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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-02-26 19:02:12 UTC

Update Date

2023-02-21 17:29:20 UTC

HMDB ID

HMDB0059752

Secondary Accession Numbers

HMDB59752

Metabolite Identification

Common Name

5-Sulfoxymethylfurfural

Description

5-Sulfoxymethylfurfural, also known as 5-SMF, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 5-Sulfoxymethylfurfural is an extremely weak basic (essentially neutral) compound (based on its pKa). These are organic compounds containing the sulfuric acid monoester functional group.

Structure

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

HEADER    PROTEIN                                 26-FEB-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-FEB-13         0                                  
HETATM    1  O   UNK     0       2.393   7.470   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0       2.393   5.930   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       0.853   5.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.933   5.930   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    7                                                       
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-Sulphoxymethylfurfural	Generator
5-Sulphooxymethylfurfural	HMDB
5-SMF	HMDB
[(5-Formylfuran-2-yl)methoxy]sulfonate	Generator
[(5-Formylfuran-2-yl)methoxy]sulphonate	Generator
[(5-Formylfuran-2-yl)methoxy]sulphonic acid	Generator
5-Sulfooxymethylfurfural	MeSH

Chemical Formula

C₆H₆O₆S

Average Molecular Weight

206.173

Monoisotopic Molecular Weight

205.988508614

IUPAC Name

[(5-formylfuran-2-yl)methoxy]sulfonic acid

Traditional Name

(5-formylfuran-2-yl)methoxysulfonic acid

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)OCC1=CC=C(O1)C=O

InChI Identifier

InChI=1S/C6H6O6S/c7-3-5-1-2-6(12-5)4-11-13(8,9)10/h1-3H,4H2,(H,8,9,10)

InChI Key

WVMJEBICTINBRO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-aldehydes

Alternative Parents

Substituents

Aryl-aldehyde
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Heteroaromatic compound
Organic sulfuric acid or derivatives
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.66 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-2.2	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	-2.7	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.81 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	41.72 m³·mol⁻¹	ChemAxon
Polarizability	17.58 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.625	31661259
DarkChem	[M-H]-	140.024	31661259
DeepCCS	[M+H]+	136.007	30932474
DeepCCS	[M-H]-	133.612	30932474
DeepCCS	[M-2H]-	168.538	30932474
DeepCCS	[M+Na]+	143.33	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.6	32859911
AllCCS	[M+NH4]+	146.6	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	136.3	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Sulfoxymethylfurfural	OS(=O)(=O)OCC1=CC=C(O1)C=O	3301.9	Standard polar	33892256
5-Sulfoxymethylfurfural	OS(=O)(=O)OCC1=CC=C(O1)C=O	1486.4	Standard non polar	33892256
5-Sulfoxymethylfurfural	OS(=O)(=O)OCC1=CC=C(O1)C=O	1751.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Sulfoxymethylfurfural,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	1844.4	Semi standard non polar	33892256
5-Sulfoxymethylfurfural,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	1759.3	Standard non polar	33892256
5-Sulfoxymethylfurfural,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	2770.5	Standard polar	33892256
5-Sulfoxymethylfurfural,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	2093.6	Semi standard non polar	33892256
5-Sulfoxymethylfurfural,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	2042.2	Standard non polar	33892256
5-Sulfoxymethylfurfural,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OCC1=CC=C(C=O)O1	2767.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Sulfoxymethylfurfural GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3910000000-19fe566986ae6f436cb2	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Sulfoxymethylfurfural 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 - 5-Sulfoxymethylfurfural 10V, Positive-QTOF	splash10-0a4i-1590000000-d9c11f6325a7b94990bd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 20V, Positive-QTOF	splash10-0a4r-4910000000-2221fc4d83d038c22ede	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 40V, Positive-QTOF	splash10-0gba-9000000000-c38a1a134f2d99aaf3a1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 10V, Negative-QTOF	splash10-0udi-0190000000-9de4cab1b9de60113e3d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 20V, Negative-QTOF	splash10-0kbb-9830000000-2d6579fde779578a9653	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 40V, Negative-QTOF	splash10-00lr-9000000000-b167d012590940b7e962	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 10V, Negative-QTOF	splash10-0udi-0190000000-6e9ac4a41050cea2b98a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 20V, Negative-QTOF	splash10-0002-9000000000-b427a7756f10c58e2353	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 40V, Negative-QTOF	splash10-000t-9000000000-c4422ccdf2ba49cfd823	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 10V, Positive-QTOF	splash10-0a4i-1190000000-1add171cb10e7916e16c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 20V, Positive-QTOF	splash10-001m-9200000000-26063d377842a18cefc1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Sulfoxymethylfurfural 40V, Positive-QTOF	splash10-000f-9000000000-b794a19d34da3a584119	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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+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

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxymethylfurfural

METLIN ID

Not Available

PubChem Compound

154718

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 5-Sulfoxymethylfurfural (HMDB0059752)

MOL for HMDB0059752 (5-Sulfoxymethylfurfural)

3D MOL for HMDB0059752 (5-Sulfoxymethylfurfural)

3D SDF for HMDB0059752 (5-Sulfoxymethylfurfural)

3D-SDF for HMDB0059752 (5-Sulfoxymethylfurfural)

PDB for HMDB0059752 (5-Sulfoxymethylfurfural)

3D PDB for HMDB0059752 (5-Sulfoxymethylfurfural)

SMILES for HMDB0059752 (5-Sulfoxymethylfurfural)

INCHI for HMDB0059752 (5-Sulfoxymethylfurfural)

Structure for HMDB0059752 (5-Sulfoxymethylfurfural)

3D Structure for HMDB0059752 (5-Sulfoxymethylfurfural)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra