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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 15:06:07 UTC
Update Date2020-02-26 21:26:30 UTC
HMDB IDHMDB0006535
Secondary Accession Numbers
  • HMDB06535
Metabolite Identification
Common Namebeta-1,4-Mannosyl-N-acetylglucosamine
Descriptionbeta-1,4-Mannosyl-N-acetylglucosamine, also known as beta-D-man-(1->4)-beta-D-glcnac or manb1-4glcnacb, 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. beta-1,4-Mannosyl-N-acetylglucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752390
Synonyms
ValueSource
2-Acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-beta-D-glucopyranoseChEBI
beta-D-Man-(1->4)-beta-D-glcnacChEBI
beta-D-Mannosyl-(1->4)-N-acetyl-beta-D-glucosamineChEBI
Manb1-4glcnacbChEBI
Manbeta1-4glcnacbetaChEBI
2-Acetamido-2-deoxy-4-O-b-D-mannopyranosyl-b-D-glucopyranoseGenerator
2-Acetamido-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranoseGenerator
b-D-Man-(1->4)-b-D-glcnacGenerator
Β-D-man-(1->4)-β-D-glcnacGenerator
b-D-Mannosyl-(1->4)-N-acetyl-b-D-glucosamineGenerator
Β-D-mannosyl-(1->4)-N-acetyl-β-D-glucosamineGenerator
b-1,4-Mannosyl-N-acetylglucosamineGenerator
Β-1,4-mannosyl-N-acetylglucosamineGenerator
2-(Acetylamino)-2-deoxy-4-O-beta-D-mannopyranosyl-beta-D-glucopyranoseHMDB
2-(Acetylamino)-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranoseHMDB
4-O-Mannopyranosyl-N-acetylglucosamineHMDB
4-O-beta-D-Mannopyranosyl-N-acetyl-D-glucosamineHMDB
4-O-Β-D-mannopyranosyl-N-acetyl-D-glucosamineHMDB
Man(beta1-4)glcnacHMDB
Man(β1-4)glcnacHMDB
Man-glcnacHMDB
Man-beta-1,4-glcnacHMDB
Man-β-1,4-glcnacHMDB
Manp(beta1-4)glcpnacHMDB
Manp(β1-4)glcpnacHMDB
Manp-glcpnacHMDB
Manp-beta-1,4-glcpnacHMDB
Manp-β-1,4-glcpnacHMDB
beta-1,4-D-Mannosyl-N-acetyl-D-glucosamineHMDB
beta-D-Man-(1→4)-beta-D-glcnacHMDB
beta-D-Mannopyranosyl-(1→4)-2-acetamido-2-deoxy-beta-D-glucopyranoseHMDB
beta-D-Mannosyl-(1→4)-N-acetyl-beta-D-glucosamineHMDB
beta-D-Manp-(1→4)-beta-D-glcpnacHMDB
Β-1,4-D-mannosyl-N-acetyl-D-glucosamineHMDB
Β-D-man-(1→4)-β-D-glcnacHMDB
Β-D-mannopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoseHMDB
Β-D-mannosyl-(1→4)-N-acetyl-β-D-glucosamineHMDB
Β-D-manp-(1→4)-β-D-glcpnacHMDB
beta-1,4-Mannosyl-N-acetylglucosamineHMDB
Chemical FormulaC14H25NO11
Average Molecular Weight383.35
Monoisotopic Molecular Weight383.142760629
IUPAC NameN-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-[(2R,3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
CAS Registry Number856224-94-7
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O
InChI Identifier
InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10+,11+,12-,13-,14+/m1/s1
InChI KeyKFEUJDWYNGMDBV-JVHZDDNZSA-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
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility259 g/LALOGPS
logP-2.8ALOGPS
logP-5ChemAxon
logS-0.17ALOGPS
pKa (Strongest Acidic)11.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area198.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.44 m³·mol⁻¹ChemAxon
Polarizability36.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Lysosome
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified169.559-190.427 umol/mmol creatinineNot SpecifiedNot Specifiedbeta-Mannosidosis details
Associated Disorders and Diseases
Disease References
beta-Mannosidosis
  1. Tjoa S, Wenger DA, Fennessey PV: Quantitative analysis of disaccharides in the urine of beta-mannosidosis patients. J Inherit Metab Dis. 1990;13(2):187-94. [PubMed:2116550 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023964
KNApSAcK IDNot Available
Chemspider ID28533652
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70698368
PDB IDNot Available
ChEBI ID71553
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available