.234  -0.644  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.356  -0.143  -1.659  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.111   1.582  -1.356  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.019   2.302   1.931  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.095   2.999   0.223  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.300   1.776   0.803  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.895  -4.195  -0.832  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.779  -2.237  -1.157  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6   16
CONECT    6    7    7    8
CONECT    8    9   10
CONECT    9   26   27   28
CONECT   10   11   11   12
CONECT   12   13   16   16
CONECT   13   14   14
CONECT   14   15   29
CONECT   15   16   30
END

HMDB0245912
     RDKit          3D
3-Isobutyl-1-methylxanthine
 30 31  0  0  0  0  0  0  0  0999 V2000
    2.1965   -0.7911    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0951    0.5379    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4423    0.7463   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.5751   -0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2908    0.3230   -0.4181 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097    1.2770    0.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377    2.4899    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3760    0.9978    0.4171 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2193    2.0821    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464   -0.2609    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.4593    0.8023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337   -1.2577   -0.0157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -2.5840   -0.1454 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0598   -3.1257   -0.6240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1934   -2.1162   -0.7919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -0.9455   -0.4311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9369   -0.6728    1.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6195   -1.5151    0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2476   -1.1088    1.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9501    1.3390    0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006    1.1729   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0865    1.4460    0.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.2344   -0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -0.1425   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1109    1.5824   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0193    2.3024    1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0951    2.9986    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3001    1.7758    0.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8948   -4.1952   -0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7788   -2.2368   -1.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16  5  1  0
 16 12  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
 15 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Methyl-3-(2-methylpropyl)-7H-purine-2,6-dione	ChEBI
1-Methyl-3-isobutylxanthine	ChEBI
3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione	ChEBI
3-Isobutyl-1-methyxanthine	ChEBI
IBMX	ChEBI
3 Isobutyl 1 methylxanthine	HMDB
1 Methyl 3 isobutylxanthine	HMDB
Isobutyltheophylline	HMDB
3-Isobutyl-1-methylxanthine	ChEBI

Chemical Formula

C₁₀H₁₄N₄O₂

Average Molecular Weight

222.2438

Monoisotopic Molecular Weight

222.111675712

IUPAC Name

1-methyl-3-(2-methylpropyl)-2,3,6,9-tetrahydro-1H-purine-2,6-dione

Traditional Name

3-isobutyl-1-methylxanthine

CAS Registry Number

Not Available

SMILES

CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

InChI Identifier

InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)

InChI Key

APIXJSLKIYYUKG-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Xanthines

Alternative Parents

Substituents

Xanthine
6-oxopurine
Purinone
Alkaloid or derivatives
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Urea
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3-isobutyl-1-methylxanthine (CHEBI:43253 )
a small molecule (CPD-5461 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.84	ALOGPS
logP	0.44	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	2.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	57.37 m³·mol⁻¹	ChemAxon
Polarizability	22.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.421	30932474
DeepCCS	[M-H]-	146.063	30932474
DeepCCS	[M-2H]-	179.187	30932474
DeepCCS	[M+Na]+	154.514	30932474
AllCCS	[M+H]+	148.1	32859911
AllCCS	[M+H-H2O]+	144.3	32859911
AllCCS	[M+NH4]+	151.6	32859911
AllCCS	[M+Na]+	152.6	32859911
AllCCS	[M-H]-	151.1	32859911
AllCCS	[M+Na-2H]-	151.4	32859911
AllCCS	[M+HCOO]-	151.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.4094 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.51 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1625.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	283.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	70.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	370.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	409.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	761.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	439.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1174.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	319.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	258.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Isobutyl-1-methylxanthine	CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O	2309.0	Standard polar	33892256
3-Isobutyl-1-methylxanthine	CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O	2106.7	Standard non polar	33892256
3-Isobutyl-1-methylxanthine	CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O	2093.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Isobutyl-1-methylxanthine,1TMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C)C=N2	1984.3	Semi standard non polar	33892256
3-Isobutyl-1-methylxanthine,1TMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C)C=N2	2189.9	Standard non polar	33892256
3-Isobutyl-1-methylxanthine,1TMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C)C=N2	2721.4	Standard polar	33892256
3-Isobutyl-1-methylxanthine,1TBDMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C(C)(C)C)C=N2	2208.7	Semi standard non polar	33892256
3-Isobutyl-1-methylxanthine,1TBDMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C(C)(C)C)C=N2	2361.4	Standard non polar	33892256
3-Isobutyl-1-methylxanthine,1TBDMS,isomer #1	CC(C)CN1C(=O)N(C)C(=O)C2=C1N([Si](C)(C)C(C)(C)C)C=N2	2754.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Isobutyl-1-methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-5910000000-dd00d48d2ce219db988c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Isobutyl-1-methylxanthine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine LC-ESI-qTof , Positive-QTOF	splash10-03xr-3900100000-d4f10d08f06745544691	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine , positive-QTOF	splash10-03xr-3900100000-d4f10d08f06745544691	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 10V, Positive-QTOF	splash10-00di-0190000000-ed2a919c53f3be26f2e9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 20V, Positive-QTOF	splash10-06di-3930000000-95a1923a4392dadd6833	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 40V, Positive-QTOF	splash10-0a4i-9500000000-85dcf34624d52be35336	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 10V, Negative-QTOF	splash10-00di-0290000000-74320dca4a38f07e7eb9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 20V, Negative-QTOF	splash10-00xr-1960000000-c5570519133d6c4dfeff	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 40V, Negative-QTOF	splash10-052v-4900000000-003e9ddbff40e87636b8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 10V, Positive-QTOF	splash10-00di-0090000000-0f3b49643c36bc32e3a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 20V, Positive-QTOF	splash10-00xr-1970000000-a1814fcc4ac7ac81e92e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 40V, Positive-QTOF	splash10-001r-9700000000-de626ddc113b1e076b0a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 10V, Negative-QTOF	splash10-00di-0090000000-14f107ab451165ea0139	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 20V, Negative-QTOF	splash10-014i-0890000000-c427729be9b332b2a539	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Isobutyl-1-methylxanthine 40V, Negative-QTOF	splash10-0670-8900000000-e4998f869a177a74fd4b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07954

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3627

KEGG Compound ID

C13708

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3758

PDB ID

Not Available

ChEBI ID

34795

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3-Isobutyl-1-methylxanthine (HMDB0245912)

MOL for HMDB0245912 (3-Isobutyl-1-methylxanthine)

3D MOL for HMDB0245912 (3-Isobutyl-1-methylxanthine)

3D SDF for HMDB0245912 (3-Isobutyl-1-methylxanthine)

3D-SDF for HMDB0245912 (3-Isobutyl-1-methylxanthine)

PDB for HMDB0245912 (3-Isobutyl-1-methylxanthine)

3D PDB for HMDB0245912 (3-Isobutyl-1-methylxanthine)

SMILES for HMDB0245912 (3-Isobutyl-1-methylxanthine)

INCHI for HMDB0245912 (3-Isobutyl-1-methylxanthine)

Structure for HMDB0245912 (3-Isobutyl-1-methylxanthine)

3D Structure for HMDB0245912 (3-Isobutyl-1-methylxanthine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra