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Showing NP-Card for Methylpyrazine (NP0047553)

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Record Information
Version2.0
Created at2022-03-17 20:42:03 UTC
Updated at2022-03-17 20:42:03 UTC
NP-MRD IDNP0047553
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethylpyrazine
DescriptionMethylpyrazine, also known as fema 3309, 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. Methylpyrazine is a moderately basic compound (based on its pKa). Methylpyrazine is a chocolate, cocoa, and green tasting compound. Outside of the human body, Methylpyrazine is found, on average, in the highest concentration within kohlrabis. Methylpyrazine has also been detected, but not quantified in, several different foods, such as milk and milk products, cocoa and cocoa products, tortilla chips, alcoholic beverages, and fenugreeks. Methylpyrazine is found in Camellia sinensis, Coffea arabica, Coffea arabica , Coffea canephora , Corynebacterium glutamicum, Panax ginseng and Sergia lucens. Methylpyrazine was first documented in 2011 (PMID: 22417522). This could make methylpyrazine a potential biomarker for the consumption of these foods (PMID: 22541463) (PMID: 22972787) (PMID: 21613503) (PMID: 21536621) (PMID: 21701755) (PMID: 22465766).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047553 (Methylpyrazine)


  Mrv1652304272018132D          

  7  7  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    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  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for NP0047553 (Methylpyrazine)

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3D SDF for NP0047553 (Methylpyrazine)

  Mrv1652304272018132D          

  7  7  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    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  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=NC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6N2/c1-5-4-6-2-3-7-5/h2-4H,1H3

> <INCHI_KEY>
CAWHJQAVHZEVTJ-UHFFFAOYSA-N

> <FORMULA>
C5H6N2

> <MOLECULAR_WEIGHT>
94.1145

> <EXACT_MASS>
94.053098202

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.732087004064836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpyrazine

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
-0.3307288689999999

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.4225769819721823

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
26.3357

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methylpyrazine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047553 (Methylpyrazine)
Download
PDB for NP0047553 (Methylpyrazine)
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   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   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      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.770   1.334   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      -0.770  -1.334   0.000  0.00  0.00           N+0
CONECT    1    5                                                            
CONECT    2    3    6                                                       
CONECT    3    2    7                                                       
CONECT    4    5    6                                                       
CONECT    5    1    4    7                                                  
CONECT    6    2    4                                                       
CONECT    7    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0047553 (Methylpyrazine)
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SMILES for NP0047553 (Methylpyrazine)
CC1=NC=CN=C1
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INCHI for NP0047553 (Methylpyrazine)
InChI=1S/C5H6N2/c1-5-4-6-2-3-7-5/h2-4H,1H3
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View in JSmol
Synonyms
ValueSource
2-MethylpyrazineHMDB
2-Methyl-1,4-diazineHMDB
2-Methyl-pyrazineHMDB
FEMA 3309HMDB
Methyl-pyrazineHMDB
Chemical FormulaC5H6N2
Average Mass94.1145 Da
Monoisotopic Mass94.05310 Da
IUPAC Name2-methylpyrazine
Traditional Name2-methylpyrazine
CAS Registry Number109-08-0
SMILES
CC1=NC=CN=C1
InChI Identifier
InChI=1S/C5H6N2/c1-5-4-6-2-3-7-5/h2-4H,1H3
InChI KeyCAWHJQAVHZEVTJ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica oleracea var. gongylodesFooDB
Camellia sinensisLOTUS Database
Coffea arabicaLOTUS Database
Coffea arabica L.Plant
Coffea canephoraPlant
Corynebacterium glutamicumLOTUS Database
Glycine maxFooDB
Panax ginsengLOTUS Database
Sergia lucensLOTUS Database
Theobroma cacaoFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Trigonella foenum-graecumFooDB
Vigna radiataFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.19ALOGPS
logP-0.33ChemAxon
logS0.55ALOGPS
pKa (Strongest Basic)1.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.34 m³·mol⁻¹ChemAxon
Polarizability9.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033112  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011112  
KNApSAcK IDNot Available
Chemspider ID7688  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7976  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Divine RD, Sommer D, Lopez-Hernandez A, Rankin SA: Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage. J Dairy Sci. 2012 May;95(5):2347-54. doi: 10.3168/jds.2011-4828. [PubMed:22541463  ] 
  2. Magi E, Bono L, Di Carro M: Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols. J Mass Spectrom. 2012 Sep;47(9):1191-7. doi: 10.1002/jms.3034. [PubMed:22972787  ] 
  3. Qin P, Ma T, Wu L, Shan F, Ren G: Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry. J Food Sci. 2011 Aug;76(6):S401-7. doi: 10.1111/j.1750-3841.2011.02223.x. Epub 2011 Jun 8. [PubMed:22417522  ] 
  4. 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  ] 
  5. Yabuki M, Scott DJ, Briand L, Taylor AJ: Dynamics of odorant binding to thin aqueous films of rat-OBP3. Chem Senses. 2011 Sep;36(7):659-71. doi: 10.1093/chemse/bjr037. Epub 2011 May 2. [PubMed:21536621  ] 
  6. Dhachapally N, Kalevaru VN, Radnik J, Martin A: Tuning the surface composition of novel metal vanadates and its effect on the catalytic performance. Chem Commun (Camb). 2011 Aug 7;47(29):8394-6. doi: 10.1039/c1cc12117k. Epub 2011  Jun 24. [PubMed:21701755  ] 
  7. Morkan IA, Celik D, Morkan AU, Guven K: Synthesis, crystal structure, spectroscopic investigations, thermal behavior and DFT calculations of pentacarbonyl(2-methylpyrazine)chromium(0). Spectrochim Acta A Mol Biomol Spectrosc. 2012 Jul;93:47-52. doi: 10.1016/j.saa.2012.02.037. Epub 2012 Feb 24. [PubMed:22465766  ] 
  8. Nicolotti L, Cordero C, Bicchi C, Rubiolo P, Sgorbini B, Liberto E: Volatile profiling of high quality hazelnuts (Corylus avellana L.): chemical indices of roasting. Food Chem. 2013 Jun 1;138(2-3):1723-33. doi: 10.1016/j.foodchem.2012.11.086. Epub 2012 Nov 29. [PubMed:23411304  ] 
  9. Treesuwan W, Hirao H, Morokuma K, Hannongbua S: Characteristic vibration patterns of odor compounds from bread-baking volatiles upon protein binding: density functional and ONIOM study and principal component analysis. J Mol Model. 2012 May;18(5):2227-40. doi: 10.1007/s00894-011-1227-9. Epub 2011 Sep 27. [PubMed:21952829  ] 
  10. El-sharkawy RG, El-din AS, El-din H Etaiw S: Kinetics and mechanism of the heterogeneous catalyzed oxidative decolorization of Acid-Blue 92 using bimetallic metal-organic frameworks. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Sep;79(5):1969-75. doi: 10.1016/j.saa.2011.05.101. Epub 2011 Jun 6. [PubMed:21703918  ]