2.0 2012-05-31 13:44:28 -0600 2015-09-17 15:41:08 -0600 ECMDB01068 M2MDB000240 D-Sedoheptulose 7-phosphate D-sedoheptulose 7-phosphate is a member of the chemical class known as Heptoses. These are monosaccharides in which the sugar unit is an heptose. D-sedoheptulose 7-phosphate is invovled in lipopolysaccharide biosynthesis, the pentose phosphate pathway (non-oxidative), the biosynthesis of secondary metabolites, the pentose phosphate pathway, and microbial metabolism in diverse environments. Sedoheptulose 7-phosphate is an intermediate in the pentose phosphate pathway. It is formed by transketolase and acted upon by transaldolase. 7-(dihydrogen phosphate) sedoheptulose 7-(Dihydrogen phosphate) sedoheptulose (6ci,7ci,8ci) 7-(Dihydrogen phosphoric acid) sedoheptulose 7-(Dihydrogen phosphoric acid) sedoheptulose (6ci,7ci,8ci) D-Altro-2-heptulose 7-(dihydrogen phosphate) D-altro-2-Heptulose 7-(dihydrogen phosphoric acid) D-Sedoheptulose 7-phosphoric acid D-Sedoheptulose-7-p D-Sedoheptulose-7-phosphate D-Sedoheptulose-7-phosphoric acid Heptulose 7-phosphate Heptulose 7-phosphoric acid Heptulose-7-phosphate Heptulose-7-phosphoric acid S7P Sedo-heptulose-7-phosphate sedo-Heptulose-7-phosphoric acid Sedoheptulose 7-phosphate Sedoheptulose 7-phosphoric acid Sedoheptulose-7-p Sedoheptulose-7-phosphate Sedoheptulose-7-phosphoric acid C7H15O10P 290.1618 290.040283212 [(2,3,4,5,7-pentahydroxy-6-oxoheptyl)oxy]phosphonic acid sedoheptulose 7-phosphate 2646-35-7 OCC1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O InChI=1S/C7H15O10P/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15/h3-6,8-12H,1-2H2,(H2,13,14,15)/t3-,4-,5-,6+,7?/m1/s1 CBIDVWSRUUODHL-QTSLKERKSA-N Cytosol logp -1.93 ALOGPS logs -1.06 ALOGPS solubility 2.51e+01 g/l ALOGPS logp -4 ChemAxon pka_strongest_acidic 1.49 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac [(2,3,4,5,7-pentahydroxy-6-oxoheptyl)oxy]phosphonic acid ChemAxon average_mass 290.1618 ChemAxon mono_mass 290.040283212 ChemAxon smiles OCC1(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H](O)[C@@H]1O ChemAxon formula C7H15O10P ChemAxon inchi InChI=1S/C7H15O10P/c8-2-7(12)6(11)5(10)4(9)3(17-7)1-16-18(13,14)15/h3-6,8-12H,1-2H2,(H2,13,14,15)/t3-,4-,5-,6+,7?/m1/s1 ChemAxon inchikey CBIDVWSRUUODHL-QTSLKERKSA-N ChemAxon polar_surface_area 184.98 ChemAxon refractivity 54.4 ChemAxon polarizability 23.37 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Carbon fixation in photosynthetic organisms ec00710 Lipopolysaccharide biosynthesis E. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA. A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and CMP-3-deoxy-α-D-manno-octulosonate. CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core. A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter. The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831 ec00540 Metabolic Biosynthesis of ansamycins ec01051 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 Pentose Phosphate PW000893 Metabolic ADP-L-glycero-Beta-D-manno-heptose biosynthesis ADP-L-glycero-β-D-manno-heptose is a precursor for the inner core lipopolysaccharide (LPS). LPS is a component of the outer membrane of Gram-negative bacteria and consists of lipid A, a core oligosaccharide, and an O-specific polysaccharide (O antigen). PW002095 Metabolic Sedoheptulose Bisphosphate Bypass Accumulation of D-sedoheptulose 7-phosphate, an intermediate of the pentose phosphate pathway (non-oxidative branch), leads to its utilization via the sedoheptulose bisphospate bypass pathway, described here. The pathway was discovered due to the unexpected near-wild type growth of a talA talB double null mutant on xylose. 6-Phosphofructokinase I is able to phosphorylate D-sedoheptulose 7-phosphate, producing D-sedoheptulose-1,7-bisphosphate, which is in turn split into glycerone phosphate and D-erythrose 4-phosphate by fructose bisphosphate aldolase. PW002098 Metabolic pentose phosphate pathway (non-oxidative branch) NONOXIPENT-PWY ADP-L-<i>glycero</i>-&beta;-D-<i>manno</i>-heptose biosynthesis PWY0-1241 sedoheptulose bisphosphate bypass PWY0-1517 Specdb::CMs 113857 Specdb::CMs 127733 Specdb::CMs 978871 Specdb::CMs 978872 Specdb::CMs 978873 Specdb::CMs 978874 Specdb::CMs 978875 Specdb::CMs 978876 Specdb::CMs 978877 Specdb::CMs 978878 Specdb::CMs 978879 Specdb::CMs 978880 Specdb::CMs 978881 Specdb::CMs 978882 Specdb::CMs 978883 Specdb::CMs 978884 Specdb::CMs 978885 Specdb::CMs 978886 Specdb::CMs 978887 Specdb::CMs 978888 Specdb::CMs 978889 Specdb::CMs 978890 Specdb::CMs 978891 Specdb::CMs 978892 Specdb::CMs 978893 Specdb::MsMs 24707 Specdb::MsMs 24708 Specdb::MsMs 24709 Specdb::MsMs 31265 Specdb::MsMs 31266 Specdb::MsMs 31267 HMDB01068 596 C05382 15721 D-SEDOHEPTULOSE-7-P sedoheptulose 7-phosphate 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 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 6-phosphofructokinase isozyme 2 P06999 K6PF2_ECOLI pfkB http://ecmdb.ca/proteins/P06999.xml 6-phosphofructokinase isozyme 1 P0A796 K6PF1_ECOLI pfkA http://ecmdb.ca/proteins/P0A796.xml Transaldolase A P0A867 TALA_ECOLI talA http://ecmdb.ca/proteins/P0A867.xml Transaldolase B P0A870 TALB_ECOLI talB http://ecmdb.ca/proteins/P0A870.xml Transketolase 1 P27302 TKT1_ECOLI tktA http://ecmdb.ca/proteins/P27302.xml Transketolase 2 P33570 TKT2_ECOLI tktB http://ecmdb.ca/proteins/P33570.xml Phosphoheptose isomerase P63224 GMHA_ECOLI gmhA http://ecmdb.ca/proteins/P63224.xml D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Erythrose 4-phosphate + Fructose 6-phosphate TRANSALDOL-RXN D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate 1TRANSKETO-RXN D-Sedoheptulose 7-phosphate > D-Glycero-D-manno-heptose 7-phosphate RXN0-4301 Adenosine triphosphate + D-Sedoheptulose 7-phosphate > ADP + Hydrogen ion + Sedoheptulose 1,7-bisphosphate RXN0-6541 D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate 1TRANSKETO-RXN Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate <> D-Ribose-5-phosphate + Xylulose 5-phosphate R01641 Sedoheptulose 7-phosphate + D-Sedoheptulose 7-phosphate <> D-Glycero-D-manno-heptose 7-phosphate R09768 Xylulose 5-phosphate + D-Ribose-5-phosphate + Xylulose 5-phosphate <> D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate PW_R003345 D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate + D-Sedoheptulose 7-phosphate + D-Glyceraldehyde 3-phosphate <> beta-D-Fructose 6-phosphate + D-Erythrose 4-phosphate PW_R003347 D-Sedoheptulose 7-phosphate > D-Glycero-D-manno-heptose 7-phosphate PW_R006111 D-Sedoheptulose 7-phosphate + Adenosine triphosphate > Sedoheptulose 1,7-bisphosphate + ADP + Hydrogen ion PW_R006120