MiMeDB: Showing metabocard for 2-Methoxy-3-isobutylpyrazine (MMDBc0033558)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:53:32 UTC

Update Date

2024-09-29 09:37:58 UTC

Metabolite ID

MMDBc0033558

Metabolite Identification

Common Name

2-Methoxy-3-isobutylpyrazine

Description

2-Methoxy-3-isobutylpyrazine is a 3-alkyl-2-methoxypyrazine, which are important compounds for the aroma of wines. 2-Methoxy-3-isobutylpyrazine has been related with the green and vegetative aromas characteristic of some wines made with Cabernet Sauvignon, Sauvignon blanc, Merlot or Cabernet Franc grapes. It it is typically found at 15-30 ng/L in these wines. The origin of 3-alkyl-2-methoxypyrazines is mostly endogenous as these compounds are part of the chemicals produced in the first stages of grape development. [PMID: 21227432 ]

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PRZ                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.326   3.026   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       0.326   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.008   0.716   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.342   1.486   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.342   3.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.008   3.796   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.659   0.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659  -0.824   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.993  -1.594   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.326  -1.594   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.008  -0.824   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.342  -1.594   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
1DZK	HMDB
2-Isobutyl-3-methoxy-pyrazine	HMDB
2-Isobutyl-3-methoxypyrazine	HMDB
2-Isobutyl-3-methoxypyrazine, 8ci	HMDB
2-Methoxy-3-(2-methyl-propyl) pyrazine	HMDB
2-Methoxy-3-(2-methylpropyl)-pyrazine	HMDB
2-Methoxy-3-isobutylpyrazine	HMDB, MeSH
3-Isobutyl-2-methoxypyrazine	HMDB, MeSH
3-Methoxy-2-isobutylpyrazine	HMDB
FEMA 3132	HMDB
Galbazine	HMDB
IBMP	HMDB
PRZ	HMDB
Pyrazine, 2-(2-methylpropyl)-3-methoxy	HMDB
Pyrazine, 2-isobutyl-3-methoxy	HMDB
Pyrazine, 2-methoxy, 3-isobutyl	HMDB
Pyrazine, 3-methoxy-2-(2-methylpropyl)	HMDB

Molecular Formula

C₉H₁₄N₂O

Average Mass

166.2203

Monoisotopic Mass

166.11061308

IUPAC Name

2-methoxy-3-(2-methylpropyl)pyrazine

Traditional Name

2-isobutyl-3-methoxypyrazine

CAS Registry Number

24683-00-9

SMILES

COC1=NC=CN=C1CC(C)C

InChI Identifier

InChI=1S/C9H14N2O/c1-7(2)6-8-9(12-3)11-5-4-10-8/h4-5,7H,6H2,1-3H3

InChI Key

UXFSPRAGHGMRSQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Methoxypyrazines

Alternative Parents

Substituents

Methoxypyrazine
Alkyl aryl ether
Heteroaromatic compound
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	20.9 g/L	ALOGPS
logP	2.11	ALOGPS
logP	1.54	ChemAxon
logS	-0.9	ALOGPS
pKa (Strongest Basic)	0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.01 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.89 m³·mol⁻¹	ChemAxon
Polarizability	18.38 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9800000000-b2a76f846c9e6cdec480	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-f195deae40b120d03a2b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-7900000000-ce68c6d37c62fbafe643	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9100000000-fdcbed3bfb97241ae911	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-f72a38590d903075c866	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2900000000-8a6a0e5c0c27143a34f1	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-02b43dab5d60f685355e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-36e5a9d0812fa5b880dc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1900000000-a3ae70c6cad1c5005bd3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1252189c65cc284d2024	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-d120bc32d136e668f60a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-b41ddec9414daee33f17	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9100000000-4674a4a6a16f025751ab	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-9800000000-0379fe3fc6cfe11798f3	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-30	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Fruit	Capsicum annuum	FooDB	31437929
Plant	Fruit	Capsicum annuum var. annuum	FooDB	31437929
Plant	Stem	Vitis vinifera	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0031860

DrugBank ID

DB04512

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008544

KNApSAcK ID

C00052644

Chemspider ID

30208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

32594

PDB ID

PRZ

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 2-Methoxy-3-isobutylpyrazine (MMDBc0033558)

MOL for #<Metabolite:0x00007f46a6355f40>

3D MOL for #<Metabolite:0x00007f46a6355f40>

3D SDF for #<Metabolite:0x00007f46a6355f40>

3D-SDF for #<Metabolite:0x00007f46a6355f40>

PDB for #<Metabolite:0x00007f46a6355f40>

3D PDB for #<Metabolite:0x00007f46a6355f40>

SMILES for #<Metabolite:0x00007f46a6355f40>

INCHI for #<Metabolite:0x00007f46a6355f40>

Structure for #<Metabolite:0x00007f46a6355f40>

3D Structure for #<Metabolite:0x00007f46a6355f40>