1.0 2018-06-25 21:50:54 UTC 2020-03-13 17:33:41 UTC BMDB0062103 BMDB62103 N-acetyl-Muramic acid N-Acetylmuramate, also known as acetylmuramic acid or 4-O-nacmur, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetylmuramate is possibly soluble (in water) and a moderately basic compound (based on its pKa). N-Acetylmuramate exists in all living organisms, ranging from bacteria to humans. N-Acetyl-D-muramoate N-Acetylmuramic acid N-Acetyl-D-muramoic acid N-Acetylisomuramic acid Acetylmuramic acid 2-Acetamido-4-O-(1-carboxyethyl)-2-deoxyglucose 2-Acetamido-3-O-((S)-1-carboxyethyl)-2-deoxy-D-glucose 2-Acetamido-4-O-(1-carboxyethyl)-2-deoxyglucose, (beta-D)-isomer 4-O-NAcMur N-Acetylmuramate N-Acetyl-D-muramate C11H19NO8 293.2705 293.111066589 (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid 61633-75-8 [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1 MNLRQHMNZILYPY-MKFCKLDKSA-N belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Acylaminosugars Acetamides Carbonyl compounds Carboxylic acids Dialkyl ethers Hemiacetals Hexoses Hydrocarbon derivatives Monocarboxylic acids and derivatives N-acyl-alpha-hexosamines Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Secondary alcohols Secondary carboxylic acid amides Sugar acids and derivatives Acetamide Acylaminosugar Alcohol Aliphatic heteromonocyclic compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Dialkyl ether Ether Hemiacetal Hexose monosaccharide Hydrocarbon derivative Monocarboxylic acid or derivatives Monosaccharide Muramic_acid N-acyl-alpha-hexosamine Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Primary alcohol Secondary alcohol Secondary carboxylic acid amide Sugar acid Aliphatic heteromonocyclic compounds Amino sugars N-acetylmuramic acid logp -1.75 ALOGPS logs -0.74 ALOGPS logp -1.7 ChemAxon pka_strongest_acidic 3.55 ChemAxon pka_strongest_basic 1.39 ChemAxon iupac (2R)-2-{[(3R,4R,5S,6R)-2,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid ChemAxon average_mass 293.2705 ChemAxon mono_mass 293.111066589 ChemAxon smiles [H][C@](C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([H])(O)[C@]1([H])N=C(C)O)C(O)=O ChemAxon formula C11H19NO8 ChemAxon inchi InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1 ChemAxon inchikey MNLRQHMNZILYPY-MKFCKLDKSA-N ChemAxon polar_surface_area 149.04 ChemAxon refractivity 62.88 ChemAxon polarizability 27.39 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 35568 Specdb::CMs 48249 Specdb::CMs 169125 Specdb::MsMs 24461 Specdb::MsMs 24462 Specdb::MsMs 24463 Specdb::MsMs 31019 Specdb::MsMs 31020 Specdb::MsMs 31021 Specdb::MsMs 437304 Specdb::MsMs 437305 Specdb::MsMs 437306 Specdb::MsMs 437307 Specdb::MsMs 437308 Specdb::MsMs 445746 Specdb::MsMs 445747 Specdb::MsMs 445748 Specdb::MsMs 445749 Specdb::MsMs 445750 Specdb::MsMs 2236330 Specdb::MsMs 2237071 Specdb::MsMs 2238460 Specdb::MsMs 2239098 Specdb::MsMs 2240588 Specdb::MsMs 2241130 Specdb::MsMs 2242621 Specdb::MsMs 2243211 Specdb::MsMs 2248801 Specdb::NmrOneD 59292 Specdb::NmrOneD 59293 Specdb::NmrOneD 59294 Specdb::NmrOneD 59295 Specdb::NmrOneD 59296 Specdb::NmrOneD 59297 Specdb::NmrOneD 59298 Specdb::NmrOneD 59299 Specdb::NmrOneD 59300 Specdb::NmrOneD 59301 Specdb::NmrOneD 59302 Specdb::NmrOneD 59303 Specdb::NmrOneD 59304 Specdb::NmrOneD 59305 Specdb::NmrOneD 59306 Specdb::NmrOneD 59307 Specdb::NmrOneD 59308 Specdb::NmrOneD 59309 Specdb::NmrOneD 59310 Specdb::NmrOneD 59311 Milk Milk from Friesuan Holstein cows (n=1035) Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. 23438684 Milk Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. 20855010 4575341 5462244 C02713 21615 N-Acetylmuramic_acid Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. 20855010