Lacto-N-fucopentaose V (CHEM036201)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:46 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036201
Identification
Common NameLacto-N-fucopentaose V
ClassSmall Molecule
DescriptionLacto-N-fucopentaose V is an oligosaccharide found in human milk and other biofluids. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system. Oligosaccharides of the blood group family decorate diverse glycoproteins and glycolipids on the surface of cells. (PMID: 17002410, 16954962, 1802622, 3927775, 6638472).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
LNFP VHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-beta-D-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-beta-delta-galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-beta-delta-galactopyranosyl-(1->4)]-delta-glucoseHMDB
N-[(3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3R,5R)-1,2,5-trihydroxy-6-oxo-4-{[(2S,3S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidateGenerator, HMDB
Chemical FormulaC32H55NO25
Average Molecular Mass853.771 g/mol
Monoisotopic Mass853.306 g/mol
CAS Registry Number60254-64-0
IUPAC NameN-[(3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3R,5R)-1,2,5-trihydroxy-6-oxo-4-{[(2S,3S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
Traditional NameN-[(3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(3R,5R)-1,2,5-trihydroxy-6-oxo-4-{[(2S,3S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
SMILESC[C@@H]1O[C@@H](OC([C@@H](O)C=O)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](OC3O[C@H](CO)[C@@H](O)C(OC4O[C@H](CO)C(O)C(O)[C@H]4O)[C@H]3NC(C)=O)[C@H]2O)C(O)CO)[C@@H](O)C(O)C1O
InChI IdentifierInChI=1S/C32H55NO25/c1-8-16(42)20(46)22(48)30(51-8)55-25(10(40)3-34)26(11(41)4-35)56-32-24(50)28(19(45)14(7-38)54-32)58-29-15(33-9(2)39)27(18(44)13(6-37)52-29)57-31-23(49)21(47)17(43)12(5-36)53-31/h3,8,10-32,35-38,40-50H,4-7H2,1-2H3,(H,33,39)/t8-,10-,11?,12+,13+,14+,15+,16?,17?,18+,19-,20?,21?,22-,23+,24+,25?,26+,27?,28-,29?,30-,31?,32-/m0/s1
InChI KeyTVVLIFCVJJSLBL-SEHWTJTBSA-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
  • Oxane
  • Fatty acyl
  • Alpha-hydroxyaldehyde
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aldehyde
  • 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 Solubility103 g/LALOGPS
logP-2.2ALOGPS
logP-9.9ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)11.37ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area423.46 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity176.56 m³·mol⁻¹ChemAxon
Polarizability81.04 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-05bo-0206019160-1cf40221a96632048fccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bc-1709248110-27d941d00181852d2eedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-2905043210-59309037b3944f5ad3edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ai-4101133690-7ea3396adb4346ccbc7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3505236490-1ec24f41e0812335bb19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mi-6956640000-7ccccd2f9860776ed127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0202009130-e13efce160be588e6abdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002e-1900028020-e599bd9797b3c865da5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9702011100-02cc82dedb7dbc1f44afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1000000190-6421d314286c20adeaafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06xw-6900004520-295b158000ca63c6fec7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vl-9700031100-1dbb2941f4bb84c06201Spectrum
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 IDHMDB0006706
FooDB IDFDB024035
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35016019
ChEBI ID88778
PubChem Compound ID53477884
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Koizumi, Satoshi; Sasaki, Katsutoshi; Endo, Tetsuo; Tabata, Kazuhiko; Ozaki, Akio. Processes for producing sugar nucleotides and complex carbohydrates. PCT Int. Appl. (1998), 119 pp.
2. Ninonuevo MR, Park Y, Yin H, Zhang J, Ward RE, Clowers BH, German JB, Freeman SL, Killeen K, Grimm R, Lebrilla CB: A strategy for annotating the human milk glycome. J Agric Food Chem. 2006 Oct 4;54(20):7471-80.
3. Musumeci M, Simpore J, D'Agata A, Sotgiu S, Musumeci S: Oligosaccharides in colostrum of Italian and Burkinabe women. J Pediatr Gastroenterol Nutr. 2006 Sep;43(3):372-8.
4. Lindenberg S: Experimental studies on the initial trophoblast endometrial interaction. Dan Med Bull. 1991 Oct;38(5):371-80.
5. Rosenfelder G, Morgelin M, Chang JY, Schonenberger CA, Braun DG, Towbin H: Chromogenic labeling of monosaccharides using 4'-N,N-dimethylamino-4-aminoazobenzene. Anal Biochem. 1985 May 15;147(1):156-65.
6. Dua VK, Bush CA: Identification and fractionation of human milk oligosaccharides by proton-nuclear magnetic resonance spectroscopy and reverse-phase high-performance liquid chromatography. Anal Biochem. 1983 Aug;133(1):1-8.