Showing metabocard for Tetramethylpyrazine (MMDBc0015898)

Plant
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 06:39:34 UTC
Update Date2024-09-29 11:07:07 UTC
Metabolite IDMMDBc0015898
Metabolite Identification
Common NameTetramethylpyrazine
DescriptionTetramethylpyrazine, or 2,3,5,6-tetramethylpyrazine, or TMP and also known as FEMA 3237, is an alkylpyrazine and belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Tetramethylpyrazine is a moderately basic compound with white crystals that are soluble in alcohol, fixed oils, propylene glycol and water. Its odor is described as nutty, musty and vanilla with dry, brown cocoa nuances and it taste is described as nutty, musty, cocoa, drying, peanut-like with raw coffee notes. Tetramethylpyrazine has been detected in roasted beef, cheddar cheese, dairy products, red and yellow bell peppers (c. annuum), potato, filberts, boiled egg, coconut endosperm, cocoa products, green tea, tea leaf, soybean products, soybean seed, macadamia nut, peanut, meat, guava fruit, shrimp, rum and whiskey. This could make tetramethylpyrazine a potential biomarker for the consumption of these foods. It has been used as a perfuming agent in soaps, detergents, toiletries, fabric softeners, bleach, alcoholic beverages, and fine fragrances. Its biosynthesis in Bacillus involves the amination of acetoin, the latter being derived from pyruvate (doi:10.1038/1951103a0). It exhibits potential nootropic (improved executive function PMID:23916742 ) and anti-inflammatory activities against induced cerebral ischemic in rats (PMID:23644042 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fc950eeedc0>


  Mrv1652304272018192D          

 10 10  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fc950eeedc0>

HMDB0036584
     RDKit          3D
Tetramethylpyrazine
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.4682    1.4235    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660    0.7223    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3844   -0.1905 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    0.6819   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479    1.3703   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576   -0.6848   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4551   -1.3976   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0037   -1.3303    0.1884 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642   -0.6409    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -1.3284    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213    2.5252    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    1.2006    1.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753    1.1358   -0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.9796    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589    2.4535   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044    1.0499   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -1.0169    0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -2.4610    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -1.3385   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.7876    0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5058   -1.6500    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -2.2909   -0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fc950eeedc0>


  Mrv1652304272018192D          

 10 10  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015898

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=NC(C)=C(C)N=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3

> <INCHI_KEY>
FINHMKGKINIASC-UHFFFAOYSA-N

> <FORMULA>
C8H12N2

> <MOLECULAR_WEIGHT>
136.1943

> <EXACT_MASS>
136.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.023429816184183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
tetramethylpyrazine

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.06338163800000016

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.189242582387245

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
40.1102

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazine, tetramethyl-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007fc950eeedc0>

HMDB0036584
     RDKit          3D
Tetramethylpyrazine
 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.4682    1.4235    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1660    0.7223    0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3844   -0.1905 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    0.6819   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479    1.3703   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576   -0.6848   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4551   -1.3976   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0037   -1.3303    0.1884 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642   -0.6409    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421   -1.3284    0.5358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213    2.5252    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    1.2006    1.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1753    1.1358   -0.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144    0.9796    0.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589    2.4535   -0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8044    1.0499   -1.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1993   -1.0169    0.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -2.4610    0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -1.3385   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190   -0.7876    0.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5058   -1.6500    1.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -2.2909   -0.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  5 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 10 21  1  0
 10 22  1  0
M  END
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PDB for #<Metabolite:0x00007fc950eeedc0>

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.770   1.334   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    1    6    9                                                  
CONECT    6    2    5   10                                                  
CONECT    7    3    8    9                                                  
CONECT    8    4    7   10                                                  
CONECT    9    5    7                                                       
CONECT   10    6    8                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x00007fc950eeedc0>

COMPND    HMDB0036584
HETATM    1  C1  UNL     1      -2.468   1.424   0.155  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.166   0.722   0.067  1.00  0.00           C  
HETATM    3  N1  UNL     1      -0.006   1.384  -0.191  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.153   0.682  -0.258  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.448   1.370  -0.538  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.158  -0.685  -0.067  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.455  -1.398  -0.153  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.004  -1.330   0.188  1.00  0.00           N  
HETATM    9  C7  UNL     1      -1.164  -0.641   0.258  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.442  -1.328   0.536  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.321   2.525   0.134  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.996   1.201   1.127  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.175   1.136  -0.635  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.214   0.980   0.166  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.359   2.453  -0.537  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.804   1.050  -1.557  1.00  0.00           H  
HETATM   17  H7  UNL     1       3.199  -1.017   0.584  1.00  0.00           H  
HETATM   18  H8  UNL     1       2.261  -2.461   0.159  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.926  -1.339  -1.143  1.00  0.00           H  
HETATM   20  H10 UNL     1      -3.319  -0.788   0.170  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.506  -1.650   1.593  1.00  0.00           H  
HETATM   22  H12 UNL     1      -2.409  -2.291  -0.057  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    3    9
CONECT    3    4
CONECT    4    5    6    6
CONECT    5   14   15   16
CONECT    6    7    8
CONECT    7   17   18   19
CONECT    8    9    9
CONECT    9   10
CONECT   10   20   21   22
END
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SMILES for #<Metabolite:0x00007fc950eeedc0>

CC1=NC(C)=C(C)N=C1C
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INCHI for #<Metabolite:0x00007fc950eeedc0>

InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
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Synonyms
ValueSource
2,3,5,6,-Tetramethyl-1,4-pyrazineChEBI
2,3,5,6-TetramethylpyrazineChEBI
FEMA 3237ChEBI
FEMA no. 3237ChEBI
LiqustrazineChEBI
TMPChEBI
TMPZMeSH
ChuanxiongzineMeSH
LigustrazineMeSH
Tetramethyl pyrazineMeSH
Tetramethylpyrazine hydrochlorideMeSH
2356-Tetramethyl-pyrazineChEMBL, HMDB
2356-TetramethylpyrazineChEMBL, HMDB
LigustizineHMDB
TetramethylpyrazinHMDB
TetrapyrazineHMDB
TMP?HMDB
Molecular FormulaC8H12N2
Average Mass136.1943
Monoisotopic Mass136.100048394
IUPAC Nametetramethylpyrazine
Traditional Namepyrazine, tetramethyl-
CAS Registry NumberNot Available
SMILES
CC1=NC(C)=C(C)N=C1C
InChI Identifier
InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
InChI KeyFINHMKGKINIASC-UHFFFAOYSA-N