ContaminantDB: p-Lacto-N-octaose

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 07:18:30 UTC

Update Date

2016-11-09 01:21:27 UTC

Accession Number

CHEM036193

Identification

Common Name

p-Lacto-N-octaose

Class

Small Molecule

Description

Para-Lacto-N-octaose is a core octasaccharide of human milk determined by a combination of proton NMR spectroscopy and fast-atom-bombardment mass spectrometry. (PMID: 8344303).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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-glucose	HMDB
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-glucose	HMDB
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]ethanimidate	HMDB

Chemical Formula

C₅₄H₉₁N₃O₄₁

Average Molecular Mass

1438.296 g/mol

Monoisotopic Mass

1437.513 g/mol

CAS Registry Number

150517-85-4

IUPAC Name

N-[(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 Name

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 Key

JUJZVMYPNJNART-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	103 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.23	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	41	ChemAxon
Hydrogen Donor Count	26	ChemAxon
Polar Surface Area	698.88 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	297.54 m³·mol⁻¹	ChemAxon
Polarizability	139.86 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0230-0752960031-d45a7ddf644ae75a3f77	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01x4-4944451021-471d587974e6871c8816	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01x1-3926440011-eddcfae059c44f7694ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014l-6129825404-9c6149243ecabd3d9cde	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066v-1416920011-37337e1039810eebc3a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00b9-2830921302-4b043a64b87fcc5eba66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1004900010-91954bb4d920137b36c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0cdr-4349500000-e959c4f6ce9e541c7688	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9402100010-0f9623799d3479570710	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0nvl-2384960110-3d8a704e726603ac0024	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kj-6635940420-12dbe2aa4505de0aee87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-6913461010-fe8b49bb9800dc5de48d	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006691

FooDB ID

FDB024026

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

17216404

ChEBI ID

Not Available

PubChem Compound ID

22833680

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. 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.

2. 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.

p-Lacto-N-octaose (CHEM036193)

Structure for CHEM036193: p-Lacto-N-octaose