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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-30 10:40:40 UTC
Update Date2021-09-14 15:45:58 UTC
HMDB IDHMDB0006691
Secondary Accession Numbers
  • HMDB06691
Metabolite Identification
Common Namep-Lacto-N-octaose
Descriptionp-Lacto-N-octaose 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. p-Lacto-N-octaose has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make p-lacto-N-octaose a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on p-Lacto-N-octaose.
Structure
Data?1582752399
Synonyms
ValueSource
O-beta-D-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-beta-delta-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
N-[(2S,3R,4R,5S,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,4R,5R,6S)-6-{[(3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(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-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]ethanimidateHMDB
Chemical FormulaC54H91N3O41
Average Molecular Weight1438.2958
Monoisotopic Molecular Weight1437.512799429
IUPAC NameN-[(2S,3R,4R,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}-5-{[(3R,4S,5S,6R)-4-{[(2S,3R,4R,6R)-3-acetamido-5-{[(2S,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional NameN-[(2S,3R,4R,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}-5-{[(3R,4S,5S,6R)-4-{[(2S,3R,4R,6R)-3-acetamido-5-{[(2S,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
CAS Registry Number150517-85-4
SMILES
CC(=O)N[C@@H]1[C@@H](O)[C@H](OC2O[C@H](CO)[C@H](O)[C@H](O[C@@H]3O[C@H](CO)C(O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@H]5NC(C)=O)[C@H]4O)[C@H](O)[C@H]3NC(C)=O)[C@H]2O)[C@@H](CO)O[C@H]1O[C@H]1[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]1O
InChI Identifier
InChI=1S/C54H91N3O41/c1-13(67)55-25-34(78)42(23(11-65)90-48(25)96-45-31(75)20(8-62)87-52(38(45)82)92-41(17(71)5-59)28(72)16(70)4-58)93-53-39(83)46(32(76)21(9-63)88-53)97-49-26(56-14(2)68)35(79)43(24(12-66)91-49)94-54-40(84)47(33(77)22(10-64)89-54)98-50-27(57-15(3)69)44(30(74)19(7-61)85-50)95-51-37(81)36(80)29(73)18(6-60)86-51/h4,16-54,59-66,70-84H,5-12H2,1-3H3,(H,55,67)(H,56,68)(H,57,69)/t16-,17+,18+,19+,20+,21+,22+,23+,24+,25+,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36-,37+,38+,39+,40+,41+,42+,43?,44+,45-,46-,47-,48-,49-,50-,51-,52-,53?,54-/m0/s1
InChI KeyJUJZVMYPNJNART-ZPNUIHFXSA-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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility103 g/LALOGPS
logP-2.1ALOGPS
logP-17ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.23ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count41ChemAxon
Hydrogen Donor Count26ChemAxon
Polar Surface Area698.88 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity297.54 m³·mol⁻¹ChemAxon
Polarizability139.86 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 10V, Positive-QTOFsplash10-0230-0752960031-d45a7ddf644ae75a3f772017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 20V, Positive-QTOFsplash10-01x4-4944451021-471d587974e6871c88162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 40V, Positive-QTOFsplash10-01x1-3926440011-eddcfae059c44f7694ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 10V, Negative-QTOFsplash10-014l-6129825404-9c6149243ecabd3d9cde2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 20V, Negative-QTOFsplash10-066v-1416920011-37337e1039810eebc3a32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 40V, Negative-QTOFsplash10-00b9-2830921302-4b043a64b87fcc5eba662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 10V, Negative-QTOFsplash10-000i-1004900010-91954bb4d920137b36c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 20V, Negative-QTOFsplash10-0cdr-4349500000-e959c4f6ce9e541c76882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 40V, Negative-QTOFsplash10-0a6r-9402100010-0f9623799d34795707102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 10V, Positive-QTOFsplash10-0nvl-2384960110-3d8a704e726603ac00242021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 20V, Positive-QTOFsplash10-03kj-6635940420-12dbe2aa4505de0aee872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Lacto-N-octaose 40V, Positive-QTOFsplash10-000b-6913461010-fe8b49bb9800dc5de48d2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024026
KNApSAcK IDNot Available
Chemspider ID17216404
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22833680
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Haeuw-Fievre S, Wieruszeski JM, Plancke Y, Michalski JC, Montreuil J, Strecker G: Primary structure of human milk octa-, dodeca- and tridecasaccharides determined by a combination of 1H-NMR spectroscopy and fast-atom-bombardment mass spectrometry. Evidence for a new core structure, the para-lacto-N-octaose. Eur J Biochem. 1993 Jul 15;215(2):361-71. [PubMed:8344303 ]
  2. Tachibana Y, Yamashita K, Kobata A: Oligosaccharides of human milk: structural studies of di-and trifucosyl derivatives of lacto-N-octaose and lacto-N-neoctaose. Arch Biochem Biophys. 1978 May;188(1):83-9. [PubMed:677898 ]