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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:01 UTC

Update Date

2022-03-07 02:52:23 UTC

HMDB ID

HMDB0029988

Secondary Accession Numbers

HMDB29988

Metabolite Identification

Common Name

Bis(2-furanylmethyl) disulfide

Description

Bis(2-furanylmethyl) disulfide 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) disulfide is a cabbage, chicken, and coffee tasting compound. Bis(2-furanylmethyl) disulfide has been detected, but not quantified in, several different foods, such as coffee and coffee products, anatidaes (Anatidae), cereals and cereal products, breakfast cereal, and chickens (Gallus gallus). This could make bis(2-furanylmethyl) disulfide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Bis(2-furanylmethyl) disulfide.

Structure

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


  Mrv1652302102020362D          

 14 15  0  0  0  0            999 V2000
    0.5974    1.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7812    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1494    0.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291    1.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099    2.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3687   -0.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7610    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    1.9475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320    1.1270    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0465    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  2  0  0  0  0
  9  3  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029988

> <DATABASE_NAME>
hmdb

> <SMILES>
C(SSCC1=CC=CO1)C1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H2

> <INCHI_KEY>
CBJPZHSWLMJQRI-UHFFFAOYSA-N

> <FORMULA>
C10H10O2S2

> <MOLECULAR_WEIGHT>
226.315

> <EXACT_MASS>
226.012220944

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
23.76669976838184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({[(furan-2-yl)methyl]disulfanyl}methyl)furan

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
2.4106437873333335

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6031880129604117

> <JCHEM_POLAR_SURFACE_AREA>
26.28

> <JCHEM_REFRACTIVITY>
61.3194

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[(furan-2-ylmethyl)disulfanyl]methyl}furan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0       1.115   2.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.658   0.816   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.146   1.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.628   1.960   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.885   3.955   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.888  -0.518   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.886   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.887   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.552   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.221   1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.392   3.635   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.382  -0.198   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0       6.220   2.104   0.000  0.00  0.00           S+0
HETATM   14  S   UNK     0       7.553   1.334   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   14                                                       
CONECT    9    3    7   11                                                  
CONECT   10    4    8   12                                                  
CONECT   11    5    9                                                       
CONECT   12    6   10                                                       
CONECT   13    7   14                                                       
CONECT   14    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis(2-furanylmethyl) disulphide	Generator
2,2'-(Dithiobis(methylene))bis-furan	HMDB
2,2'-(Dithiobis(methylene))bisfuran	HMDB
2,2'-(Dithiodimethylene)di-furan	HMDB
2,2'-(Dithiodimethylene)difuran	HMDB
2,2'-[Dithiobis(methylene)]bis-furan	HMDB
2,2'-[Dithiobis(methylene)]bisfuran	HMDB
2,2'-[Dithiobis(methylene)]bisfuran, 9ci	HMDB
2-([(2-Furylmethyl)disulfanyl]methyl)furan	HMDB
2-Difurfuryl disulfide	HMDB
2-Furfuryl disulfide	HMDB
Bis(2-furfuryl) disulfide	HMDB
Bis(2-furfuryl)disulfide	HMDB
Bis(2-furylmethyl) disulphide	HMDB
Bis(2-furylmethyl)disulfide	HMDB
Bis-(furylmethyl) disulfide	HMDB
Bis-2-furfuryldisulphide	HMDB
Bis-furfuryl disulfide	HMDB
Di-2-furfuryl disulfide	HMDB
Difurfuryl disulfide	HMDB
Difurfuryldisulfide	HMDB
FEMA 3146	HMDB
Furfuryl disulfide	HMDB
2-({[(furan-2-yl)methyl]disulphanyl}methyl)furan	Generator

Chemical Formula

C₁₀H₁₀O₂S₂

Average Molecular Weight

226.315

Monoisotopic Molecular Weight

226.012220944

IUPAC Name

2-({[(furan-2-yl)methyl]disulfanyl}methyl)furan

Traditional Name

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

CAS Registry Number

4437-20-1

SMILES

C(SSCC1=CC=CO1)C1=CC=CO1

InChI Identifier

InChI=1S/C10H10O2S2/c1-3-9(11-5-1)7-13-14-8-10-4-2-6-12-10/h1-6H,7-8H2

InChI Key

CBJPZHSWLMJQRI-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
Dialkyldisulfide
Organic disulfide
Oxacycle
Sulfenyl compound
Organic oxygen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	10 - 11 °C	Not Available
Boiling Point	229.00 to 230.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	11.56 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.030	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	3.22	ALOGPS
logP	2.41	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-2.6	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	5	ChemAxon
Refractivity	61.32 m³·mol⁻¹	ChemAxon
Polarizability	23.77 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]+	146.374	31661259
DarkChem	[M-H]-	145.908	31661259
DeepCCS	[M+H]+	146.878	30932474
DeepCCS	[M-H]-	144.471	30932474
DeepCCS	[M-2H]-	180.162	30932474
DeepCCS	[M+Na]+	155.587	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.3	32859911
AllCCS	[M-H]-	145.7	32859911
AllCCS	[M+Na-2H]-	145.9	32859911
AllCCS	[M+HCOO]-	146.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(2-furanylmethyl) disulfide	C(SSCC1=CC=CO1)C1=CC=CO1	2286.5	Standard polar	33892256
Bis(2-furanylmethyl) disulfide	C(SSCC1=CC=CO1)C1=CC=CO1	1694.5	Standard non polar	33892256
Bis(2-furanylmethyl) disulfide	C(SSCC1=CC=CO1)C1=CC=CO1	1652.6	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 - Bis(2-furanylmethyl) disulfide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9100000000-695c41cfbd193f9ee2db	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(2-furanylmethyl) disulfide 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) disulfide 10V, Positive-QTOF	splash10-004i-0190000000-6513dfd7ccc2c0fe2781	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 20V, Positive-QTOF	splash10-01t9-1970000000-54dc2e0918efabb6ff5b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 40V, Positive-QTOF	splash10-03yi-8900000000-1e716c0c77cceaca9d0e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 10V, Negative-QTOF	splash10-004i-0090000000-d789644f67b7bbc21aac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 20V, Negative-QTOF	splash10-03di-1910000000-c5a98e6d0877a6f503c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 40V, Negative-QTOF	splash10-01pc-9610000000-433edcf7998fe872054f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 10V, Positive-QTOF	splash10-004i-1950000000-705199837ef47f0e21f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 20V, Positive-QTOF	splash10-01q9-9710000000-a03ce2925906065ebc79	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 40V, Positive-QTOF	splash10-001i-9100000000-d7bd21f6b85214e3f06f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 10V, Negative-QTOF	splash10-03di-0900000000-914fd82d32599c15e5e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 20V, Negative-QTOF	splash10-03di-2900000000-d90a11ec6203520f359e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-furanylmethyl) disulfide 40V, Negative-QTOF	splash10-02t9-9300000000-0c1cf1cfab4f950b5b96	2021-09-24	Wishart 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

FDB001276

KNApSAcK ID

Not Available

Chemspider ID

19306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20499

PDB ID

Not Available

ChEBI ID

855724

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1021291

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) disulfide (HMDB0029988)

MOL for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

3D MOL for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

3D SDF for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

3D-SDF for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

PDB for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

3D PDB for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

SMILES for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

INCHI for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

Structure for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

3D Structure for HMDB0029988 (Bis(2-furanylmethyl) disulfide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra