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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:23:38 UTC

Update Date

2023-02-21 17:25:38 UTC

HMDB ID

HMDB0037149

Secondary Accession Numbers

HMDB37149

Metabolite Identification

Common Name

6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine

Description

6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 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-5-methyl-5H-cyclopenta[b]pyrazine is a baked, earthy, and nut tasting compound. 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine has been detected, but not quantified in, several different foods, such as robusta coffees (Coffea canephora), arabica coffees (Coffea arabica), teas (Camellia sinensis), black tea, and coffee and coffee products. This could make 6,7-dihydro-5-methyl-5H-cyclopenta[b]pyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Methyl -6,7-dihydrocyclopentapyrazine	HMDB
5-Methyl-(5H)-6,7-dihydrocyclo- pentapyrazine	HMDB
5-Methyl-5H-cyclopenta[b]pyrazine	HMDB
5-Methyl-6,7-dihydro-(5H)-cyclopentapyrazine	HMDB
5-Methyl-6,7-dihydro-5H-cyclopenta[b]pyrazine	HMDB
FEMA 3306	HMDB

Chemical Formula

C₈H₁₀N₂

Average Molecular Weight

134.1784

Monoisotopic Molecular Weight

134.08439833

IUPAC Name

5-methyl-5H,6H,7H-cyclopenta[b]pyrazine

Traditional Name

5-methyl-5H,6H,7H-cyclopenta[b]pyrazine

CAS Registry Number

23747-48-0

SMILES

CC1CCC2=C1N=CC=N2

InChI Identifier

InChI=1S/C8H10N2/c1-6-2-3-7-8(6)10-5-4-9-7/h4-6H,2-3H2,1H3

InChI Key

YZEFQPIMXZVPKP-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0037149)
Cytoplasm (HMDB: HMDB0037149)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037149)

Source

Exogenous

Exogenous (HMDB: HMDB0037149)

Food

Food (HMDB: HMDB0037149)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Not Available

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037149)

Biological role

Nutrient (HMDB: HMDB0037149)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	46 g/L	ALOGPS
logP	1.27	ALOGPS
logP	0.84	ChemAxon
logS	-0.46	ALOGPS
pKa (Strongest Basic)	1.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.35 m³·mol⁻¹	ChemAxon
Polarizability	14.81 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.038	31661259
DarkChem	[M-H]-	124.276	31661259
DeepCCS	[M+H]+	127.3	30932474
DeepCCS	[M-H]-	124.263	30932474
DeepCCS	[M-2H]-	161.121	30932474
DeepCCS	[M+Na]+	135.97	30932474
AllCCS	[M+H]+	128.2	32859911
AllCCS	[M+H-H2O]+	123.5	32859911
AllCCS	[M+NH4]+	132.6	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	130.1	32859911
AllCCS	[M+HCOO]-	131.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine	CC1CCC2=C1N=CC=N2	1633.7	Standard polar	33892256
6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine	CC1CCC2=C1N=CC=N2	1094.9	Standard non polar	33892256
6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine	CC1CCC2=C1N=CC=N2	1142.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05nf-6900000000-2906b3f1a60c022f3783	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 10V, Positive-QTOF	splash10-000i-0900000000-406813d8116863ccf1e3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 20V, Positive-QTOF	splash10-000i-1900000000-9a26cc4a02bda4731c35	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 40V, Positive-QTOF	splash10-00kf-9300000000-f2102f670590a6dda4cb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 10V, Negative-QTOF	splash10-001i-0900000000-65295988de494826aaa5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 20V, Negative-QTOF	splash10-001i-0900000000-46823726a0670447c9b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 40V, Negative-QTOF	splash10-0pc0-6900000000-8a95ebe63e999ab7bf96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 10V, Negative-QTOF	splash10-001i-0900000000-01d3d9050ab710b33e95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 20V, Negative-QTOF	splash10-001i-0900000000-08f65d2671144611677b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 40V, Negative-QTOF	splash10-0a4i-3900000000-b7066717cdb0f4c4d8a5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 10V, Positive-QTOF	splash10-000i-0900000000-ac53f30f5946fcc05e5c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 20V, Positive-QTOF	splash10-000i-2900000000-f8b041142d824b822c6b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine 40V, Positive-QTOF	splash10-00mo-9200000000-7a9b4bb0887f0de3613a	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016144

KNApSAcK ID

C00054446

Chemspider ID

29734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32065

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine (HMDB0037149)

MOL for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

3D MOL for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

3D SDF for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

3D-SDF for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

PDB for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

3D PDB for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

SMILES for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

INCHI for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

Structure for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

3D Structure for HMDB0037149 (6,7-Dihydro-5-methyl-5H-cyclopenta[b]pyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra