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Showing metabocard for 2-Ethyl-3,5-dimethylpyrazine (HMDB0040299)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:49:55 UTC
Update Date2023-02-21 17:28:09 UTC
HMDB IDHMDB0040299
Secondary Accession Numbers
  • HMDB40299
Metabolite Identification
Common Name2-Ethyl-3,5-dimethylpyrazine
Description2-Ethyl-3,5-dimethylpyrazine 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. 2-Ethyl-3,5-dimethylpyrazine is a burnt almonds, coffee, and potato tasting compound. 2-Ethyl-3,5-dimethylpyrazine has been detected, but not quantified in, several different foods, such as tortilla chip, green tea, cereals and cereal products, teas (Camellia sinensis), and green vegetables. This could make 2-ethyl-3,5-dimethylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Ethyl-3,5-dimethylpyrazine.
Structure
Data?1677000489
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)


  Mrv1652304272018152D          

 10 10  0  0  0  0            999 V2000
   -0.4125    2.1434    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    1.4290    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   -0.7145    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    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  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 10  2  0  0  0  0
  8  9  2  0  0  0  0
M  END
Download

3D MOL for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

HMDB0040299
     RDKit          3D
2-Ethyl-3,5-dimethylpyrazine
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.7823   -0.4803   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    0.0095    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298   -0.1525    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -1.1746    1.1416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -1.3746    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.4654    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -0.6195    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207    0.5577   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.7561   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026    1.8822   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    0.2869   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4450   -1.3689   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993   -0.8075   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795   -0.5952    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258    1.0329    0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -2.2062    1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659   -1.6078   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323    0.1439   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386   -0.4724    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662    2.6894   -1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    2.3838   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460    1.5824   -1.8683 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  3  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 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 HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)


  Mrv1652304272018152D          

 10 10  0  0  0  0            999 V2000
   -0.4125    2.1434    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    1.4290    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   -0.7145    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    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  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 10  2  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040299

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1=NC=C(C)N=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2/c1-4-8-7(3)10-6(2)5-9-8/h5H,4H2,1-3H3

> <INCHI_KEY>
JZBCTZLGKSYRSF-UHFFFAOYSA-N

> <FORMULA>
C8H12N2

> <MOLECULAR_WEIGHT>
136.1943

> <EXACT_MASS>
136.100048394

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.880172197593655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-3,5-dimethylpyrazine

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
0.6325473160000005

> <ALOGPS_LOGS>
-0.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0188851388263607

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
40.1456

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.15e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl-3,5-dimethylpyrazine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

HMDB0040299
     RDKit          3D
2-Ethyl-3,5-dimethylpyrazine
 22 22  0  0  0  0  0  0  0  0999 V2000
    2.7823   -0.4803   -0.5950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0973    0.0095    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298   -0.1525    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -1.1746    1.1416 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -1.3746    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0508   -0.4654    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5307   -0.6195    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207    0.5577   -0.3182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739    0.7561   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6026    1.8822   -0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010    0.2869   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4450   -1.3689   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9993   -0.8075   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795   -0.5952    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4258    1.0329    0.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8459   -2.2062    1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659   -1.6078   -0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9323    0.1439   -0.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0386   -0.4724    1.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662    2.6894   -1.0614 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651    2.3838   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9460    1.5824   -1.8683 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
  6  8  1  0
  8  9  2  0
  9 10  1  0
  9  3  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 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 HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

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      -0.770   4.001   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      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.540   2.667   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      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   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    4                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    1    8                                                       
CONECT    5    6    9                                                       
CONECT    6    2    5   10                                                  
CONECT    7    3    8   10                                                  
CONECT    8    4    7    9                                                  
CONECT    9    5    8                                                       
CONECT   10    6    7                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

COMPND    HMDB0040299
HETATM    1  C1  UNL     1       2.782  -0.480  -0.595  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.097   0.009   0.676  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.630  -0.152   0.542  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.010  -1.175   1.142  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.339  -1.375   1.044  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.051  -0.465   0.284  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.531  -0.620   0.134  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.421   0.558  -0.318  1.00  0.00           N  
HETATM    9  C7  UNL     1      -0.074   0.756  -0.217  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.603   1.882  -0.878  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.401   0.287  -1.083  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.445  -1.369  -0.379  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.999  -0.807  -1.330  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.479  -0.595   1.555  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.426   1.033   0.838  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.846  -2.206   1.535  1.00  0.00           H  
HETATM   17  H7  UNL     1      -3.766  -1.608  -0.319  1.00  0.00           H  
HETATM   18  H8  UNL     1      -3.932   0.144  -0.566  1.00  0.00           H  
HETATM   19  H9  UNL     1      -4.039  -0.472   1.111  1.00  0.00           H  
HETATM   20  H10 UNL     1      -0.166   2.689  -1.061  1.00  0.00           H  
HETATM   21  H11 UNL     1       1.365   2.384  -0.246  1.00  0.00           H  
HETATM   22  H12 UNL     1       0.946   1.582  -1.868  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4    4    9
CONECT    4    5
CONECT    5    6    6   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 HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

CCC1=NC=C(C)N=C1C
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INCHI for HMDB0040299 (2-Ethyl-3,5-dimethylpyrazine)

InChI=1S/C8H12N2/c1-4-8-7(3)10-6(2)5-9-8/h5H,4H2,1-3H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,6-Dimethyl-3-ethyl-pyrazineHMDB
2,6-Dimethyl-3-ethylpyrazineHMDB
2-Ethyl-3,5(6)-dimethyl-pyrazineHMDB
2-Ethyl-3,5-dimethyl pyrazineHMDB
2-Ethyl-3,5-dimethyl-pyrazineHMDB
3,5-Dimethyl-2-ethyl-pyrazineHMDB
3,5-Dimethyl-2-ethylpyrazineHMDB
3-Ethyl-2,6-dimethylpyrazineHMDB
FEMA 3150HMDB
Pyrazine, 3-ethyl-2,6-dimethylHMDB
Chemical FormulaC8H12N2
Average Molecular Weight136.1943
Monoisotopic Molecular Weight136.100048394
IUPAC Name2-ethyl-3,5-dimethylpyrazine
Traditional Name2-ethyl-3,5-dimethylpyrazine
CAS Registry Number13925-07-0
SMILES
CCC1=NC=C(C)N=C1C
InChI Identifier
InChI=1S/C8H12N2/c1-4-8-7(3)10-6(2)5-9-8/h5H,4H2,1-3H3
InChI KeyJZBCTZLGKSYRSF-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
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point180.00 to 182.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1473 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.457 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility21.5 g/LALOGPS
logP1.59ALOGPS
logP0.63ChemAxon
logS-0.8ALOGPS
pKa (Strongest Basic)2.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.15 m³·mol⁻¹ChemAxon
Polarizability15.88 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]+128.99731661259
DarkChem[M-H]-128.25331661259
DeepCCS[M+H]+133.30630932474
DeepCCS[M-H]-129.47830932474
DeepCCS[M-2H]-166.84730932474
DeepCCS[M+Na]+142.21430932474
AllCCS[M+H]+128.632859911
AllCCS[M+H-H2O]+124.032859911
AllCCS[M+NH4]+132.932859911
AllCCS[M+Na]+134.232859911
AllCCS[M-H]-131.832859911
AllCCS[M+Na-2H]-133.732859911
AllCCS[M+HCOO]-135.832859911

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. 2.7 minutes32390414
Predicted by Siyang on May 30, 20228.9389 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.13 minutes32390414

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Ethyl-3,5-dimethylpyrazineCCC1=C(C)N=C(C)C=N11429.3Standard polar33892256
2-Ethyl-3,5-dimethylpyrazineCCC1=C(C)N=C(C)C=N11033.5Standard non polar33892256
2-Ethyl-3,5-dimethylpyrazineCCC1=C(C)N=C(C)C=N11083.9Semi standard non polar33892256
Spectra
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 IDFDB020021
KNApSAcK IDNot Available
Chemspider ID24536
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26334
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1008281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .