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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:14:48 UTC

Update Date

2023-02-21 17:25:12 UTC

HMDB ID

HMDB0036187

Secondary Accession Numbers

HMDB36187

Metabolite Identification

Common Name

2-[(2-Furanylmethyl)thio]-6-methylpyrazine

Description

2-[(2-Furanylmethyl)thio]-6-methylpyrazine belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. Based on a literature review very few articles have been published on 2-[(2-Furanylmethyl)thio]-6-methylpyrazine.

Structure

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


  Mrv0541 02241216132D          

 14 15  0  0  0  0            999 V2000
   -2.0817   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0817   -0.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679   -1.3203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -0.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3679    0.3287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0599    0.3287    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -0.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4903    0.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2426   -0.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955    0.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3828    1.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741    1.1484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7955    0.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036187

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CN=CC(SCC2=CC=CO2)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N2OS/c1-8-5-11-6-10(12-8)14-7-9-3-2-4-13-9/h2-6H,7H2,1H3

> <INCHI_KEY>
KVROPEIAOPWQEV-UHFFFAOYSA-N

> <FORMULA>
C10H10N2OS

> <MOLECULAR_WEIGHT>
206.264

> <EXACT_MASS>
206.051383642

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.758141210536657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(furan-2-ylmethyl)sulfanyl]-6-methylpyrazine

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.416980136333333

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.30662856403950467

> <JCHEM_POLAR_SURFACE_AREA>
38.92

> <JCHEM_REFRACTIVITY>
56.61480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(furan-2-ylmethyl)sulfanyl]-6-methylpyrazine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.886  -0.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.886  -1.694   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.553  -2.465   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.223  -1.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.223  -0.154   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.553   0.614   0.000  0.00  0.00           N+0
HETATM    7  S   UNK     0       0.112   0.614   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       1.447  -0.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.782   0.614   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.186  -0.013   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.218   1.130   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.448   2.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.938   2.144   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.218   0.616   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    5                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    9   12                                                       
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(((2-Furanylmethyl)thio)methyl)-pyrazine	HMDB
((furfurylthio)Methyl)pyrazine	HMDB
2-(((2-Furanylmethyl)thio)methyl)-pyrazine	HMDB
6-Methyl-2-pyrazinyl 2-furfuryl sulfide	HMDB
FEMA 3189	HMDB
2-{[(furan-2-yl)methyl]sulphanyl}-6-methylpyrazine	Generator

Chemical Formula

C₁₀H₁₀N₂OS

Average Molecular Weight

206.264

Monoisotopic Molecular Weight

206.051383642

IUPAC Name

2-[(furan-2-ylmethyl)sulfanyl]-6-methylpyrazine

Traditional Name

2-[(furan-2-ylmethyl)sulfanyl]-6-methylpyrazine

CAS Registry Number

59021-05-5

SMILES

CC1=CN=CC(SCC2=CC=CO2)=N1

InChI Identifier

InChI=1S/C10H10N2OS/c1-8-5-11-6-10(12-8)14-7-9-3-2-4-13-9/h2-6H,7H2,1H3

InChI Key

KVROPEIAOPWQEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Aryl thioethers

Alternative Parents

Substituents

Aryl thioether
Alkylarylthioether
Pyrazine
Furan
Heteroaromatic compound
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036187)
Cytoplasm (HMDB: HMDB0036187)

Source

Exogenous

Exogenous (HMDB: HMDB0036187)

Food

Food (HMDB: HMDB0036187)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036187)

Biological role

Nutrient (HMDB: HMDB0036187)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	317.36 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1579 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.247 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	2.15	ALOGPS
logP	1.42	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	0.31	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	56.61 m³·mol⁻¹	ChemAxon
Polarizability	20.76 Å³	ChemAxon
Number of Rings	2	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]+	145.257	31661259
DarkChem	[M-H]-	144.534	31661259
DeepCCS	[M+H]+	144.709	30932474
DeepCCS	[M-H]-	141.028	30932474
DeepCCS	[M-2H]-	178.513	30932474
DeepCCS	[M+Na]+	154.052	30932474
AllCCS	[M+H]+	143.4	32859911
AllCCS	[M+H-H2O]+	139.1	32859911
AllCCS	[M+NH4]+	147.4	32859911
AllCCS	[M+Na]+	148.6	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	146.0	32859911
AllCCS	[M+HCOO]-	146.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.52 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4442 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.29 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1200.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	409.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	248.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	115.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	381.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	543.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1075.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	171.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1079.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	490.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	52.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-[(2-Furanylmethyl)thio]-6-methylpyrazine	CC1=CN=CC(SCC2=CC=CO2)=N1	2180.4	Standard polar	33892256
2-[(2-Furanylmethyl)thio]-6-methylpyrazine	CC1=CN=CC(SCC2=CC=CO2)=N1	1606.4	Standard non polar	33892256
2-[(2-Furanylmethyl)thio]-6-methylpyrazine	CC1=CN=CC(SCC2=CC=CO2)=N1	1643.3	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 - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0563-9420000000-6eb58943c3485f6f7e34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 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 - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 10V, Positive-QTOF	splash10-0a4i-1090000000-8253367a68045b56962f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 20V, Positive-QTOF	splash10-0a4i-2490000000-0dbf9158ac7d449a7e05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 40V, Positive-QTOF	splash10-0w29-9400000000-25cce80a893ec771fdeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 10V, Negative-QTOF	splash10-0a4i-0190000000-701256d74d61147f0a96	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 20V, Negative-QTOF	splash10-0a4l-8390000000-d196b367f5ec077497d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 40V, Negative-QTOF	splash10-0006-9100000000-bacd7a3945f098b6e0c7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 10V, Negative-QTOF	splash10-0a4i-0090000000-b4e97b8b7a11063c39f0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 20V, Negative-QTOF	splash10-0a4i-7890000000-b0045be6121ad6dace62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 40V, Negative-QTOF	splash10-052f-9200000000-6e2f4bebeb716598f75f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 10V, Positive-QTOF	splash10-0a4i-2290000000-401da465eb35e3cef49c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 20V, Positive-QTOF	splash10-052f-9020000000-9b86f72529277f0d435a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-[(2-Furanylmethyl)thio]-6-methylpyrazine 40V, Positive-QTOF	splash10-0udi-9200000000-57c78107b775831f7693	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

FDB015041

KNApSAcK ID

Not Available

Chemspider ID

91254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101005

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1464241

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 2-[(2-Furanylmethyl)thio]-6-methylpyrazine (HMDB0036187)

MOL for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

3D MOL for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

3D SDF for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

3D-SDF for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

PDB for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

3D PDB for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

SMILES for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

INCHI for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

Structure for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

3D Structure for HMDB0036187 (2-[(2-Furanylmethyl)thio]-6-methylpyrazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra