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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:22:15 UTC
Update Date2022-03-07 02:56:21 UTC
HMDB IDHMDB0039831
Secondary Accession Numbers
  • HMDB39831
Metabolite Identification
Common Name6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine
Description6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 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. 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine is a burnt, earthy, and nutty tasting compound. 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine has been detected, but not quantified in, several different foods, such as breakfast cereal, coffee and coffee products, nuts, cocoa beans (Theobroma cacao), and arabica coffees (Coffea arabica). This could make 6,7-dihydro-2,5-dimethyl-5H-cyclopentapyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine.
Structure
Data?1563863445
Synonyms
ValueSource
2,5-Dimethyl-6,7-dihydro-(5H)-cyclopentapyrazineHMDB
2,5-Dimethyl-6,7-dihydro-5H-cyclopenta[b]pyrazineHMDB
Chemical FormulaC9H12N2
Average Molecular Weight148.205
Monoisotopic Molecular Weight148.100048394
IUPAC Name2,5-dimethyl-5H,6H,7H-cyclopenta[b]pyrazine
Traditional Name2,5-dimethyl-5H,6H,7H-cyclopenta[b]pyrazine
CAS Registry Number38917-61-2
SMILES
CC1CCC2=C1N=CC(C)=N2
InChI Identifier
InChI=1S/C9H12N2/c1-6-3-4-8-9(6)10-5-7(2)11-8/h5-6H,3-4H2,1-2H3
InChI KeyCTFGVWCFSGCLHZ-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 heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point110.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point222.08 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility719 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.794 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.5 g/LALOGPS
logP1.83ALOGPS
logP0.97ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)1.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area25.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity42.94 m³·mol⁻¹ChemAxon
Polarizability17.07 ųChemAxon
Number of Rings2ChemAxon
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]+132.62831661259
DarkChem[M-H]-130.09431661259
DeepCCS[M+H]+134.49330932474
DeepCCS[M-H]-130.66530932474
DeepCCS[M-2H]-168.03330932474
DeepCCS[M+Na]+143.57230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazineCC1CCC2=C1N=CC(C)=N21659.9Standard polar33892256
6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazineCC1CCC2=C1N=CC(C)=N21168.9Standard non polar33892256
6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazineCC1CCC2=C1N=CC(C)=N21223.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2900000000-c1e83c8d2e97432002a82017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 10V, Positive-QTOFsplash10-0002-0900000000-b4c5580d24ab87d771fa2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 20V, Positive-QTOFsplash10-0002-1900000000-481f96962d72558f84b32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 40V, Positive-QTOFsplash10-0kcr-9600000000-c34ab3e7e7465bfd9d372015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 10V, Negative-QTOFsplash10-0002-0900000000-276f718afdf772401b482015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 20V, Negative-QTOFsplash10-0002-0900000000-a469551d4046723681002015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 40V, Negative-QTOFsplash10-014l-4900000000-55ff7fded4e49a96f9362015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 10V, Positive-QTOFsplash10-0002-0900000000-2ef1a63f0d174650da9c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 20V, Positive-QTOFsplash10-0002-1900000000-392e18cabc33199fe3542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 40V, Positive-QTOFsplash10-005c-9200000000-0a5cda27313684a9b33b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 10V, Negative-QTOFsplash10-0002-0900000000-aff21bfca25e06c854232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 20V, Negative-QTOFsplash10-0002-0900000000-4127051532b1d57df8b22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6,7-Dihydro-2,5-dimethyl-5H-cyclopentapyrazine 40V, Negative-QTOFsplash10-014l-5900000000-f5a9d7cb47a3f7a9f9c12021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDFDB019484
KNApSAcK IDC00054445
Chemspider ID462010
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound530404
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1595401
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.. .