Showing metabocard for 2-Methoxy-3-isobutylpyrazine (MMDBc0033558)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:53:32 UTC
Update Date2022-08-31 22:36:44 UTC
Metabolite IDMMDBc0033558
Metabolite Identification
Common Name2-Methoxy-3-isobutylpyrazine
Description2-Methoxy-3-isobutylpyrazine is a 3-alkyl-2-methoxypyrazine, which are important compounds for the aroma of wines. 2-Methoxy-3-isobutylpyrazine has been related with the green and vegetative aromas characteristic of some wines made with Cabernet Sauvignon, Sauvignon blanc, Merlot or Cabernet Franc grapes. It it is typically found at 15-30 ng/L in these wines. The origin of 3-alkyl-2-methoxypyrazines is mostly endogenous as these compounds are part of the chemicals produced in the first stages of grape development. [PMID: 21227432 ]
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1240ce8f98>

PRZ
  Mrv0541 02231217442D          

 12 12  0  0  0  0            999 V2000
    0.1744    1.6210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    0.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    0.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    1.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400    2.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f1240ce8f98>

HMDB0031860
     RDKit          3D
2-Methoxy-3-(2-methylpropyl)pyrazine
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.0916   -2.1866    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -1.5629   -0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789   -0.1905   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406    0.5784    0.2385 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    1.9307    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977    2.4834    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402    1.6999   -0.1341 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317    0.3544   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -0.5343   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    0.1609   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    0.9442    0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -0.9238   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275   -1.6225    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.2062    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6545   -2.2584   -0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072    2.5167    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115    3.5728    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0555   -1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983   -1.2992    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    0.8338   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    0.2894    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    1.8185    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    1.2782    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -1.3594   -2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349   -1.7678   -0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.4942   -0.8971 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  8  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  6 17  1  0
  9 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f1240ce8f98>

PRZ
  Mrv0541 02231217442D          

 12 12  0  0  0  0            999 V2000
    0.1744    1.6210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    0.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    0.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545    1.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400    2.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -0.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5400   -0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2545   -0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033558

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=NC=CN=C1CC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3

> <INCHI_KEY>
UXFSPRAGHGMRSQ-UHFFFAOYSA-N

> <FORMULA>
C9H14N2O

> <MOLECULAR_WEIGHT>
166.2203

> <EXACT_MASS>
166.11061308

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.380994541168764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-3-(2-methylpropyl)pyrazine

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.5381810036666668

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.9760616216891669

> <JCHEM_POLAR_SURFACE_AREA>
35.010000000000005

> <JCHEM_REFRACTIVITY>
46.8889

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isobutyl-3-methoxypyrazine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f1240ce8f98>

HMDB0031860
     RDKit          3D
2-Methoxy-3-(2-methylpropyl)pyrazine
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.0916   -2.1866    0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -1.5629   -0.1257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789   -0.1905   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7406    0.5784    0.2385 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6432    1.9307    0.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977    2.4834    0.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3402    1.6999   -0.1341 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4317    0.3544   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6926   -0.5343   -0.5306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9986    0.1609   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    0.9442    0.4732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0439   -0.9238   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275   -1.6225    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9167   -3.2062    0.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6545   -2.2584   -0.8787 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5072    2.5167    0.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115    3.5728    0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0555   -1.4928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7983   -1.2992    0.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952    0.8338   -1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1442    0.2894    1.0728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    1.8185    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    1.2782    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724   -1.3594   -2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349   -1.7678   -0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0486   -0.4942   -0.8971 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  8  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  5 16  1  0
  6 17  1  0
  9 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 11 22  1  0
 11 23  1  0
 12 24  1  0
 12 25  1  0
 12 26  1  0
M  END
Download

PDB for #<Metabolite:0x00007f1240ce8f98>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PRZ                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.326   3.026   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.326   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.008   0.716   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.342   1.486   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.342   3.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.008   3.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.659   0.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659  -0.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.993  -1.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.326  -1.594   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.008  -0.824   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.342  -1.594   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for #<Metabolite:0x00007f1240ce8f98>

COMPND    HMDB0031860
HETATM    1  C1  UNL     1       3.092  -2.187   0.068  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.828  -1.563  -0.126  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.679  -0.190  -0.036  1.00  0.00           C  
HETATM    4  N1  UNL     1       2.741   0.578   0.239  1.00  0.00           N  
HETATM    5  C3  UNL     1       2.643   1.931   0.337  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.398   2.483   0.141  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.340   1.700  -0.134  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.432   0.354  -0.233  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.693  -0.534  -0.531  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.999   0.161  -0.719  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.459   0.944   0.473  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.044  -0.924  -1.017  1.00  0.00           C  
HETATM   13  H1  UNL     1       3.628  -1.622   0.857  1.00  0.00           H  
HETATM   14  H2  UNL     1       2.917  -3.206   0.444  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.654  -2.258  -0.879  1.00  0.00           H  
HETATM   16  H4  UNL     1       3.507   2.517   0.557  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.311   3.573   0.218  1.00  0.00           H  
HETATM   18  H6  UNL     1      -0.458  -1.056  -1.493  1.00  0.00           H  
HETATM   19  H7  UNL     1      -0.798  -1.299   0.259  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.995   0.834  -1.614  1.00  0.00           H  
HETATM   21  H9  UNL     1      -3.144   0.289   1.073  1.00  0.00           H  
HETATM   22  H10 UNL     1      -3.095   1.818   0.174  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.628   1.278   1.130  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.872  -1.359  -2.018  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.935  -1.768  -0.277  1.00  0.00           H  
HETATM   26  H14 UNL     1      -4.049  -0.494  -0.897  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5
CONECT    5    6    6   16
CONECT    6    7   17
CONECT    7    8    8
CONECT    8    9
CONECT    9   10   18   19
CONECT   10   11   12   20
CONECT   11   21   22   23
CONECT   12   24   25   26
END
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SMILES for #<Metabolite:0x00007f1240ce8f98>

COC1=NC=CN=C1CC(C)C
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INCHI for #<Metabolite:0x00007f1240ce8f98>

InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3
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Synonyms
ValueSource
1DZKHMDB
2-Isobutyl-3-methoxy-pyrazineHMDB
2-Isobutyl-3-methoxypyrazineHMDB
2-Isobutyl-3-methoxypyrazine, 8ciHMDB
2-Methoxy-3-(2-methyl-propyl) pyrazineHMDB
2-Methoxy-3-(2-methylpropyl)-pyrazineHMDB
2-Methoxy-3-isobutylpyrazineHMDB, MeSH
3-Isobutyl-2-methoxypyrazineHMDB, MeSH
3-Methoxy-2-isobutylpyrazineHMDB
FEMA 3132HMDB
GalbazineHMDB
IBMPHMDB
PRZHMDB
Pyrazine, 2-(2-methylpropyl)-3-methoxyHMDB
Pyrazine, 2-isobutyl-3-methoxyHMDB
Pyrazine, 2-methoxy, 3-isobutylHMDB
Pyrazine, 3-methoxy-2-(2-methylpropyl)HMDB
Molecular FormulaC9H14N2O
Average Mass166.2203
Monoisotopic Mass166.11061308
IUPAC Name2-methoxy-3-(2-methylpropyl)pyrazine
Traditional Name2-isobutyl-3-methoxypyrazine
CAS Registry Number24683-00-9
SMILES
COC1=NC=CN=C1CC(C)C
InChI Identifier
InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3
InChI KeyUXFSPRAGHGMRSQ-UHFFFAOYSA-N