Showing metabocard for N-Acetylmannosamine (BMDB0001129)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:41:29 UTC
Update Date2020-05-11 20:50:51 UTC
BMDB IDBMDB0001129
Secondary Accession Numbers
  • BMDB01129
Metabolite Identification
Common NameN-Acetylmannosamine
DescriptionN-Acetylmannosamine, also known as 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. N-Acetylmannosamine is possibly soluble (in water) and a moderately basic 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 through its interaction with 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 cattle, N-acetylmannosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Acetamido-2-deoxy-D-mannoseChEBI
ManNAcChEBI
N-Acetylmannosamine, (D)-isomerMeSH
N-Acetylmannosamine, (L)-isomerMeSH
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidic acid
Traditional NameN-acetylmannosamine
CAS Registry Number3615-17-6
SMILES
[H]C1(O)O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@]1([H])N=C(C)O
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-ZTVVOAFPSA-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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Milk
  • Prostate Tissue
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00019583
Chemspider IDNot Available
KEGG Compound IDC00645
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Acetylmannosamine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID63153
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)Not Available
General References
  1. Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53. [PubMed:11556330 ]

Enzymes

Enzyme Details
1. N-acetylneuraminate lyase
General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
NPL
Uniprot ID:
Q29RY9
Molecular weight:
35166.0