NP-MRD: Showing NP-Card for alpha-D-fructofuranose (NP0044229)

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Record Information

Version

1.0

Created at

2022-01-25 17:34:06 UTC

Updated at

2022-01-25 18:11:58 UTC

NP-MRD ID

NP0044229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-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. It was first documented in 2012 (PMID: 22129837). Dahlia and Jerusalem artichoke tubers.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 04-DEC-21   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-DEC-21         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

View in JSmol

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

Chemical Formula

C₆H₁₂O₆

Average Mass

180.1559 Da

Monoisotopic Mass

180.06339 Da

IUPAC Name

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

Traditional Name

fruit sugar

CAS Registry Number

Not Available

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-ZXXMMSQZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, experimental)	Ahselim			2022-01-25	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

General References

Barclay T, Ginic-Markovic M, Johnston MR, Cooper P, Petrovsky N: Observation of the keto tautomer of D-fructose in D(2)O using (1)H NMR spectroscopy. Carbohydr Res. 2012 Jan 10;347(1):136-41. doi: 10.1016/j.carres.2011.11.003. Epub 2011 Nov 12. [PubMed:22129837 ]

Showing NP-Card for alpha-D-fructofuranose (NP0044229)

MOL for NP0044229 (alpha-D-fructofuranose)

3D MOL for NP0044229 (alpha-D-fructofuranose)

3D SDF for NP0044229 (alpha-D-fructofuranose)

3D-SDF for NP0044229 (alpha-D-fructofuranose)

PDB for NP0044229 (alpha-D-fructofuranose)

3D PDB for NP0044229 (alpha-D-fructofuranose)

SMILES for NP0044229 (alpha-D-fructofuranose)

INCHI for NP0044229 (alpha-D-fructofuranose)

Structure for NP0044229 (alpha-D-fructofuranose)

3D Structure for NP0044229 (alpha-D-fructofuranose)