2.0 2012-07-30 14:54:39 -0600 2015-06-03 17:20:39 -0600 ECMDB21112 M2MDB001521 1,6-Anhydrous-N-Acetylmuramyl-tripeptide 1,6-anhydrous-n-acetylmuramyl-tripeptide belongs to the class of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (inferred from compound structure) C26H43N5O14 649.6447 649.280651109 (6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid (6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid [H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=O)C(O)=O InChI=1S/C26H43N5O14/c1-11(28-23(38)12(2)45-21-17(29-13(3)33)10-44-18(9-32)20(21)36)22(37)30-15(7-8-19(34)35)24(39)31-16(26(42)43)6-4-5-14(27)25(40)41/h11-12,14-18,20-21,32,36H,4-10,27H2,1-3H3,(H,28,38)(H,29,33)(H,30,37)(H,31,39)(H,34,35)(H,40,41)(H,42,43)/t11-,12+,14?,15+,16-,17-,18+,20+,21+/m0/s1 KGVLFEPQSVUIRC-FYQNUYSYSA-N Cytosol logp -1.80 ALOGPS logs -3.71 ALOGPS solubility 1.26e-01 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}heptanedioic acid ChemAxon average_mass 649.6447 ChemAxon mono_mass 649.280651109 ChemAxon smiles [H]C(N)(CCC[C@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N=C(O)[C@@]([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=O)C(O)=O ChemAxon formula C26H43N5O14 ChemAxon inchi InChI=1S/C26H43N5O14/c1-11(28-23(38)12(2)45-21-17(29-13(3)33)10-44-18(9-32)20(21)36)22(37)30-15(7-8-19(34)35)24(39)31-16(26(42)43)6-4-5-14(27)25(40)41/h11-12,14-18,20-21,32,36H,4-10,27H2,1-3H3,(H,28,38)(H,29,33)(H,30,37)(H,31,39)(H,34,35)(H,40,41)(H,42,43)/t11-,12+,14?,15+,16-,17-,18+,20+,21+/m0/s1 ChemAxon inchikey KGVLFEPQSVUIRC-FYQNUYSYSA-N ChemAxon polar_surface_area 327.2 ChemAxon refractivity 149.24 ChemAxon polarizability 63.89 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 19 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon D-Alanine metabolism L-alanine is an essential component of protein and peptidoglycan. The latter also contains about three molecules of D-alanine for every L-alanine. Only about 10 percent of the total alanine synthesized flows into peptidoglycan. Refer to L-alanine metabolism (pathway PW000788 ). Through this single pathway D-alanine can be degraded to pyruvate through a D-amino acid dehydrogenase, which enters central metabolism and thereby can serve as a total source of carbon and energy. This pathway is unique among those through which L-amino acids are degraded, in that the L form must first be converted to the D form. This first step of the pathway, which can be catalyzed by either of two racemases( biosynthetic or catabolic), also serves an essential role in biosynthesis because its product, D-alanine, is an essential component of cell wall peptidoglycan (murein). D-alanine is metabolized by an ATP driven D-alanine ligase A and B resulting in D-alanyl-D-alanine. This product is incorporated into the peptidoglycan biosynthesis. PW000768 ec00473 Metabolic Specdb::CMs 1083648 Specdb::EiMs 4412 Specdb::NmrOneD 289955 Specdb::NmrOneD 289956 Specdb::NmrOneD 289957 Specdb::NmrOneD 289958 Specdb::NmrOneD 289959 Specdb::NmrOneD 289960 Specdb::NmrOneD 289961 Specdb::NmrOneD 289962 Specdb::NmrOneD 289963 Specdb::NmrOneD 289964 Specdb::NmrOneD 289965 Specdb::NmrOneD 289966 Specdb::NmrOneD 289967 Specdb::NmrOneD 289968 Specdb::NmrOneD 289969 Specdb::NmrOneD 289970 Specdb::NmrOneD 289971 Specdb::NmrOneD 289972 Specdb::NmrOneD 289973 Specdb::NmrOneD 289974 Specdb::MsMs 25865 Specdb::MsMs 25866 Specdb::MsMs 25867 Specdb::MsMs 32423 Specdb::MsMs 32424 Specdb::MsMs 32425 46173119 CPD0-2284 Beta-hexosaminidase P75949 NAGZ_ECOLI nagZ http://ecmdb.ca/proteins/P75949.xml Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD P13016 AMPD_ECOLI ampD http://ecmdb.ca/proteins/P13016.xml 1,6-Anhydrous-N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + 1,6-Anhydro-N-acetylmuramate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide