2.0 2012-10-10 12:12:11 -0600 2015-06-03 17:25:43 -0600 ECMDB23011 M2MDB003401 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate is a substrate for 2-O-(6-phospho-alpha-D-mannosyl)-D-glycerate acylhydrolase. The enzyme participates in the mannosylglycerate degradation pathway of some bacteria. Mannosylglycerate is phosphorylated during transport into the cell, and the phosphorylated form is hydrolysed by this enzyme. It is involved in 2-O-alpha-mannosyl-D-glycerate degradation. (2R)-3-Hydroxy-2-(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yloxypropanoate (2R)-3-hydroxy-2-(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(phosphonooxymethyl)oxan-2-yloxypropanoic acid (2R)-3-Hydroxy-2-(6-O-phosphono-a-D-mannopyranosyl)oxypropanoate (2R)-3-Hydroxy-2-(6-O-phosphono-a-D-mannopyranosyl)oxypropanoic acid (2R)-3-Hydroxy-2-(6-O-phosphono-alpha-D-mannopyranosyl)oxypropanoate (2R)-3-Hydroxy-2-(6-O-phosphono-alpha-D-mannopyranosyl)oxypropanoic acid (2R)-3-Hydroxy-2-(6-O-phosphono-α-D-mannopyranosyl)oxypropanoate (2R)-3-Hydroxy-2-(6-O-phosphono-α-D-mannopyranosyl)oxypropanoic acid 2(α-D-mannosyl-6-phosphate)-D-glycerate 2(α-D-mannosyl-6-phosphoric acid)-D-glyceric acid 2-O-(6-phospho-a-D-Mannosyl)-D-glycerate 2-O-(6-phospho-a-D-Mannosyl)-D-glyceric acid 2-O-(6-Phospho-a-mannosyl)-D-glycerate 2-O-(6-Phospho-a-mannosyl)-D-glyceric acid 2-O-(6-phospho-a-Mannosyl)-delta-glycerate 2-O-(6-phospho-a-Mannosyl)-delta-glyceric acid 2-O-(6-phospho-a-Mannosyl)-δ-glycerate 2-O-(6-phospho-a-Mannosyl)-δ-glyceric acid 2-O-(6-phospho-alpha-D-Mannosyl)-D-glyceric acid 2-O-(6-Phospho-alpha-mannosyl)-D-glycerate 2-O-(6-Phospho-alpha-mannosyl)-D-glyceric acid 2-O-(6-Phospho-alpha-mannosyl)-delta-glycerate 2-O-(6-Phospho-alpha-mannosyl)-delta-glyceric acid 2-O-(6-phospho-α-D-Mannosyl)-D-glycerate 2-O-(6-phospho-α-D-Mannosyl)-D-glyceric acid 2-O-(6-phospho-α-Mannosyl)-D-glycerate 2-O-(6-phospho-α-Mannosyl)-D-glyceric acid 2-O-(6-phospho-α-Mannosyl)-δ-glycerate 2-O-(6-phospho-α-Mannosyl)-δ-glyceric acid C9H17O12P 348.1978 348.04576252 (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid OC[C@@H](O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O InChI=1S/C9H17O12P/c10-1-3(8(14)15)20-9-7(13)6(12)5(11)4(21-9)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/t3-,4-,5-,6+,7+,9+/m1/s1 BOLXAGHGKNGVBE-MTXRGOKVSA-N Solid logp -2.41 ALOGPS logs -1.09 ALOGPS solubility 2.84e+01 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-3-hydroxy-2-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(phosphonooxy)methyl]oxan-2-yl]oxy}propanoic acid ChemAxon average_mass 348.1978 ChemAxon mono_mass 348.04576252 ChemAxon smiles OC[C@@H](O[C@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O)C(O)=O ChemAxon formula C9H17O12P ChemAxon inchi InChI=1S/C9H17O12P/c10-1-3(8(14)15)20-9-7(13)6(12)5(11)4(21-9)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/t3-,4-,5-,6+,7+,9+/m1/s1 ChemAxon inchikey BOLXAGHGKNGVBE-MTXRGOKVSA-N ChemAxon polar_surface_area 203.44 ChemAxon refractivity 63.67 ChemAxon polarizability 28.12 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon 2-O-alpha-mannosyl-D-glycerate degradation 2-O-α-Mannosyl-D-glycerate (MG) is an osmolyte utilized by hyperthermophilic archaea and bacteria. E. coli is able to utilize MG as a carbon source but not as protection against osmotic stress. MG utilization is controlled by the divergently transcribed mngR gene and mngAB operon. MngR acts as a repressor of the expression both mngR and mngAB. MngA is the EII of a PEP-dependent sugar phosphotransferase system responsible for the uptake and phosphorylation of MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate, which is subsequently converted to mannose-6-phosphate and glycerate by the α-mannosidase MngB. Glycerate can be converted to 2-phosphoglycerate by glycerate kinase I encoded by the garK gene which is also induced when cells are grown in MG. (EcoCyc) PW002096 Metabolic Specdb::CMs 10664 Specdb::CMs 39836 Specdb::CMs 149188 Specdb::CMs 149190 Specdb::CMs 149192 Specdb::CMs 154911 Specdb::CMs 279713 Specdb::NmrOneD 11462 Specdb::NmrOneD 11463 Specdb::NmrOneD 11464 Specdb::NmrOneD 11465 Specdb::NmrOneD 11466 Specdb::NmrOneD 11467 Specdb::NmrOneD 11468 Specdb::NmrOneD 11469 Specdb::NmrOneD 11470 Specdb::NmrOneD 11471 Specdb::NmrOneD 11472 Specdb::NmrOneD 11473 Specdb::NmrOneD 11474 Specdb::NmrOneD 11475 Specdb::NmrOneD 11476 Specdb::NmrOneD 11477 Specdb::NmrOneD 11478 Specdb::NmrOneD 11479 Specdb::NmrOneD 11480 Specdb::NmrOneD 11481 Specdb::MsMs 26288 Specdb::MsMs 26289 Specdb::MsMs 26290 Specdb::MsMs 32846 Specdb::MsMs 32847 Specdb::MsMs 32848 Specdb::MsMs 2313710 Specdb::MsMs 2313711 Specdb::MsMs 2313712 Specdb::MsMs 2652449 Specdb::MsMs 2652450 Specdb::MsMs 2652451 HMDB12152 24892815 C16699 61001 CPD0-1063 FDB028809 Ryu J, Kanapathipillai M, Lentzen G, Park CB: Inhibition of beta-amyloid peptide aggregation and neurotoxicity by alpha-d-mannosylglycerate, a natural extremolyte. Peptides. 2008 Apr;29(4):578-84. Epub 2008 Jan 9. 18304694 Alpha-mannosidase mngB P54746 MNGB_ECOLI mngB http://ecmdb.ca/proteins/P54746.xml Mannosyl-D-glycerate transport/metabolism system repressor MngR P13669 MNGR_ECOLI mngR http://ecmdb.ca/proteins/P13669.xml 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid PW_R006116 2(alpha-D-Mannosyl)-D-glycerate + HPr - phosphorylated > 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + HPr PW_RCT000192