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Showing metabocard for Tetramethylpyrazine (HMDB0036584)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:44:31 UTC
Update Date2023-02-21 17:25:26 UTC
HMDB IDHMDB0036584
Secondary Accession Numbers
  • HMDB36584
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
Data?1677000326
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0036584 (Tetramethylpyrazine)


  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 HMDB0036584 (Tetramethylpyrazine)

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 HMDB0036584 (Tetramethylpyrazine)


  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>
HMDB0036584

> <DATABASE_NAME>
hmdb

> <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 HMDB0036584 (Tetramethylpyrazine)

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

PDB for HMDB0036584 (Tetramethylpyrazine)

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 HMDB0036584 (Tetramethylpyrazine)

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 HMDB0036584 (Tetramethylpyrazine)

CC1=NC(C)=C(C)N=C1C
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INCHI for HMDB0036584 (Tetramethylpyrazine)

InChI=1S/C8H12N2/c1-5-6(2)10-8(4)7(3)9-5/h1-4H3
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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Nametetramethylpyrazine
Traditional Namepyrazine, tetramethyl-
CAS Registry Number1124-11-4
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
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazines
Alternative Parents
Substituents
  • Pyrazine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling Point190.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility7007 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.28Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility15 g/LALOGPS
logP1.46ALOGPS
logP0.063ChemAxon
logS-0.96ALOGPS
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.11 m³·mol⁻¹ChemAxon
Polarizability16.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.92331661259
DarkChem[M-H]-126.26331661259
DeepCCS[M+H]+136.0430932474
DeepCCS[M-H]-133.11730932474
DeepCCS[M-2H]-169.88830932474
DeepCCS[M+Na]+145.21130932474
AllCCS[M+H]+129.032859911
AllCCS[M+H-H2O]+124.432859911
AllCCS[M+NH4]+133.232859911
AllCCS[M+Na]+134.432859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-131.632859911
AllCCS[M+HCOO]-133.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.46 minutes32390414
Predicted by Siyang on May 30, 20228.7788 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.65 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid153.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid394.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid296.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid105.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid167.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid47.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid284.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid269.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)546.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid651.5 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid47.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1126.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid199.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid250.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate533.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA496.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water380.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TetramethylpyrazineCC1=NC(C)=C(C)N=C1C1450.6Standard polar33892256
TetramethylpyrazineCC1=NC(C)=C(C)N=C1C1044.8Standard non polar33892256
TetramethylpyrazineCC1=NC(C)=C(C)N=C1C1079.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetramethylpyrazine EI-B (Non-derivatized)splash10-0udu-9300000000-5d317f2dc804e043f2b92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetramethylpyrazine EI-B (Non-derivatized)splash10-0udu-9300000000-5d317f2dc804e043f2b92018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetramethylpyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-68c7df3c47d48f17b27b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetramethylpyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-9300000000-33fe7599448be6d9a1f02015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine Orbitrap 5V, positive-QTOFsplash10-000i-2900000000-825affe0aeefbf7abe2a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine Orbitrap 6V, positive-QTOFsplash10-052r-9800000000-0e691fbfc32545d1b1aa2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine Orbitrap 8V, positive-QTOFsplash10-0a4r-9300000000-bd32b31ff50928daf2612020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine Orbitrap 9V, positive-QTOFsplash10-0pb9-9100000000-80bdd2f5e9e721213dba2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine Orbitrap 11V, positive-QTOFsplash10-0ue9-9000000000-a8ff866cfac430f29e972020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine n/a 9V, positive-QTOFsplash10-0002-9000000000-acc42c048c36b7492ded2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tetramethylpyrazine n/a 9V, positive-QTOFsplash10-0a4i-9000000000-e10afcdf21ddde828d7c2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 10V, Positive-QTOFsplash10-000i-0900000000-4ea5d7454e8109b365d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 20V, Positive-QTOFsplash10-000i-0900000000-f797c5b258bf45ed58012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 40V, Positive-QTOFsplash10-0udl-9100000000-465d4f375262ee01acb32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 10V, Negative-QTOFsplash10-000i-0900000000-ca8b41e13886eb5f390f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 20V, Negative-QTOFsplash10-000i-0900000000-9c6dd6eec8dafc56f8252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 40V, Negative-QTOFsplash10-00kr-4900000000-a04f3b4c94a247e992322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 10V, Positive-QTOFsplash10-000i-0900000000-ac299646e14f1770c4b52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 20V, Positive-QTOFsplash10-000i-3900000000-997da2b6ee4b7359f4d62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 40V, Positive-QTOFsplash10-00kf-9000000000-38545d1df73cc3f6ffdc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 10V, Negative-QTOFsplash10-000i-1900000000-22a6232d9fbf0c94bc772021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 20V, Negative-QTOFsplash10-000l-9800000000-d3294b56735618c40d872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetramethylpyrazine 40V, Negative-QTOFsplash10-00kf-9100000000-63057d96e8a5e31397952021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015495
KNApSAcK IDC00056171
Chemspider ID13658
KEGG Compound IDNot Available
BioCyc IDCPD-15901
BiGG IDNot Available
Wikipedia LinkTetramethylpyrazine
METLIN IDNot Available
PubChem Compound14296
PDB IDNot Available
ChEBI ID133246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009291
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhu XL, Xiong LZ, Wang Q, Liu ZG, Ma X, Zhu ZH, Hu S, Gong G, Chen SY: Therapeutic time window and mechanism of tetramethylpyrazine on transient focal cerebral ischemia/reperfusion injury in rats. Neurosci Lett. 2009 Jan 2;449(1):24-7. doi: 10.1016/j.neulet.2008.09.007. Epub 2008 Sep 6. [PubMed:18790005 ]
  2. Dai XZ, Bache RJ: Coronary and systemic hemodynamic effects of tetramethylpyrazine in the dog. J Cardiovasc Pharmacol. 1985 Sep-Oct;7(5):841-9. [PubMed:2413290 ]
  3. Li M, Handa S, Ikeda Y, Goto S: Specific inhibiting characteristics of tetramethylpyrazine, one of the active ingredients of the Chinese herbal medicine 'Chuanxiong,' on platelet thrombus formation under high shear rates. Thromb Res. 2001 Oct 1;104(1):15-28. [PubMed:11583735 ]
  4. Wu W, Yu X, Luo XP, Yang SH, Zheng D: Tetramethylpyrazine protects against scopolamine-induced memory impairments in rats by reversing the cAMP/PKA/CREB pathway. Behav Brain Res. 2013 Sep 15;253:212-6. doi: 10.1016/j.bbr.2013.07.052. Epub 2013 Aug 2. [PubMed:23916742 ]
  5. Kao TK, Chang CY, Ou YC, Chen WY, Kuan YH, Pan HC, Liao SL, Li GZ, Chen CJ: Tetramethylpyrazine reduces cellular inflammatory response following permanent focal cerebral ischemia in rats. Exp Neurol. 2013 Sep;247:188-201. doi: 10.1016/j.expneurol.2013.04.010. Epub 2013 Apr 30. [PubMed:23644042 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .