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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2018-04-16 16:59:20 UTC |
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HMDB ID | HMDB0000660 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Fructose |
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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). |
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Structure | |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C6H12O6 |
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Average Molecular Weight | 180.1559 |
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Monoisotopic Molecular Weight | 180.063388116 |
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IUPAC Name | (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol |
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Traditional Name | fructose |
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CAS Registry Number | 53188-23-1 |
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SMILES | OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O |
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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 |
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InChI Key | RFSUNEUAIZKAJO-ARQDHWQXSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | C-glycosyl compounds |
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Alternative Parents | |
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Substituents | - C-glycosyl compound
- Pentose monosaccharide
- Monosaccharide
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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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 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-076r-9600000000-f2c06850d0c3db9ec103 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-0fb9-5614950000-6ef14e948d063026f7ee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0002-0900000000-2ce9036c30158be73d60 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00ri-9600000000-a826b29724713036f579 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-007a-9200000000-7621d8d96132cc999f4c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-2afc98a319bf6041adf0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-3900000000-1dd0cdea93f529e6ccb2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9100000000-d0f08ad6c9dee008067a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-74b62c8ea3678afcff8a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ta-1900000000-5a0f3f01ddf8c11c6370 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-93c2b00aa44481aa8630 | View in MoNA |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Location | |
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Pathways | Name | SMPDB/Pathwhiz | KEGG | Amino Sugar Metabolism |    |  | Fructose and Mannose Degradation |    |  | Fructose intolerance, hereditary |    | Not Available | Fructosuria |    | Not Available | G(M2)-Gangliosidosis: Variant B, Tay-sachs disease |    | Not Available |
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Normal Concentrations |
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Blood | Detected and Quantified | 31.0 +/- 3.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 48.0 +/- 16.0 uM | Adult (>18 years old) | Male | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 240.0 (220.0 -260.0) uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 160 +/- 91 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | | Infant (0-1 year old) | Both | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 129.518 +/- 61.708 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 70.38 +/- 107.54 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 12.00 +/- 3.8 uM | Adult (>18 years old) | Both | Diabetes | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal Cancer | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Colorectal cancer | | details | Urine | Detected and Quantified | 8.4 +/- 7.0 umol/mmol creatinine | Adult (>18 years old) | Both | Diabetes | | details | Urine | Detected and Quantified | 94.126 +/- 154.083 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Associated Disorders and Diseases |
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Disease References | Diabetes mellitus type 2 |
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- 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 ]
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Associated OMIM IDs | - 125853 (Diabetes mellitus type 2)
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB012528 |
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KNApSAcK ID | C00001117 |
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Chemspider ID | 388775 |
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KEGG Compound ID | C02336 |
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BioCyc ID | BETA-D-FRUCTOSE |
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BiGG ID | 33835 |
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Wikipedia Link | Fructose |
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METLIN ID | 135 |
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PubChem Compound | 439709 |
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PDB ID | FRU |
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ChEBI ID | 28645 |
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References |
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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. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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 ]
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