Muramic acid (Compound)

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ID	2024
Name	Muramic acid
Synonyms	2-Amino-3-(O-(D-1-carboxyethyl)-2-deoxy-D-glucose; (R)-2-Amino-3-O-(1-carboxyethyl)-2-deoxy-D-glucose
Structure	MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure Structure for EE002024 (Muramic acid) 3D Structure for EE002024 (Muramic acid) 441038 -OEChem-12292200423D 34 34 0 1 0 0 0 0 0999 V2000 -2.7021 -0.4788 -0.1644 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3515 -0.0413 -0.6988 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2058 2.1848 0.2482 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5402 -2.8014 -0.1931 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4268 1.5633 0.4511 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4898 0.5553 0.9463 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6671 -1.2694 -0.1241 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3057 -2.6147 0.2249 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1441 -0.1751 0.0533 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7820 0.9964 -0.2872 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5117 -1.5154 -0.2969 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1789 0.7682 0.2983 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9321 -1.5986 0.2747 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1646 1.8543 -0.1211 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3078 0.7413 -0.0020 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6475 1.9445 -0.8642 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5310 -0.1133 0.2551 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3591 -0.1724 1.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8291 1.1078 -1.3781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5489 -1.6279 -1.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1437 0.7477 1.3960 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9224 -1.6255 1.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2886 1.8857 -1.2085 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8547 2.8430 0.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3591 -2.5536 1.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2626 -2.5165 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9519 1.0812 0.9781 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6853 2.9421 -0.1271 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2382 -3.0336 0.4428 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1694 1.6284 -1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3047 2.6409 -0.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7581 2.4871 -1.1939 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6963 0.6831 0.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2833 -0.0001 1.1014 H 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 1 13 1 0 0 0 0 2 9 1 0 0 0 0 2 15 1 0 0 0 0 3 10 1 0 0 0 0 3 28 1 0 0 0 0 4 13 1 0 0 0 0 4 29 1 0 0 0 0 5 14 1 0 0 0 0 5 33 1 0 0 0 0 6 17 1 0 0 0 0 6 34 1 0 0 0 0 7 17 2 0 0 0 0 8 11 1 0 0 0 0 8 25 1 0 0 0 0 8 26 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 16 32 1 0 0 0 0 M END > <PUBCHEM_COMPOUND_CID> 441038 > <PUBCHEM_CONFORMER_RMSD> 0.6 > <PUBCHEM_CONFORMER_DIVERSEORDER> 1 44 57 61 64 76 63 73 84 45 88 50 16 56 83 68 81 48 74 38 91 26 75 55 21 59 82 20 77 79 85 46 62 51 30 92 18 87 23 49 5 66 22 10 53 7 42 43 67 36 33 35 60 39 54 80 89 25 32 41 13 90 86 71 15 9 65 70 78 58 47 72 14 69 34 12 2 37 8 24 11 29 28 31 40 6 4 27 17 52 3 19 > <PUBCHEM_MMFF94_PARTIAL_CHARGES> 22 1 -0.56 10 0.28 11 0.27 12 0.28 13 0.56 14 0.28 15 0.34 17 0.66 2 -0.56 25 0.36 26 0.36 28 0.4 29 0.4 3 -0.68 33 0.4 34 0.5 4 -0.68 5 -0.68 6 -0.65 7 -0.57 8 -0.99 9 0.28 > <PUBCHEM_EFFECTIVE_ROTOR_COUNT> 5.2 > <PUBCHEM_PHARMACOPHORE_FEATURES> 14 1 1 acceptor 1 2 acceptor 1 3 acceptor 1 3 donor 1 4 acceptor 1 4 donor 1 5 acceptor 1 5 donor 1 6 acceptor 1 7 acceptor 1 8 cation 1 8 donor 3 6 7 17 anion 6 1 9 10 11 12 13 rings > <PUBCHEM_HEAVY_ATOM_COUNT> 17 > <PUBCHEM_ATOM_DEF_STEREO_COUNT> 5 > <PUBCHEM_ATOM_UDEF_STEREO_COUNT> 1 > <PUBCHEM_BOND_DEF_STEREO_COUNT> 0 > <PUBCHEM_BOND_UDEF_STEREO_COUNT> 0 > <PUBCHEM_ISOTOPIC_ATOM_COUNT> 0 > <PUBCHEM_COMPONENT_COUNT> 1 > <PUBCHEM_CACTVS_TAUTO_COUNT> 1 > <PUBCHEM_CONFORMER_ID> 0006BACE00000001 > <PUBCHEM_MMFF94_ENERGY> 35.8181 > <PUBCHEM_FEATURE_SELFOVERLAP> 71.171 > <PUBCHEM_SHAPE_FINGERPRINT> 10967382 1 18266179422348467902 11132069 177 18411135827061572808 11680986 33 18193569873721848963 12251169 10 18334295349037598396 12500047 106 18341887511382049144 12553582 1 17835244823734873854 12592029 89 18189341177818134387 13140716 1 18409167727112596752 13380535 76 18340487764365753239 13544592 145 18199756838963222294 14178342 30 18336249220250475282 14897335 6 18339641140391240655 15196674 1 18411136926926582922 15442244 35 18335701671838566164 16945 1 18337682892617174189 17804303 29 18340772538104239486 17846911 113 18341611473523056105 18186145 218 18339643347798878132 18511873 20 18333731295330206120 20510252 161 18270966867769248019 20645476 183 17897187877185405924 20711985 365 18337672035177311046 21501502 16 18263647436249052292 21524375 3 18411137996489334773 2334 1 18338241594863750964 23402539 116 18272078371167585253 23419403 2 16987143049868602427 23463225 33 18407760343791862134 23557571 272 18131073778985775926 23558518 356 18116433845754041344 23559900 14 18272089371327481086 23598291 2 17967535722368855004 2748010 2 18194139425414206383 335352 9 18266460906221192094 5104073 3 18409442622758469392 53812653 166 18342737382251760137 58051976 100 18261115192139777836 58051976 378 18339641119233220893 58807428 26 18335980857181288915 69090 78 18410853231325121245 6992083 37 18113619010040389164 7364860 26 17982452594353519735 81228 2 18046056322895280897 9709674 26 18343023293940464542 > <PUBCHEM_SHAPE_MULTIPOLES> 303.79 6.9 2.72 0.73 2.63 1.05 0.01 -2 -1.08 -1.67 0.14 0.29 -0.12 -0.37 > <PUBCHEM_SHAPE_SELFOVERLAP> 608.189 > <PUBCHEM_SHAPE_VOLUME> 176.2 > <PUBCHEM_COORDINATE_TYPE> 2 5 10 $$$$
Description	Muramic acid is an amino sugar acid. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls.
Classification	Compounds > Chemical entities > Organic compounds > Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Sugar acids and derivatives
CAS number	484-57-1
PubChem ID	441038
ChEBI ID	7027
FooDB ID	FDB023131
HMDB ID	HMDB0003254

Chemical data

MolDBi data

IUPAC Name	(2R)-2-{[(3R,4R,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
Traditional IUPAC Name	muramic acid
Formula	C9H17NO7
InChI	InChI=1S/C9H17NO7/c1-3(8(13)14)16-7-5(10)9(15)17-4(2-11)6(7)12/h3-7,9,11-12,15H,2,10H2,1H3,(H,13,14)/t3-,4-,5-,6-,7-,9?/m1/s1
InChI Key	MSFSPUZXLOGKHJ-PGYHGBPZSA-N
Molecular weight	251.235
Exact mass	251.100501891
SMILES	C[C@@H](O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O)C(O)=O

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Sugar acids and derivatives
Alternative Parents	Hexoses Aminosaccharides Oxanes Secondary alcohols Amino acids Hemiacetals Oxacyclic compounds Carboxylic acids Dialkyl ethers Monocarboxylic acids and derivatives Organopnictogen compounds Carbonyl compounds Organic oxides Hydrocarbon derivatives Monoalkylamines Primary alcohols

Publications with Muramic acid

ID	Title	First author	Authors	Year	Journal	Volume	Issue	Pages	PubMed ID	DOI	Study design	No. of Biomarkers	No. of Intake values	No. of Concentration values	No. of Reproducibility values	No. of Correlation values	No. of Metabolomic associations	No. of Microbiota associations	No. of Cancer associations

Biomarker data

Measurements of Muramic acid in biospecimens

Concentration values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Reproducibility values

ID	Excretion ID	Subject group	Population	Country	Cohort	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Arithmetic mean	Geometric mean	Median	Unit	Adjusted on	Reproducibility size	ICC	ICC 95% CI lower	ICC 95% CI upper	CV% WS	CV% BS	VAR WS	VAR BS	Publication

Associations of Muramic acid with exposures

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication

Metabolomic associations

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	Intake Assessment method	Intake	Intervention dose	Biospecimen	Analytical method	Biomarker	Structural identification	Feature selection	Area under curve	Sensitivity	Specificity	PLS-DA VIP	Beta coefficient	Beta coefficient p-value	ANOVA p-value	Publication

Microbiota associations

ID	Biomarker	Experimental evidence	Organism	Biospecimen	Antibiotic	Bacterial source	Substrate	Publication

Associations of Muramic acid with cancer risk

Cancer associations

ID	Excretion ID	Subject group	Population	Country	Cohort	No. of subjects	No. of cases	No. of controls	Biospecimen	Analytical method	Biomarker	Biomarker detail	Cancer	Study design	Publication

Exposure data

Measurements of Muramic acid exposures in populations

Intake values

ID	Parent ID	Depth	Subject group	Population	Country	Cohort	Intake Time definition	Intake assessment tool	Intake food coverage	Intake time coverage	Intake Assessment method	Intake	Intake detail	Food description	Supplement intakes included?	Measurement size	Detected (nb)	Detected (%)	Detected only?	Arithmethic mean	Arithmethic SD	Geometric mean	Geometric SD	Min	Min (detected)	Percentile_05	Percentile_10	Percentile_25	Median	Percentile_75	Percentile_90	Percentile_95	Max	Interquartile range	Mean 95% CI lower	Mean 95% CI upper	GMean 95% CI lower	GMean 95% CI upper	Unit	Converted arithmetic mean	Converted geometric mean	Converted median	Converted unit	Adjustment type	Adjusted on	Regressed on	Expressed as	Publication

Associations of Muramic acid exposures with biomarkers

Correlation values

ID	Intake ID	Excretion ID	Subject group	Population	Country	Cohort	Intake Time definition	Intake Assessment method	Intake	Intake detail	Supplement intakes included?	Intake Arithmetic mean	Intake Geometric mean	Intake Median	Intake Unit	Intake Adjusted on	Biomarker Time definition	Biospecimen	Analytical method	Biomarker	Biomarker detail	Biomarker Arithmetic mean	Biomarker Geometric mean	Biomarker Median	Biomarker Unit	Biomarker Adjusted on	Correlation size	Correlation type	Correlation value	Correlation 95% CI lower	Correlation 95% CI upper	Correlation p-value	Significant?	Measurement adjustment	Deattenuated?	Covariates	Publication