Bovine Metabolome Database: Showing metabocard for Lacto-N-tetraose (BMDB0006566)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:23:27 UTC

Update Date

2020-04-22 15:17:53 UTC

BMDB ID

BMDB0006566

Secondary Accession Numbers

BMDB06566

Metabolite Identification

Common Name

Lacto-N-tetraose

Description

Lacto-N-tetraose, also known as gal-glcnac-gal-GLC or LNT, belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Based on a literature review a significant number of articles have been published on Lacto-N-tetraose.

Structure

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

Synonyms

Value	Source
beta-D-Gal-(1->3)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-beta-D-GLC	ChEBI
beta-D-Galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucose	ChEBI
Galb1-3glcnacb1-3galb1-4GLCB	ChEBI
Galbeta1-3glcnacbeta1-3galbeta1-4glcbeta	ChEBI
WURCS=2.0/3,4,3/[a2122h-1b_1-5][a2112h-1b_1-5][a2122h-1b_1-5_2*ncc/3=o]/1-2-3-2/a4-b1_b3-c1_c3-D1	ChEBI
b-D-Gal-(1->3)-b-D-glcnac-(1->3)-b-D-gal-(1->4)-b-D-GLC	Generator
Β-D-gal-(1->3)-β-D-glcnac-(1->3)-β-D-gal-(1->4)-β-D-GLC	Generator
b-D-Galactosyl-(1->3)-N-acetyl-b-D-glucosaminyl-(1->3)-b-D-galactosyl-(1->4)-b-D-glucose	Generator
Β-D-galactosyl-(1->3)-N-acetyl-β-D-glucosaminyl-(1->3)-β-D-galactosyl-(1->4)-β-D-glucose	Generator
Gal(beta1->3)glcnac(beta1->3)gal(beta1->4)GLC	HMDB
Gal(β1→3)glcnac(β1→3)gal(β1→4)GLC	HMDB
Gal-glcnac-gal-GLC	HMDB
Galp(beta1->3)glcpnac(beta1->3)galp(beta1->4)GLCP	HMDB
Galp(β1→3)glcpnac(β1→3)galp(β1→4)GLCP	HMDB
LNT	HMDB
O-beta-D-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-D-glucose	HMDB
O-beta-D-Galactopyranosyl-(1->3)-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose	HMDB
O-Β-D-galactopyranosyl-(1→3)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-D-glucose	HMDB
O-Β-D-galactopyranosyl-(1→3)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose	HMDB
beta-D-Gal-(1->3)-beta-D-glcnac-(1->3)-beta-D-gal-(1->4)-D-GLC	HMDB
beta-D-Galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucose	HMDB
Β-D-gal-(1→3)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-D-GLC	HMDB
Β-D-gal-(1→3)-β-D-glcnac-(1→3)-β-D-gal-(1→4)-β-D-GLC	HMDB
Β-D-galactosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-D-glucose	HMDB
Β-D-galactosyl-(1→3)-N-acetyl-β-D-glucosaminyl-(1→3)-β-D-galactosyl-(1→4)-β-D-glucose	HMDB
Galp-glcpnac-galp-GLCP	HMDB
beta-D-Galactopyranosyl-(1->3)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-D-glucopyranose	HMDB
beta-D-Galactopyranosyl-(1->3)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranose	HMDB
beta-D-Galp-(1->3)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-D-GLCP	HMDB
beta-D-Galp-(1->3)-beta-D-glcpnac-(1->3)-beta-D-galp-(1->4)-beta-D-GLCP	HMDB
Β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-D-glucopyranose	HMDB
Β-D-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranose	HMDB
Β-D-galp-(1→3)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-D-GLCP	HMDB
Β-D-galp-(1→3)-β-D-glcpnac-(1→3)-β-D-galp-(1→4)-β-D-GLCP	HMDB
b-D-Galp-(1->3)-b-D-glcpnac-(1->3)-b-D-galp-(1->4)-b-D-GLCP	HMDB
Β-D-galp-(1->3)-β-D-glcpnac-(1->3)-β-D-galp-(1->4)-β-D-GLCP	HMDB
Lacto-N-tetraose	HMDB

Chemical Formula

C₂₆H₄₅NO₂₁

Average Molecular Weight

707.632

Monoisotopic Molecular Weight

707.248407473

IUPAC Name

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

Traditional Name

CAS Registry Number

14116-68-8

SMILES

CC(=O)N[C@H]1[C@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](O)O[C@@H]3CO)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H45NO21/c1-6(32)27-11-21(47-25-18(39)15(36)12(33)7(2-28)44-25)13(34)8(3-29)43-24(11)48-22-14(35)9(4-30)45-26(19(22)40)46-20-10(5-31)42-23(41)17(38)16(20)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32)/t7-,8-,9-,10-,11-,12+,13-,14+,15+,16-,17-,18-,19-,20-,21-,22+,23-,24+,25+,26+/m1/s1

InChI Key

AXQLFFDZXPOFPO-UNTPKZLMSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Oligosaccharides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-Gal-(1->3)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc (CHEBI:53481 )

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	-2.6	ALOGPS
logP	-8.5	ChemAxon
logS	-0.51	ALOGPS
pKa (Strongest Acidic)	11.16	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	356.7 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	144.26 m³·mol⁻¹	ChemAxon
Polarizability	66.21 Å³	ChemAxon
Number of Rings	4	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_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0001066900-89a9b0290f4b568a8e80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054p-0203159300-3bef2f7d7c5da99c109c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ss-9511067000-465c9e1255258dcdb8a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1010009600-75ed1df9cc5a4ad1d48f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-6202009200-695014bdccbea236ee6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100221000-31c7145387c493f5339e	View in MoNA
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

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

HMDB0006566

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB019386

KNApSAcK ID

Not Available

Chemspider ID

4443269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lacto-N-tetraose

METLIN ID

Not Available

PubChem Compound

5279514

PDB ID

Not Available

ChEBI ID

53481

References

Synthesis Reference

Yamashita, Katsuko; Tachibana, Yoko; Kobata, Akira. Oligosaccharides of human milk: structures of three lacto-N-hexaose derivatives with H-haptenic structure. Archives of Biochemistry and Biophysics (1977), 182(2), 546-55.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Lacto-N-tetraose (BMDB0006566)

Structure for BMDB0006566 (Lacto-N-tetraose)