Record Information
Version2.0
Creation Date2012-05-31 13:45:54 -0600
Update Date2015-10-15 16:13:51 -0600
Secondary Accession Numbers
  • ECMDB01129
Identification
Name:N-Acetylmannosamine
DescriptionN-Acetylmannosamine is a monosaccharide that is used as a precursor in the chemical or enzymatic synthesis of the neuraminic acids found in glycolipids and glycoproteins.
Structure
Thumb
Synonyms:
  • 2-Acetamido-2-deoxy-D-mannopyranose
  • 2-Acetamido-2-deoxy-D-mannose
  • ManNAc
  • N-Acetyl-D-mannosamine
  • N-Acetylmannosamine
Chemical Formula:C8H15NO6
Weight:Average: 221.2078
Monoisotopic: 221.089937217
InChI Key:OVRNDRQMDRJTHS-OZRXBMAMSA-N
InChI:InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8-/m1/s1
CAS number:3615-17-6
IUPAC Name:N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional IUPAC Name:N-acetylmannosamine
SMILES:[H][C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • N-acyl-alpha-hexosamine
  • Hexose monosaccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility82.5 g/LALOGPS
logP-2.3ALOGPS
logP-2.4ChemAxon
logS-0.43ALOGPS
pKa (Strongest Acidic)7.38ChemAxon
pKa (Strongest Basic)1.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area122.74 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability20.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Amino sugar and nucleotide sugar metabolism ec00520
EcoCyc Pathways:
  • N-acetylneuraminate and N-acetylmannosamine degradation PWY0-1324
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0690000000-76eea9cfdbd489aa104eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imi-1930000000-2084256295351ad89bfdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07p4-9600000000-b97b52aa812bc5c8403eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-9820000000-0f80f0084f73d8c0b639View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-8920000000-cabfb7f1d41c43ccf556View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-ac54532e68f9cc588dbaView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Satoh, Chiyoko; Akio, Kiyomoto. Nitrogen-containing sugars. I. Synthesis of 2-acetamido-2-deoxy-D-mannose from 1-deoxy-1-nitro-D-mannitol pentaacetate. Chemical & Pharmaceutical Bulletin (1964), 12(5), 615-19.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17122
HMDB IDHMDB01129
Pubchem Compound ID439281
Kegg IDC00645
ChemSpider ID388414
WikipediaN-Acetylmannosamine
BioCyc IDN-ACETYL-D-MANNOSAMINE
EcoCyc IDN-ACETYL-D-MANNOSAMINE

Enzymes

General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cleavage of N-acetylneuraminic acid (sialic acid) to form pyruvate and N-acetylmannosamine via a Schiff base intermediate
Gene Name:
nanA
Uniprot ID:
P0A6L4
Molecular weight:
32593
Reactions
N-acetylneuraminate = N-acetyl-D-mannosamine + pyruvate.
General function:
Involved in UDP-N-acetylglucosamine 2-epimerase activity
Specific function:
Catalyzes the reversible epimerization at C-2 of UDP-N- acetylglucosamine (UDP-GlcNAc) and thereby provides bacteria with UDP-N-acetylmannosamine (UDP-ManNAc), the activated donor of ManNAc residues. Also involved in bacteriophage N4 adsorption
Gene Name:
wecB
Uniprot ID:
P27828
Molecular weight:
42244
Reactions
UDP-N-acetyl-D-glucosamine = UDP-N-acetyl-D-mannosamine.
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of N-acetylmannosamine (ManNAc) to ManNAc-6-P. Has also low level glucokinase activity in vitro
Gene Name:
nanK
Uniprot ID:
P45425
Molecular weight:
29644
Reactions
ATP + N-acyl-D-mannosamine = ADP + N-acyl-D-mannosamine 6-phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manX
Uniprot ID:
P69797
Molecular weight:
35047
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yniC
Uniprot ID:
P77247
Molecular weight:
Not Available
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfbT
Uniprot ID:
P77625
Molecular weight:
Not Available

Transporters

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manY
Uniprot ID:
P69801
Molecular weight:
27636
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in mannose transport
Gene Name:
manZ
Uniprot ID:
P69805
Molecular weight:
31303
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368