2.0 2012-10-10 12:17:09 -0600 2015-06-03 17:25:57 -0600 ECMDB23112 M2MDB003502 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate or MECDP is a highly unusual cyclodiphosphate-containing intermediate in the mevalonate-independent pathway to isopentenyl diphosphate and dimethylallyl diphosphate (i.e. isoprenoid biosynthesis). It is a product of the enzyme 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (MECDP) synthase which catalyzes the conversion of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to MECDP [PMID: 11786530] (6S,7R)-2,4-dihydroxy-6-(hydroxymethyl)-6-methyl-2,4-dioxo-1,3,5,2$l^{5},4$l^{5}-trioxadiphosphocan-7-ol (6S,7R)-6-(Hydroxymethyl)-6-methyl-1,3,5,2,4-trioxadiphosphocane-2,4,7-triol 2,4-dioxide 2-C-Methyl-D-erythritol 2,4-cyclodiphosphoric acid 3-Methyl-1,2,3,4-tetrahydroxybutane-1,3-cyclic bisphosphate 3-Methyl-1,2,3,4-tetrahydroxybutane-1,3-cyclic bisphosphoric acid C5H12O9P2 278.0909 277.995655006 (6S,7R)-2,4,7-trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ⁵,4λ⁵-trioxadiphosphocane-2,4-dione 3-mthbcp [H][C@@]1(O)COP(O)(=O)OP(O)(=O)O[C@@]1(C)CO InChI=1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-,5+/m1/s1 SFRQRNJMIIUYDI-UHNVWZDZSA-N logp -0.81 ALOGPS logs -1.11 ALOGPS solubility 2.14e+01 g/l ALOGPS logp -1.8 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (6S,7R)-2,4,7-trihydroxy-6-(hydroxymethyl)-6-methyl-1,3,5,2λ⁵,4λ⁵-trioxadiphosphocane-2,4-dione ChemAxon average_mass 278.0909 ChemAxon mono_mass 277.995655006 ChemAxon smiles [H][C@@]1(O)COP(O)(=O)OP(O)(=O)O[C@@]1(C)CO ChemAxon formula C5H12O9P2 ChemAxon inchi InChI=1S/C5H12O9P2/c1-5(3-6)4(7)2-12-15(8,9)14-16(10,11)13-5/h4,6-7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-,5+/m1/s1 ChemAxon inchikey SFRQRNJMIIUYDI-UHNVWZDZSA-N ChemAxon polar_surface_area 142.75 ChemAxon refractivity 49.08 ChemAxon polarizability 20.4 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 1084595 Specdb::EiMs 2552 Specdb::NmrOneD 332538 Specdb::NmrOneD 332539 Specdb::NmrOneD 332540 Specdb::NmrOneD 332541 Specdb::NmrOneD 332542 Specdb::NmrOneD 332543 Specdb::NmrOneD 332544 Specdb::NmrOneD 332545 Specdb::NmrOneD 332546 Specdb::NmrOneD 332547 Specdb::NmrOneD 332548 Specdb::NmrOneD 332549 Specdb::NmrOneD 332550 Specdb::NmrOneD 332551 Specdb::NmrOneD 332552 Specdb::NmrOneD 332553 Specdb::NmrOneD 332554 Specdb::NmrOneD 332555 Specdb::NmrOneD 332556 Specdb::NmrOneD 332557 Specdb::MsMs 27728 Specdb::MsMs 27729 Specdb::MsMs 27730 Specdb::MsMs 34286 Specdb::MsMs 34287 Specdb::MsMs 34288 C11453 18425 CDI 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase P62617 ISPF_ECOLI ispF http://ecmdb.ca/proteins/P62617.xml 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase P62620 ISPG_ECOLI ispG http://ecmdb.ca/proteins/P62620.xml 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate + Cytidine monophosphate 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + 2 oxidized ferredoxin > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate +2 reduced ferredoxin 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol + 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate + Cytidine monophosphate + Cytidine monophosphate PW_R003842