1.0 2016-09-30 22:34:28 UTC 2020-06-04 20:58:44 UTC BMDB0000660 BMDB00660 D-Fructose D-Fructose, also known as D-tagatose or D-lyxo-2-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. D-Fructose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. D-Fructose exists in all living species, ranging from bacteria to humans. D-Fructose participates in a number of enzymatic reactions, within cattle. In particular, D-Fructose can be biosynthesized from sorbitol through its interaction with the enzyme sorbitol dehydrogenase. In addition, D-Fructose can be biosynthesized from Beta-D-fructose 2-phosphate through the action of the enzyme 14 kda phosphohistidine phosphatase. In cattle, D-fructose is involved in the metabolic pathway called the fructose and mannose degradation pathway. D-Fructose is a potentially toxic compound. beta-D-Arabino-hexulose beta-D-Fructose beta-Fruit sugar beta-Levulose FRUCTOSE b-D-Arabino-hexulose Β-D-arabino-hexulose b-D-Fructose Β-D-fructose b-Fruit sugar Β-fruit sugar b-Levulose Β-levulose beta-D-Fructofuranose beta-delta-Arabino-hexulose beta-delta-Fructofuranose beta-delta-Fructose D-(-)-Fructose delta-(-)-Fructose delta-Fructose FRU Fructon Levulose Braun brand OF fructose Fleboplast levulosa Fresenius kabi brand OF fructose Instituto farmacologico brand OF fructose Levulosa Levulosa ife Grifols brand OF fructose Levulosa baxter Levulosado braun Ern brand OF fructose Levulosa grifols Levulosa mein Levulosado vitulia Apir levulosa Baxter brand OF fructose Bieffe brand OF fructose Levulosa braun Levulosa ibys Levulosa, apir Levulosa, fleboplast Levulosado bieffe medit Plast apyr levulosa mein C6H12O6 180.1559 180.063388116 (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol fructose 53188-23-1 OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O 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 RFSUNEUAIZKAJO-ARQDHWQXSA-N 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. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates C-glycosyl compounds Hemiacetals Hydrocarbon derivatives Oxacyclic compounds Pentoses Polyols Primary alcohols Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteromonocyclic compound C-glycosyl compound Hemiacetal Hydrocarbon derivative Monosaccharide Organoheterocyclic compound Oxacycle Pentose monosaccharide Polyol Primary alcohol Secondary alcohol Tetrahydrofuran Aliphatic heteromonocyclic compounds D-fructofuranose Solid melting_point 119 - 122 °C water_solubility 778 mg/mL at 20 °C YALKOWSKY,SH & DANNENFELSER,RM (1992) logp -2.45 ALOGPS logs 0.79 ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 10.28 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol ChemAxon average_mass 180.1559 ChemAxon mono_mass 180.063388116 ChemAxon smiles OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O ChemAxon formula C6H12O6 ChemAxon inchi 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 ChemAxon inchikey RFSUNEUAIZKAJO-ARQDHWQXSA-N ChemAxon polar_surface_area 110.38 ChemAxon refractivity 36.36 ChemAxon polarizability 16.26 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1029 Specdb::NmrTwoD 1405 Specdb::MsIr 709 Specdb::MsIr 710 Specdb::MsIr 711 Specdb::NmrOneD 1246 Specdb::NmrOneD 1460 Specdb::NmrOneD 144750 Specdb::NmrOneD 144751 Specdb::NmrOneD 144752 Specdb::NmrOneD 144753 Specdb::NmrOneD 144754 Specdb::NmrOneD 144755 Specdb::NmrOneD 144756 Specdb::NmrOneD 144757 Specdb::NmrOneD 144758 Specdb::NmrOneD 144759 Specdb::NmrOneD 144760 Specdb::NmrOneD 144761 Specdb::NmrOneD 144762 Specdb::NmrOneD 144763 Specdb::NmrOneD 144764 Specdb::NmrOneD 144765 Specdb::NmrOneD 144766 Specdb::NmrOneD 144767 Specdb::NmrOneD 144768 Specdb::NmrOneD 144769 Specdb::NmrOneD 166524 Specdb::CMs 25898 Specdb::CMs 37678 Specdb::CMs 134210 Specdb::CMs 141944 Specdb::CMs 1071907 Specdb::CMs 1071909 Specdb::CMs 1071911 Specdb::CMs 1071913 Specdb::CMs 1071915 Specdb::CMs 1071917 Specdb::CMs 1071918 Specdb::CMs 1071920 Specdb::CMs 1071922 Specdb::CMs 1071924 Specdb::CMs 1071926 Specdb::CMs 1071928 Specdb::CMs 1071929 Specdb::CMs 1071931 Specdb::CMs 1071933 Specdb::CMs 1071934 Specdb::CMs 1071936 Specdb::CMs 1071938 Specdb::CMs 1071940 Specdb::CMs 1071942 Specdb::CMs 1071943 Specdb::MsMs 900 Specdb::MsMs 901 Specdb::MsMs 902 Specdb::MsMs 323386 Specdb::MsMs 323387 Specdb::MsMs 323388 Specdb::MsMs 371530 Specdb::MsMs 371531 Specdb::MsMs 371532 Specdb::MsMs 1471235 Specdb::MsMs 1471236 Specdb::MsMs 1471237 Specdb::MsMs 2252958 Specdb::MsMs 2253528 Specdb::MsMs 2255570 Specdb::MsMs 2757510 Specdb::MsMs 2757511 Specdb::MsMs 2757512 Specdb::MsMs 2948001 Specdb::MsMs 2948002 Specdb::MsMs 2948003 Liver Metabolomics analysis was performed using GC-MS/LC-MS in multiparous Holstein dairy cows Shahzad K, Lopreiato V, Liang Y, Trevisi E, Osorio JS, Xu C, Loor JJ: Hepatic metabolomics and transcriptomics to study susceptibility to ketosis in response to prepartal nutritional management. J Anim Sci Biotechnol. 2019 Dec 18;10:96. doi: 10.1186/s40104-019-0404-z. eCollection 2019. 31867104 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under alfalfa hay based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Mammary Gland 8 multiparous Chinese Holstein dairy cows fed in the Hangzhou Hangjiang Dairy Farm based on the milk production under corn stover based diets. Detection used gas chromatography time-of-flight/mass spectrometry (GC-TOF/MS) platform. Sun HZ, Zhou M, Wang O, Chen Y, Liu JX, Guan LL: Multi-omics reveals functional genomic and metabolic mechanisms of milk production and quality in dairy cows. Bioinformatics. 2020 Apr 15;36(8):2530-2537. doi: 10.1093/bioinformatics/btz951. 31873721 Milk Whole milk from markets Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Ruminal Fluid 763.813 +/- 751.731 uM Fozia Saleem, Souhaila Bouatra, An Chi Guo, Nikolaos Psychogios, Rupasri Mandal, Suzanna M. Dunn, Burim N. Ametaj, David S. Wishart. The Bovine Ruminal Fluid Metabolome. Metabolomics (2013) 9:360–378. Ruminal Fluid Samples collected from 16 multiparous Holstein cows Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. 25599412 Semen Analysis was performed using GC-MS in Holstein bulls (n = 16). Compound was authenticated by external standard reference(s). Velho ALC, Menezes E, Dinh T, Kaya A, Topper E, Moura AA, Memili E: Metabolomic markers of fertility in bull seminal plasma. PLoS One. 2018 Apr 10;13(4):e0195279. doi: 10.1371/journal.pone.0195279. eCollection 2018. 29634739 FDB031286 388775 C02336 439709 FRU 28645 BETA-D-FRUCTOSE C00001117 33835 Fructose 135 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. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. 25108860 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00784 Sorbitol dehydrogenase Q58D31 SORD Enzyme BMDBP00803 Lysosomal alpha-glucosidase Q9MYM4 GAA Enzyme BMDBP00912 Hexokinase-1 P27595 HK1 Enzyme BMDBP01874 Sodium/myo-inositol cotransporter 2 Q3ZC26 SLC5A11 Enzyme BMDBP02036 Solute carrier family 2, facilitated glucose transporter member 8 P58354 SLC2A8 Enzyme BMDBP02075 Solute carrier family 2, facilitated glucose transporter member 5 P58353 SLC2A5 Enzyme BMDBP02885 14 kDa phosphohistidine phosphatase Q32PA4 PHPT1 Enzyme BMDBP03186 Ketohexokinase Q0II75 KHK Enzyme