Livestock Metabolome Database: Showing metabocard for 6'-Sialyllactose (LMDB00481)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:50:48 UTC

Update Date

2016-09-23 18:45:36 UTC

Lmdb

LMDB00481

Secondary Accession Numbers

None

Metabolite Identification

Common Name

6'-Sialyllactose

Description

Sialyllactose is an oligossaccharide found in both animal breast milk and cow's milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2>6')-a-sialyllactose	HMDB
(2>6')-alpha-sialyllactose	HMDB
(2>6')-sialyllactose	HMDB
6'-a-Sialyllactose	HMDB
6'-alpha-Sialyllactose	HMDB
6'-Monosialyllactose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-D-glucose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2-3)-O-beta-delta-galactopyranosyl-(1-4)-delta-glucose	HMDB
(2R,4S,5R,6R)-4-Hydroxy-5-[(1-hydroxyethylidene)amino]-2-{[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-2-yl]methoxy}-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	HMDB
6'-Sialyllactose	MeSH

Chemical Formula

C₂₃H₃₉NO₁₉

Average Molecular Weight

633.5511

Monoisotopic Molecular Weight

633.211628071

IUPAC Name

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

Traditional Name

CAS Registry Number

35890-39-2

SMILES

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

InChI Identifier

InChI=1S/C23H39NO19/c1-7(28)24-13-8(29)2-23(22(38)39,43-20(13)15(34)10(31)4-26)40-6-12-16(35)17(36)18(37)21(41-12)42-19(11(32)5-27)14(33)9(30)3-25/h3,8-21,26-27,29-37H,2,4-6H2,1H3,(H,24,28)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17-,18+,19+,20+,21-,23+/m0/s1

InChI Key

VMWYCXKMRSTDSP-GIGDJUIZSA-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
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Polyol
Organopnictogen compound
Primary alcohol
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-Gal-(1->3)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:53481 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
logP	-2.8	ALOGPS
logP	-7.7	ChemAxon
logS	-0.8	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	342.92 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	130.03 m³·mol⁻¹	ChemAxon
Polarizability	58.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-9202158000-b439176314d868764595	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-1912068000-d17393334dafaf316409	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-4915020000-385305279dc06c3aaa7b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9731010000-4f4bfea7ead4ea37990b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-022c-4941064000-38270a81e0872f5d02ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06tr-9834012000-cba3a4d93580b3f5dcca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9621000000-a0a6a1c6d1648d30d616	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-053r-2110179000-d87b6bf93bb8407d5ed0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06si-3070292000-8de17e6149de52927b16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-073b06a22652a7d8fb8b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0hmt-2700894000-f3241190fd335bd642d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9702210000-02ffe0a958770e124e24	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03nc-8935100000-a0569e822448ca14eebb	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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Colostrum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Colostrum	Detected and Quantified	30 uM	Not Available	Bovine	11242449	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0006569

FooDB ID

FDB021796

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

559069

ChEBI ID

Not Available

PubChem Compound ID

643987

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 6'-Sialyllactose (LMDB00481)

Structure for LMDB00481 (6'-Sialyllactose)