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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:08 UTC
HMDB IDHMDB0001129
Secondary Accession Numbers
  • HMDB0062724
  • HMDB01129
  • HMDB62724
Metabolite Identification
Common NameN-Acetylmannosamine
DescriptionN-Acetylmannosamine, also known as beta-ManNAcc or β-ManNAc, 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. Within humans, N-acetylmannosamine participates in a number of enzymatic reactions. 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; which is mediated by the enzyme bifunctional UDP-N-acetyl glucosamine 2-epimerase / N-acetylmannosamine kinase. In humans, N-acetylmannosamine is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway. In the rate-limiting step of the pathway, UDP-GlcNAc is converted into ManNAc by UDP-GlcNAc 2-epimerase, encoded by the epimerase domain of GNE. Improved sialylation after the addition of ManNAc and other supporting ingredients to the culture medium not only increases manufacturing yield, but also improves therapeutic efficacy by increasing solubility, increasing half-life and reducing immunogenicity by reducing the formation of antibodies to the therapeutic glycoprotein When the GNE epimerase kinase does not function correctly in the human body thereby reducing the available ManNAc, it is reasonable to assume that treatment with ManNAc could assist with improving health benefits. There is no available therapy to treat GNE myopathy. ManNAc is the first committed biological precursor of N-acetylneuraminic acid (Neu5Ac, sialic acid).
Structure
Data?1582752178
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 Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-acetylmannosamine
CAS Registry Number7772-94-3
SMILES
CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI Identifier
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
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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.22Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.59131661259
DarkChem[M-H]-144.7431661259
AllCCS[M+H]+149.73532859911
AllCCS[M-H]-145.93132859911
DeepCCS[M+H]+151.0930932474
DeepCCS[M-H]-148.69430932474
DeepCCS[M-2H]-183.06930932474
DeepCCS[M+Na]+157.60230932474
AllCCS[M+H]+149.732859911
AllCCS[M+H-H2O]+145.932859911
AllCCS[M+NH4]+153.332859911
AllCCS[M+Na]+154.332859911
AllCCS[M-H]-145.932859911
AllCCS[M+Na-2H]-146.432859911
AllCCS[M+HCOO]-147.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetylmannosamineCC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O3657.7Standard polar33892256
N-AcetylmannosamineCC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O2082.8Standard non polar33892256
N-AcetylmannosamineCC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O2104.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylmannosamine,1TMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O1894.9Semi standard non polar33892256
N-Acetylmannosamine,1TMS,isomer #2CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O1900.1Semi standard non polar33892256
N-Acetylmannosamine,1TMS,isomer #3CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O1898.0Semi standard non polar33892256
N-Acetylmannosamine,1TMS,isomer #4CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C1908.2Semi standard non polar33892256
N-Acetylmannosamine,1TMS,isomer #5CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C1835.0Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O1915.8Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #10CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1897.1Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #2CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O1930.3Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #3CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C1938.6Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #4CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C1890.6Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #5CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O1939.6Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #6CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C1939.6Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #7CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C1911.9Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #8CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1933.2Semi standard non polar33892256
N-Acetylmannosamine,2TMS,isomer #9CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1895.9Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O2003.5Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #10CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1967.8Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #2CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C2011.5Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #3CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C1939.5Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #4CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2016.7Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #5CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1961.8Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #6CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1981.0Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #7CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2006.4Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #8CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C1967.9Semi standard non polar33892256
N-Acetylmannosamine,3TMS,isomer #9CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C1970.5Semi standard non polar33892256
N-Acetylmannosamine,4TMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C2036.2Semi standard non polar33892256
N-Acetylmannosamine,4TMS,isomer #2CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O)[Si](C)(C)C2024.8Semi standard non polar33892256
N-Acetylmannosamine,4TMS,isomer #3CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2040.9Semi standard non polar33892256
N-Acetylmannosamine,4TMS,isomer #4CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2039.6Semi standard non polar33892256
N-Acetylmannosamine,4TMS,isomer #5CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2031.3Semi standard non polar33892256
N-Acetylmannosamine,5TMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2092.3Semi standard non polar33892256
N-Acetylmannosamine,5TMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2154.1Standard non polar33892256
N-Acetylmannosamine,5TMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)[Si](C)(C)C2100.6Standard polar33892256
N-Acetylmannosamine,1TBDMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O2151.2Semi standard non polar33892256
N-Acetylmannosamine,1TBDMS,isomer #2CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2148.3Semi standard non polar33892256
N-Acetylmannosamine,1TBDMS,isomer #3CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2164.7Semi standard non polar33892256
N-Acetylmannosamine,1TBDMS,isomer #4CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2166.9Semi standard non polar33892256
N-Acetylmannosamine,1TBDMS,isomer #5CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2109.9Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O2423.5Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #10CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2384.2Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #2CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2439.8Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #3CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2433.2Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #4CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2371.0Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #5CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2427.0Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #6CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2436.0Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #7CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2406.0Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #8CC(=O)N[C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2423.5Semi standard non polar33892256
N-Acetylmannosamine,2TBDMS,isomer #9CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2389.3Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2686.1Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #10CC(=O)N([C@@H]1[C@H](O)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2624.3Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #2CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2664.9Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #3CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O)[Si](C)(C)C(C)(C)C2622.2Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #4CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2659.1Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #5CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2629.1Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #6CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2628.6Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #7CC(=O)N[C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2682.8Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #8CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2658.8Semi standard non polar33892256
N-Acetylmannosamine,3TBDMS,isomer #9CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2650.9Semi standard non polar33892256
N-Acetylmannosamine,4TBDMS,isomer #1CC(=O)N[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2872.7Semi standard non polar33892256
N-Acetylmannosamine,4TBDMS,isomer #2CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O)[Si](C)(C)C(C)(C)C2860.6Semi standard non polar33892256
N-Acetylmannosamine,4TBDMS,isomer #3CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2859.4Semi standard non polar33892256
N-Acetylmannosamine,4TBDMS,isomer #4CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2849.9Semi standard non polar33892256
N-Acetylmannosamine,4TBDMS,isomer #5CC(=O)N([C@@H]1[C@H](O)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2868.3Semi standard non polar33892256
N-Acetylmannosamine,5TBDMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3101.4Semi standard non polar33892256
N-Acetylmannosamine,5TBDMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3050.3Standard non polar33892256
N-Acetylmannosamine,5TBDMS,isomer #1CC(=O)N([C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2705.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - N-Acetylmannosamine GC-MS (4 TMS)splash10-00di-1910000000-c54e9f9969c7d963036f2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 5 TMS)splash10-0pvi-1951000000-56398608d2dd4355e1f62018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 4 TMS)splash10-0kw0-3940000000-02993315f1b1a700b7ec2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - N-Acetylmannosamine GC-MS (1 MEOX; 5 TMS)splash10-0pvi-2941000000-c2e3ada4d3e27dc6890a2018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-7920000000-9991e74281c314048f5e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (4 TMS) - 70eV, Positivesplash10-0007-3331900000-c6fab10d67507eecce652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylmannosamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004r-0920000000-26c87e12e0c8c5f919b72012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9400000000-f0d2f81f4292b627f0ef2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylmannosamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001j-9000000000-fcbf9adb619f826e3cd32012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Positive-QTOFsplash10-00di-0390000000-ce54c5d356ec2fc8ab9f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Positive-QTOFsplash10-0il0-2950000000-e4e02ffea74d8dfd08102017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Positive-QTOFsplash10-01ox-9400000000-180503dcc7682bb1753b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Negative-QTOFsplash10-00dr-9830000000-a5028d14de09cabbb3032017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Negative-QTOFsplash10-0ac0-9820000000-d3017a9fb13bdc3aa8472017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Negative-QTOFsplash10-0a4l-9200000000-ce24407926ce180ba3652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Positive-QTOFsplash10-0udi-0390000000-3820a7eec5a8c72f49d92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Positive-QTOFsplash10-0h90-9740000000-db880363194a3979c6372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Positive-QTOFsplash10-0229-9200000000-cdcf015aa799dc7d6d8b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 10V, Negative-QTOFsplash10-0a4i-9500000000-2c2b09cb6bfb290390852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 20V, Negative-QTOFsplash10-0abc-9540000000-a1f7d557237a521d306a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylmannosamine 40V, Negative-QTOFsplash10-0a4i-9000000000-18eabe9e3d36578883602021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Fibroblasts
  • Prostate
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028419
KNApSAcK IDNot Available
Chemspider ID9271300
KEGG Compound IDC00645
BioCyc IDN-ACETYL-D-MANNOSAMINE
BiGG ID35606
Wikipedia LinkN-acetylmannosamine
METLIN ID6024
PubChem Compound11096158
PDB IDNot Available
ChEBI ID63154
Food Biomarker OntologyNot Available
VMH IDACMANA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSatoh, 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)
General References
  1. 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. [PubMed:19212411 ]
  2. 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. [PubMed:12409508 ]
  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. [PubMed:15670773 ]
  4. 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. [PubMed:1511450 ]
  5. 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. [PubMed:444571 ]
  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. [PubMed:7216169 ]
  7. 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. [PubMed:7772033 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Regulates and initiates biosynthesis of N-acetylneuraminic acid (NeuAc), a precursor of sialic acids. Plays an essential role in early development (By similarity). Required for normal sialylation in hematopoietic cells. Sialylation is implicated in cell adhesion, signal transduction, tumorigenicity and metastatic behavior of malignant cells.
Gene Name:
GNE
Uniprot ID:
Q9Y223
Molecular weight:
83065.25
Reactions
Uridine diphosphate-N-acetylglucosamine + Water → N-Acetylmannosamine + Uridine 5'-diphosphatedetails
Adenosine triphosphate + N-Acetylmannosamine → ADP + N-Acetyl-D-mannosamine 6-phosphatedetails
General function:
Involved in catalytic activity
Specific function:
Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:
NANS
Uniprot ID:
Q9NR45
Molecular weight:
40307.26
Reactions
Phosphoenolpyruvic acid + N-Acetylmannosamine + Water → Phosphate + N-Acetylneuraminic aciddetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes the interconversion of N-acetylglucosamine to N-acetylmannosamine. Binds to renin forming a protein complex called high molecular weight (HMW) renin and inhibits renin activity. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway: although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded.
Gene Name:
RENBP
Uniprot ID:
P51606
Molecular weight:
48830.6
Reactions
N-Acetyl-D-glucosamine → N-Acetylmannosaminedetails
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. It prevents sialic acids from being recycled and returning to the cell surface. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Although human is not able to catalyze formation of Neu5Gc due to the inactive CMAHP enzyme, Neu5Gc is present in food and must be degraded (By similarity).
Gene Name:
NPL
Uniprot ID:
Q9BXD5
Molecular weight:
33116.95
Reactions
N-Acetylneuraminic acid → N-Acetylmannosamine + Pyruvic aciddetails
General function:
Involved in phosphohistidine phosphatase activity
Specific function:
Exhibits phosphohistidine phosphatase activity.
Gene Name:
PHPT1
Uniprot ID:
Q9NRX4
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Lipid phosphatase that acts on phosphatidylinositol 3-phosphate and phosphatidylinositol (3,5)-bisphosphate.
Gene Name:
MTMR1
Uniprot ID:
Q13613
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup. Has phosphatase activity towards phosphatidylinositol 3-phosphate and phosphatidylinositol 3,5-bisphosphate.
Gene Name:
MTMR2
Uniprot ID:
Q13614
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup. Acts as a negative regulator of KCNN4/KCa3.1 channel activity in CD4+ T-cells possibly by decreasing intracellular levels of phosphatidylinositol 3 phosphatase. Negatively regulates proliferation of reactivated CD4+ T-cells.
Gene Name:
MTMR6
Uniprot ID:
Q9Y217
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails
General function:
Not Available
Specific function:
Phosphatase that acts on lipids with a phosphoinositol headgroup (Probable).
Gene Name:
MTMR7
Uniprot ID:
Q9Y216
Molecular weight:
Not Available
Reactions
N-Acetylmannosamine + Phosphate → N-Acetyl-D-mannosamine 6-phosphate + Waterdetails