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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 17:54:03 UTC

Update Date

2023-02-21 17:23:09 UTC

HMDB ID

HMDB0033154

Secondary Accession Numbers

HMDB33154

Metabolite Identification

Common Name

5,6,7,8-Tetrahydroquinoxaline

Description

5,6,7,8-Tetrahydroquinoxaline 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. 5,6,7,8-Tetrahydroquinoxaline is a bean, cereal, and cheese tasting compound. 5,6,7,8-Tetrahydroquinoxaline has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, arabica coffees (Coffea arabica), cocoa beans (Theobroma cacao), and nuts. This could make 5,6,7,8-tetrahydroquinoxaline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,6,7,8-Tetrahydroquinoxaline.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5,6,7,8-tetrahydro-Quinoxaline	HMDB
Cyclohexapyrazine	HMDB
FEMA 3321	HMDB
Tetrahydroquinoxaline	HMDB

Chemical Formula

C₈H₁₀N₂

Average Molecular Weight

134.1784

Monoisotopic Molecular Weight

134.08439833

IUPAC Name

5,6,7,8-tetrahydroquinoxaline

Traditional Name

5,6,7,8-tetrahydroquinoxaline

CAS Registry Number

34413-35-9

SMILES

C1CCC2=C(C1)N=CC=N2

InChI Identifier

InChI=1S/C8H10N2/c1-2-4-8-7(3-1)9-5-6-10-8/h5-6H,1-4H2

InChI Key

XCZPDOCRSYZOBI-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: HMDB0033154)
Cytoplasm (HMDB: HMDB0033154)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033154)

Source

Exogenous

Food

Food (HMDB: HMDB0033154)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

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

Nutrient (HMDB: HMDB0033154)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	29 - 30 °C	Not Available
Boiling Point	108.00 to 111.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.158 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	42.6 g/L	ALOGPS
logP	1.29	ALOGPS
logP	0.74	ChemAxon
logS	-0.5	ALOGPS
pKa (Strongest Basic)	1.36	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	38.38 m³·mol⁻¹	ChemAxon
Polarizability	14.82 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]+	127.213	31661259
DarkChem	[M-H]-	124.674	31661259
DeepCCS	[M+H]+	128.816	30932474
DeepCCS	[M-H]-	125.261	30932474
DeepCCS	[M-2H]-	162.489	30932474
DeepCCS	[M+Na]+	137.574	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.0	32859911
AllCCS	[M+NH4]+	134.2	32859911
AllCCS	[M+Na]+	135.5	32859911
AllCCS	[M-H]-	128.6	32859911
AllCCS	[M+Na-2H]-	130.0	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,6,7,8-Tetrahydroquinoxaline	C1CCC2=C(C1)N=CC=N2	1715.8	Standard polar	33892256
5,6,7,8-Tetrahydroquinoxaline	C1CCC2=C(C1)N=CC=N2	1155.1	Standard non polar	33892256
5,6,7,8-Tetrahydroquinoxaline	C1CCC2=C(C1)N=CC=N2	1228.8	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 - 5,6,7,8-Tetrahydroquinoxaline GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-3900000000-21a3100a6a1b969bf3a6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 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 - 5,6,7,8-Tetrahydroquinoxaline 10V, Positive-QTOF	splash10-000i-0900000000-8488e8d4156f9644bf9f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 20V, Positive-QTOF	splash10-000i-0900000000-80a01f42708ef40682bc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 40V, Positive-QTOF	splash10-0pb9-9300000000-563eb106f34d86592e21	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 10V, Negative-QTOF	splash10-001i-0900000000-ce495fa4a12361cb030b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 20V, Negative-QTOF	splash10-001i-0900000000-b361b129a00df334d538	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 40V, Negative-QTOF	splash10-0a4i-1900000000-9cdaf721a18c26510dc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 10V, Negative-QTOF	splash10-001i-0900000000-01d3d9050ab710b33e95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 20V, Negative-QTOF	splash10-001i-0900000000-01d3d9050ab710b33e95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 40V, Negative-QTOF	splash10-0a4i-2900000000-d9fb8710ba5cc72c5fa3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 10V, Positive-QTOF	splash10-000i-0900000000-ac53f30f5946fcc05e5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 20V, Positive-QTOF	splash10-000i-0900000000-341c37e106bc53df46cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6,7,8-Tetrahydroquinoxaline 40V, Positive-QTOF	splash10-014l-9400000000-1fea450155e2f81df2a8	2021-09-22	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

FDB011159

KNApSAcK ID

Not Available

Chemspider ID

33794

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

36822

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035871

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 5,6,7,8-Tetrahydroquinoxaline (HMDB0033154)

MOL for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

3D MOL for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

3D SDF for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

3D-SDF for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

PDB for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

3D PDB for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

SMILES for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

INCHI for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

Structure for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

3D Structure for HMDB0033154 (5,6,7,8-Tetrahydroquinoxaline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra