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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:11:58 UTC

Update Date

2023-02-21 17:25:06 UTC

HMDB ID

HMDB0036134

Secondary Accession Numbers

HMDB36134

Metabolite Identification

Common Name

4-[(2-Furanylmethyl)thio]-2-pentanone

Description

4-[(2-Furanylmethyl)thio]-2-pentanone 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. 4-[(2-Furanylmethyl)thio]-2-pentanone is a meaty tasting compound. 4-[(2-Furanylmethyl)thio]-2-pentanone 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 4-[(2-furanylmethyl)thio]-2-pentanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-[(2-Furanylmethyl)thio]-2-pentanone.

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       7.196   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.197   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.636   2.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.605   3.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.866   0.816   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.863   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.864   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.530   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.197   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.198   2.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.530   4.977   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      15.359   1.136   0.000  0.00  0.00           O+0
HETATM   13  S   UNK     0      12.531   2.667   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   12                                                       
CONECT    6    8    9                                                       
CONECT    7   10   13                                                       
CONECT    8    1    6   11                                                  
CONECT    9    2    6   13                                                  
CONECT   10    4    7   12                                                  
CONECT   11    8                                                            
CONECT   12    5   10                                                       
CONECT   13    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0036134
HETATM    1  C1  UNL     1      -3.408   1.795   0.652  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.484   0.640   0.812  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.451   0.085   1.892  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.658   0.237  -0.356  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.789  -0.937  -0.020  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.611  -2.112   0.385  1.00  0.00           C  
HETATM    7  S1  UNL     1       0.285  -1.269  -1.436  1.00  0.00           S  
HETATM    8  C6  UNL     1       1.417   0.104  -1.641  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.371   0.189  -0.468  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.592  -0.438  -0.373  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.117  -0.090   0.846  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.197   0.732   1.440  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.194   0.864   0.631  1.00  0.00           O  
HETATM   14  H1  UNL     1      -4.249   1.424  -0.003  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.838   2.114   1.632  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.845   2.612   0.162  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.367  -0.013  -1.183  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.039   1.111  -0.692  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.119  -0.643   0.838  1.00  0.00           H  
HETATM   20  H7  UNL     1      -1.811  -2.112   1.476  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.124  -3.088   0.174  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.624  -2.055  -0.106  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.981   0.092  -2.588  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.818   1.046  -1.590  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.048  -1.079  -1.114  1.00  0.00           H  
HETATM   26  H13 UNL     1       5.081  -0.400   1.272  1.00  0.00           H  
HETATM   27  H14 UNL     1       3.315   1.190   2.439  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5   17   18
CONECT    5    6    7   19
CONECT    6   20   21   22
CONECT    7    8
CONECT    8    9   23   24
CONECT    9   10   10   13
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(furfurylthio)Pentan-2-one	HMDB
4-furfurylthio-2-Pentanone	HMDB
FEMA 3840	HMDB
4-{[(furan-2-yl)methyl]sulphanyl}pentan-2-one	Generator

Chemical Formula

C₁₀H₁₄O₂S

Average Molecular Weight

198.282

Monoisotopic Molecular Weight

198.071450382

IUPAC Name

4-[(furan-2-ylmethyl)sulfanyl]pentan-2-one

Traditional Name

4-[(furan-2-ylmethyl)sulfanyl]pentan-2-one

CAS Registry Number

180031-78-1

SMILES

CC(CC(C)=O)SCC1=CC=CO1

InChI Identifier

InChI=1S/C10H14O2S/c1-8(11)6-9(2)13-7-10-4-3-5-12-10/h3-5,9H,6-7H2,1-2H3

InChI Key

IUNKNKANRUMCNL-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
Ketone
Oxacycle
Dialkylthioether
Sulfenyl compound
Thioether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Odor

Meaty

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036134)
Cytoplasm (HMDB: HMDB0036134)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036134)

Source

Exogenous

Food

Food (HMDB: HMDB0036134)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Endogenous

Plant

Coffea (HMDB: HMDB0036134)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0036134)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036134)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	288.00 to 289.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1203 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.313 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.081 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	54.95 m³·mol⁻¹	ChemAxon
Polarizability	21.71 Å³	ChemAxon
Number of Rings	1	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]+	144.165	31661259
DarkChem	[M-H]-	139.075	31661259
DeepCCS	[M+H]+	141.074	30932474
DeepCCS	[M-H]-	138.601	30932474
DeepCCS	[M-2H]-	174.285	30932474
DeepCCS	[M+Na]+	149.453	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.9	32859911
AllCCS	[M+NH4]+	146.3	32859911
AllCCS	[M+Na]+	147.3	32859911
AllCCS	[M-H]-	146.0	32859911
AllCCS	[M+Na-2H]-	147.1	32859911
AllCCS	[M+HCOO]-	148.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-[(2-Furanylmethyl)thio]-2-pentanone	CC(CC(C)=O)SCC1=CC=CO1	2143.6	Standard polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone	CC(CC(C)=O)SCC1=CC=CO1	1450.3	Standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone	CC(CC(C)=O)SCC1=CC=CO1	1430.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-[(2-Furanylmethyl)thio]-2-pentanone,1TMS,isomer #1	CC(=CC(C)SCC1=CC=CO1)O[Si](C)(C)C	1657.6	Semi standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TMS,isomer #1	CC(=CC(C)SCC1=CC=CO1)O[Si](C)(C)C	1547.0	Standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TMS,isomer #2	C=C(CC(C)SCC1=CC=CO1)O[Si](C)(C)C	1630.8	Semi standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TMS,isomer #2	C=C(CC(C)SCC1=CC=CO1)O[Si](C)(C)C	1553.3	Standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TBDMS,isomer #1	CC(=CC(C)SCC1=CC=CO1)O[Si](C)(C)C(C)(C)C	1890.2	Semi standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TBDMS,isomer #1	CC(=CC(C)SCC1=CC=CO1)O[Si](C)(C)C(C)(C)C	1764.9	Standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TBDMS,isomer #2	C=C(CC(C)SCC1=CC=CO1)O[Si](C)(C)C(C)(C)C	1867.1	Semi standard non polar	33892256
4-[(2-Furanylmethyl)thio]-2-pentanone,1TBDMS,isomer #2	C=C(CC(C)SCC1=CC=CO1)O[Si](C)(C)C(C)(C)C	1759.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-9300000000-a6fd329c8e125d5ef958	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 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 - 4-[(2-Furanylmethyl)thio]-2-pentanone 10V, Positive-QTOF	splash10-00l2-2900000000-0078342403e118aeba19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 20V, Positive-QTOF	splash10-014i-3900000000-9012831454ec1bfc9c6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 40V, Positive-QTOF	splash10-00kb-9300000000-2837ffce6feaba3cbeba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 10V, Negative-QTOF	splash10-0002-1900000000-1a14be2cbbd596ab8e3c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 20V, Negative-QTOF	splash10-03ea-5900000000-090616584057643fc5a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 40V, Negative-QTOF	splash10-01q9-9200000000-b9415326adc37dd9e676	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 10V, Negative-QTOF	splash10-01ot-1900000000-fc4aa855b4001aaf27b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 20V, Negative-QTOF	splash10-03di-3900000000-99ea38bd68d30a23b273	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 40V, Negative-QTOF	splash10-02t9-9300000000-7bb36f2d54aaec4840c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 10V, Positive-QTOF	splash10-00ko-9100000000-bbc3d65365ff4d67b4e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 20V, Positive-QTOF	splash10-01qc-9300000000-39302159028ef0e22a13	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[(2-Furanylmethyl)thio]-2-pentanone 40V, Positive-QTOF	splash10-001l-9100000000-24c12e00d36413e2544a	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

FDB014983

KNApSAcK ID

Not Available

Chemspider ID

2291568

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3025939

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1586611

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 4-[(2-Furanylmethyl)thio]-2-pentanone (HMDB0036134)

MOL for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

3D MOL for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

3D SDF for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

3D-SDF for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

PDB for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

3D PDB for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

SMILES for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

INCHI for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

Structure for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

3D Structure for HMDB0036134 (4-[(2-Furanylmethyl)thio]-2-pentanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra