Showing Compound Poly-N-acetyllactosamine (FDB023985)

Record Information

Version

1.0

Creation date

2011-09-21 00:38:03 UTC

Update date

2015-07-21 06:57:57 UTC

Primary ID

FDB023985

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Poly-N-acetyllactosamine

Description

Poly-N-acetyllactosamine is a unique carbohydrate composed of N-acetyllactosamine repeats. In particular, poly-N-acetyllactosamine chains are synthesized by repeated alternating additions of N-acetylglucosamine and galactose, catalyzed by -1,3-N-acetylglucosaminyltransferases (poly-N-acetyllactosamine synthase) and -1,4-galactosyltransferases. What is depicted and described in this MetaboCard is a single subunit structure. Poly-N-acetyllactosamine structures occur in mammalian glycoproteins in both N- and O-linked glycans. They represent a backbone for additional modifications by fucosyltransferases, sialyltransferases and sulfotransferases. These glycans have been suggested to be involved in biospecific interactions with selectins and other glycan-binding proteins. Moreover, the poly-Nacetyllactosamine chains in N-glycans have been found to promote tumor progression and metastasis (PMID: 12570780) [HMDB]

CAS Number

82441-98-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucose	HMDB
2-(acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-D-Glucose	hmdb
2-(acetylamino)-2-Deoxy-4-O-beta-D-galactopyranosyl-D-glucose homopolymer	HMDB
2-(Acetylamino)-2-deoxy-4-O-beta-D-galactopyranosyl-D-glucose homopolymer	hmdb
N-[(2R,3R,4S,5R)-3,5,6-Trihydroxy-1-oxo-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexan-2-yl]ethanimidate	Generator, HMDB
N-Acetyl-4-O-beta-D-galactopyranosyl-D-glucosamine	HMDB
N-Acetyl-lactosamine	HMDB
O-beta-D-Galactopyranosyl-(14)-2-deoxy-2-acetamido-D-glucose	HMDB
PNALA	MeSH
Poly(N-acetyllactosamine)	MeSH

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	152 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-5.6	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	206.24 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	80.86 m³·mol⁻¹	ChemAxon
Polarizability	35.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C14H25NO11

IUPAC name

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

InChI Identifier

InChI=1S/C14H25NO11/c1-5(19)15-6(2-16)9(21)13(7(20)3-17)26-14-12(24)11(23)10(22)8(4-18)25-14/h2,6-14,17-18,20-24H,3-4H2,1H3,(H,15,19)/t6-,7+,8+,9+,10-,11-,12+,13+,14-/m0/s1

InChI Key

HESSGHHCXGBPAJ-ZBELOFFLSA-N

Isomeric SMILES

CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@H](O)CO

Average Molecular Weight

383.3484

Monoisotopic Molecular Weight

383.142760647

Classification

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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Amino saccharide
Beta-hydroxy aldehyde
Monosaccharide
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Aldehyde
Hydrocarbon derivative
Organic oxide
Alcohol
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Primary alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Biofluid and excreta:

Urine

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

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	Poly-N-acetyllactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03xr-9316000000-514f29613692706435a9	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-3712049000-933f6d8f5aa1b5a54dc3	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_4_49, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_4_54, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_4_125, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_28, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_33, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_48, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_58, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_63, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_67, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_68, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_70, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_104, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_5_124, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_23, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_28, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_32, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_33, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_35, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_38, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Poly-N-acetyllactosamine, TMS_6_47, 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	splash10-0g59-1169000000-63db2012e8740c82b427	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-8941000000-2ca60fa57b84220edb6a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-9631000000-58c2e7db43bf8480de15	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0230-2459000000-2641dc1f4ac5d1460232	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0nvi-6933000000-a34db716f8f4a9226b7b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvi-9720000000-40688a14c35dffff6e68	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0029000000-8d1cda2ae623d4833595	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9326000000-a1029f8a5bcae64f40fd	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-2359ed48cc77289858d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0129000000-94456d35aba7fa29da93	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-6902000000-f697198a1216b3cc23d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9710000000-9cb6df3a5b03d0b10b97	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

106753

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

119547

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06583

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

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB

Showing 1 to 10 of 29 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Beta-1,3-N-acetylglucosaminyltransferase bGnT-2	bGnT-2	Q9NY97
Carbohydrate sulfotransferase 5	CHST5	Q9GZS9
Carbohydrate sulfotransferase 6	CHST6	Q9GZX3
N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase	B3GNT1	O43505
N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase, isoform B	GCNT2	Q06430
UDP-GlcNAc:betaGal beta-1,3-N-acetylglucosaminyltransferase 8	B3GNT8	Q7Z7M8