Livestock Metabolome Database: Showing metabocard for 3'-Sialyllactose (LMDB00254)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:45 UTC

Update Date

2016-09-23 18:45:01 UTC

Lmdb

LMDB00254

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3'-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>3')-a-sialyllactose	HMDB
(2>3')-alpha-sialyllactose	HMDB
3'-(N-Acetyl-a-neuraminosyl)lactose	HMDB
3'-(N-Acetyl-alpha-neuraminosyl)lactose	HMDB
3'-a-Sialyllactose	HMDB
3'-alpha-Sialyllactose	HMDB
3'-Monosialyllactose	HMDB
3'-N-Acetylneuraminyl-D-lactose	HMDB
3'-N-Acetylneuraminyl-delta-lactose	HMDB
3'-Sialyl-D-lactose	HMDB
3'-Sialyl-delta-lactose	HMDB
32-N-Acetyl-a-neuraminyllactose	HMDB
32-N-Acetyl-alpha-neuraminyllactose	HMDB
a-Neu5ac-(2>3)-b-D-gal-(1>4)-D-GLC	HMDB
a2,3-Sialyllactose	HMDB
alpha-Neu5ac-(2>3)-beta-D-gal-(1>4)-D-GLC	HMDB
alpha-Neu5ac-(2>3)-beta-delta-gal-(1>4)-delta-GLC	HMDB
N-Acetylneuraminoyllactose	HMDB
N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranose	HMDB
(2S,4S,5R,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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate	HMDB
3'-Sialyllactose	MeSH

Chemical Formula

C₂₃H₃₉NO₁₉

Average Molecular Weight

633.5511

Monoisotopic Molecular Weight

633.211628071

IUPAC Name

(2S,4S,5R,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-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

CAS Registry Number

35890-38-1

SMILES

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

InChI Identifier

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

InChI Key

OIZGSVFYNBZVIK-FHHHURIISA-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
C-glucuronide
Alkyl glycoside
C-glycosyl compound
O-glycosyl compound
Glycosyl compound
Ketal
Beta-hydroxy aldehyde
Fatty acyl
Oxane
Pyran
Acetamide
Alpha-hydroxyaldehyde
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Aldehyde
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Organic oxide
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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	-2.6	ALOGPS
logP	-7.7	ChemAxon
logS	-0.85	ALOGPS
pKa (Strongest Acidic)	2.84	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	58.66 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	splash10-0329-9200136000-fffce6abd054ee490a92	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-0091000000-7e22772e5e2744079301	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0229-0390000000-002eec5ec089f1eb0e5b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00xs-1930000000-89aed3dbc59d2c137408	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02u1-1905068000-8188f1508e1a6fe4b08a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0059-1619000000-56b3f7f1b9406974b2ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-8953000000-14875e5817ba52578c18	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-5910085000-1d9e7dc1c1b15e596033	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a73-9647001000-3efe2b78863a5580b526	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9843000000-ba45a1d17f709c61e7b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-2120279000-b879570d20ee857cbdc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08gl-2010291000-4d99393826350dc02114	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9110000000-cc64071c39126f0d8560	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0frb-1400894000-dfbfe52cc93f55bebc01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0irr-9414852000-d2182ab82f00048d4b3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-024l-9614210000-0ef934abaed3d29bcc58	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
1D NMR	13C 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	50 uM	Not Available	Bovine	11242449	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000825

FooDB ID

FDB021795

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5788

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

110445

ChEBI ID

Not Available

PubChem Compound ID

123914

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 3'-Sialyllactose (LMDB00254)

Structure for LMDB00254 (3'-Sialyllactose)