Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:51:09 UTC

Update Date

2021-09-26 23:02:22 UTC

HMDB ID

HMDB0250747

Secondary Accession Numbers

None

Metabolite Identification

Common Name

D-Fructofuranose

Description

2,5-bis(hydroxymethyl)oxolane-2,3,4-triol belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (6-{oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate. It is generated by EC.3.2.1.X enzyme via a glycoside-hydrolysis reaction. This glycoside-hydrolysis occurs in human gut microbiota. This compound has been identified in human blood as reported by (PMID: 31557052 ). D-fructofuranose is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically D-Fructofuranose is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 19-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-AUG-19         0                                  
HETATM    1  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.477   2.904   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.090   3.224   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
CONECT    1    3    7                                                       
CONECT    2    6    8                                                       
CONECT    3    1    4   12                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    2    5   11   12                                             
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    3    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.156

Monoisotopic Molecular Weight

180.063388106

IUPAC Name

2,5-bis(hydroxymethyl)oxolane-2,3,4-triol

Traditional Name

β-fruit sugar

CAS Registry Number

Not Available

SMILES

OCC1OC(O)(CO)C(O)C1O

InChI Identifier

InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2

InChI Key

RFSUNEUAIZKAJO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-fructofuranose (CPD-10730 )

Ontology

Not Available

Endogenous (HMDB: HMDB0125599)

Process

Not Available

Role

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
logP	-2.4	ALOGPS
logP	-2.8	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.28 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
DeepCCS	[M+H]+	137.419	30932474
DeepCCS	[M-H]-	134.737	30932474
DeepCCS	[M-2H]-	171.367	30932474
DeepCCS	[M+Na]+	146.601	30932474
AllCCS	[M+H]+	140.4	32859911
AllCCS	[M+H-H2O]+	136.2	32859911
AllCCS	[M+NH4]+	144.3	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	131.7	32859911
AllCCS	[M+Na-2H]-	132.7	32859911
AllCCS	[M+HCOO]-	133.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Fructofuranose	OCC1OC(O)(CO)C(O)C1O	3518.1	Standard polar	33892256
D-Fructofuranose	OCC1OC(O)(CO)C(O)C1O	1818.8	Standard non polar	33892256
D-Fructofuranose	OCC1OC(O)(CO)C(O)C1O	1748.1	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 - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (5 TMS) - 70eV, Positive	splash10-0fb9-5614950000-6ef14e948d063026f7ee	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (Non-derivatized) - 70eV, Positive	splash10-076r-9600000000-f2c06850d0c3db9ec103	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-bis(hydroxymethyl)oxolane-2,3,4-triol GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-03	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 - D-Fructofuranose 10V, Negative-QTOF	splash10-004i-2900000000-74b62c8ea3678afcff8a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 20V, Negative-QTOF	splash10-01ta-1900000000-5a0f3f01ddf8c11c6370	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 40V, Negative-QTOF	splash10-0006-9000000000-93c2b00aa44481aa8630	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 10V, Negative-QTOF	splash10-056r-9800000000-b033c19e1db6b17bf7cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 20V, Negative-QTOF	splash10-0a4i-9500000000-01306ef5e3c5a271dfb2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 40V, Negative-QTOF	splash10-0a4l-9000000000-4e87bfc49b1664133053	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 10V, Positive-QTOF	splash10-001i-0900000000-2afc98a319bf6041adf0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 20V, Positive-QTOF	splash10-03ea-3900000000-1dd0cdea93f529e6ccb2	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 40V, Positive-QTOF	splash10-0007-9100000000-d0f08ad6c9dee008067a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 10V, Positive-QTOF	splash10-001i-0900000000-6aefe19f3e63c1b3fbef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 20V, Positive-QTOF	splash10-03gm-9500000000-d2f178dbda765758ef3d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Fructofuranose 40V, Positive-QTOF	splash10-0btd-9000000000-62631cc26542b523e7d7	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

METLIN ID

Not Available

PubChem Compound

716

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for D-Fructofuranose (HMDB0250747)

MOL for HMDB0250747 (D-Fructofuranose)

3D MOL for HMDB0250747 (D-Fructofuranose)

3D SDF for HMDB0250747 (D-Fructofuranose)

3D-SDF for HMDB0250747 (D-Fructofuranose)

PDB for HMDB0250747 (D-Fructofuranose)

3D PDB for HMDB0250747 (D-Fructofuranose)

SMILES for HMDB0250747 (D-Fructofuranose)

INCHI for HMDB0250747 (D-Fructofuranose)

Structure for HMDB0250747 (D-Fructofuranose)

3D Structure for HMDB0250747 (D-Fructofuranose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra