N-Acetylneuraminic acid (Compound)

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ID	2262
Name	N-Acetylneuraminic acid
Synonyms	Neu5Ac; NANA; 5-N-Acetyl-beta-D-neuraminic acid
Structure	MOL SDF PDB SMILES InChI Structure for EE002262 (N-Acetylneuraminic acid) 3D Structure for EE002262 (N-Acetylneuraminic acid) Mrv1652311131907572D 22 22 0 0 0 0 999 V2000 9985.8394 9985.0642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9986.5531 9985.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9987.2688 9985.0642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9987.9824 9985.4756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9986.5531 9986.3007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9985.8394 9984.2391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9984.4098 9984.2391 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9983.6953 9983.8255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9982.9808 9984.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9983.6953 9983.0005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9982.9788 9985.0642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9984.4098 9987.5383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9983.6953 9987.9508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9985.1243 9987.9508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9985.1243 9987.1258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9985.1243 9984.6506 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9984.4098 9986.7122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9983.6964 9986.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9983.6964 9985.4764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9984.4098 9985.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9985.1233 9985.4764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9985.1233 9986.3003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 6 1 1 0 0 0 2 3 1 0 0 0 0 2 5 1 6 0 0 0 3 4 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 17 22 1 0 0 0 0 21 22 1 0 0 0 0 1 21 1 0 0 0 0 21 16 1 6 0 0 0 20 7 1 6 0 0 0 19 11 1 1 0 0 0 17 12 1 0 0 0 0 17 15 1 6 0 0 0 M END > <DATABASE_ID> EE002262 > <DATABASE_NAME> ExposomeExplorer > <SMILES> [H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO > <INCHI_IDENTIFIER> InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1 > <INCHI_KEY> SQVRNKJHWKZAKO-PFQGKNLYSA-N > <FORMULA> C11H19NO9 > <MOLECULAR_WEIGHT> 309.2699 > <EXACT_MASS> 309.105981211 > <JCHEM_ACCEPTOR_COUNT> 9 > <JCHEM_ATOM_COUNT> 40 > <JCHEM_AVERAGE_POLARIZABILITY> 27.818468332190793 > <JCHEM_BIOAVAILABILITY> 1 > <JCHEM_DONOR_COUNT> 7 > <JCHEM_FORMAL_CHARGE> 0 > <JCHEM_GHOSE_FILTER> 0 > <JCHEM_IUPAC> (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid > <ALOGPS_LOGP> -2.78 > <JCHEM_LOGP> -3.5639375190000004 > <ALOGPS_LOGS> -0.13 > <JCHEM_MDDR_LIKE_RULE> 0 > <JCHEM_NUMBER_OF_RINGS> 1 > <JCHEM_PHYSIOLOGICAL_CHARGE> -1 > <JCHEM_PKA> 11.10700253474434 > <JCHEM_PKA_STRONGEST_ACIDIC> 2.9966581465692994 > <JCHEM_PKA_STRONGEST_BASIC> -1.3430861642982186 > <JCHEM_POLAR_SURFACE_AREA> 176.78 > <JCHEM_REFRACTIVITY> 63.7814 > <JCHEM_ROTATABLE_BOND_COUNT> 5 > <JCHEM_RULE_OF_FIVE> 0 > <ALOGPS_SOLUBILITY> 2.27e+02 g/l > <JCHEM_TRADITIONAL_IUPAC> β-neu5ac > <JCHEM_VEBER_RULE> 0 $$$$
Description
Classification	Compounds > Chemical entities > Organic compounds > Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Sugar acids and derivatives > Sugar amino acids and derivatives > Pyranoid amino acids and derivatives > Neuraminic acids and derivatives > N-acylneuraminic acids and derivatives > N-acylneuraminic acids
CAS number	19342-33-7
PubChem ID	445063
ChEBI ID	45744
FooDB ID
HMDB ID	HMDB0000230

Chemical data

MolDBi data

IUPAC Name	(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional IUPAC Name	β-neu5ac
Formula	C11H19NO9
InChI	InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11-/m0/s1
InChI Key	SQVRNKJHWKZAKO-PFQGKNLYSA-N
Molecular weight	309.2699
Exact mass	309.105981211
SMILES	[H][C@]1(O[C@@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

ClassyFire Taxonomy

Description	belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	N-acylneuraminic acids
Alternative Parents	Neuraminic acids C-glucuronides C-glycosyl compounds Pyrans Alpha hydroxy acids and derivatives Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Hemiacetals Polyols Oxacyclic compounds Carboxylic acids Monocarboxylic acids and derivatives Primary alcohols Carbonyl compounds Organonitrogen compounds Hydrocarbon derivatives Organopnictogen compounds Organic oxides

Publications with N-Acetylneuraminic 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 N-Acetylneuraminic 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 N-Acetylneuraminic 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 N-Acetylneuraminic 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 N-Acetylneuraminic 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 N-Acetylneuraminic 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