MiMeDB: Showing metabocard for D-Fructose (MMDBc0000360)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:06 UTC

Update Date

2024-04-30 19:31:55 UTC

Metabolite ID

MMDBc0000360

Metabolite Identification

Common Name

D-Fructose

Description

Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). Pure fructose has a sweet taste similar to cane sugar, but with a "fruity" aroma. Pure, dry fructose is a sweet, white, odorless, crystalline solid, and is the most water-soluble of all the sugars. 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 a reducing sugar, as are all monosaccharides. Fructose is found in many foods including honey, tree fruits, berries, melons, and some root vegetables, such as beets, sweet potatoes, parsnips, and onions. Commercially, fructose is derived from sugar cane, sugar beets, and maize. 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. Excessive consumption of fructose (especially from sugar-sweetened beverages) may contribute to insulin resistance, obesity, elevated LDL cholesterol and triglycerides, leading to metabolic syndrome (PMID: 26429086 ). Fructose exists in foods either as a monosaccharide (free fructose) or as a unit of a disaccharide (sucrose). Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. As sucrose comes into contact with the membrane of the small intestine, the enzyme sucrase catalyzes the cleavage of sucrose to yield one glucose unit and one fructose unit, which are then each absorbed. After absorption, it enters the hepatic portal vein and is directed toward the liver. fructose absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 transport proteins. Since the concentration of fructose is higher in the lumen, fructose is able to flow down a concentration gradient into the enterocytes, assisted by transport proteins. Fructose may be transported out of the enterocyte across the basolateral membrane by either GLUT2 or GLUT5, although the GLUT2 transporter has a greater capacity for transporting fructose, and, therefore, the majority of fructose is transported out of the enterocyte through GLUT2. The catabolism of fructose is sometimes referred to as fructolysis. In fructolysis, the enzyme fructokinase produces fructose 1-phosphate, which is split by aldolase B to produce the trioses dihydroxyacetone phosphate (DHAP) and glyceraldehyde. Unlike glycolysis, in fructolysis the triose glyceraldehyde lacks a phosphate group. A third enzyme, triokinase, is therefore required to phosphorylate glyceraldehyde, producing glyceraldehyde 3-phosphate. The resulting trioses can enter the gluconeogenic pathway for glucose or glycogen synthesis, or be further catabolized through the lower glycolytic pathway to pyruvate. Fructose metabolism leads to significant increases of plasma uric acid levels (PMID: 28420204 ). In fructolysis, fructose 1-phosphate accumulates, and intracellular phosphate decreases. This decrease stimulates AMP deaminase (AMPD), which catalyzes the degradation of AMP to inosine monophosphate, increasing the rate of purine degradation (PMID: 28420204 ). The purine degradation produces uric acid and generates mitochondrial oxidants. Mitochondrial oxidative stress then induces aconitase inhibition in the Krebs cycle, with accumulation of citrate and stimulation of ATP citrate lyase and fatty acid synthase (PMID: 28420204 ). The result is de novo lipogenesis and hepatic fat accumulation. Physiologically, the increase in intracellular uric acid is followed by an acute rise in circulating levels of uric acid, which is likely due to its release from the liver. Fructose also stimulates uric acid synthesis from amino acid precursors such as glycine. Moreover, long-term fructose administration suppresses renal excretion of uric acid, resulting in elevated serum uric acid levels.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         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      23.667 -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      20.775 -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
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	HMDB
Fleboplast levulosa	HMDB
Fresenius kabi brand OF fructose	HMDB
Instituto farmacologico brand OF fructose	HMDB
Levulosa	HMDB
Levulosa ife	HMDB
Grifols brand OF fructose	HMDB
Levulosa baxter	HMDB
Levulosado braun	HMDB
Ern brand OF fructose	HMDB
Levulosa grifols	HMDB
Levulosa mein	HMDB
Levulosado vitulia	HMDB
Apir levulosa	HMDB
Baxter brand OF fructose	HMDB
Bieffe brand OF fructose	HMDB
Levulosa braun	HMDB
Levulosa ibys	HMDB
Levulosa, apir	HMDB
Levulosa, fleboplast	HMDB
Levulosado bieffe medit	HMDB
Plast apyr levulosa mein	HMDB

Molecular Formula

C₆H₁₂O₆

Average Mass

180.1559

Monoisotopic Mass

180.063388116

IUPAC Name

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

Traditional Name

fructose

CAS Registry Number

Not Available

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Liver
Placenta
Prostate
Saliva
Semen
Urine

Tissue Locations

Liver
Placenta
Prostate
Semen

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191882	Hexokinase-3	Enzyme	P52790	Homo sapiens
MMDBp0191883	Hexokinase-2	Enzyme	P52789	Homo sapiens
MMDBp0191885	Hexokinase-1	Enzyme	P19367	Homo sapiens
MMDBp0191960	Sucrase-isomaltase, intestinal	Enzyme	P14410	Homo sapiens
MMDBp0192160	Sorbitol dehydrogenase	Unknown	Q00796	Homo sapiens
MMDBp0192803	Ketohexokinase	Enzyme	P50053	Homo sapiens
MMDBp0193281	Lysosomal alpha-glucosidase	Enzyme	P10253	Homo sapiens
MMDBp0193796	Maltase-glucoamylase, intestinal	Enzyme	O43451	Homo sapiens
MMDBp0194024	Neutral alpha-glucosidase C	Enzyme	Q8TET4	Homo sapiens
MMDBp0196656	14 kDa phosphohistidine phosphatase	Enzyme	Q9NRX4	Homo sapiens
MMDBp0196842	Putative hexokinase HKDC1	Unknown	Q2TB90
MMDBp0196890	Myotubularin-related protein 1	Unknown	Q13613
MMDBp0196891	Myotubularin-related protein 2	Unknown	Q13614
MMDBp0196892	Myotubularin-related protein 6	Unknown	Q9Y217
MMDBp0196893	Myotubularin-related protein 7	Unknown	Q9Y216

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018593	Sucrose	D-Glucose	Maltodextrin glucosidase	Carbohydrate hydrolysis	PathBank	31602464
MMDBr0018594	D-Fructose	beta-D-Fructofuranose 6-phosphate	Fructokinase	Phosphorylation	PathBank	31602464
MMDBr0018605	D-Fructose	Sucrose	Glucosylglycerate phosphorylase	Phosphorylation	PathBank	31602464
MMDBr0019474	D-Fructose	beta-D-Fructose 6-phosphate	Hexokinase-1	Phosphorylation	PathBank	31602464
MMDBr0019477	Sucrose-6-phosphate	D-Fructose	Invertase		PathBank	31602464
MMDBr0019478	Sucrose	D-Fructose	Invertase		PathBank	31602464
MMDBr0019554	D-Fructose	beta-D-Fructose 6-phosphate	Hexokinase-1	Phosphorylation	PathBank	31602464
MMDBr0019881	D-Fructose	beta-D-Fructose 6-phosphate	Putative glucokinase-2	Phosphorylation	PathBank	31602464
MMDBr0019884	D-Fructose	Sucrose	Glucosidase 2 subunit alpha	Carbohydrate hydrolysis	PathBank	31602464
MMDBr0019896	Sucrose-6-phosphate	D-Fructose	Invertase		PathBank	31602464
MMDBr0024529	D-Fructofuranose	Sucrose	Sucrose synthase	Synthesis	RHEA	34755880
MMDBr0024607	Sucrose	D-Fructofuranose	Dextransucrase 1	Transfer of a glucosyl group	RHEA	34755880
MMDBr0024786	Sucrose	D-Fructofuranose	Amylosucrase	Synthesis of alpha-glucan from sucrose	RHEA	34755880
MMDBr0025318	D-Fructofuranose	L-Histidine	PTS system fructose-specific EIIB component	Phosphorylation	RHEA	34755880
MMDBr0026042	CDPglucose	Uridine 5'-diphosphate	Sucrose synthase	Synthesis	RHEA	34755880
MMDBr0026043	ADP-alpha-D-glucose	Sucrose	Sucrose synthase	Synthesis	RHEA	34755880
MMDBr0026044	GDP-alpha-D-glucose	Guanosine 3',5'-bis(diphosphate)	Sucrose synthase	Synthesis	RHEA	34755880
MMDBr0026045	UDP-alpha-D-glucose	Uridine 5'-diphosphate	Sucrose synthase	Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Diabetes mellitus type 2	Decreased	Association	Human Blood	HMDB	11815509
Diabetes mellitus type 2		Association	Human Urine	HMDB	11815509
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	807	Human ; Human supragingival plaque; Human stool; Human feces; Human saliva; Human mucosa; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human pleural fluid plaque; Pig ; Cattle ; Goat feces; Sheep feces	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	331	Human feces; Human stool; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human supragingival plaque; Human mucosa; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Archaea	Euryarchaeota	4	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Actinobacteria	25	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	241	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Human stool	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	187	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque; Human mucosa; Human sputum	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	5	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	55	Human ; Human supragingival plaque; Human stool; Human feces; Human saliva; Human mucosa; Human urine; Human sputum; Human subgingival plaque; Human vaginal fluid; Human pleural fluid plaque; Pig ; Cattle ; Goat feces; Sheep feces	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	20	Human feces; Human stool; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human feces; pleural fluid plaque; bal; Human subgingival plaque; Human supragingival plaque; Human mucosa; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	2	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	30	Human feces; Human ; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Metabolic reconstruction
Bacteria	Candidatus melainabacteria	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	21	Human feces; Human supragingival plaque; Human saliva	Unknown
Eukaryota/Fungi	Basidiomycota	2	Human feces
Bacteria/Eubacteria	Cyanobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	12.00	3.8			uM	Adult (>18 years old)	Both	Diabetes	HMDB	11815509
Human Urine	Detected and Quantified	8.4	7.0			umol/mmol creatinine	Adult (>18 years old)	Both	Diabetes	HMDB	11815509
Human Cerebrospinal fluid (csf)	Detected and Quantified	160	91			uM	Adult (>18 years old)	Both	Normal	HMDB	18502700
Human Urine	Detected and Quantified	70.38	107.54			umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	2026685
Human Urine	Detected and Quantified	94.126	154.083			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	129.518	61.708			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Cerebrospinal fluid (csf)	Detected and Quantified	240.0		220.0	260.0	uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	31.0	3.0			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Blood	Detected and Quantified	48.0	16.0			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Semen	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	20669995
Human Feces	Detected but not Quantified						Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24029555
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24424155
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	28157703

External Links

HMDB ID

HMDB0000660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1006/rtph.1999.1298. [PubMed:10341166 ]
Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11. doi: 10.1023/a:1007136209970. [PubMed:10408311 ]
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. doi: 10.1053/meta.2000.9532. [PubMed:11079825 ]
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 ]
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. doi: 10.1046/j.1365-2605.2001.00306.x. [PubMed:11554981 ]
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. doi: 10.1080/01485010390219728. [PubMed:12893512 ]
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. doi: 10.1007/s11255-005-0254-9. [PubMed:16502061 ]
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. doi: 10.1007/BF03349172. [PubMed:16553029 ]
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 ]
Malik VS, Hu FB: Fructose and Cardiometabolic Health: What the Evidence From Sugar-Sweetened Beverages Tells Us. J Am Coll Cardiol. 2015 Oct 6;66(14):1615-1624. doi: 10.1016/j.jacc.2015.08.025. [PubMed:26429086 ]
Caliceti C, Calabria D, Roda A, Cicero AFG: Fructose Intake, Serum Uric Acid, and Cardiometabolic Disorders: A Critical Review. Nutrients. 2017 Apr 18;9(4). pii: nu9040395. doi: 10.3390/nu9040395. [PubMed:28420204 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for D-Fructose (MMDBc0000360)

MOL for #<Metabolite:0x00005645c9301118>

3D MOL for #<Metabolite:0x00005645c9301118>

3D SDF for #<Metabolite:0x00005645c9301118>

3D-SDF for #<Metabolite:0x00005645c9301118>

PDB for #<Metabolite:0x00005645c9301118>

3D PDB for #<Metabolite:0x00005645c9301118>

SMILES for #<Metabolite:0x00005645c9301118>

INCHI for #<Metabolite:0x00005645c9301118>

Structure for #<Metabolite:0x00005645c9301118>

3D Structure for #<Metabolite:0x00005645c9301118>