Lacto-N-fucopentaose I (CHEM036200)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:18:45 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036200
Identification
Common NameLacto-N-fucopentaose I
ClassSmall Molecule
DescriptionLacto-n-fucopentaose I is an oligosaccharide found in human milk and other biofluids. Oligosaccharides of the blood group family decorate diverse glycoproteins and glycolipids on the surface of cells. Lacto-n-fucopentaose I and its sulfated and sialylated analogs, SuLNFPI and SLNFPI, are potent oligosaccharide ligands for the animal lectins, E- and L-selectin, and the natural killer cell receptor, NKR-P1. Burkinabe women show lower concentrations of lacto-n-fucopentaose I while Italian women show a higher concentrations of lacto-n-fucopentaose I. Lacto-n-fucopentaose I inhibits blastocyst attachment to uterine epithelial cells in vitro; component(s) carrying LNF-1 in the secretion might be regulatory molecules helping to secure the proper time for implantation. (PMID: 8639679, 16954962, 1802622, 3927775, 2988366).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
lacto-N-fuco-Pentaose IHMDB
LNF 1HMDB
LNF IHMDB
LNFP IHMDB
N-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidateGenerator, HMDB
Chemical FormulaC32H55NO25
Average Molecular Mass853.771 g/mol
Monoisotopic Mass853.306 g/mol
CAS Registry Number7578-25-8
IUPAC NameN-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2S,3R,5S,6R)-2-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-4-{[(2R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILESC[C@@H]1O[C@@H](OC2[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]2OC2[C@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)[C@@H]2NC(C)=O)[C@@H](O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C32H55NO25/c1-8-16(42)21(47)23(49)30(51-8)58-28-22(48)18(44)12(5-36)54-32(28)56-26-15(33-9(2)39)29(52-13(6-37)19(26)45)57-27-20(46)14(7-38)53-31(24(27)50)55-25(11(41)4-35)17(43)10(40)3-34/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 KeyDTVXXTISAIGIBA-GZPGEGJMSA-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 Solubility104 g/LALOGPS
logP-2.2ALOGPS
logP-9.9ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)11.42ChemAxon
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
Polarizability80.07 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, Positivesplash10-01s6-1901064260-b850d4506c68ae23b85eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sl-3903053100-843ce6fc87bb82149f17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-5901142210-9dcef2ef52d6b6dabcbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-9404004680-cfea312901a010ffc3dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08ir-5904013250-2bcda8ccf32d0f157a66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-5932200000-783cf0aae99e8b970083Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3300002790-5636de176459b02ce309Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bvl-5200002940-bcab4b1d4b9bab38322bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-3b57957d9f2906046749Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0l73-1200017090-299bba1644298b53180cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-3201079000-1d80c2471306f799a46cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000b-9300010100-3d28da60d5c2704681e9Spectrum
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 IDHMDB0006705
FooDB IDFDB024034
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35016018
ChEBI IDNot Available
PubChem Compound ID53477883
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yamashita, Katsuko; Tachibana, Yoko; Kobata, Akira. Oligosaccharides of human milk: structures of three lacto-N-hexaose derivatives with H-haptenic structure. Archives of Biochemistry and Biophysics (1977), 182(2), 546-55.
2. Kogelberg H, Frenkiel TA, Homans SW, Lubineau A, Feizi T: Conformational studies on the selectin and natural killer cell receptor ligands sulfo- and sialyl-lacto-N-fucopentaoses (SuLNFPII and SLNFPII) using NMR spectroscopy and molecular dynamics simulations. Comparisons with the nonacidic parent molecule LNFPII. Biochemistry. 1996 Feb 13;35(6):1954-64.
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. Bush CA, Panitch MM, Dua VK, Rohr TE: Carbon nuclear magnetic resonance spectra of oligosaccharides isolated from human milk and ovarian cyst mucin. Anal Biochem. 1985 Feb 15;145(1):124-36.