2.0 2012-05-31 13:03:52 -0600 2015-09-13 15:15:21 -0600 ECMDB01051 M2MDB000233 D-Glyceraldehyde Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet colorless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde. &alpha;,&beta;-dihydroxypropionaldehyde (+/-)-2,3-dihydroxy-Propanal (+/-)-Glyceraldehyde 2, 3-Dihydroxy-Propanal 2,3-Dihydroxy-Propionaldehyde 2,3-Dihydroxypropanal 2,3-Dihydroxypropionaldehyde A,b-Dihydroxypropionaldehyde Alpha,beta-Dihydroxypropionaldehyde D-(+)-Glyceraldehyde D-2,3-Dihydroxypropanal D-2,3-Dihydroxypropionaldehyde D-Aldotriose D-Glycerose Delta-(+)-Glyceraldehyde Delta-2,3-dihydroxypropanal Delta-2,3-dihydroxypropionaldehyde Delta-aldotriose Delta-Glyceraldehyde Delta-glycerose Dihydroxypropionaldehyde DL-GLYC DL-Glyceraldehyde DL-Glyceric aldehyde DLG Glyceraldehyde Glyceric aldehyde Glycerinaldehyde Glycerinformal Glycerose α,β-Dihydroxypropionaldehyde δ-(+)-Glyceraldehyde δ-2,3-Dihydroxypropanal δ-2,3-Dihydroxypropionaldehyde δ-Aldotriose δ-Glyceraldehyde δ-Glycerose C3H6O3 90.0779 90.031694058 2,3-dihydroxypropanal (+/-)-glyceraldehyde 56-82-6 OCC(O)C=O InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 MNQZXJOMYWMBOU-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.63 ALOGPS logs 0.96 ALOGPS solubility 8.14e+02 g/l ALOGPS melting_point 145 oC logp -1.7 ChemAxon pka_strongest_acidic 12.84 ChemAxon pka_strongest_basic -3 ChemAxon iupac 2,3-dihydroxypropanal ChemAxon average_mass 90.0779 ChemAxon mono_mass 90.031694058 ChemAxon smiles OCC(O)C=O ChemAxon formula C3H6O3 ChemAxon inchi InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2 ChemAxon inchikey MNQZXJOMYWMBOU-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 19.46 ChemAxon polarizability 8.07 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 699 Specdb::CMs 700 Specdb::CMs 2653 Specdb::CMs 30144 Specdb::CMs 30145 Specdb::CMs 30554 Specdb::CMs 30555 Specdb::CMs 37905 Specdb::CMs 120025 Specdb::CMs 171346 Specdb::CMs 868161 Specdb::CMs 868162 Specdb::CMs 868163 Specdb::CMs 868164 Specdb::CMs 868165 Specdb::CMs 868166 Specdb::CMs 868167 Specdb::CMs 868168 Specdb::CMs 868169 Specdb::CMs 868170 Specdb::CMs 868171 Specdb::NmrOneD 1637 Specdb::NmrOneD 5146 Specdb::NmrOneD 8402 Specdb::NmrOneD 8403 Specdb::NmrOneD 8404 Specdb::NmrOneD 8405 Specdb::NmrOneD 8406 Specdb::NmrOneD 8407 Specdb::NmrOneD 8408 Specdb::NmrOneD 8409 Specdb::NmrOneD 8410 Specdb::NmrOneD 8411 Specdb::NmrOneD 8412 Specdb::NmrOneD 8413 Specdb::NmrOneD 8414 Specdb::NmrOneD 8415 Specdb::NmrOneD 8416 Specdb::NmrOneD 8417 Specdb::NmrOneD 8418 Specdb::NmrOneD 8419 Specdb::NmrOneD 8420 Specdb::NmrOneD 8421 Specdb::MsMs 1403 Specdb::MsMs 1404 Specdb::MsMs 1405 Specdb::MsMs 182691 Specdb::MsMs 182692 Specdb::MsMs 182693 Specdb::MsMs 183039 Specdb::MsMs 183040 Specdb::MsMs 183041 Specdb::MsMs 440063 Specdb::MsMs 2831011 Specdb::MsMs 2831012 Specdb::MsMs 2831013 Specdb::MsMs 2847251 Specdb::MsMs 2847252 Specdb::MsMs 2847253 Specdb::NmrTwoD 1052 Specdb::NmrTwoD 1578 HMDB01051 731 C00577 5445 GLYCERALD Glyceraldehyde Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Gugliucci A: A practical method to study functional impairment of proteins by glycation and effects of inhibitors using current coagulation/fibrinolysis reagent kits. Clin Biochem. 2003 Mar;36(2):155-8. 12633766 Beard KM, Shangari N, Wu B, O'Brien PJ: Metabolism, not autoxidation, plays a role in alpha-oxoaldehyde- and reducing sugar-induced erythrocyte GSH depletion: relevance for diabetes mellitus. Mol Cell Biochem. 2003 Oct;252(1-2):331-8. 14577607 Iwata H, Ukeda H, Maruyama T, Fujino T, Sawamura M: Effect of carbonyl compounds on red blood cells deformability. Biochem Biophys Res Commun. 2004 Aug 27;321(3):700-6. 15358163 Zakrzewska I, Prokopowicz J, Worowski K, Skrzydlewska E, Puchalski Z, Piotrowski Z: Low molecular organic inactivators in differentiating organ origin of alpha-amylase in humans. Part I. Mater Med Pol. 1989 Oct-Dec;21(4):274-6. 2518736 Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. 3402055 Fujita T, Funako T, Hayashi H: 8-Hydroxydaidzein, an aldose reductase inhibitor from okara fermented with Aspergillus sp. HK-388. Biosci Biotechnol Biochem. 2004 Jul;68(7):1588-90. 15277768 Haraguchi H, Hayashi R, Ishizu T, Yagi A: A flavone from Manilkara indica as a specific inhibitor against aldose reductase in vitro. Planta Med. 2003 Sep;69(9):853-5. 14598214 Yamagishi S, Nakamura K, Inoue H, Kikuchi S, Takeuchi M: Serum or cerebrospinal fluid levels of glyceraldehyde-derived advanced glycation end products (AGEs) may be a promising biomarker for early detection of Alzheimer's disease. Med Hypotheses. 2005;64(6):1205-7. 15823718 Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol (Berl). 2004 Sep;108(3):189-93. Epub 2004 Jun 17. 15221334 Jonas AJ, Lin SN, Conley SB, Schneider JA, Williams JC, Caprioli RC: Urine glyceraldehyde excretion is elevated in the renal Fanconi syndrome. Kidney Int. 1989 Jan;35(1):99-104. 2709665 Takeuchi M, Yamagishi S: Alternative routes for the formation of glyceraldehyde-derived AGEs (TAGE) in vivo. Med Hypotheses. 2004;63(3):453-5. 15288367 Nagaraj RH, Oya-Ito T, Padayatti PS, Kumar R, Mehta S, West K, Levison B, Sun J, Crabb JW, Padival AK: Enhancement of chaperone function of alpha-crystallin by methylglyoxal modification. Biochemistry. 2003 Sep 16;42(36):10746-55. 12962499 Wan, Xin-Jun; Song, Ming-You; Wu, Rong; Chu, Dao-Bao. Synthesis of glyceraldehyde by indirect electrooxidation. Yingyong Huaxue (2003), 20(6), 578-581. http://hmdb.ca/system/metabolites/msds/000/000/945/original/HMDB01051.pdf?1358462747 Fructose-bisphosphate aldolase class 1 P0A991 ALF1_ECOLI fbaB http://ecmdb.ca/proteins/P0A991.xml Fructose-bisphosphate aldolase class 2 P0AB71 ALF_ECOLI fbaA http://ecmdb.ca/proteins/P0AB71.xml S-(hydroxymethyl)glutathione dehydrogenase P25437 FRMA_ECOLI frmA http://ecmdb.ca/proteins/P25437.xml Sugar efflux transporter C P31436 SETC_ECOLI setC http://ecmdb.ca/proteins/P31436.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Glycerol uptake facilitator protein P0AER0 GLPF_ECOLI glpF http://ecmdb.ca/proteins/P0AER0.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml D-Glyceraldehyde + Hydrogen ion + NADH <> Glycerol + NAD 2-Keto-3-deoxy-D-gluconic acid D-Glyceraldehyde + Pyruvic acid DHDOGALDOL-RXN