ContaminantDB: Lewis a trisaccharide

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

Record Information

Version

1.0

Creation Date

2016-05-26 07:16:27 UTC

Update Date

2016-11-09 01:21:26 UTC

Accession Number

CHEM036154

Identification

Common Name

Lewis a trisaccharide

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-O-b-D-Galactopyranosyl-4-O-a-L-fucopyranosyl-N-acetyl-D-glucosamine	HMDB
3-O-beta-D-Galactopyranosyl-4-O-alpha-L-fucopyranosyl-N-acetyl-D-glucosamine	HMDB
Lea	HMDB
Lea tri	HMDB
Lea trisaccharide	HMDB
Lewis a	HMDB
N-Acetyl-4-O-a-L-fucosyl-3-O-b-D-galactosyl-glucosamine	HMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-D-galactosyl-glucosamine	HMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-delta-galactosyl-glucosamine	HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-glucose	HMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-glucose	HMDB
O-a-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucose	HMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-delta-glucose	HMDB
N-[(2R,3R,4R,5R)-5,6-Dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidate	Generator, HMDB

Chemical Formula

C₂₀H₃₅NO₁₅

Average Molecular Mass

529.490 g/mol

Monoisotopic Mass

529.201 g/mol

CAS Registry Number

56570-03-7

IUPAC Name

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

Traditional Name

N-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide

SMILES

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

InChI Identifier

InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1

InChI Key

HHQLEBOUBWWITP-MBKDEEHCSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Amino saccharide
Monosaccharide
Oxane
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Aldehyde
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	121 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.4	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.16 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	111.73 m³·mol⁻¹	ChemAxon
Polarizability	49.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03xr-8621950000-6c5362f47107bdfe2c3a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-08fr-8422129000-28c650c37eaaacc1181f	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_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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0i0r-0019130000-363d4b547844359483d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4i-3569000000-c5945405a01b88cc67a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-4294000000-2d2ce9890f58b891e2c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0400-4528790000-3999d8e6f911f16d66f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6529230000-025259eea3091321d8a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03xr-9774000000-c06b221f4453d2c7625d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-6202390000-751a8aa5a69ad8130951	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0r01-6901620000-6608ec28b9ba1e71247e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3191000000-19ad84406dbadaf10329	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0119020000-d69bf66a9061ee5dc4d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-3295000000-c801ce02be3ae8dd85d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-9740000000-c496b3fcffdf0af5e81f	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

HMDB0006582

FooDB ID

FDB023984

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

30776578

ChEBI ID

Not Available

PubChem Compound ID

53477858

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Makimura, Yutaka; Ishida, Hideharu; Kiso, Makoto; Hasegawa, Akira. Synthetic studies of sialoglycoconjugates. 93. Synthetic studies on tumor-associated antigens: efficient syntheses of Lea and sialyl-Lea oligosaccharides, and their deaminated analogs. ChemInform 28(35) · August 2010

2. Morrow AL, Ruiz-Palacios GM, Altaye M, Jiang X, Guerrero ML, Meinzen-Derr JK, Farkas T, Chaturvedi P, Pickering LK, Newburg DS: Human milk oligosaccharides are associated with protection against diarrhea in breast-fed infants. J Pediatr. 2004 Sep;145(3):297-303.

3. Asakuma S, Urashima T, Akahori M, Obayashi H, Nakamura T, Kimura K, Watanabe Y, Arai I, Sanai Y: Variation of major neutral oligosaccharides levels in human colostrum. Eur J Clin Nutr. 2008 Apr;62(4):488-94. Epub 2007 Mar 21.

4. Sumiyoshi W, Urashima T, Nakamura T, Arai I, Saito T, Tsumura N, Wang B, Brand-Miller J, Watanabe Y, Kimura K: Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation. Br J Nutr. 2003 Jan;89(1):61-9.

5. Ford DS, Condon JA, Bacon J, Richards VL, Kronenberg H: A family exhibiting the cis-AB genotype. Pathology. 1989 Jan;21(1):23-6.

Lewis a trisaccharide (CHEM036154)

Structure for CHEM036154: Lewis a trisaccharide