2.0 2012-05-31 13:58:54 -0600 2015-09-13 12:56:13 -0600 ECMDB03406 M2MDB000497 D-Serine Serine is important in metabolism in that it participates in the biosynthesis of purines and pyrimidines. It is the precursor to several amino acids including glycine and cysteine, and tryptophan in bacteria. It is also the precursor to numerous of other metabolites, including sphingolipids and folate, which is the principal donor of one-carbon fragments in biosynthesis. Serine dehydratase is an enzyme that converts serine to pyruvate. (2R)-2-amino-3-hydroxypropanoate (2R)-2-amino-3-hydroxypropanoic acid (R)-2-amino-3-hydroxypropanoate (R)-2-amino-3-hydroxypropanoic acid D-Ser D-Serin DL-Serine DSN Serine D-form C3H7NO3 105.0926 105.042593095 (2R)-2-amino-3-hydroxypropanoic acid D-serine 312-84-5 N[C@H](CO)C(O)=O InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1 MTCFGRXMJLQNBG-UWTATZPHSA-N Solid Cytosol Extra-organism Periplasm logp -3.42 ALOGPS logs 0.66 ALOGPS solubility 4.80e+02 g/l ALOGPS melting_point 229 oC logp -3.9 ChemAxon pka_strongest_acidic 2.03 ChemAxon pka_strongest_basic 8.93 ChemAxon iupac (2R)-2-amino-3-hydroxypropanoic acid ChemAxon average_mass 105.0926 ChemAxon mono_mass 105.042593095 ChemAxon smiles N[C@H](CO)C(O)=O ChemAxon formula C3H7NO3 ChemAxon inchi InChI=1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1 ChemAxon inchikey MTCFGRXMJLQNBG-UWTATZPHSA-N ChemAxon polar_surface_area 83.55 ChemAxon refractivity 22.04 ChemAxon polarizability 9.39 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Glycine, serine and threonine metabolism ec00260 Methane metabolism ec00680 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 D-serine degradation The degradation of D-serine begins with the transport of D-serine into the cytosol through a cycA. Once in the cytosol D-serine reacts with ammonia-lyase resulting in the release of a hydrogen ion, water and a 2-aminoprop-2-enoate. This compound in turn reacts spontaneously to produces 2-iminipropanoate. This compound in turn reacts with water and hydrogen ion spontaneously resulting in the release of ammonium and apyruvate. PW002101 Metabolic D-serine degradation PWY0-1535 Specdb::CMs 2447 Specdb::CMs 38591 Specdb::CMs 166908 Specdb::NmrOneD 1963 Specdb::NmrOneD 21682 Specdb::NmrOneD 21683 Specdb::NmrOneD 21684 Specdb::NmrOneD 21685 Specdb::NmrOneD 21686 Specdb::NmrOneD 21687 Specdb::NmrOneD 21688 Specdb::NmrOneD 21689 Specdb::NmrOneD 21690 Specdb::NmrOneD 21691 Specdb::NmrOneD 21692 Specdb::NmrOneD 21693 Specdb::NmrOneD 21694 Specdb::NmrOneD 21695 Specdb::NmrOneD 21696 Specdb::NmrOneD 21697 Specdb::NmrOneD 21698 Specdb::NmrOneD 21699 Specdb::NmrOneD 21700 Specdb::NmrOneD 21701 Specdb::MsMs 2283 Specdb::MsMs 2284 Specdb::MsMs 2285 Specdb::MsMs 180477 Specdb::MsMs 180478 Specdb::MsMs 180479 Specdb::MsMs 2962509 Specdb::MsMs 2962510 Specdb::MsMs 2962511 Specdb::MsMs 178161 Specdb::MsMs 178162 Specdb::MsMs 178163 Specdb::MsMs 2716473 Specdb::MsMs 2716474 Specdb::MsMs 2716475 Specdb::NmrTwoD 1098 Specdb::NmrTwoD 1898 HMDB03406 71077 64231 C00740 16523 D-SERINE DSN DSN Keseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 4pp. http://hmdb.ca/system/metabolites/msds/000/002/987/original/HMDB03406.pdf?1358894051 D-serine dehydratase P00926 SDHD_ECOLI dsdA http://ecmdb.ca/proteins/P00926.xml NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG P39831 YDFG_ECOLI ydfG http://ecmdb.ca/proteins/P39831.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml DsdX permease P08555 DSDX_ECOLI dsdX http://ecmdb.ca/proteins/P08555.xml Serine transporter P0AAD6 SDAC_ECOLI sdaC http://ecmdb.ca/proteins/P0AAD6.xml Threonine/serine transporter tdcC P0AAD8 TDCC_ECOLI tdcC http://ecmdb.ca/proteins/P0AAD8.xml D-serine/D-alanine/glycine transporter P0AAE0 CYCA_ECOLI cycA http://ecmdb.ca/proteins/P0AAE0.xml Serine/threonine transporter sstT P0AGE4 SSTT_ECOLI sstT http://ecmdb.ca/proteins/P0AGE4.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 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 NADP + D-Serine <> 2-Aminomalonate semialdehyde + Hydrogen ion + NADPH D-Serine > Ammonium + Pyruvic acid D-Serine <> Pyruvic acid + Ammonia R00221 D-Serine > Hydrogen ion + Pyruvic acid + Ammonia R00221 DSERDEAM-RXN D-Serine > Pyruvic acid + Ammonia D-Serine + 2-Aminoacrylic acid + 2-Iminopropanoate + Water <> Pyruvic acid + Ammonia R00221 Phosphoserine + O-Phospho-D-serine + Water <> L-Serine + D-Serine + Phosphate R00582 R02853 D-Serine > Water + Hydrogen ion + 2-Aminoacrylic acid PW_R006128 D-Serine <> Pyruvic acid + Ammonia