Trifucosyllacto-N-hexaose (CHEM036179)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:17:28 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036179
Identification
Common NameTrifucosyllacto-N-hexaose
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TFLNH(a)HMDB
trifucosyllacto-N-Hexaose-aHMDB
N-[2-({4-[(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-2-yl}methoxy)-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]ethanimidateGenerator, HMDB
Chemical FormulaC58H98N2O43
Average Molecular Mass1511.386 g/mol
Monoisotopic Mass1510.554 g/mol
CAS Registry Number116883-09-1
IUPAC NameN-(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-2-{[2-({[3-acetamido-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)acetamide
Traditional NameN-(4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-2-{[2-({[3-acetamido-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)acetamide
SMILESCC1OC(OC2C(O)C(O)C(CO)OC2OC2C(NC(C)=O)C(OC3C(O)C(COC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(OC5OC(C)C(O)C(O)C5O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)OC(CO)C2OC2OC(C)C(O)C(O)C2O)C(O)C(O)C1O
InChI IdentifierInChI=1S/C58H98N2O43/c1-13-27(71)34(78)39(83)53(89-13)98-46-23(11-66)95-52(26(60-17(5)68)48(46)101-58-50(38(82)32(76)21(9-64)93-58)103-55-41(85)36(80)29(73)15(3)91-55)102-49-33(77)24(96-57(43(49)87)97-44(19(70)7-62)30(74)18(69)6-61)12-88-51-25(59-16(4)67)47(100-54-40(84)35(79)28(72)14(2)90-54)45(22(10-65)94-51)99-56-42(86)37(81)31(75)20(8-63)92-56/h6,13-15,18-58,62-66,69-87H,7-12H2,1-5H3,(H,59,67)(H,60,68)
InChI KeyYOTBLRKYLWEPOA-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 Solubility156 g/LALOGPS
logP-1.4ALOGPS
logP-15ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)11.28ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count43ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area708.47 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity314.22 m³·mol⁻¹ChemAxon
Polarizability143.4 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-0007-1339700000-55ef8b1f3d8eddcc22f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uem-4597400010-4b8a012123d14120f6b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uyl-4695500000-036684be26fb316df7baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-5324900011-5cfb86a872fb9fa09041Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01r6-1813900201-a23760692fd9924d325bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4800190504-7683a8e993850838398bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0539410000-7a5945f8401a7869f9b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gc1-0596010000-5ba75e72eb13f081f0e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g1-9101132000-c8a90c188970fceb4b95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1312970000-2a935b34849eab92f3bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-3401920000-624f5596c555188d8bd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-6923320000-a8d706a57f95b4386442Spectrum
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 IDHMDB0006621
FooDB IDFDB024010
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID2637308
ChEBI IDNot Available
PubChem Compound ID3392565
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pfenninger A, Karas M, Finke B, Stahl B: Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nano-electrospray MS(n) (part 1: methodology). J Am Soc Mass Spectrom. 2002 Nov;13(11):1331-40.
2. Bode L, Kunz C, Muhly-Reinholz M, Mayer K, Seeger W, Rudloff S: Inhibition of monocyte, lymphocyte, and neutrophil adhesion to endothelial cells by human milk oligosaccharides. Thromb Haemost. 2004 Dec;92(6):1402-10.
3. Strecker G, Wieruszeski JM, Michalski JC, Montreuil J: Primary structure of human milk nona- and decasaccharides determined by a combination of fast atom bombardment mass spectrometry and 1H-/13C-nuclear magnetic resonance spectroscopy. Evidence for a new core structure, iso-lacto-N-octaose. Glycoconj J. 1989;6(2):169-82.