Np mrd loader

Record Information
Version2.0
Created at2024-09-12 10:43:59 UTC
Updated at2024-09-12 10:44:00 UTC
NP-MRD IDNP0341759
Secondary Accession NumbersNone
Natural Product 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. It was first documented in 2009 (PMID: 19443021). Beta-1,4-Mannosyl-N-acetylglucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 25568069) (PMID: 31537530).
Structure
Thumb
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
b-D-Manp-(1->4)-b-D-glcpnacGenerator
Β-D-manp-(1->4)-β-D-glcpnacGenerator
Chemical FormulaC14H25NO11
Average Mass383.3500 Da
Monoisotopic Mass383.14276 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0006535
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS: Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. J Allergy Clin Immunol. 2009 Jun;123(6):1268-76.e15. doi: 10.1016/j.jaci.2009.03.013. Epub 2009 May 13. [PubMed:19443021 ]
  2. Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S: The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Sci Transl Med. 2015 Jan 7;7(269):269ra1. doi: 10.1126/scitranslmed.3010524. [PubMed:25568069 ]
  3. Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S: The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies. Blood. 2019 Nov 28;134(22):1941-1950. doi: 10.1182/blood.2019001705. [PubMed:31537530 ]