Showing Compound 6-Sialyllactosamine (FDB022413)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:39 UTC

Update date

2019-11-26 03:21:03 UTC

Primary ID

FDB022413

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6-Sialyllactosamine

Description

(N-acetylneuraminosyl(alpha2-6)lactosamine) is widely distributed among tissues and is involved in biological processes such as the regulation of the immune response and the progression of colon cancer. Sialylation represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. Sialic acid is commonly found alpha,6-linked to N-acetylgalactosamine (GalNAc). The biosynthesis of the linkage is mediated by a member of the sialyltransferase family, the beta-galactoside alpha,6-sialyltransferase (EC 2.4.99.1, ST6Gal.I). Although expressed by a single gene, this enzyme shows a complex pattern of regulation which allows its tissue- and stage-specific modulation. (PMID 11425186)

6'-Sialyllactosamine is an oligosaccharide found in human milk. Oligosaccharides in human milk inhibit enteric pathogens in vitro and in vivo. (PMID:10683228)

[HMDB]

CAS Number

64364-50-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	Generator
(2R,4S,5R,6R)-5-Acetamido-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid	ChEBI
(N-acetylneuraminosyl(a2-6)lactosamine)	hmdb
(N-Acetylneuraminosyl(alpha2-6)lactosamine)	ChEBI
(N-acetylneuraminosyl(alpha2-6)lactosamine)	hmdb
(N-Acetylneuraminosyl(α2-6)lactosamine)	Generator
6'-Sialyllactosamine	ChEBI
6-Sialyllactosamine	ChEBI
a-N-Acetylneuraminyl-(2->6)-b-D-galactosyl-(1->4)-N-acetyl-b-D-glucosamine	Generator, HMDB
a-N-Acetylneuraminyl-2,6-b-D-galactosyl-1,4-N-acetyl-b-D-glucosamine	Generator

Showing 1 to 10 of 50 entries

Predicted Properties

Property	Value	Source
Water Solubility	72.5 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-7.4	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	343.95 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	139.71 m³·mol⁻¹	ChemAxon
Polarizability	63.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C25H42N2O19

IUPAC name

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

InChI Identifier

InChI=1S/C25H42N2O19/c1-7(30)26-13-9(32)3-25(24(40)41,46-21(13)15(34)10(33)4-28)42-6-12-16(35)18(37)19(38)23(44-12)45-20-11(5-29)43-22(39)14(17(20)36)27-8(2)31/h9-23,28-29,32-39H,3-6H2,1-2H3,(H,26,30)(H,27,31)(H,40,41)/t9-,10+,11+,12+,13+,14+,15+,16-,17+,18-,19+,20+,21+,22+,23-,25+/m0/s1

InChI Key

RPSBVJXBTXEJJG-LURNZOHQSA-N

Isomeric SMILES

[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](NC(C)=O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O)C(O)=O)[C@H](O)[C@H](O)CO

Average Molecular Weight

674.603

Monoisotopic Molecular Weight

674.238177172

Classification

Description

Belongs to the class of organic compounds known as neuraminic acids. These are carbohydrate derivatives containing a neuraminic acid moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Neuraminic acids

Alternative Parents

Substituents

Neuraminic acid
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Disaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Pyran
Oxane
Hemiacetal
Secondary alcohol
Acetal
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic 1,3-dipolar compound
Polyol
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine oligosaccharide (CHEBI:17725 )
amino trisaccharide (CHEBI:17725 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Breast milk

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	6-Sialyllactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0nmi-5235119000-5a6aa8ff9e0838274a4b	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_1_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	6-Sialyllactosamine, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0avi-0051009000-92d7600cf12a3e43b8da	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0g4i-2294002000-8d29637be46c1d8fd36f	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-022c-4391001000-847f9d4addc27d2b4d8d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-4942473000-7edd91cc87dbeead8022	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-9881203000-a60297bc793daed18eb2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9641000000-bc983c803272c7ccce3c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0020039000-18d48851f2beb9db3adf	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3090022000-8c7f3399bee970f68a60	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052o-9520001000-9d39a2f319fe4cae1e7c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000009000-6626f23b078e7b6b89e8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0267029000-d0aa4fdac515d5c38553	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f8c-4987000000-3cdf54155f61766e6711	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

111381

ChEMBL ID

Not Available

KEGG Compound ID

C04886

Pubchem Compound ID

125128

Pubchem Substance ID

Not Available

ChEBI ID

17725

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB01081

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 6-Sialyllactosamine (FDB022413)

Structure for FDB022413 (6-Sialyllactosamine)