AFCDB: D-Fructose (FDB012528)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:13 UTC

Update date

2019-11-26 03:06:58 UTC

Primary ID

FDB012528

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Fructose

Description

D-Fructose occurs in honey and a large number of fruits, particularly apples and tomatoes. It is fluid and nutrient replenisher, and nutritive sweetener. Inulin from dandelion roots has also been used as a source. Present in polymeric form in the inulins, the energy reserve polysaccharides of many plants, e.g. dahlia and Jerusalem artichoke tubers. D-Fructose is also found in many other foods, some of which are sweet cherry, anise, and tinda.

CAS Number

53188-23-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

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

Chemical Formula

C18H36O18

IUPAC name

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

InChI Identifier

InChI=1S/3C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6;7-1-3-4(9)5(10)6(11,2-8)12-3;7-1-3(9)5(11)6(12)4(10)2-8/h2*3-5,7-11H,1-2H2;3,5-9,11-12H,1-2H2

InChI Key

JCOXAIPZGMCTBN-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C(O)C(O)C(=O)CO.OCC1OC(O)(CO)C(O)C1O.OCC1(O)OCC(O)C(O)C1O

Average Molecular Weight

540.4676

Monoisotopic Molecular Weight

540.190164348

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	Mp 102-104°	DFC
Boiling Point	Not Available
Experimental Water Solubility	778 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	Not Available
Experimental pKa	pKa1 12.03 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -92.4 (c, 4 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2900000000-e83683f33312f7b8a1e1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-4900000000-c14d4be56a78c5647ddc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05a7-9100000000-0fb431a2d8f04450b6a0	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900000000-2255549937d454d405a0	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-2900000000-b640e9d3b37f0787f857	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-a51d0897073ec10f04bd	2015-09-15	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

48095

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00660

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

HET ID

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1098991

SuperScent ID

Not Available

Wikipedia ID

Fructose

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti alcoholic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti diabetic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hangover	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti ketotic			DUKE
anti nauseant	50919	A drug used to prevent nausea or vomiting. An antiemetic may act by a wide range of mechanisms: it might affect the medullary control centres (the vomiting centre and the chemoreceptive trigger zone) or affect the peripheral receptors.	DUKE
laxative	50503	An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.	DUKE
neoplastic			DUKE
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Sucrase-isomaltase, intestinal	SI	P14410
Lysosomal alpha-glucosidase	GAA	P10253
Maltase-glucoamylase, intestinal	MGAM	O43451
Neutral alpha-glucosidase C	GANC	Q8TET4
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789
Hexokinase-1	HK1	P19367
Ketohexokinase	KHK	P50053
14 kDa phosphohistidine phosphatase	PHPT1	Q9NRX4

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Fructose and Mannose Degradation	SMP00064	map00051
Galactose Metabolism	SMP00043	map00052
Starch and Sucrose Metabolism	SMP00058	map00500

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

D-Fructose (FDB012528)

Structure for FDB012528 (D-Fructose)