Human Metabolome Database: Showing metabocard for D-Fructose (HMDB0000660)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (15) Show 15 proteins XML

enzymes (15) Show 15 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2019-05-23 18:27:18 UTC

HMDB ID

HMDB0000660

Secondary Accession Numbers

HMDB00660

Metabolite Identification

Common Name

D-Fructose

Description

Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). The chemical composition of fructose is (C6H12O6). Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Although fructose is a hexose (6-carbon sugar), it generally exists as a 5-member hemiketal ring (a furanose). This structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is found in many foods and is one of the three most important blood sugars along with glucose and galactose. Honey, tree fruits, berries, melons, and some root vegetables, such as beets, sweet potatoes, parsnips, and onions contain fructose, usually in combination with sucrose and glucose. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a reducing sugar, as are all monosaccharides. The spontaneous addition of single sugar molecules to proteins, known as glycation, is a significant cause of damage in diabetics. Fructose appears to be as dangerous as glucose in this regard, and therefore does not seem to be the answer for diabetes (McPherson et al, 1988). This may be an important contribution to senescence and many age-related chronic diseases (Levi & Werman 1998).

Structure

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

Synonyms

Value	Source
beta-D-arabino-Hexulose	ChEBI
beta-D-Fructose	ChEBI
beta-Fruit sugar	ChEBI
beta-Levulose	ChEBI
FRUCTOSE	ChEBI
b-D-arabino-Hexulose	Generator
β-D-arabino-hexulose	Generator
b-D-Fructose	Generator
β-D-fructose	Generator
b-Fruit sugar	Generator
β-fruit sugar	Generator
b-Levulose	Generator
β-levulose	Generator
beta-D-Fructofuranose	HMDB
beta-delta-arabino-Hexulose	HMDB
beta-delta-Fructofuranose	HMDB
beta-delta-Fructose	HMDB
D-(-)-Fructose	HMDB
delta-(-)-Fructose	HMDB
delta-Fructose	HMDB
FRU	HMDB
Fructon	HMDB
Levulose	HMDB
Braun brand OF fructose	MeSH
Fleboplast levulosa	MeSH
Fresenius kabi brand OF fructose	MeSH
instituto farmacologico Brand OF fructose	MeSH
Levulosa	MeSH
Levulosa ife	MeSH
Grifols brand OF fructose	MeSH
Levulosa baxter	MeSH
levulosado Braun	MeSH
Ern brand OF fructose	MeSH
Levulosa grifols	MeSH
Levulosa mein	MeSH
levulosado Vitulia	MeSH
Apir levulosa	MeSH
Baxter brand OF fructose	MeSH
Bieffe brand OF fructose	MeSH
Levulosa braun	MeSH
Levulosa ibys	MeSH
Levulosa, apir	MeSH
Levulosa, fleboplast	MeSH
levulosado Bieffe medit	MeSH
Plast apyr levulosa mein	MeSH

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

fructose

CAS Registry Number

53188-23-1

SMILES

OC[C@H]1O[C@](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-ARQDHWQXSA-N

Chemical Taxonomy

Description

This compound 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-fructofuranose (CHEBI:28645 )

Ontology

Hypertension

Metabolism and nutrition disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	119 - 122 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	778 mg/mL at 20 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1110 g/L	ALOGPS
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	16.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-076r-9600000000-f2c06850d0c3db9ec103	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0fb9-5614950000-6ef14e948d063026f7ee	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-2ce9036c30158be73d60	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9600000000-a826b29724713036f579	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9200000000-7621d8d96132cc999f4c	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2afc98a319bf6041adf0	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-1dd0cdea93f529e6ccb2	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9100000000-d0f08ad6c9dee008067a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-74b62c8ea3678afcff8a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-1900000000-5a0f3f01ddf8c11c6370	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-93c2b00aa44481aa8630	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Liver
Prostate
Sperm

Pathways

Name	SMPDB/Pathwhiz	KEGG
Starch and Sucrose Metabolism
Galactose Metabolism
Fructose and Mannose Degradation
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	31.0 +/- 3.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	48.0 +/- 16.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	240.0 (220.0 -260.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	160 +/- 91 uM	Adult (>18 years old)	Both	Normal	18502700	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24424155	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified		Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified		Infant (0-1 year old)	Both	Normal	22411374	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified		Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	28157703	details
Urine	Detected and Quantified	129.518 +/- 61.708 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	70.38 +/- 107.54 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	2026685	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	12.00 +/- 3.8 uM	Adult (>18 years old)	Both	Diabetes	11815509	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified		Adult (>18 years old)	Both	Colorectal cancer	24424155	details
Urine	Detected and Quantified	8.4 +/- 7.0 umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	11815509	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	94.126 +/- 154.083 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Phua LC, Chue XP, Koh PK, Cheah PY, Ho HK, Chan EC: Non-invasive fecal metabonomic detection of colorectal cancer. Cancer Biol Ther. 2014 Apr;15(4):389-97. doi: 10.4161/cbt.27625. Epub 2014 Jan 14. [PubMed:24424155 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Diabetes mellitus type 2
Kawasaki T, Akanuma H, Yamanouchi T: Increased fructose concentrations in blood and urine in patients with diabetes. Diabetes Care. 2002 Feb;25(2):353-7. [PubMed:11815509 ]
Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

114500 (Colorectal cancer)
125853 (Diabetes mellitus type 2)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Liu, Hong; Han, Dong; Meng, Xiang-bao; Li, Zhong-jun. Improved synthesis of fructose-derived 1,3,4-oxadiazole as novel antitumor agents. Journal of Chinese Pharmaceutical Sciences (2005), 14(4), 209-212.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Vicari E, La Vignera S, Castiglione R, Calogero AE: Sperm parameter abnormalities, low seminal fructose and reactive oxygen species overproduction do not discriminate patients with unilateral or bilateral post-infectious inflammatory prostato-vesiculo-epididymitis. J Endocrinol Invest. 2006 Jan;29(1):18-25. [PubMed:16553029 ]
Bar A: Characteristics and significance of D-tagatose-induced liver enlargement in rats: An interpretative review. Regul Toxicol Pharmacol. 1999 Apr;29(2 Pt 2):S83-93. [PubMed:10341166 ]
Andrade-Rocha FT: Semen analysis in an infertile man with seminal vesicles cysts associated with ipsilateral renal agenesis. Int Urol Nephrol. 2006;38(1):101-3. [PubMed:16502061 ]
Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11. [PubMed:10408311 ]
Gonzales GF, Villena A: True corrected seminal fructose level: a better marker of the function of seminal vesicles in infertile men. Int J Androl. 2001 Oct;24(5):255-60. [PubMed:11554981 ]
Buemann B, Gesmar H, Astrup A, Quistorff B: Effects of oral D-tagatose, a stereoisomer of D-fructose, on liver metabolism in man as examined by 31P-magnetic resonance spectroscopy. Metabolism. 2000 Oct;49(10):1335-9. [PubMed:11079825 ]
Koca Y, Ozdal OL, Celik M, Unal S, Balaban N: Antioxidant activity of seminal plasma in fertile and infertile men. Arch Androl. 2003 Sep-Oct;49(5):355-9. [PubMed:12893512 ]
Williams AC, Ford WC: The role of glucose in supporting motility and capacitation in human spermatozoa. J Androl. 2001 Jul-Aug;22(4):680-95. [PubMed:11451366 ]

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Hexokinase-3

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK3
Uniprot ID:: P52790
Molecular weight:: 99024.56

Reactions

Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details
Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details

Enzyme Details

2. Hexokinase-2

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK2
Uniprot ID:: P52789
Molecular weight:: 102379.06

Reactions

Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details
Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details

Enzyme Details

3. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK1
Uniprot ID:: P19367
Molecular weight:: 102485.1

Reactions

Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details
Adenosine triphosphate + D-Fructose → ADP + Beta-D-Fructose 6-phosphate	details

Enzyme Details

4. Sucrase-isomaltase, intestinal

General function:: Involved in catalytic activity
Specific function:: Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:: SI
Uniprot ID:: P14410
Molecular weight:: Not Available

Reactions

Sucrose + Water → D-Fructose + D-Glucose	details
Sucrose + Water → D-Fructose + alpha-D-Glucose	details
Neohancoside D + Water → D-Fructose + D-Glucose	details
Neohancoside D + Water → D-Fructose + alpha-D-Glucose	details

Enzyme Details

5. Sorbitol dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:: SORD
Uniprot ID:: Q00796
Molecular weight:: 38324.25

Reactions

Sorbitol + NAD → D-Fructose + NADH + Hydrogen Ion	details

Enzyme Details

6. Ketohexokinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: KHK
Uniprot ID:: P50053
Molecular weight:: 32730.055

Reactions

Adenosine triphosphate + D-Fructose → ADP + D-fructose 1-phosphate	details

Enzyme Details

7. Lysosomal alpha-glucosidase

General function:: Involved in catalytic activity
Specific function:: Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name:: GAA
Uniprot ID:: P10253
Molecular weight:: Not Available

Reactions

Sucrose + Water → D-Fructose + D-Glucose	details
Sucrose + Water → D-Fructose + alpha-D-Glucose	details

Enzyme Details

8. Maltase-glucoamylase, intestinal

General function:: Involved in catalytic activity
Specific function:: May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
Gene Name:: MGAM
Uniprot ID:: O43451
Molecular weight:: Not Available

Reactions

Sucrose + Water → D-Fructose + D-Glucose	details
Sucrose + Water → D-Fructose + alpha-D-Glucose	details
Neohancoside D + Water → D-Fructose + D-Glucose	details
Neohancoside D + Water → D-Fructose + alpha-D-Glucose	details

Enzyme Details

9. Neutral alpha-glucosidase C

General function:: Involved in catalytic activity
Specific function:: Has alpha-glucosidase activity.
Gene Name:: GANC
Uniprot ID:: Q8TET4
Molecular weight:: Not Available

Reactions

Sucrose + Water → D-Fructose + D-Glucose	details
Sucrose + Water → D-Fructose + alpha-D-Glucose	details

Enzyme Details

10. 14 kDa phosphohistidine phosphatase

General function:: Involved in phosphohistidine phosphatase activity
Specific function:: Exhibits phosphohistidine phosphatase activity.
Gene Name:: PHPT1
Uniprot ID:: Q9NRX4
Molecular weight:: Not Available

Reactions

Beta-D-Fructose 2-phosphate + Water → D-Fructose + Phosphoric acid	details

Only showing the first 10 proteins. There are 15 proteins in total.

Show all enzymes and transporters

Showing metabocard for D-Fructose (HMDB0000660)

Structure for HMDB0000660 (D-Fructose)

Enzymes

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