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Showing metabocard for Lacto-N-fucoheptaose (HMDB06643)

Record Information
Version 3.5
Creation Date 2007-05-28 07:50:34 -0600
Update Date 2013-02-08 17:15:08 -0700
HMDB ID HMDB06643
Secondary Accession Numbers None
Metabolite Identification
Common Name Lacto-N-fucoheptaose
Description Lacto-N-fucoheptaose is a heptasaccharide found in human breast milk. It contains D(+)-galactose, D(+)-glucose, L(-)-fucose and N-acetyl-D(+)-glucosamine in a 3 : 1 : 1 : 2 ratio. The glucose residue is at the reducing end of the oligosaccharide. Milk oligosaccharides vary among individuals and over the course of lactation. Oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound oligosaccharides have potential biological activity and are known to inhibit viral infection. (PMID: 10744332 Link_out, 7138030 Link_out, 1132510 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Lacto-N-fucoheptaose
  2. O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-[O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-O-beta-D-galactopyranosyl-(1->4)- D-Glucose
  3. O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-[O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)]-O-beta-delta-galactopyranosyl-(1->4)- D-Glucose
Chemical Formula C46H78N2O35
Average Molecular Weight 1219.1039
Monoisotopic Molecular Weight 1218.438512276
IUPAC Name N-{2-[(4-{[3-acetamido-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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]-4-hydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl}acetamide
Traditional IUPAC Name N-{2-[(4-{[3-acetamido-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-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]-4-hydroxy-6-(hydroxymethy
CAS Registry Number 56501-25-8
SMILES CC1OC(OC2(CC(NC(C)=O)C(OC3C(O)C(COC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)OC2CO)OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O
InChI Identifier InChI=1S/C46H78N2O35/c1-12-24(59)30(65)34(69)44(73-12)82-46(83-45-35(70)32(67)27(62)19(8-52)75-45)4-15(47-13(2)55)40(78-22(46)10-54)81-39-28(63)21(77-43(36(39)71)79-37(17(58)6-50)25(60)16(57)5-49)11-72-41-23(48-14(3)56)29(64)38(20(9-53)76-41)80-42-33(68)31(66)26(61)18(7-51)74-42/h5,12,15-45,50-54,57-71H,4,6-11H2,1-3H3,(H,47,55)(H,48,56)
InChI Key DUUXDOCGEHMZIH-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Oligosaccharides
Sub Class Hexose Oligosaccharides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glycosyl Compound
  • Mannosamine
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent Hexose Oligosaccharides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 152 g/L ALOGPS
LogP -2.36 ALOGPS
LogP -13 ChemAxon
LogS -0.90 ALOGPS
pKa (strongest acidic) 11.36 ChemAxon
pKa (strongest basic) -3.9 ChemAxon
Hydrogen Acceptor Count 35 ChemAxon
Hydrogen Donor Count 22 ChemAxon
Polar Surface Area 590.63 A2 ChemAxon
Rotatable Bond Count 24 ChemAxon
Refractivity 252.44 ChemAxon
Polarizability 115.23 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024017
KNApSAcK ID Not Available
Chemspider ID 2339104 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06643 Link_out
Metagene Link HMDB06643 Link_out
METLIN ID Not Available
PubChem Compound 3081510 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Zhang Y; Dausse B; Sinay P; Afsahi M; Berthault P; Desvaux H Synthesis and NMR study of a heptasaccharide, epitope of the stage-specific embryonic antigen-1 (SSEA-1). Carbohydrate research (2000), 324(4), 231-41. PubMed ID 10744332
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Grimmonprez L, Delautre M, Bouquelet S, Montreuil J: [Determination of the structure of a heptasaccharide isolated from human milk: lacto-n-fucoheptaose] FEBS Lett. 1975 Jun 15;54(2):221-3. Pubmed: 1132510 Link_out