Bovine Metabolome Database: Showing metabocard for N-Acetyllactosamine (BMDB0001542)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:26 UTC

Update Date

2020-05-11 20:53:28 UTC

BMDB ID

BMDB0001542

Secondary Accession Numbers

BMDB01542

Metabolite Identification

Common Name

N-Acetyllactosamine

Description

N-Acetyllactosamine, also known as galb1-4glcnacb or lacnac, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyllactosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyllactosamine exists in all living organisms, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-D-Galactosyl-1,4-N-acetyl-D-glucosamine	ChEBI
Galb1-4glcnacb	ChEBI
Galbeta1-4glcnacbeta	ChEBI
LacNAc	ChEBI
N-Acetyl-beta-lactosamine	ChEBI
beta-D-Galactosyl-1,4-N-acetyl-beta-D-glucosamine	Kegg
b-D-Galactosyl-1,4-N-acetyl-D-glucosamine	Generator
Β-D-galactosyl-1,4-N-acetyl-D-glucosamine	Generator
N-Acetyl-b-lactosamine	Generator
N-Acetyl-β-lactosamine	Generator
b-D-Galactosyl-1,4-N-acetyl-b-D-glucosamine	Generator
Β-D-galactosyl-1,4-N-acetyl-β-D-glucosamine	Generator
beta-delta-Galactosyl-1,4-N-acetyl-beta-delta-glucosamine	HMDB
beta-delta-Galactosyl-1,4-N-acetyl-delta-glucosamine	HMDB
D-Galactopyranosyl	HMDB
delta-Galactopyranosyl	HMDB
N-Acetyl-lactosamine	HMDB
ACETYL lactosamine	HMDB

Chemical Formula

C₁₄H₂₅NO₁₁

Average Molecular Weight

383.3484

Monoisotopic Molecular Weight

383.142760647

IUPAC Name

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

Traditional Name

N-acetyllactosamine

CAS Registry Number

32181-59-2

SMILES

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

InChI Identifier

InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1

InChI Key

KFEUJDWYNGMDBV-LODBTCKLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-galactopyranosyl-(1->4)-N-acetyl-D-glucosamine (CHEBI:16153 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

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	-2.8	ALOGPS
logP	-5	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	35.66 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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uy3-5539000000-9001b4ffdf2686f61fdb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0a4i-3410139000-490a44b54a788af499ad	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0g4i-0294000000-eba3eabd1634e1f899d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-002r-0900000000-65d60bd6a084f5fb8a03	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0019-9800000000-5cfef19dd8c8707bef7a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00yi-0179000000-d117b299438bee3a1a40	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0592000000-db6f5abfab26c98d8af4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wbc-5960000000-915e1f050484eedb63d2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2492000000-1208b9128bdb1fd8688e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0h90-7984000000-2636a4af2a05389c39e5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-7910000000-dce1bda7d8788ebd90af	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-1169000000-37af2930ba0a18fdfe2d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bu3-9317000000-05676e3bb792b14a9ea9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9410000000-9f5dbeeb51b744740d72	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-0659000000-98f0c5a2f817d77728ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0951000000-f475151e03af91aeeac3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-9410000000-abd7ef88c6f0a3d44980	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Epidermis
Intestine
Spleen

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001542

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019860

KNApSAcK ID

Not Available

Chemspider ID

388404

KEGG Compound ID

C00611

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetyllactosamine

METLIN ID

4231

PubChem Compound

439271

PDB ID

Not Available

ChEBI ID

16153

References

Synthesis Reference

Dekany, Gyula; Agoston, Karoly; Bajza, Istvan; Boejstrup, Marie; Kroeger, Lars. Process for the large-scale preparation of N-acetyllactosamine, lactosamine, lactosamine salts and lactosamine-containing oligosaccharides. PCT Int. Appl. (2007), 44pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Beta-1,4-galactosyltransferase 1

General function:: Involved in alpha-tubulin binding
Specific function:: The Golgi complex form catalyzes the production of lactose in the lactating mammary gland and could also be responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:: B4GALT1
Uniprot ID:: P08037
Molecular weight:: 44843.0

Enzyme Details

2. Beta-1,4-galactosyltransferase 3

General function:: Involved in beta-N-acetylglucosaminylglycopeptide beta-
Specific function:: Responsible for the synthesis of complex-type N-linked oligosaccharides in many glycoproteins as well as the carbohydrate moieties of glycolipids.
Gene Name:: B4GALT3
Uniprot ID:: Q5EA87
Molecular weight:: 44371.0

Enzyme Details

3. Beta-galactoside alpha-2,6-sialyltransferase 2

General function:: Involved in beta-galactoside alpha-2,6-sialyltransferas
Specific function:: Transfers sialic acid from the donor of substrate CMP-sialic acid to galactose containing acceptor substrates. Has alpha-2,6-sialyltransferase activity toward oligosaccharides that have the Gal-beta-1,4-GlcNAc sequence at the non-reducing end of their carbohydrate groups, but it has weak or no activities toward glycoproteins and glycolipids.
Gene Name:: ST6GAL2
Uniprot ID:: A5D7T4
Molecular weight:: 55418.0

Showing metabocard for N-Acetyllactosamine (BMDB0001542)

Structure for BMDB0001542 (N-Acetyllactosamine)

Enzymes