Bovine Metabolome Database: Showing metabocard for 3-Sialyl Lewis (BMDB0006579)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:23:37 UTC

Update Date

2020-04-22 15:17:56 UTC

BMDB ID

BMDB0006579

Secondary Accession Numbers

BMDB06579

Metabolite Identification

Common Name

3-Sialyl Lewis

Description

3-Sialyl Lewis belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Based on a literature review very few articles have been published on 3-Sialyl Lewis.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3'-Sialyl lewis a	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy- D-glucose	HMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-2-(acetylamino)-2-deoxy- D-glucose	HMDB
Sialyl lea tri	HMDB
Sialyl lewis a	HMDB
SLea	HMDB
(2S,4S,5R,6R)-2-{[(2R,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-5,6-dihydroxy-2-[(1-hydroxyethylidene)amino]-1-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-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

Chemical Formula

C₃₁H₅₂N₂O₂₃

Average Molecular Weight

820.7442

Monoisotopic Molecular Weight

820.29608598

IUPAC Name

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

Traditional Name

sialyl-lewis A

CAS Registry Number

92448-22-1

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

InChI Identifier

InChI=1S/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)54-25(15(42)7-36)24(12(5-34)32-10(2)38)53-29-23(48)27(20(45)16(8-37)52-29)56-31(30(49)50)4-13(40)17(33-11(3)39)26(55-31)19(44)14(41)6-35/h5,9,12-29,35-37,40-48H,4,6-8H2,1-3H3,(H,32,38)(H,33,39)(H,49,50)/t9-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28-,29-,31-/m0/s1

InChI Key

INZOTETZQBPBCE-NYLDSJSYSA-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

N-acylneuraminic acid
Neuraminic acid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
C-glucuronide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
C-glycosyl compound
Amino saccharide
Ketal
Oxane
Pyran
Monosaccharide
Fatty acyl
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
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

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

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	-2.7	ALOGPS
logP	-8.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.89	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	410.71 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	172 m³·mol⁻¹	ChemAxon
Polarizability	77.25 Å³	ChemAxon
Number of Rings	3	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_16) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0039047780-a6a6eefa31eb1cd8aa37	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1219050000-24ed19da17cf8095551a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ht9-2197012000-e61172bbfcd93fa7dc71	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kml-3811003940-bfbedd8c5c1a742e1588	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pdr-9847130210-b52a4b20d0eb31cc3b79	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8659000000-a3d562e1e1522405c2b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0002201290-3aa7a8d28cf5c288102b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05gi-0035397460-100165c981288423ab19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02ai-9742023200-8f288fed4a7cfc3f3b4a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0le9-6141001890-f11d5c1fbe0826e11e5f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-2160031930-ba7fd20ea109f7ae0aef	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-4297000000-12c687ed5acc9af26505	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0006579

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023981

KNApSAcK ID

Not Available

Chemspider ID

559075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

643993

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Reddy, Gurijala V.; Jain, Rakesh K.; Locke, Robert D.; Matta, Khushi L. Synthesis of precursors for the dimeric 3-O-SO3Na LewisX and LewisA structures. Carbohydrate Research (1996), 280(2), 261-76.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Sialyl Lewis (BMDB0006579)

Structure for BMDB0006579 (3-Sialyl Lewis)