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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:32:15 UTC

Update Date

2023-02-21 17:27:17 UTC

HMDB ID

HMDB0039982

Secondary Accession Numbers

HMDB39982

Metabolite Identification

Common Name

Trimethyl-2-propenylpyrazine

Description

Trimethyl-2-propenylpyrazine 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. Trimethyl-2-propenylpyrazine has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make trimethyl-2-propenylpyrazine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Trimethyl-2-propenylpyrazine.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
CONECT    1    5                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    9                                                            
CONECT    5    1    6                                                       
CONECT    6    5   10                                                       
CONECT    7    2    8   11                                                  
CONECT    8    3    7   12                                                  
CONECT    9    4   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    7    9                                                       
CONECT   12    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Allyl-3,5,6-trimethylpyrazine	HMDB

Chemical Formula

C₁₀H₁₄N₂

Average Molecular Weight

162.2316

Monoisotopic Molecular Weight

162.115698458

IUPAC Name

2,3,5-trimethyl-6-(prop-2-en-1-yl)pyrazine

Traditional Name

2,3,5-trimethyl-6-(prop-2-en-1-yl)pyrazine

CAS Registry Number

55138-71-1

SMILES

CC1=NC(C)=C(CC=C)N=C1C

InChI Identifier

InChI=1S/C10H14N2/c1-5-6-10-9(4)11-7(2)8(3)12-10/h5H,1,6H2,2-4H3

InChI Key

ZFPORMYSWAHSAQ-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 heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039982)
Cytoplasm (HMDB: HMDB0039982)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039982)

Source

Exogenous

Food

Food (HMDB: HMDB0039982)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0039982)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039982)

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	192.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.26 g/L	ALOGPS
logP	2.07	ALOGPS
logP	0.9	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Basic)	1.85	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	2	ChemAxon
Refractivity	49.38 m³·mol⁻¹	ChemAxon
Polarizability	19.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	136.258	31661259
DarkChem	[M-H]-	135.777	31661259
DeepCCS	[M+H]+	140.837	30932474
DeepCCS	[M-H]-	138.301	30932474
DeepCCS	[M-2H]-	174.038	30932474
DeepCCS	[M+Na]+	149.402	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	130.7	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.3	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.5	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trimethyl-2-propenylpyrazine	CC1=NC(C)=C(CC=C)N=C1C	1681.6	Standard polar	33892256
Trimethyl-2-propenylpyrazine	CC1=NC(C)=C(CC=C)N=C1C	1220.0	Standard non polar	33892256
Trimethyl-2-propenylpyrazine	CC1=NC(C)=C(CC=C)N=C1C	1258.1	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 - Trimethyl-2-propenylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03gj-5900000000-8a8e906775dfd47485ca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethyl-2-propenylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trimethyl-2-propenylpyrazine 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 - Trimethyl-2-propenylpyrazine 10V, Positive-QTOF	splash10-03di-0900000000-a63abb0926d582df35a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 20V, Positive-QTOF	splash10-03di-0900000000-83483876e3c98197327e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 40V, Positive-QTOF	splash10-0f6x-9200000000-34339d41fe60b3af5428	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 10V, Negative-QTOF	splash10-03di-0900000000-f3e536c5bee6b625d308	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 20V, Negative-QTOF	splash10-03di-0900000000-0eceddbc3804c480efc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 40V, Negative-QTOF	splash10-000b-4900000000-c5a15230a268c754da1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 10V, Negative-QTOF	splash10-03di-0900000000-517d8a3479f28b47c705	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 20V, Negative-QTOF	splash10-0229-2900000000-c553d5fe8ffae93c3d36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 40V, Negative-QTOF	splash10-014l-9600000000-8bd84577d8923cb91efe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 10V, Positive-QTOF	splash10-03di-0900000000-d5505f5ad7b83fea0dde	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 20V, Positive-QTOF	splash10-03dr-2900000000-abd34dabe2006b011f44	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trimethyl-2-propenylpyrazine 40V, Positive-QTOF	splash10-00nf-9200000000-b7cb09b73cb12dc41f94	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

FDB019664

KNApSAcK ID

Not Available

Chemspider ID

517459

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

595263

PDB ID

Not Available

ChEBI ID

166528

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1881281

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 Trimethyl-2-propenylpyrazine (HMDB0039982)

MOL for HMDB0039982 (Trimethyl-2-propenylpyrazine)

3D MOL for HMDB0039982 (Trimethyl-2-propenylpyrazine)

3D SDF for HMDB0039982 (Trimethyl-2-propenylpyrazine)

3D-SDF for HMDB0039982 (Trimethyl-2-propenylpyrazine)

PDB for HMDB0039982 (Trimethyl-2-propenylpyrazine)

3D PDB for HMDB0039982 (Trimethyl-2-propenylpyrazine)

SMILES for HMDB0039982 (Trimethyl-2-propenylpyrazine)

INCHI for HMDB0039982 (Trimethyl-2-propenylpyrazine)

Structure for HMDB0039982 (Trimethyl-2-propenylpyrazine)

3D Structure for HMDB0039982 (Trimethyl-2-propenylpyrazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra