alpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-D-GlcNAcp (CHEM036197)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:40 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036197
Identification
Common Namealpha-D-Manp-(1->2)-alpha-D-Manp-(1->2)-alpha-D-Manp-(1->3)-beta-D-Manp-(1->4)-D-GlcNAcp
ClassSmall Molecule
DescriptionAlpha-D-Manp-(1 -> 2)-a-D-Manp-(1 -> 2)-a-D-Manp-(1 -> 3)-b-D-Manp-(1 -> 4)-D-GlcNAcp is a pentasaccharide found in the urine of patients with mannosidosis (PMID: 953057). It is a glycan structure of human milk glycoprotein glycopeptides (PMID: 6698017). This oligosaccharide is derived from high-mannose and different complex and hybrid asparagine-linked glycans and from the storage products in alpha-mannosidosis. The human liver lysosomal alpha-mannosidase (EC 3.2.1.24) enzyme that specifically hydrolyzes all alpha(1-2)-, alpha(1-3)- and alpha(1-6)-mannosidic linkages in these glycans. (PMID: 1872811).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-D-Manp-(1 -> 2)-a-D-manp-(1 -> 2)-a-D-manp-(1 -> 3)-b-D-manp-(1 -> 4)-D-glcnacpGenerator
Α-D-manp-(1 -> 2)-a-D-manp-(1 -> 2)-a-D-manp-(1 -> 3)-b-D-manp-(1 -> 4)-D-glcnacpGenerator
a-D-Manp-(1 -> 2)-a-D-manp-(1 -> 2)-a-D-manp-(1 -> 3)-b-D-manp-(1 -> 4)-D-glcnacpo-alpha-D-mannopyranosyl-(1->2)-O-alpha-D-mannopyranosyl-(1->3)-O-beta-D-mannopyranosyl-(1->4)-2-(acetylamino)-2-deoxy- D-glucoseHMDB
alpha-D-Manp-(1 -> 2)-alpha-D-manp-(1 -> 2)-alpha-D-manp-(1 -> 3)-beta-D-manp-(1 -> 4)-D-glcnacpo-alpha-D-mannopyranosyl-(1->2)-O-alpha-D-mannopyranosyl-(1->3)-O-beta-D-mannopyranosyl-(1->4)-2-(acetylamino)-2-deoxy- D-glucoseHMDB
O-alpha-delta-Mannopyranosyl-(1->2)-O-alpha-delta-mannopyranosyl-(1->3)-O-beta-delta-mannopyranosyl-(1->4)-2-(acetylamino)-2-deoxy- D-glucoseHMDB
N-[(2R,3R,4S,5R)-4-{[(2S,3S,4S,5R,6R)-4-{[(2R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]ethanimidateGenerator, HMDB
a-D-Manp-(1->2)-a-D-manp-(1->2)-a-D-manp-(1->3)-b-D-manp-(1->4)-D-glcnacpGenerator
Α-D-manp-(1->2)-α-D-manp-(1->2)-α-D-manp-(1->3)-β-D-manp-(1->4)-D-glcnacpGenerator
Chemical FormulaC26H45NO21
Average Molecular Mass707.630 g/mol
Monoisotopic Mass707.248 g/mol
CAS Registry Number52134-33-5
IUPAC NameN-[(2R,3R,4S,5R)-4-{[(2S,3S,4S,5R,6R)-4-{[(2R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4S,5R)-4-{[(2S,3S,4S,5R,6R)-4-{[(2R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5,6-trihydroxy-1-oxohexan-2-yl]acetamide
SMILESCC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)C2O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O)[C@H](O)CO
InChI IdentifierInChI=1S/C26H45NO21/c1-7(33)27-8(2-28)13(35)21(9(34)3-29)46-25-20(42)22(16(38)12(6-32)44-25)47-26-23(18(40)15(37)11(5-31)45-26)48-24-19(41)17(39)14(36)10(4-30)43-24/h2,8-26,29-32,34-42H,3-6H2,1H3,(H,27,33)/t8-,9+,10+,11+,12+,13+,14+,15+,16+,17-,18-,19-,20-,21+,22-,23?,24+,25-,26+/m0/s1
InChI KeyPOROYQINIQHUGJ-APJJTYCFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Amino saccharide
  • Beta-hydroxy aldehyde
  • Oxane
  • Fatty acyl
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Aldehyde
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organic nitrogen compound
  • Alcohol
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility122 g/LALOGPS
logP-2.5ALOGPS
logP-9.2ChemAxon
logS-0.76ALOGPS
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area364.54 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity145.69 m³·mol⁻¹ChemAxon
Polarizability66.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-4201009000-c6e66f8c14f635ec35a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_15) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0g7m-1298076100-fbbcf6d368dbfd23d88aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-5965031000-6eca7dcd817dc7bfa4b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h90-5895112000-65f1f72d04c1493d4e9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-2411049100-8e3078875dc766a955efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kdr-4932126000-4f2ee786d727032ffc94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-5942000000-cf4dc592b49043b4ac96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a5i-1100029200-3dd477a70746e5e07478Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a59-9000018000-c3821bde3976d5552037Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200011000-722711dbd6bb1da308c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abm-0210019200-20c2d8c3a16452738a07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c0s-9800016200-9f35a70b731460efd89eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5l-9200001000-c9aee2c23d79b119f4f3Spectrum
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
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 IDHMDB0006699
FooDB IDFDB024031
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35016016
ChEBI IDNot Available
PubChem Compound ID53477881
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. al Daher S, de Gasperi R, Daniel P, Hall N, Warren CD, Winchester B: The substrate-specificity of human lysosomal alpha-D-mannosidase in relation to genetic alpha-mannosidosis. Biochem J. 1991 Aug 1;277 ( Pt 3):743-51.
2. Yanagida K, Natsuka S, Hase S: Structural diversity of cytosolic free oligosaccharides in the human hepatoma cell line, HepG2. Glycobiology. 2006 Apr;16(4):294-304. Epub 2005 Dec 27.
3. De Gasperi R, Daniel PF, Warren CD: A human lysosomal alpha-mannosidase specific for the core of complex glycans. J Biol Chem. 1992 May 15;267(14):9706-12.
4. Strecker G, Fournet B, Bouquelet S, Montreuil J, Dhondt JL, Farriaux JP: [Chemistry of urinary mannosides excreted in mannosidosis]. Biochimie. 1976;58(5):579-86.
5. Pierce-Cretel A, Debray H, Montreuil J, Spik G, Van Halbeek H, Mutsaers JH, Vliegenthart JF: Primary structure of N-glycosidically linked asialoglycans of secretory immunoglobulins A from human milk. Eur J Biochem. 1984 Mar 1;139(2):337-49.