MiMeDB: Showing metabocard for D-Fructofuranose (MMDBc0000293)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-28 00:08:54 UTC

Update Date

2022-08-31 00:17:13 UTC

Metabolite ID

MMDBc0000293

Metabolite Identification

Common Name

D-Fructofuranose

Description

D-Fructose, also known as fruit sugar or levulose, 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. D-Fructose is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, D-fructose participates in a number of enzymatic reactions. In particular, D-fructose can be biosynthesized from sorbitol; which is catalyzed by the enzyme sorbitol dehydrogenase. In addition, D-fructose can be biosynthesized from β-D-fructose 2-phosphate; which is mediated by the enzyme 14 kda phosphohistidine phosphatase. Inulin from dandelion roots has also been used as a source. In humans, D-fructose is involved in fructose intolerance, hereditary. D-Fructose is an odorless tasting compound. Outside of the human body, D-Fructose is found, on average, in the highest concentration within a few different foods, such as honey, agaves, and dates and in a lower concentration in white cabbages, italian sweet red peppers, and tortilla. D-Fructose has also been detected, but not quantified in, several different foods, such as fruit preserves, malus (crab apple), groundcherries, carp breams, and crayfish. This could make D-fructose a potential biomarker for the consumption of these foods. D-Fructose occurs in honey and a large number of fruits, particularly apples and tomatoes. It is fluid and nutrient replenisher, and nutritive sweetener. D-Fructose is also found in many other foods, some of which are sweet cherry, anise, and tinda. Present in polymeric form in the inulins, the energy reserve polysaccharides of many plants, e.g. dahlia and Jerusalem artichoke tubers.

Structure

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0      25.688 -16.394   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.220 -17.818   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      24.412 -15.470   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      26.766 -15.291   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      27.099 -16.907   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      23.668 -17.818   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      26.124 -19.075   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      23.167 -16.362   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      28.171 -15.939   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.769 -19.082   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      21.698 -15.900   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      20.774 -17.138   0.000  0.00  0.00           O+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8                                                       
CONECT    4    1    9                                                       
CONECT    5    1                                                            
CONECT    6    2   10    8                                                  
CONECT    7    2                                                            
CONECT    8    3   11    6                                                  
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    8   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
D-Arabino-hexulose	ChEBI
Fruit sugar	ChEBI
Levulose	ChEBI
D-Fructose	ChEBI
Baxter brand OF fructose	MeSH
Bieffe brand OF fructose	MeSH
Ern brand OF fructose	MeSH
Fleboplast levulosa	MeSH
Levulosa	MeSH
Levulosa braun	MeSH
Levulosa grifols	MeSH
Levulosa ife	MeSH
Levulosa mein	MeSH
Levulosa, fleboplast	MeSH
levulosado Bieffe medit	MeSH
Braun brand OF fructose	MeSH
instituto farmacologico Brand OF fructose	MeSH
Levulosa baxter	MeSH
levulosado Braun	MeSH
Fresenius kabi brand OF fructose	MeSH
Fructose	MeSH
Grifols brand OF fructose	MeSH
Apir levulosa	MeSH
Levulosa ibys	MeSH
Levulosa, apir	MeSH
levulosado Vitulia	MeSH
Plast apyr levulosa mein	MeSH

Molecular Formula

C₆H₁₂O₆

Average Mass

180.1559

Monoisotopic Mass

180.063388116

IUPAC Name

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

Traditional Name

fruit sugar

CAS Registry Number

57-48-7

SMILES

OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6?/m1/s1

InChI Key

RFSUNEUAIZKAJO-VRPWFDPXSA-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

D-fructose (CHEBI:37721 )
fructofuranose (CHEBI:37721 )
Ketoses (C00095 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.8	ChemAxon
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-e83683f33312f7b8a1e1	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-4900000000-c14d4be56a78c5647ddc	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05a7-9100000000-0fb431a2d8f04450b6a0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900000000-2255549937d454d405a0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-2900000000-b640e9d3b37f0787f857	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-a51d0897073ec10f04bd	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	87	Human stool; Human ; Human feces; Human vaginal fluid; Human subgingival plaque; Human saliva; Goat feces; Sheep feces; Human mucosa; Human sputum; Human urine; Human supragingival plaque	Microbial culture
Bacteria	Bacteroidetes	17	Human saliva; Human ; Human subgingival plaque; Human feces; Human stool; Human urine	Microbial culture
Eukaryota	Apicomplexa	1		Microbial culture
Bacteria	Proteobacteria	20	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human sputum; Human subgingival plaque	Microbial culture
Archaea	Crenarchaeota	1	Human feces	Microbial culture
Bacteria	Deinococcus-thermus	3		Microbial culture
Bacteria	Actinobacteria	12	Human ; Human feces; Human urine; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Microbial culture
Bacteria	Ignavibacteriae	1	Human	Microbial culture
Eukaryota/Fungi	Ascomycota	21	Human feces; Human saliva; Human supragingival plaque	Microbial culture
Bacteria	Tenericutes	1		Microbial culture
Bacteria	Chloroflexi	1		Microbial culture
Bacteria	Fusobacteria	2	Human ; Human feces	Microbial culture
Bacteria	Spirochaetes	2		Microbial culture
Eukaryota	Parabasalia	1		Microbial culture
Eukaryota/Fungi	Basidiomycota	2	Human feces
Bacteria	Cyanobacteria	1

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012528

KNApSAcK ID

C00001117

Chemspider ID

Not Available

KEGG Compound ID

C00095

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fructose

METLIN ID

Not Available

PubChem Compound

439163

PDB ID

Not Available

ChEBI ID

37721

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Showing metabocard for D-Fructofuranose (MMDBc0000293)

MOL for #<Metabolite:0x00007fdb5079dbb8>

3D MOL for #<Metabolite:0x00007fdb5079dbb8>

3D SDF for #<Metabolite:0x00007fdb5079dbb8>

3D-SDF for #<Metabolite:0x00007fdb5079dbb8>

PDB for #<Metabolite:0x00007fdb5079dbb8>

3D PDB for #<Metabolite:0x00007fdb5079dbb8>

SMILES for #<Metabolite:0x00007fdb5079dbb8>

INCHI for #<Metabolite:0x00007fdb5079dbb8>

Structure for #<Metabolite:0x00007fdb5079dbb8>

3D Structure for #<Metabolite:0x00007fdb5079dbb8>