NP-MRD: Showing NP-Card for Trimethylpyrazine (NP0001446)

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Record Information

Version

1.0

Created at

2012-09-11 17:45:55 UTC

Updated at

2021-08-19 23:59:08 UTC

NP-MRD ID

NP0001446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trimethylpyrazine

Description

Trimethylpyrazine, also known as fema 3244, 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. Trimethylpyrazine is a cocoa, earthy, and hazelnut tasting compound. Trimethylpyrazine is found, on average, in the highest concentration in kohlrabis. Trimethylpyrazine has also been detected, but not quantified, in several different foods, such as green vegetables, pepper (c. Annuum), orange bell peppers, potato, and red bell peppers. This could make trimethylpyrazine a potential biomarker for the consumption of these foods. Found in many foodstuffs e.G. Asparagus, baked potato, wheat bread, Swiss cheese, coffee, black tea, roasted filbert and peanut, and soybean.

Structure

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


  Mrv1652306242117433D          

 19 19  0  0  0  0            999 V2000
    3.1316    0.5056    0.3565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    0.1326    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -0.8343   -0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1464   -1.1869   -1.1690 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8951   -0.6024   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041   -0.9632   -0.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997    0.3662    0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    1.0109    1.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748    0.7154    0.6759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2626    0.7887    1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238   -0.3269    0.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    1.3608   -0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513   -1.3147   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3820   -2.0064   -1.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9354   -0.9428    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7747   -0.2972   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270    1.8738    1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3386    0.2648    1.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4698    1.4558    0.3274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  3 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  6 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(N=C(C(=N1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3

> <INCHI_KEY>
IAEGWXHKWJGQAZ-UHFFFAOYSA-N

> <FORMULA>
C7H10N2

> <MOLECULAR_WEIGHT>
122.1677

> <EXACT_MASS>
122.08439833

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.94124903813873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,3,5-trimethylpyrazine

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
-0.06798853099999991

> <ALOGPS_LOGS>
-0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0771269222209257

> <JCHEM_POLAR_SURFACE_AREA>
25.78

> <JCHEM_REFRACTIVITY>
35.5187

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pyrazine, trimethyl-

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.132   0.506   0.357  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.716   0.133   0.055  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.413  -0.834  -0.881  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.146  -1.187  -1.169  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.895  -0.602  -0.547  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.304  -0.963  -0.836  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.600   0.366   0.392  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.762   1.011   1.079  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.675   0.715   0.676  0.00  0.00           N+0
HETATM   10  H   UNK     0       3.263   0.789   1.419  0.00  0.00           H+0
HETATM   11  H   UNK     0       3.824  -0.327   0.156  0.00  0.00           H+0
HETATM   12  H   UNK     0       3.469   1.361  -0.278  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.251  -1.315  -1.392  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.382  -2.006  -1.229  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.935  -0.943   0.088  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.775  -0.297  -1.575  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.427   1.874   1.709  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.339   0.265   1.650  0.00  0.00           H+0
HETATM   19  H   UNK     0      -2.470   1.456   0.327  0.00  0.00           H+0
CONECT    1    2   10   11   12                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5   14   15   16                                             
CONECT    7    5    8    9                                                  
CONECT    8    7   17   18   19                                             
CONECT    9    7    2                                                       
CONECT   10    1                                                            
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    3                                                            
CONECT   14    6                                                            
CONECT   15    6                                                            
CONECT   16    6                                                            
CONECT   17    8                                                            
CONECT   18    8                                                            
CONECT   19    8                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
235-Trimethyl-pyrazine	HMDB
2,3,5-TRIMETHYL pyrazine	HMDB
2,3,5-Trimethyl-pyrazine	HMDB
2,3,6-Trimethylpyrazine	HMDB
FEMA 3244	HMDB
Pyrazine, 2,3,5-trimethyl	HMDB
Trimethyl-pyrazine	HMDB

Chemical Formula

C₇H₁₀N₂

Average Mass

122.1677 Da

Monoisotopic Mass

122.08440 Da

IUPAC Name

2,3,5-trimethylpyrazine

Traditional Name

pyrazine, trimethyl-

CAS Registry Number

14667-55-1

SMILES

[H]C1=C(N=C(C(=N1)C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3

InChI Key

IAEGWXHKWJGQAZ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Bubalus bubalis	FooDB	FooDB
Camellia sinensis	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cocos nucifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Coffea arabica	LOTUS Database	35616633
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corynebacterium glutamicum	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glycine max	FooDB	10995351
Glycyrrhiza glabra	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Mandragora autumnalis	KNApSAcK Database	22123792
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Panax ginseng	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Sergia lucens	LOTUS Database	35616633
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vigna radiata	FooDB	10995351

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

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	171.00 to 172.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	15210 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.95	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	51.6 g/L	ALOGPS
logP	1.11	ALOGPS
logP	-0.068	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Basic)	2.08	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	35.52 m³·mol⁻¹	ChemAxon
Polarizability	13.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008527

KNApSAcK ID

C00053868

Chemspider ID

24972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

26808

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1012941

References

General References

Van Lancker F, Adams A, De Kimpe N: Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems. J Agric Food Chem. 2012 May 9;60(18):4697-708. doi: 10.1021/jf301315b. Epub 2012 Apr 25. [PubMed:22463717 ]
Bohman B, Jeffares L, Flematti G, Byrne LT, Skelton BW, Phillips RD, Dixon KW, Peakall R, Barrow RA: Discovery of tetrasubstituted pyrazines as semiochemicals in a sexually deceptive orchid. J Nat Prod. 2012 Sep 28;75(9):1589-94. Epub 2012 Sep 18. [PubMed:22988937 ]
Zhai L, Zhang P, Sun RY, Liu XY, Liu WG, Guo XL: Cytoprotective effects of CSTMP, a novel stilbene derivative, against H2O2-induced oxidative stress in human endothelial cells. Pharmacol Rep. 2011;63(6):1469-80. [PubMed:22358095 ]
Li S, Chen H, Wang X, Wu J, Jiang J, Wang Y: Pharmacokinetic study of a novel stroke therapeutic, 2-[[(1,1-dimethylethyl)oxidoimino]methyl]-3,5,6-trimethylpyrazine, by a simple HPLC-UV method in rats. Eur J Drug Metab Pharmacokinet. 2011 Jun;36(2):95-101. doi: 10.1007/s13318-011-0032-2. Epub 2011 Mar 22. [PubMed:21424683 ]
Divine RD, Sommer D, Lopez-Hernandez A, Rankin SA: Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage. J Dairy Sci. 2012 May;95(5):2347-54. doi: 10.3168/jds.2011-4828. [PubMed:22541463 ]
Yang XZ, Yang WH, Xu YG, Diao XJ, He GW, Gong GQ: Synthesis and antithrombotic evaluation of novel dabigatran prodrugs containing a cleavable moiety with anti-platelet activity. Eur J Med Chem. 2012 Nov;57:21-8. doi: 10.1016/j.ejmech.2012.09.016. Epub 2012 Sep 18. [PubMed:23043765 ]
Ren M, Dong J, Xu Y, Wen N, Gong G: Synthesis of novel ligustrazine derivatives as NA+/H+ exchange inhibitors. Chem Biodivers. 2010 Nov;7(11):2727-36. doi: 10.1002/cbdv.200900353. [PubMed:21072772 ]
Huang Y, Barringer SA: Alkylpyrazines and other volatiles in cocoa liquors at pH 5 to 8, by Selected Ion Flow Tube-Mass Spectrometry (SIFT-MS). J Food Sci. 2010 Jan-Feb;75(1):C121-7. doi: 10.1111/j.1750-3841.2009.01455.x. [PubMed:20492142 ]
Magi E, Bono L, Di Carro M: Characterization of cocoa liquors by GC-MS and LC-MS/MS: focus on alkylpyrazines and flavanols. J Mass Spectrom. 2012 Sep;47(9):1191-7. doi: 10.1002/jms.3034. [PubMed:22972787 ]
Qin P, Ma T, Wu L, Shan F, Ren G: Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry. J Food Sci. 2011 Aug;76(6):S401-7. doi: 10.1111/j.1750-3841.2011.02223.x. Epub 2011 Jun 8. [PubMed:22417522 ]
Huang Y, Barringer SA: Monitoring of cocoa volatiles produced during roasting by selected ion flow tube-mass spectrometry (SIFT-MS). J Food Sci. 2011 Mar;76(2):C279-86. doi: 10.1111/j.1750-3841.2010.01984.x. Epub 2011 Feb 1. [PubMed:21535747 ]
Sun Y, Yu P, Zhang G, Wang L, Zhong H, Zhai Z, Wang L, Wang Y: Therapeutic effects of tetramethylpyrazine nitrone in rat ischemic stroke models. J Neurosci Res. 2012 Aug;90(8):1662-9. doi: 10.1002/jnr.23034. Epub 2012 Mar 19. [PubMed:22431378 ]
Sharp MD, Kocaoglu-Vurma NA, Langford V, Rodriguez-Saona LE, Harper WJ: Rapid discrimination and characterization of vanilla bean extracts by attenuated total reflection infrared spectroscopy and selected ion flow tube mass spectrometry. J Food Sci. 2012 Mar;77(3):C284-92. doi: 10.1111/j.1750-3841.2011.02544.x. [PubMed:22384952 ]
Guerra PV, Yaylayan VA: Double Schiff base adducts of 2,3-butanedione with glycine: formation of pyrazine rings with the participation of amino acid carbon atoms. J Agric Food Chem. 2012 Nov 14;60(45):11440-5. doi: 10.1021/jf303658m. Epub 2012 Nov 6. [PubMed:23106172 ]
Ishida T, Takechi S, Yamaguchi T: Possible involvement of glutathione balance disruption in dihydropyrazine-induced cytotoxicity on human hepatoma HepG2 cells. J Toxicol Sci. 2012;37(5):1065-9. [PubMed:23038014 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Trimethylpyrazine (NP0001446)

MOL for NP0001446 (Trimethylpyrazine)

3D MOL for NP0001446 (Trimethylpyrazine)

3D SDF for NP0001446 (Trimethylpyrazine)

3D-SDF for NP0001446 (Trimethylpyrazine)

PDB for NP0001446 (Trimethylpyrazine)

3D PDB for NP0001446 (Trimethylpyrazine)

SMILES for NP0001446 (Trimethylpyrazine)

INCHI for NP0001446 (Trimethylpyrazine)

Structure for NP0001446 (Trimethylpyrazine)

3D Structure for NP0001446 (Trimethylpyrazine)