Disialyllacto-N-hexaose I (CHEM036192)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:27 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036192
Identification
Common NameDisialyllacto-N-hexaose I
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DSLNH-IHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->6)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->6)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)]-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
2-({2-[(2-{[2-({[5-({6-[({2-carboxy-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl)oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-6-hydroxy-5-[(1-hydroxyethylidene)amino]-4-(1,2,3-trihydroxypropyl)oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC62H102N4O47
Average Molecular Mass1655.472 g/mol
Monoisotopic Mass1654.571 g/mol
CAS Registry Number137636-98-7
IUPAC Name2-{[2-({2-[(2-{[(5-{[6-({[2-carboxy-5-acetamido-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]methyl}-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-6-hydroxy-4-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name2-{[2-({2-[(2-{[(5-{[6-({[2-carboxy-5-acetamido-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-4-hydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]methyl}-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl)oxy]-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-4-yl}oxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-6-hydroxy-4-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
SMILESCC(=O)NC1C(O)OC(CC1C(O)C(O)CO)(OC1C(O)C(CO)OC(OC2C(O)C(CO)OC(OC3C(O)C(COC4OC(CO)C(OC5OC(COC6(CC(O)C(NC(C)=O)C(O6)C(O)C(O)CO)C(O)=O)C(O)C(O)C5O)C(O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)C2NC(C)=O)C1O)C(O)=O
InChI IdentifierInChI=1S/C62H102N4O47/c1-16(74)63-31-20(35(83)22(79)7-67)5-62(60(98)99,113-53(31)95)112-52-40(88)27(12-72)103-58(46(52)94)109-49-34(66-19(4)77)55(102-26(11-71)39(49)87)110-51-41(89)29(105-57(45(51)93)107-47(25(82)10-70)36(84)23(80)8-68)14-100-54-33(65-18(3)76)42(90)48(28(13-73)104-54)108-56-44(92)43(91)38(86)30(106-56)15-101-61(59(96)97)6-21(78)32(64-17(2)75)50(111-61)37(85)24(81)9-69/h8,20-58,67,69-73,78-95H,5-7,9-15H2,1-4H3,(H,63,74)(H,64,75)(H,65,76)(H,66,77)(H,96,97)(H,98,99)
InChI KeyUUZWLWYXBNTJDG-UHFFFAOYSA-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 Solubility98 g/LALOGPS
logP-2.3ALOGPS
logP-18ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count47ChemAxon
Hydrogen Donor Count30ChemAxon
Polar Surface Area822.81 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity342.73 m³·mol⁻¹ChemAxon
Polarizability155.83 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0824019000-1bd38e1a69403805188fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-3419000104-6b385ddaec6cbaa67926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ea-4889031411-3cb4a50389dedc730410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-059l-3111149000-bfa7427443e9cb44cd24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-3159128000-eaa18a643341470d7f2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9758143100-279490a640698a344160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0100069000-5a5742a88104bde218b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1015093000-e0389ca61c1962ae5804Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9220011000-42e136edb14f2f7885bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0300529000-464581e548da13e99124Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-4430219000-52771798f63cf635991bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-1925214041-96f8821cd3f01ce2828eSpectrum
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
1D NMR13C 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 IDHMDB0006681
FooDB IDFDB024025
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216403
ChEBI IDNot Available
PubChem Compound ID22833679
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kim, Hyunjin M.; Kim, In Jong; Danishefsky, Samuel J. Total Syntheses of Tumor-Related Antigens N3: Probing the Feasibility Limits of the Glycal Assembly Method. Journal of the American Chemical Society (2001), 123(1), 35-48.
2. Shen Z, Warren CD, Newburg DS: High-performance capillary electrophoresis of sialylated oligosaccharides of human milk. Anal Biochem. 2000 Mar 1;279(1):37-45.
3. Kitagawa H, Takaoka M, Nakada H, Fukui S, Funakoshi I, Kawasaki T, Tate S, Inagaki F, Yamashina I: Isolation and structural studies of human milk oligosaccharides that are reactive with a monoclonal antibody MSW 113. J Biochem. 1991 Oct;110(4):598-604.