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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:44:24 UTC

Update Date

2022-03-07 02:56:30 UTC

HMDB ID

HMDB0040201

Secondary Accession Numbers

HMDB40201

Metabolite Identification

Common Name

3,3'-Dithiobis[2-methylfuran]

Description

3,3'-Dithiobis[2-methylfuran], also known as bis(2-methyl-3-furyl) disulfide or 3,3'-dithio-2,2'-dimethyldifuran, 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. 3,3'-Dithiobis[2-methylfuran] is a meaty, onion, and roasted tasting compound. 3,3'-dithiobis[2-methylfuran] has been detected, but not quantified, in tea. This could make 3,3'-dithiobis[2-methylfuran] a potential biomarker for the consumption of this food.

Structure

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

  Mrv1652305261923582D          

 14 15  0  0  0  0            999 V2000
   -2.6563    3.3986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1735    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0688    1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7610    2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438    1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5860    2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563    2.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1735    1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3237    2.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5061    2.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    2.0887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8410    2.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1084    2.3436    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215    1.7916    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040201

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(SSC2=C(C)OC=C2)C=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2S2/c1-7-9(3-5-11-7)13-14-10-4-6-12-8(10)2/h3-6H,1-2H3

> <INCHI_KEY>
OHDFENKFSKIFBJ-UHFFFAOYSA-N

> <FORMULA>
C10H10O2S2

> <MOLECULAR_WEIGHT>
226.315

> <EXACT_MASS>
226.012220944

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
22.256614296825838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-3-[(2-methylfuran-3-yl)disulfanyl]furan

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
3.253358637333333

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5545969375585726

> <JCHEM_POLAR_SURFACE_AREA>
26.28

> <JCHEM_REFRACTIVITY>
57.78640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-3-[(2-methylfuran-3-yl)disulfanyl]furan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.958   6.344   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.524   1.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.728   2.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.754   5.285   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.188   2.434   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.294   5.285   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.958   4.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.524   2.915   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.204   3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.278   3.820   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.713   3.899   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0     -12.770   3.820   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      -7.669   4.375   0.000  0.00  0.00           S+0
HETATM   14  S   UNK     0      -8.813   3.344   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    5    9                                                       
CONECT    4    6   10                                                       
CONECT    5    3   11                                                       
CONECT    6    4   12                                                       
CONECT    7    1    9   11                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3    7   13                                                  
CONECT   10    4    8   14                                                  
CONECT   11    5    7                                                       
CONECT   12    6    8                                                       
CONECT   13    9   14                                                       
CONECT   14   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Bis(2-methylfuran-3-yl)disulfane	ChEBI
2-Methyl-3-[(2-methylfuran-3-yl)disulfanyl]furan	ChEBI
3,3'-Dithio-2,2'-dimethyldifuran	ChEBI
3,3'-Dithiobis(2-methylfuran)	ChEBI
Bis(2-methyl-3-furanyl) disulfide	ChEBI
Bis(2-methyl-3-furyl) disulfide	ChEBI
Bis(2-methyl-3-furyl)disulphide	ChEBI
FEMA 3259	ChEBI
1,2-Bis(2-methylfuran-3-yl)disulphane	Generator
2-Methyl-3-[(2-methylfuran-3-yl)disulphanyl]furan	Generator
Bis(2-methyl-3-furanyl) disulphide	Generator
Bis(2-methyl-3-furyl) disulphide	Generator
Bis(2-methyl-3-furyl)disulfide	Generator
2-Methyl-3-furyl disulfide	HMDB
3,3'-Dithiobis(2-methyl-furan	HMDB
3,3'-Dithiobis[2-methyl-furan	HMDB
Bis(2-methyl-3-furyi)-disulfide	HMDB
Bis(2-methylfuryl) disulfide	HMDB
Bis-(2-methyl-3-furyl)-disulphide	HMDB
Bis-(2-methylfuryl-3-) disulfide	HMDB
Bis-[(2-methylfuryl-3)] disulfide	HMDB

Chemical Formula

C₁₀H₁₀O₂S₂

Average Molecular Weight

226.315

Monoisotopic Molecular Weight

226.012220944

IUPAC Name

2-methyl-3-[(2-methylfuran-3-yl)disulfanyl]furan

Traditional Name

2-methyl-3-[(2-methylfuran-3-yl)disulfanyl]furan

CAS Registry Number

28588-75-2

SMILES

CC1=C(SSC2=C(C)OC=C2)C=CO1

InChI Identifier

InChI=1S/C10H10O2S2/c1-7-9(3-5-11-7)13-14-10-4-6-12-8(10)2/h3-6H,1-2H3

InChI Key

OHDFENKFSKIFBJ-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
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

Cellular substructure

Membrane (HMDB: HMDB0040201)
Cell membrane (HMDB: HMDB0040201)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040201)

Source

Exogenous

Exogenous (HMDB: HMDB0040201)

Food

Food (HMDB: HMDB0040201)

Tea

Endogenous

Plant

Plant (HMDB: HMDB0040201)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040201)

Biological role

Nutrient (HMDB: HMDB0040201)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	277.00 to 280.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	9.27 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.345 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.25	ChemAxon
logS	-3.8	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	3	ChemAxon
Refractivity	57.79 m³·mol⁻¹	ChemAxon
Polarizability	22.26 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]+	148.352	31661259
DarkChem	[M-H]-	144.944	31661259
DeepCCS	[M+H]+	146.624	30932474
DeepCCS	[M-H]-	144.266	30932474
DeepCCS	[M-2H]-	179.353	30932474
DeepCCS	[M+Na]+	154.637	30932474
AllCCS	[M+H]+	145.0	32859911
AllCCS	[M+H-H2O]+	140.9	32859911
AllCCS	[M+NH4]+	148.9	32859911
AllCCS	[M+Na]+	150.0	32859911
AllCCS	[M-H]-	142.1	32859911
AllCCS	[M+Na-2H]-	142.2	32859911
AllCCS	[M+HCOO]-	142.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,3'-Dithiobis[2-methylfuran]	CC1=C(SSC2=C(C)OC=C2)C=CO1	2098.8	Standard polar	33892256
3,3'-Dithiobis[2-methylfuran]	CC1=C(SSC2=C(C)OC=C2)C=CO1	1557.4	Standard non polar	33892256
3,3'-Dithiobis[2-methylfuran]	CC1=C(SSC2=C(C)OC=C2)C=CO1	1601.1	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 - 3,3'-Dithiobis[2-methylfuran] GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2910000000-cdb4efbaa82b9b108b49	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dithiobis[2-methylfuran] GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 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 - 3,3'-Dithiobis[2-methylfuran] 10V, Positive-QTOF	splash10-004i-0290000000-0dc77ae1e33b5f290c53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 20V, Positive-QTOF	splash10-004i-0490000000-32873febf58206c30575	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 40V, Positive-QTOF	splash10-044r-9400000000-46d9a0378ccfe9acc998	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 10V, Negative-QTOF	splash10-004i-0090000000-c4dd5de4fdc36365c566	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 20V, Negative-QTOF	splash10-03di-2920000000-3f3cbd8e03c0bc7e3e55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 40V, Negative-QTOF	splash10-03di-0900000000-9e29374b2b2440aa28b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 10V, Positive-QTOF	splash10-03xr-0910000000-95917524accec18b6393	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 20V, Positive-QTOF	splash10-03xr-3900000000-0cfc6df2cbe67dc0f058	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 40V, Positive-QTOF	splash10-03di-6900000000-505d9ee1f301e572bdfa	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 10V, Negative-QTOF	splash10-03di-2900000000-b593a34adf581c3d9d54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 20V, Negative-QTOF	splash10-03dl-9700000000-6bf8cd06aa54ed8a9187	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,3'-Dithiobis[2-methylfuran] 40V, Negative-QTOF	splash10-03dl-9500000000-ed12606a67618ad88e93	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

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

FDB019913

KNApSAcK ID

Not Available

Chemspider ID

459081

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

526624

PDB ID

Not Available

ChEBI ID

172109

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1035721

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 3,3'-Dithiobis[2-methylfuran] (HMDB0040201)

MOL for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

3D MOL for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

3D SDF for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

3D-SDF for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

PDB for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

3D PDB for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

SMILES for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

INCHI for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

Structure for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

3D Structure for HMDB0040201 (3,3'-Dithiobis[2-methylfuran])

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra