ChemFOnt: Showing chemical card for Glucosylgalactosyl hydroxylysine (CFc000000456)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:51 UTC

Chemfont ID

CFc000000456

Molecule Identification

Common Name

Glucosylgalactosyl hydroxylysine

Definition

Glucosylgalactosyl hydroxylysine is a Glycoside of hydroxylysine. Hydroxylation of lysine is an important post-translational modification of collagen, (PMID 10928217 ) a reaction catalyzed by the enzyme Lysyl hydroxylase (EC 1.14.11.4) forming hydroxylysine in collagens and other proteins with collagen-like amino acid sequences, by the hydroxylation of lysine residues in X-lys-gly sequences. The hydroxylysine residues formed in the lysyl hydroxylase reaction have 2 important functions: first, their hydroxy groups serve as sites of attachment for carbohydrate units, either the monosaccharide galactose or the disaccharide glucosylgalactose; and second, they are essential for the stability of the intermolecular collagen crosslinks. (OMIM 153454 ). Hydroxylysine-deficient skin collagen is manifested in Ehlers-Danlos syndrome, type VIA, A heritable disorder of connective tissue (PMID 5016372 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2alpha-Glucosylgalactosyl-O-hydroxylysine	HMDB
2-O-a-D-Glucopyranosyl-O-b-D-galactopyranosylhydroxylysine	HMDB
2-O-alpha-D-Glucopyranosyl-O-beta-D-galactopyranosylhydroxylysine	HMDB
2-O-alpha-delta-Glucopyranosyl-O-beta-delta-galactopyranosylhydroxylysine	HMDB
5-[O-a-D-Glucopyranosyl-(1->2)-b-D-galactopyranosyloxy]-L-lysine	HMDB
5-[O-alpha-D-Glucopyranosyl-(1->2)-beta-D-galactopyranosyloxy]-L-lysine	HMDB
5-[O-alpha-delta-Glucopyranosyl-(1->2)-beta-delta-galactopyranosyloxy]-L-lysine	HMDB
Glucopyranosylgalactopyranosylhydroxylysine	HMDB
Glucosido-galactosyl-hydroxylysine	HMDB
Glucosyl galactosyl-D-hydroxylysine	HMDB
Glucosyl galactosyl-delta-hydroxylysine	HMDB
Glucosylgalactosylhydroxylysine	HMDB
Hydroxylysine-galactose-glucose	HMDB
Hydroxylysine-glucose-galactose	HMDB
L-5-((2-O-alpha-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy)-lysine	HMDB
L-5-((2-O-alpha-delta-Glucopyranosyl-beta-delta-galactopyranosyl)oxy)-lysine	HMDB
1,2 alpha-Glucosylgalactosyl-O-hydroxylysine	HMDB
(2S)-2,6-Diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoate	HMDB

Chemical Formula

C₁₈H₃₄N₂O₁₃

Average Molecular Weight

486.4682

Monoisotopic Molecular Weight

486.206089184

IUPAC Name

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

Traditional Name

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

CAS Registry Number

32448-35-4

SMILES

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

InChI Identifier

InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1

InChI Key

UTIRJVJBKWSIOX-SRMFCGEKSA-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
Disaccharide
Glycosyl compound
O-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acid
Oxane
Amino acid or derivatives
Amino acid
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Primary amine
Primary alcohol
Primary aliphatic amine
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000585)

Excreta

Biofluid or Excreta

Urine (PMID: 5472370)

Cellular substructure

Cytoplasm (HMDB: HMDB0000585)
Cell membrane (HMDB: HMDB0000585)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000585)

Source

Endogenous

Endogenous (HMDB: HMDB0000585)

Animal

Animal (HMDB: HMDB0000585)

Exogenous

Food

Food (HMDB: HMDB0000585)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000585)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000585)

Lipid metabolism pathway (HMDB: HMDB0000585)

Biochemical process

Lipid transport (HMDB: HMDB0000585)

Role

Biological role

Energy source (HMDB: HMDB0000585)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	82.2 g/L	ALOGPS
logP	-3.6	ALOGPS
logP	-8	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	1.76	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	267.87 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	104 m³·mol⁻¹	ChemAxon
Polarizability	46.29 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000585

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022130

KNApSAcK ID

Not Available

Chemspider ID

109059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5567

PubChem Compound

122304

PDB ID

Not Available

ChEBI ID

89573

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Garza, Hector; Bennett, Nelson Jr.; Rodriguez, Gladys P. Improved rapid method for the isolation, purification and identification of collagen glycosides. Journal of Chromatography, A (1996), 732(2), 385-389.

Showing chemical card for Glucosylgalactosyl hydroxylysine (CFc000000456)

MOL for CFc000000456 (Glucosylgalactosyl hydroxylysine)

3D MOL for CFc000000456 (Glucosylgalactosyl hydroxylysine)

3D SDF for CFc000000456 (Glucosylgalactosyl hydroxylysine)

3D-SDF for CFc000000456 (Glucosylgalactosyl hydroxylysine)

PDB for CFc000000456 (Glucosylgalactosyl hydroxylysine)

3D PDB for CFc000000456 (Glucosylgalactosyl hydroxylysine)

SMILES for CFc000000456 (Glucosylgalactosyl hydroxylysine)

INCHI for CFc000000456 (Glucosylgalactosyl hydroxylysine)

Structure for CFc000000456 (Glucosylgalactosyl hydroxylysine)

3D Structure for CFc000000456 (Glucosylgalactosyl hydroxylysine)