alpha-Tetrasaccharide (CHEM034866)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:17:16 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034866
Identification
Common Namealpha-Tetrasaccharide
ClassSmall Molecule
DescriptionAlpha-Tetrasaccharide is a metabolite that accumulates in the urine of glucosidase I deficiency patients, a defect due to missense mutations in the glucosidase I gene. (PMID 10788335) A tetrasaccharide is a carbohydrate which gives upon hydrolysis four molecules of the same or different monosaccharides. For example, stachyose upon hydrolysis gives one molecule each of glucose and fructose and two molecules of galactose. The general formula of a tetrasaccharide is typically C24H42O21. [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
a-TetrasaccharideGenerator
Α-tetrasaccharideGenerator
a-D-GalNAc-(1->3)[a-L-fuc-(1->2)]-b-D-gal-(1->4)-D-GLCHMDB
alpha-D-GalNAc-(1->3)[a-L-fuc-(1->2)]-beta-D-gal-(1->4)-D-GLCHMDB
alpha-delta-GalNAc-(1->3)[a-L-fuc-(1->2)]-beta-delta-gal-(1->4)-delta-GLCHMDB
O-2-(Acetylamino)-2-deoxy-a-D-galactopyranosyl-(1->3)-O-[6-deoxy-a-L-galactopyranosyl-(1->2)]-O-b-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-2-(Acetylamino)-2-deoxy-alpha-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->2)]-O-beta-D-galactopyranosyl-(1->4)-D-glucoseHMDB
O-2-(Acetylamino)-2-deoxy-alpha-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->2)]-O-beta-delta-galactopyranosyl-(1->4)-delta-glucoseHMDB
GalNAc-1-3-(fuc-1-2)gal-1-4-GLC-paHMDB
N-Acetylgalactosaminyl-1-3-(fucopyranosyl-1-2)-galactopyranosyl-1-4-glucopyranosyl-pyridylaminoHMDB
N-[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]ethanimidateHMDB
Chemical FormulaC26H45NO20
Average Molecular Mass691.630 g/mol
Monoisotopic Mass691.253 g/mol
CAS Registry Number59957-92-5
IUPAC NameN-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-{[(2R,3S,4S,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES[H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])O[C@H](CO)[C@H](O)[C@H](O)[C@H]2NC(C)=O)[C@H]1O[C@]1([H])O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O
InChI IdentifierInChI=1S/C26H45NO20/c1-7-14(35)19(40)20(41)25(42-7)47-23-22(46-24-13(27-8(2)32)18(39)16(37)11(5-30)43-24)17(38)12(6-31)44-26(23)45-21(10(34)4-29)15(36)9(33)3-28/h3,7,9-26,29-31,33-41H,4-6H2,1-2H3,(H,27,32)/t7-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20-,21+,22-,23+,24+,25-,26-/m0/s1
InChI KeyDLJLMAWPOOWMRF-BFJQYDNNSA-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
  • N-acyl-alpha-hexosamine
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aldehyde
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • 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 Solubility102 g/LALOGPS
logP-2.2ALOGPS
logP-8.1ChemAxon
logS-0.83ALOGPS
pKa (Strongest Acidic)11.47ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area344.31 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity144.14 m³·mol⁻¹ChemAxon
Polarizability64.14 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, Positivesplash10-03k9-8100019000-a3169055fc49c837f653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0259-1900168000-6e8612d8535ac393dc1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-4903241000-572debae5a05629928dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08ir-9802431000-30fd58020758ef98bd12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-5200294000-be9380baa9c2f155e5d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08or-6921145000-f49caa255ebecf201c95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08or-7910300000-fe0416b6f491d7a24bdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ox-2000009000-3076432becd489fcb683Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-9300127000-c3f2b2a8bdf06f1a202aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9013412000-670dc9d932a1be208dcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-076u-0000059000-dc8e874db552714387baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2219262000-eabe0d5734f7f24904fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fs-9202000000-7b3bbe0e246a747e54a9Spectrum
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 IDHMDB0000445
FooDB IDFDB022050
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5434
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID13628089
ChEBI IDNot Available
PubChem Compound ID21252248
Kegg Compound IDC06768
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Narimatsu, Hisashi; Kudo, Takashi; Sasaki, Katsutoshi. Cloning of cDNA or gene for a1,3-Fucosyltransferase Fuc-TIX from mouse and human and use of the encoding sequences and protein products. PCT Int. Appl. (2000), 172 pp. CODEN: PIXXD2 WO 2000006708 A1 20000210 CAN 132:148489 AN 2000:98730
2. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58.
3. De Praeter CM, Gerwig GJ, Bause E, Nuytinck LK, Vliegenthart JF, Breuer W, Kamerling JP, Espeel MF, Martin JJ, De Paepe AM, Chan NW, Dacremont GA, Van Coster RN: A novel disorder caused by defective biosynthesis of N-linked oligosaccharides due to glucosidase I deficiency. Am J Hum Genet. 2000 Jun;66(6):1744-56. Epub 2000 Apr 28.