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MetaCyc Compound: N-acetyl-β-D-galactosamine

Synonyms: β-GalNAc

Superclasses: all carbohydratesa carbohydratea glycana sugara monosaccharidean amino sugara hexosaminean N-acetyl-D-hexosaminean N-acetyl-beta-D-hexosamine
all carbohydratesa carbohydratea glycana sugara monosaccharidean amino sugara hexosaminean N-acetyl-D-hexosamineN-acetyl-D-galactosamine

Chemical Formula: C8H15NO6

Molecular Weight: 221.21 Daltons

Monoisotopic Molecular Weight: 221.0899372193 Daltons

<i>N</i>-acetyl-β-D-galactosamine compound structure

Glycan icon:

<i>N</i>-acetyl-β-D-galactosamine compound structure

SMILES: CC(NC1(C(C(C(OC1O)CO)O)O))=O

InChI: InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6+,7-,8-/m1/s1

InChIKey: InChIKey=OVRNDRQMDRJTHS-JAJWTYFOSA-N

Unification Links: ChEBI:28497, ChemSpider:389452, HMDB:HMDB00853, KEGG:C05021, MetaboLights:MTBLC28497, PubChem:440552

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -58.563206Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

N-acetyl-D-galactosamine degradation :
N-acetyl-D-galactosamine + ATP → N-acetyl-D-galactosamine 6-phosphate + ADP + H+

Reactions known to produce the compound:

chondroitin sulfate degradation (metazoa) :
chondroitin sulfate → N-acetyl-β-D-galactosamine + D-glucopyranuronate

dermatan sulfate degradation (metazoa) :
dermatan sulfate → N-acetyl-β-D-galactosamine + α-L-iduronate + sulfate

Not in pathways:
4-deoxy-β-D-gluc-4-enuronosyl-2-sulfate-(1,3)-N-acetyl-β-D-galactosamine + H2O → 5-dehydro-4-deoxy-2-O-sulfo-D-glucuronate + N-acetyl-β-D-galactosamine

Not in pathways:
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol

chondroitin sulfate degradation I (bacterial) , dermatan sulfate degradation I (bacterial) :
4-deoxy-β-D-gluc-4-enuronosyl-(1,3)-N-acetyl-D-galactosamine + H2O → 4-deoxy-L-threo-hex-4-enopyranuronate + N-acetyl-D-galactosamine

Not in pathways:
4-deoxy-β-D-gluc-4-enuronosyl-(1,4)-N-acetyl-D-galactosamine + H2O → 4-deoxy-L-threo-hex-4-enopyranuronate + N-acetyl-D-galactosamine
an N-acetyl-β-D-galactosaminide + H2O → N-acetyl-D-galactosamine + a non glycosylated sugar acceptor

Not in pathways:
a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + 2 H2O → a protopanaxatriol-type ginsenoside with no glycosidic modification at position 6 + a monosaccharide + D-glucopyranose
a protopanaxadiol-type ginsenoside with two glycosyl residues at position 20 + H2O → a protopanaxadiol-type ginsenoside with a single glucosyl residue at position 20 + a monosaccharide

Not in pathways:
a thioglucoside + H2O → a sugar + a thiol
a sugar phosphate + H2O → a sugar + phosphate
glycosyl-N-acylsphingosine + H2O → a ceramide + a sugar

In Reactions of unknown directionality:

Not in pathways:
an N-acetyl-D-hexosamine + ATP = an N-acetyl-α-D-hexosamine 1-phosphate + ADP + H+

Not in pathways:
a protopanaxatriol-type ginsenoside with two glycosyl residues at position 6 + H2O = a protopanaxatriol-type ginsenoside with a single glucosyl at position 6 + a monosaccharide

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + N-acetyl-D-galactosamine[periplasm]N-acetyl-D-galactosamine 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine,
a monosaccharide[extracellular space] + ATP + H2O ↔ a monosaccharide[cytosol] + ADP + phosphate,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Credits:
Created 04-Aug-2010 by Caspi R, SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Thu Feb 11, 2016, biocyc13.