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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:58:10 UTC
Update Date2022-03-07 02:54:00 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
Data?1563862522
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
Disposition

Biological location

Source

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
PropertyValueSource
Water Solubility534 g/LALOGPS
logP-0.29ALOGPS
logP-0.46ChemAxon
logS0.82ALOGPS
pKa (Strongest Basic)0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.74 m³·mol⁻¹ChemAxon
Polarizability7.62 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]+110.28631661259
DarkChem[M-H]-104.13431661259
DeepCCS[M+H]+123.18430932474
DeepCCS[M-H]-120.38630932474
DeepCCS[M-2H]-156.67630932474
DeepCCS[M+Na]+131.27530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrazineC1=CN=CC=N11192.4Standard polar33892256
PyrazineC1=CN=CC=N1691.3Standard non polar33892256
PyrazineC1=CN=CC=N1729.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Pyrazine EI-B (Non-derivatized)splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrazine EI-B (Non-derivatized)splash10-0f89-9000000000-0df782a68a2c1241b0fa2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrazine EI-B (Non-derivatized)splash10-0ue9-9000000000-a9ecb71c1f0bcbaaf11b2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Pyrazine EI-B (Non-derivatized)splash10-0f89-9000000000-0df782a68a2c1241b0fa2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-0d169680fbd08985c9dd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-004i-9000000000-4ab2302c1f18fb7499142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-94a5f82e15da219f831a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-94a5f82e15da219f831a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine ESI-ITFT , positive-QTOFsplash10-001i-9000000000-e12a532426f546e879652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-a5db0ef57f8fb44329022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-a5db0ef57f8fb44329022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-67966ad1ea4c70f962242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-a5db0ef57f8fb44329022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-67966ad1ea4c70f962242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-67966ad1ea4c70f962242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-67966ad1ea4c70f962242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-a5db0ef57f8fb44329022017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrazine APCI-ITFT , positive-QTOFsplash10-001i-9000000000-67966ad1ea4c70f962242017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 10V, Positive-QTOFsplash10-001i-9000000000-73d255a36568e9413c782016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 20V, Positive-QTOFsplash10-001i-9000000000-c9bce48c51da920d5cd52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 40V, Positive-QTOFsplash10-0zgi-9000000000-fdb72ce6f5a40ea431f82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 10V, Negative-QTOFsplash10-004i-9000000000-7b4264e953d5ba3b2c752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 20V, Negative-QTOFsplash10-004i-9000000000-88728ef69d13e92d73d62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrazine 40V, Negative-QTOFsplash10-004i-9000000000-461c3e6869f2758a24af2016-08-03Wishart 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
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 IDrw1040421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .