N-Acetylmannosamine (CHEM022822)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:55:13 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022822
Identification
Common NameN-Acetylmannosamine
ClassSmall Molecule
DescriptionN-Acetylmannosamine, also known as n-acetylmannosamine or n-acetylmannosamine, 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-Acetylmannosamine is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetylmannosamine participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylmannosamine can be biosynthesized from N-acetyl-D-glucosamine; which is catalyzed by the enzyme N-acylglucosamine 2-epimerase. In addition, N-Acetylmannosamine and uridine 5'-diphosphate can be biosynthesized from uridine diphosphate-N-acetylglucosamine through the action of the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In cattle, N-acetylmannosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
beta-ManNAcChEBI
N-Acetyl-beta-mannosamineChEBI
b-ManNAcGenerator
Β-mannacGenerator
N-Acetyl-b-mannosamineGenerator
N-Acetyl-β-mannosamineGenerator
2-Acetamido-2-deoxy-D-mannopyranoseHMDB
2-Acetamido-2-deoxy-D-mannoseHMDB
ManNAcHMDB
N-Acetyl-D-mannosamineHMDB
N-Acetylmannosamine, (D)-isomerHMDB
N-Acetylmannosamine, (L)-isomerHMDB
Chemical FormulaC8H15NO6
Average Molecular Mass221.208 g/mol
Monoisotopic Mass221.090 g/mol
CAS Registry Number3615-17-6
IUPAC NameN-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-acetylmannosamine
SMILES[H][C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1NC(C)=O
InChI IdentifierInChI=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
InChI KeyOVRNDRQMDRJTHS-OZRXBMAMSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility254 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (Strongest Acidic)11.6ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.02 m³·mol⁻¹ChemAxon
Polarizability20.82 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-00di-1910000000-c54e9f9969c7d963036fSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0pvi-1951000000-56398608d2dd4355e1f6Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0kw0-3940000000-02993315f1b1a700b7ecSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 5 TMS)splash10-0pvi-2941000000-c2e3ada4d3e27dc6890aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-7920000000-9991e74281c314048f5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3331900000-c6fab10d67507eecce65Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004r-0920000000-26c87e12e0c8c5f919b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9400000000-f0d2f81f4292b627f0efSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001j-9000000000-fcbf9adb619f826e3cd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0390000000-ce54c5d356ec2fc8ab9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0il0-2950000000-e4e02ffea74d8dfd0810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9400000000-180503dcc7682bb1753bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dr-9830000000-a5028d14de09cabbb303Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ac0-9820000000-d3017a9fb13bdc3aa847Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-ce24407926ce180ba365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0390000000-3820a7eec5a8c72f49d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h90-9740000000-db880363194a3979c637Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-9200000000-cdcf015aa799dc7d6d8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9500000000-2c2b09cb6bfb29039085Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abc-9540000000-a1f7d557237a521d306aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-18eabe9e3d3657888360Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001129
FooDB IDFDB028419
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35606
BioCyc IDN-ACETYL-D-MANNOSAMINE
METLIN ID6024
PDB IDNot Available
Wikipedia LinkN-acetylmannosamine
Chemspider ID9271300
ChEBI ID63154
PubChem Compound ID11096158
Kegg Compound IDC00645
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Sugawara T, Irie K, Iwasawa H, Yoshikawa T, Okuno S, Watanabe HK, Kato T, Shibukawa M, Ito Y: Synthesis of omega-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates. Carbohydr Res. 1992 Jun 4;230(1):117-49.
3. Salama I, Hinderlich S, Shlomai Z, Eisenberg I, Krause S, Yarema K, Argov Z, Lochmuller H, Reutter W, Dabby R, Sadeh M, Ben-Bassat H, Mitrani-Rosenbaum S: No overall hyposialylation in hereditary inclusion body myopathy myoblasts carrying the homozygous M712T GNE mutation. Biochem Biophys Res Commun. 2005 Mar 4;328(1):221-6.
4. Kamerling JP, Strecker G, Farriaux JP, Dorland L, Haverkamp J, Vliegenthart JF: 2-Acetamidoglucal, a new metabolite isolated from the urine of a patient with sialuria. Biochim Biophys Acta. 1979 Mar 22;583(3):403-8.
5. Sala G, Dupre T, Seta N, Codogno P, Ghidoni R: Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts. Pediatr Res. 2002 Nov;52(5):645-51.
6. von Nicolai H, Esser P, Lauer E: Partial purification and properties of neuraminidase from Bifidobacterium lactentis. Hoppe Seylers Z Physiol Chem. 1981 Feb;362(2):153-62.
7. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
8. Rodriguez-Aparicio LB, Ferrero MA, Reglero A: N-acetyl-D-neuraminic acid synthesis in Escherichia coli K1 occurs through condensation of N-acetyl-D-mannosamine and pyruvate. Biochem J. 1995 Jun 1;308 ( Pt 2):501-5.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15280054
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15936003
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=8154046