ContaminantDB: O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-D-Glu

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

Record Information

Version

1.0

Creation Date

2016-05-26 07:18:05 UTC

Update Date

2016-11-09 01:21:27 UTC

Accession Number

CHEM036187

Identification

Common Name

O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-D-Glu

Class

Small Molecule

Description

O-(N-acetyl-α-neuraminosyl)-(2->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)- D-Gluc is a naturally occurring sialylated oligosaccharide. Oligosaccharide chains in glycoproteins, glycolipids, and proteoglycans have been reported which reveal that carbohydrate structures participate in various biological events as well as in modifying protein function. (PMID: 16503611).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-(N-Acetyl-a-neuraminosyl)-(2->3)-O-b-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1->3)-O-b-D-galactopyranosyl-(1->4)- D-gluc	Generator
O-(N-Acetyl-α-neuraminosyl)-(2->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)- D-gluc	Generator
O-(N-Acetyl-alpha-neuraminosyl)-(2->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-(N-Acetyl-alpha-neuraminosyl)-(2->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
O-(N-Acetyl-α-neuraminosyl)-(2->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1->3)-O-β-D-galactopyranosyl-(1->;4)- D-glucose	HMDB
O-(N-Acetyl-α-neuraminosyl)-(2->3)-O-β-δ-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-δ-glucopyranosyl-(1->3)-O-β-δ-galactopyranosyl-(1->4)-O-2-(acetylamino)-2-deoxy-β-δ-glucopyranosyl-(1->3)-O-β-δ-galactopyranosyl-(1->;4)- D-glucose	HMDB
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator, HMDB
O-(N-Acetyl-a-neuraminosyl)-(2->3)-O-b-D-gal-(1->4)-O-2-(acetylamino)-2-deoxy-b-D-glu-(1->3)-O-b-D-gal-(1->4)-O-2-(acetylamino)-2-deoxy-b-D-glu-(1->3)-O-b-D-gal-(1->4)-D-glu	Generator, HMDB
O-(N-Acetyl-α-neuraminosyl)-(2->3)-O-β-D-gal-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glu-(1->3)-O-β-D-gal-(1->4)-O-2-(acetylamino)-2-deoxy-β-D-glu-(1->3)-O-β-D-gal-(1->4)-D-glu	Generator, HMDB

Chemical Formula

C₅₁H₈₅N₃O₃₉

Average Molecular Mass

1364.217 g/mol

Monoisotopic Mass

1363.476 g/mol

CAS Registry Number

118023-86-2

IUPAC Name

(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-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}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O[C@@]5(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O5)[C@H](O)[C@H](O)CO)C(O)=O)[C@H]4O)[C@H](O)[C@H]3NC(C)=O)[C@H]2O)[C@@H](CO)OC1O[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/C51H85N3O39/c1-13(63)52-25-16(66)4-51(50(80)81,92-41(25)29(71)18(68)6-56)93-44-32(74)22(10-60)84-49(37(44)79)89-40-24(12-62)86-46(27(34(40)76)54-15(3)65)91-43-31(73)21(9-59)83-48(36(43)78)88-39-23(11-61)85-45(26(33(39)75)53-14(2)64)90-42-30(72)20(8-58)82-47(35(42)77)87-38(19(69)7-57)28(70)17(67)5-55/h5,16-49,56-62,66-79H,4,6-12H2,1-3H3,(H,52,63)(H,53,64)(H,54,65)(H,80,81)/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-,51-/m0/s1

InChI Key

WUGAMWNNHSAGPE-ZDXMHWJZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

Oligosaccharide
N-acylneuraminic acid
Neuraminic acid
Fatty acyl glycoside
N-acyl-alpha-hexosamine
C-glucuronide
Alkyl glycoside
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Ketal
Beta-hydroxy aldehyde
Fatty acyl
Pyran
Oxane
Acetamide
Alpha-hydroxyaldehyde
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Primary alcohol
Aldehyde
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Alcohol
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	96.5 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-15	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.84	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	39	ChemAxon
Hydrogen Donor Count	25	ChemAxon
Polar Surface Area	677.26 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	281.89 m³·mol⁻¹	ChemAxon
Polarizability	130.95 Å³	ChemAxon
Number of Rings	6	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	splash10-0002-3409030021-b8002fdba1b3a54f7229	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-9302020011-dbe226dd82bc09a5d7e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qa-9723140031-d4dea08f8bce636e04c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1419120201-a879593045bc95130779	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054o-6449110010-0ee9074b7b7d3d0043f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-6935520200-7a47d20804642c6ff99e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0hja-2829410010-a4935b17d2116810b47c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-5319110330-60c772a70b8658beb519	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-7426590030-5bed041e962dda531d35	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dr-9088000000-6f1f2c4d46c766214640	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07i6-2195000000-b8eb0837955a6398670d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9101000000-ecf5a5b303dbbea717d0	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

HMDB0006668

FooDB ID

FDB024020

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

17216398

ChEBI ID

Not Available

PubChem Compound ID

22833674

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yamashita K, Umetsu K, Suzuki T, Iwaki Y, Endo T, Kobata A: Carbohydrate binding specificity of immobilized Allomyrina dichotoma lectin II. J Biol Chem. 1988 Nov 25;263(33):17482-9.

2. Chai W, Piskarev VE, Mulloy B, Liu Y, Evans PG, Osborn HM, Lawson AM: Analysis of chain and blood group type and branching pattern of sialylated oligosaccharides by negative ion electrospray tandem mass spectrometry. Anal Chem. 2006 Mar 1;78(5):1581-92.

O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-D-Glu (CHEM036187)

Structure for CHEM036187: O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-O-2-(acetylamino)-2-deoxy-beta-D-Glu-(1->3)-O-beta-D-Gal-(1->4)-D-Glu