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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:11:32 UTC

Update Date

2023-02-21 17:28:47 UTC

HMDB ID

HMDB0041503

Secondary Accession Numbers

HMDB41503

Metabolite Identification

Common Name

Bis(2-furanylmethyl) sulfide

Description

Bis(2-furanylmethyl) sulfide belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Bis(2-furanylmethyl) sulfide is a coffee, earthy, and meaty tasting compound. Bis(2-furanylmethyl) sulfide has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make bis(2-furanylmethyl) sulfide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bis(2-furanylmethyl) sulfide.

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      -4.045   7.218   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.014   6.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.275   8.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.768   8.232   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      -0.274   4.390   0.000  0.00  0.00           S+0
CONECT    1    3    5                                                       
CONECT    2    4    6                                                       
CONECT    3    1    9                                                       
CONECT    4    2   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   12                                                       
CONECT    7    9   13                                                       
CONECT    8   10   13                                                       
CONECT    9    3    7   11                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5    9                                                       
CONECT   12    6   10                                                       
CONECT   13    7    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis(2-furanylmethyl) sulphide	Generator
2,2'-(Thiobis(methylene))bis-furan	HMDB
2,2'-(Thiobis(methylene))bisfuran	HMDB
2,2'-(Thiodimethylene) difuran	HMDB
2,2'-(Thiodimethylene)di-furan	HMDB
2,2'-(Thiodimethylene)difuran	HMDB
2,2'-(Thiodimethylene)difuran, 9ci	HMDB
2,2'-[Thiobis(methylene)]bis-furan	HMDB
2,2-(Thiodimethylene)-difuran	HMDB
2-([(2-Furylmethyl)sulfanyl]methyl)furan	HMDB
2-Difurfuryl sulfide	HMDB
2-Furfuryl monosulfide	HMDB
Bis(2-furfuryl) sulfide	HMDB
Bis(2-furylmethyl) sulfide	HMDB
Bis-furfuryl sulfide	HMDB
Di-2-furfuryl sulfide	HMDB
Difurfuryl monosulfide	HMDB
Difurfuryl sulfide	HMDB
FEMA 3238	HMDB
Furfuryl sulfide	HMDB
2-({[(furan-2-yl)methyl]sulphanyl}methyl)furan	Generator

Chemical Formula

C₁₀H₁₀O₂S

Average Molecular Weight

194.25

Monoisotopic Molecular Weight

194.040150254

IUPAC Name

2-{[(furan-2-ylmethyl)sulfanyl]methyl}furan

Traditional Name

2-{[(furan-2-ylmethyl)sulfanyl]methyl}furan

CAS Registry Number

13678-67-6

SMILES

C(SCC1=CC=CO1)C1=CC=CO1

InChI Identifier

InChI=1S/C10H10O2S/c1-3-9(11-5-1)7-13-8-10-4-2-6-12-10/h1-6H,7-8H2

InChI Key

UYLKDZXJEKFFHJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Furan
Oxacycle
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxygen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0041503)
Cell membrane (HMDB: HMDB0041503)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041503)

Source

Exogenous

Food

Food (HMDB: HMDB0041503)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0041503)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0041503)

Biological role

Nutrient (HMDB: HMDB0041503)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	31 - 32 °C	Not Available
Boiling Point	130.00 to 131.00 °C. @ 9.00 mm Hg	The Good Scents Company Information System
Water Solubility	110.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.365 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	2.72	ALOGPS
logP	2.27	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.31 m³·mol⁻¹	ChemAxon
Polarizability	20.84 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]+	139.801	31661259
DarkChem	[M-H]-	139.23	31661259
DeepCCS	[M+H]+	142.065	30932474
DeepCCS	[M-H]-	139.567	30932474
DeepCCS	[M-2H]-	175.38	30932474
DeepCCS	[M+Na]+	150.771	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	141.6	32859911
AllCCS	[M+Na-2H]-	142.0	32859911
AllCCS	[M+HCOO]-	142.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(2-furanylmethyl) sulfide	C(SCC1=CC=CO1)C1=CC=CO1	2152.0	Standard polar	33892256
Bis(2-furanylmethyl) sulfide	C(SCC1=CC=CO1)C1=CC=CO1	1485.3	Standard non polar	33892256
Bis(2-furanylmethyl) sulfide	C(SCC1=CC=CO1)C1=CC=CO1	1449.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Bis(2-furanylmethyl) sulfide EI-B (Non-derivatized)	splash10-001i-9100000000-ee8816bbffcfcc47f2dd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Bis(2-furanylmethyl) sulfide EI-B (Non-derivatized)	splash10-001i-9100000000-ee8816bbffcfcc47f2dd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(2-furanylmethyl) sulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-cecac0b5e06adbe96e3d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(2-furanylmethyl) sulfide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(2-furanylmethyl) sulfide 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 - Bis(2-furanylmethyl) sulfide 10V, Negative-QTOF	splash10-0006-0900000000-0818729c41032384cbf0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 20V, Negative-QTOF	splash10-0006-0900000000-87503236343d0b3b6020	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 40V, Negative-QTOF	splash10-0w39-9200000000-ce0938ed5a22fbf6acab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 10V, Negative-QTOF	splash10-0006-2900000000-f4a1749b6cba558499df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 20V, Negative-QTOF	splash10-03ec-9500000000-eedf8c18dae597ed7bf3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 40V, Negative-QTOF	splash10-03di-9200000000-e6ec82de5a43a9e113fc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 10V, Positive-QTOF	splash10-0002-0900000000-c3800a9e6b7017714873	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 20V, Positive-QTOF	splash10-03di-3900000000-4d28ce0ba0f40e162083	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 40V, Positive-QTOF	splash10-03e9-9400000000-648f5ad9b9e40a51bbfd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 10V, Positive-QTOF	splash10-0gz9-9400000000-b7b204964841fb3cc36f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 20V, Positive-QTOF	splash10-0ue9-9000000000-915b8f3a0771f1b550ef	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) sulfide 40V, Positive-QTOF	splash10-0ue9-9000000000-8cc7db4e565d0ff63022	2021-09-21	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

Membrane

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

FDB021475

KNApSAcK ID

Not Available

Chemspider ID

55564

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61659

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035661

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 Bis(2-furanylmethyl) sulfide (HMDB0041503)

MOL for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

3D MOL for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

3D SDF for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

3D-SDF for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

PDB for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

3D PDB for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

SMILES for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

INCHI for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

Structure for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

3D Structure for HMDB0041503 (Bis(2-furanylmethyl) sulfide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra