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Showing metabocard for Pyrazine (HMDB0034176)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:58:10 UTC
Update Date2023-02-21 17:23:59 UTC
HMDB IDHMDB0034176
Secondary Accession Numbers
  • HMDB34176
Metabolite Identification
Common NamePyrazine
DescriptionPyrazine is found in fenugreek. Pyrazine is a maillard product In the Staedel-Rugheimer pyrazine synthesis (1876) 2-chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine A variation is the Gutknecht Pyrazine Synthesis (1879) also based on this selfcondensation but differing in the way the alpha-ketoamine is synthesised (the chlorine compound in the above method is a lachrymatory agent); Pyrazine is a heterocyclic aromatic organic compound. Pyrazine is a symmetrical molecule with point group D2h. It is found in folic acid in the form of pterin. Derivatives like Phenazine are well known for their antitumor, antibiotic and diuretic activity. Pyrazine is less basic in nature than pyridine, pyridazine and pyrimidine. Tetramethylpyrazine (also known as ligustrazine) is reported to scavenge superoxide anion and decrease nitric oxide production in human polymorphonuclear leukocytes. Tetramethylpyrazine is also a component of some herbs in Traditional Chinese Medicine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034176 (Pyrazine)

  Mrv0541 02241215422D          

  6  6  0  0  0  0            999 V2000
    0.0409   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0034176 (Pyrazine)

HMDB0034176
     RDKit          3D
Pyrazine
 10 10  0  0  0  0  0  0  0  0999 V2000
   -1.1978    0.5904   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1428   -0.7875    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.3444    0.0586 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -0.5955    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    0.7801   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0852    1.3418   -0.0585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    1.0441   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -1.3953    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973   -1.0354    0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    1.4016   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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3D SDF for HMDB0034176 (Pyrazine)

  Mrv0541 02241215422D          

  6  6  0  0  0  0            999 V2000
    0.0409   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034176

> <DATABASE_NAME>
hmdb

> <SMILES>
C1=CN=CC=N1

> <INCHI_IDENTIFIER>
InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H

> <INCHI_KEY>
KYQCOXFCLRTKLS-UHFFFAOYSA-N

> <FORMULA>
C4H4N2

> <MOLECULAR_WEIGHT>
80.088

> <EXACT_MASS>
80.037448138

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.621774410675052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pyrazine

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-0.4620990379999999

> <ALOGPS_LOGS>
0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.8793918998266385

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
21.7442

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.34e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034176 (Pyrazine)

HMDB0034176
     RDKit          3D
Pyrazine
 10 10  0  0  0  0  0  0  0  0999 V2000
   -1.1978    0.5904   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1428   -0.7875    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.3444    0.0586 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1999   -0.5955    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    0.7801   -0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0852    1.3418   -0.0585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774    1.0441   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -1.3953    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1973   -1.0354    0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333    1.4016   -0.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  2  8  1  0
  4  9  1  0
  5 10  1  0
M  END
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PDB for HMDB0034176 (Pyrazine)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.076  -1.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.311  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.311   0.770   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.076   1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.311   0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.311  -0.770   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for HMDB0034176 (Pyrazine)

COMPND    HMDB0034176
HETATM    1  C1  UNL     1      -1.198   0.590  -0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.143  -0.788   0.034  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.083  -1.344   0.059  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.200  -0.596   0.026  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.137   0.780  -0.034  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.085   1.342  -0.058  1.00  0.00           N  
HETATM    7  H1  UNL     1      -2.177   1.044  -0.046  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.048  -1.395   0.060  1.00  0.00           H  
HETATM    9  H3  UNL     1       2.197  -1.035   0.046  1.00  0.00           H  
HETATM   10  H4  UNL     1       2.033   1.402  -0.060  1.00  0.00           H  
CONECT    1    2    2    6    7
CONECT    2    3    8
CONECT    3    4    4
CONECT    4    5    9
CONECT    5    6    6   10
END
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SMILES for HMDB0034176 (Pyrazine)

C1=CN=CC=N1
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INCHI for HMDB0034176 (Pyrazine)

InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,4-DiazinChEBI
1,4-DiazineChEBI
p-DiazineChEBI
ParadiazineChEBI
PyrazinChEBI
pyzChEBI
PyrazinesMeSH
1, 4-DiazabenzeneHMDB
1,4-DiazabenzeneHMDB
2-CyanopyrazineHMDB
CyanopyrazineHMDB
PiazineHMDB
Piazine (obsol.)HMDB
Chemical FormulaC4H4N2
Average Molecular Weight80.088
Monoisotopic Molecular Weight80.037448138
IUPAC Namepyrazine
Traditional Namepyrazine
CAS Registry Number290-37-9
SMILES
C1=CN=CC=N1
InChI Identifier
InChI=1S/C4H4N2/c1-2-6-4-3-5-1/h1-4H
InChI KeyKYQCOXFCLRTKLS-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 Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point54 - 56 °CNot Available
Boiling Point115.00 to 116.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility218100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.26Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
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 IDFDB012468
KNApSAcK IDC00053733
Chemspider ID8904
KEGG Compound IDC02018
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrazine
METLIN IDNot Available
PubChem Compound9261
PDB IDNot Available
ChEBI ID30953
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .