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Showing NP-Card for 2-Ethylpyrazine (NP0001356)

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Record Information
Version2.0
Created at2012-09-11 17:45:57 UTC
Updated at2024-09-03 04:22:06 UTC
NP-MRD IDNP0001356
Natural Product DOIhttps://doi.org/10.57994/2743
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Ethylpyrazine
Description2-Ethylpyrazine, also known as fema 3281 or moldin, 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-Ethylpyrazine is a bitter, cocoa, and musty tasting compound. 2-Ethylpyrazine has been detected, but not quantified, in several different foods, such as asparagus, pulses, cocoa and cocoa products, cereals and cereal products, and tortilla chips.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0001356 (2-Ethylpyrazine)


  Mrv1652304272019192D          

  8  8  0  0  0  0            999 V2000
   -2.0625    0.7145    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   -0.7145    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 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  2  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
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3D MOL for NP0001356 (2-Ethylpyrazine)

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3D SDF for NP0001356 (2-Ethylpyrazine)

  Mrv1652304272019192D          

  8  8  0  0  0  0            999 V2000
   -2.0625    0.7145    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   -0.7145    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 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  2  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=NC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2/c1-2-6-5-7-3-4-8-6/h3-5H,2H2,1H3

> <INCHI_KEY>
KVFIJIWMDBAGDP-UHFFFAOYSA-N

> <FORMULA>
C6H8N2

> <MOLECULAR_WEIGHT>
108.1411

> <EXACT_MASS>
108.068748266

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.662644797923807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethylpyrazine

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.36980697799999995

> <ALOGPS_LOGS>
0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.270611241657058

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
30.9626

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.06e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl pyrazine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0001356 (2-Ethylpyrazine)
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PDB for NP0001356 (2-Ethylpyrazine)
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      -3.850   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.770   1.334   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    7                                                       
CONECT    4    3    8                                                       
CONECT    5    6    7                                                       
CONECT    6    2    5    8                                                  
CONECT    7    3    5                                                       
CONECT    8    4    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0001356 (2-Ethylpyrazine)
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SMILES for NP0001356 (2-Ethylpyrazine)
CCC1=NC=CN=C1
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INCHI for NP0001356 (2-Ethylpyrazine)
InChI=1S/C6H8N2/c1-2-6-5-7-3-4-8-6/h3-5H,2H2,1H3
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View in JSmol
Synonyms
ValueSource
2-Ethyl-1,4-diazineChEBI
FEMA 3281ChEBI
FEMA no. 3281ChEBI
2-Ethyl-pyrazineHMDB
Ethyl-pyrazineHMDB
EthylpyrazineHMDB
MoldinHMDB
Chemical FormulaC6H8N2
Average Mass108.1411 Da
Monoisotopic Mass108.06875 Da
IUPAC Name2-ethylpyrazine
Traditional Name2-ethyl pyrazine
CAS Registry Number13925-00-3
SMILES
CCC1=CN=CC=N1
InChI Identifier
InChI=1S/C6H8N2/c1-2-6-5-7-3-4-8-6/h3-5H,2H2,1H3
InChI KeyKVFIJIWMDBAGDP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-04View Spectrum
Species
Species of Origin
Species NameSourceReference
Camellia sinensis
Coffea arabica
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Perilla frutescens
Solanum tuberosumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Trigonella foenum-graecumFooDB
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 Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.69Not Available
Predicted Properties
PropertyValueSource
Water Solubility206 g/LALOGPS
logP0.87ALOGPS
logP0.37ChemAxon
logS0.28ALOGPS
pKa (Strongest Basic)1.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity30.96 m³·mol⁻¹ChemAxon
Polarizability11.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031849  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008533  
KNApSAcK IDNot Available
Chemspider ID24533  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound26331  
PDB IDNot Available
ChEBI ID73232  
Good Scents IDNot Available
References
General References
  1. Rappert S, Li R, Kokova M, Antholz M, Nagorny S, Francke W, Muller R: Degradation of 2,5-dimethylpyrazine by Rhodococcus erythropolis strain DP-45 isolated from a waste gas treatment plant of a fishmeal processing company. Biodegradation. 2007 Oct;18(5):585-96. Epub 2006 Nov 22. [PubMed:17120096  ] 
  2. Melkonian G, Eckelhoefer H, Wu M, Wang Y, Tong C, Riveles K, Talbot P: Growth and angiogenesis are inhibited in vivo in developing tissues by pyrazine and its derivatives. Toxicol Sci. 2003 Oct;75(2):393-401. Epub 2003 May 28. [PubMed:12773771  ] 
  3. Fan W, Qian MC: Characterization of aroma compounds of chinese "Wuliangye" and "Jiannanchun" liquors by aroma extract dilution analysis. J Agric Food Chem. 2006 Apr 5;54(7):2695-704. [PubMed:16569063  ] 
  4. Shu CK: Pyrazine formation from serine and threonine. J Agric Food Chem. 1999 Oct;47(10):4332-5. [PubMed:10552811  ] 
  5. Jung MY, Bock JY, Baik SO, Lee JH, Lee TK: Effects of roasting on pyrazine contents and oxidative stability of red pepper seed oil prior to its extraction. J Agric Food Chem. 1999 Apr;47(4):1700-4. [PubMed:10564041  ] 
  6. Jess I, Nather C: Investigations on the synthesis, structures, and properties of new copper(I) 2,3-dimethylpyrazine coordination compounds. Inorg Chem. 2006 Sep 4;45(18):7446-54. [PubMed:16933949  ] 
  7. Counet C, Callemien D, Ouwerx C, Collin S: Use of gas chromatography-olfactometry to identify key odorant compounds in dark chocolate. Comparison of samples before and after conching. J Agric Food Chem. 2002 Apr 10;50(8):2385-91. [PubMed:11929301  ] 
  8. Montague SA, Mathew D, Carlson JR: Similar odorants elicit different behavioral and physiological responses, some supersustained. J Neurosci. 2011 May 25;31(21):7891-9. doi: 10.1523/JNEUROSCI.6254-10.2011. [PubMed:21613503  ] 
  9. Piccone P, Lonzarich V, Navarini L, Fusella G, Pittia P: Effect of sugars on liquid-vapour partition of volatile compounds in ready-to-drink coffee beverages. J Mass Spectrom. 2012 Sep;47(9):1120-31. doi: 10.1002/jms.3073. [PubMed:22972780  ] 
  10. Qian M, Reineccius G: Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry. J Dairy Sci. 2002 Jun;85(6):1362-9. [PubMed:12146465  ] 
  11. Le Guen S, Prost C, Demaimay M: Critical comparison of three olfactometric methods for the identification of the most potent odorants in cooked mussels (Mytilus edulis). J Agric Food Chem. 2000 Apr;48(4):1307-14. [PubMed:10775390  ] 
  12. Morais VM, Miranda MS, Matos MA: Thermochemical study of the ethylpyridine and ethylpyrazine isomers. Org Biomol Chem. 2003 Dec 7;1(23):4329-34. Epub 2003 Oct 27. [PubMed:14685337  ] 
  13.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .