Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:03 UTC
HMDB IDHMDB00212
Secondary Accession Numbers
  • HMDB00835
Metabolite Identification
Common NameN-Acetylgalactosamine
DescriptionAcetylgalactosamine is an important constituent of brain heteropolysaccharides (glycoproteins). The concentration of the N-acetylgalactosamine-containing glycoproteins in the 3-year-old cerebral gray matter from human brain is 7-15 times greater than in 8-year old tissue and 15-30 times greater than in 72-year-old tissue. (PMID 1207868 ). Acetylgalactosamine patterns of the composition of the soluble glycoproteins from endoscopic mucosal biopsies tends to decrease in the tumor area in cancer of the stomach (compared with the antrum and corpus of control stomachs). (PMID: 7151277 ). Chondroitin 6-sulfotransferase (C6ST) is the key enzyme in the biosynthesis of chondroitin 6-sulfate, a glycosaminoglycan implicated in chondrogenesis, neoplasia, atherosclerosis, and other processes. C6ST catalyzes the transfer of sulfate from 3'-phosphoadenosine 5'-phosphosulfate to carbon 6 of the N- Acetylgalactosamine residues of chondroitin. (PMID: 9639683 ).
Structure
Thumb
Synonyms
  1. 2-Acetamido-2-deoxy-a-D-allopyranose
  2. 2-Acetamido-2-deoxy-a-D-glucopyranose
  3. 2-Acetamido-2-deoxy-alpha-D-allopyranose
  4. 2-Acetamido-2-deoxy-alpha-D-glucopyranose
  5. 2-Acetamido-2-deoxy-alpha-delta-allopyranose
  6. 2-Acetamido-2-deoxy-alpha-delta-glucopyranose
  7. 2-Acetamido-2-deoxy-b-D-glucopyranose
  8. 2-Acetamido-2-deoxy-beta-D-glucopyranose
  9. 2-Acetamido-2-deoxy-beta-delta-glucopyranose
  10. 2-Acetamido-2-desoxy-b-D-talofuranose
  11. 2-Acetamido-2-desoxy-beta-D-talofuranose
  12. 2-Acetamido-2-desoxy-beta-delta-talofuranose
  13. 2-Acetamino-2-deoxy-a-D-glucose
  14. 2-Acetamino-2-deoxy-alpha-D-glucose
  15. 2-Acetamino-2-deoxy-alpha-delta-glucose
  16. 2-Acetamino-2-desoxy-a-D-glucopyranose
  17. 2-Acetamino-2-desoxy-alpha-D-glucopyranose
  18. 2-Acetamino-2-desoxy-alpha-delta-glucopyranose
  19. 2-Acetamino-2-desoxy-D-galaktose
  20. 2-Acetamino-2-desoxy-D-glucose
  21. 2-Acetamino-2-desoxy-delta-galaktose
  22. 2-Acetamino-2-desoxy-delta-glucose
  23. 2-Acetylamino-2-deoxy-a-D-galactopyranose
  24. 2-Acetylamino-2-deoxy-a-D-glucopyranose
  25. 2-Acetylamino-2-deoxy-a-D-mannopyranose
  26. 2-Acetylamino-2-deoxy-alpha-D-galactopyranose
  27. 2-Acetylamino-2-deoxy-alpha-D-glucopyranose
  28. 2-Acetylamino-2-deoxy-alpha-D-mannopyranose
  29. 2-Acetylamino-2-deoxy-alpha-delta-galactopyranose
  30. 2-Acetylamino-2-deoxy-alpha-delta-glucopyranose
  31. 2-Acetylamino-2-deoxy-alpha-delta-mannopyranose
  32. 2-Acetylamino-2-deoxy-b-D-allopyranose
  33. 2-Acetylamino-2-deoxy-b-D-altropyranose
  34. 2-Acetylamino-2-deoxy-b-D-galactopyranose
  35. 2-Acetylamino-2-deoxy-b-D-glucopyranose
  36. 2-Acetylamino-2-deoxy-b-D-mannopyranose
  37. 2-Acetylamino-2-deoxy-beta-D-allopyranose
  38. 2-Acetylamino-2-deoxy-beta-D-altropyranose
  39. 2-Acetylamino-2-deoxy-beta-D-galactopyranose
  40. 2-Acetylamino-2-deoxy-beta-D-glucopyranose
  41. 2-Acetylamino-2-deoxy-beta-D-mannopyranose
  42. 2-Acetylamino-2-deoxy-beta-delta-allopyranose
  43. 2-Acetylamino-2-deoxy-beta-delta-altropyranose
  44. 2-Acetylamino-2-deoxy-beta-delta-galactopyranose
  45. 2-Acetylamino-2-deoxy-beta-delta-glucopyranose
  46. 2-Acetylamino-2-deoxy-beta-delta-mannopyranose
  47. 2-Acetylamino-2-desoxy-a-D-galaktose
  48. 2-Acetylamino-2-desoxy-a-D-mannose
  49. 2-Acetylamino-2-desoxy-alpha-D-galaktose
  50. 2-Acetylamino-2-desoxy-alpha-D-mannose
  51. 2-Acetylamino-2-desoxy-alpha-delta-galaktose
  52. 2-Acetylamino-2-desoxy-alpha-delta-mannose
  53. 2-Acetylamino-2-desoxy-b-D-galaktose
  54. 2-Acetylamino-2-desoxy-b-D-mannose
  55. 2-Acetylamino-2-desoxy-beta-D-galaktose
  56. 2-Acetylamino-2-desoxy-beta-D-mannose
  57. 2-Acetylamino-2-desoxy-beta-delta-galaktose
  58. 2-Acetylamino-2-desoxy-beta-delta-mannose
  59. 2-Acetylamino-2-desoxy-D-mannose
  60. 2-Acetylamino-2-desoxy-delta-mannose
  61. 2-Acetylamino-2-desoxy-DL-glucopyranose
  62. 2-Acetylamino-a-D-2-deoxy-galactopyranose
  63. 2-Acetylamino-a-D-2-deoxy-glucopyranose
  64. 2-Acetylamino-a-D-2-deoxy-glucose
  65. 2-Acetylamino-a-D-2-deoxy-mannopyranose
  66. 2-Acetylamino-alpha-D-2-deoxy-galactopyranose
  67. 2-Acetylamino-alpha-D-2-deoxy-glucopyranose
  68. 2-Acetylamino-alpha-D-2-deoxy-glucose
  69. 2-Acetylamino-alpha-D-2-deoxy-mannopyranose
  70. 2-Acetylamino-alpha-delta-2-deoxy-galactopyranose
  71. 2-Acetylamino-alpha-delta-2-deoxy-glucopyranose
  72. 2-Acetylamino-alpha-delta-2-deoxy-glucose
  73. 2-Acetylamino-alpha-delta-2-deoxy-mannopyranose
  74. 2-Acetylamino-b-D-2-deoxy-galactopyranose
  75. 2-Acetylamino-b-D-2-deoxy-glucopyranose
  76. 2-Acetylamino-b-D-2-deoxy-mannopyranose
  77. 2-Acetylamino-beta-D-2-deoxy-galactopyranose
  78. 2-Acetylamino-beta-D-2-deoxy-glucopyranose
  79. 2-Acetylamino-beta-D-2-deoxy-mannopyranose
  80. 2-Acetylamino-beta-delta-2-deoxy-galactopyranose
  81. 2-Acetylamino-beta-delta-2-deoxy-glucopyranose
  82. 2-Acetylamino-beta-delta-2-deoxy-mannopyranose
  83. 2-Acetylamino-D-2-deoxy-galactose
  84. 2-Acetylamino-D-2-deoxy-glucose
  85. 2-Acetylamino-D-2-deoxy-gulose
  86. 2-Acetylamino-D-2-deoxy-idose
  87. 2-Acetylamino-D-2-deoxy-mannose
  88. 2-Acetylamino-D-2-deoxy-talose
  89. 2-Acetylamino-delta-2-deoxy-galactose
  90. 2-Acetylamino-delta-2-deoxy-glucose
  91. 2-Acetylamino-delta-2-deoxy-gulose
  92. 2-Acetylamino-delta-2-deoxy-idose
  93. 2-Acetylamino-delta-2-deoxy-mannose
  94. 2-Acetylamino-delta-2-deoxy-talose
  95. 2-Acetylamino-L-2-deoxy-galactose
  96. 2-Acetylamino-L-2-deoxy-mannose
  97. a-2-Acetamido-2-deoxy-D-galactose
  98. alpha-2-Acetamido-2-deoxy-D-galactose
  99. alpha-2-Acetamido-2-deoxy-delta-galactose
  100. GalNAc
  101. N-(2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide
  102. N-Acetyl-a-D-glucosamine
  103. N-Acetyl-alpha-D-glucosamine
  104. N-Acetyl-alpha-delta-glucosamine
  105. N-Acetyl-D-allosamine
  106. N-Acetyl-D-galactosamine
  107. N-Acetyl-delta-allosamine
  108. N-Acetyl-delta-galactosamine
  109. N-Acetylgalactosamin
  110. N-Acetylgalactosamine
  111. N-Acetylglucosamin
  112. N-Acetylgluosamin
  113. N-Acetylmannosamin
Chemical FormulaC8H15NO6
Average Molecular Weight221.2078
Monoisotopic Molecular Weight221.089937217
IUPAC NameN-[(2S,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Traditional IUPAC NameN-[(2S,3R,4R,5R,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
CAS Registry Number1811-31-0
SMILES
CC(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@H](O)[C@@H]1O
InChI Identifier
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
InChI KeyOVRNDRQMDRJTHS-CBQIKETKSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Amino Sugars
  • Amino sugars(KEGG)
  • Carbohydrates and Carbohydrate Conjugates
  • N-acetylglucosamine(ChEBI)
Substituents
  • 1,2 Diol
  • Carboxamide Group
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
  • Component of Globoside metabolism
  • Component of Glutamate metabolism
  • Component of Keratan sulfate biosynthesis
  • Component of N-Glycan biosynthesis
  • Component of O-Glycan biosynthesis
ApplicationNot Available
Cellular locations
  • Lysosome
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility254 g/LALOGPS
logP-2.6ALOGPS
logP-3.2ChemAxon
logS0.06ALOGPS
pKa (strongest acidic)11.6ChemAxon
pKa (strongest basic)-0.78ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count5ChemAxon
polar surface area119.25ChemAxon
rotatable bond count2ChemAxon
refractivity47.02ChemAxon
polarizability20.84ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Lysosome
  • Golgi apparatus
Biofluid LocationsNot Available
Tissue Location
  • Adipose Tissue
  • Brain
  • Epidermis
  • Intestine
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021906
KNApSAcK IDNot Available
Chemspider ID76020
KEGG Compound IDC01074
BioCyc IDN-ACETYL-D-GLUCOSAMINE
BiGG ID36880
Wikipedia LinkN-Acetylgalactosamine
NuGOwiki LinkHMDB00212
Metagene LinkHMDB00212
METLIN ID5222
PubChem Compound84265
PDB IDA2G
ChEBI ID40356
References
Synthesis ReferenceCardini, C. E.; Leloir, Luis F. Enzymic formation of acetylgalactosamine. Journal of Biological Chemistry (1957), 225 317-24.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mazany KD, Peng T, Watson CE, Tabas I, Williams KJ: Human chondroitin 6-sulfotransferase: cloning, gene structure, and chromosomal localization. Biochim Biophys Acta. 1998 Jul 1;1407(1):92-7. Pubmed: 9639683
  2. Zhang Y, Iwasaki H, Wang H, Kudo T, Kalka TB, Hennet T, Kubota T, Cheng L, Inaba N, Gotoh M, Togayachi A, Guo J, Hisatomi H, Nakajima K, Nishihara S, Nakamura M, Marth JD, Narimatsu H: Cloning and characterization of a new human UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase, designated pp-GalNAc-T13, that is specifically expressed in neurons and synthesizes GalNAc alpha-serine/threonine antigen. J Biol Chem. 2003 Jan 3;278(1):573-84. Epub 2002 Oct 28. Pubmed: 12407114
  3. White T, Bennett EP, Takio K, Sorensen T, Bonding N, Clausen H: Purification and cDNA cloning of a human UDP-N-acetyl-alpha-D-galactosamine:polypeptide N-acetylgalactosaminyltransferase. J Biol Chem. 1995 Oct 13;270(41):24156-65. Pubmed: 7592619
  4. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  5. Nakagawa F, Schulte BA, Spicer SS: Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man. Cell Tissue Res. 1986;245(3):579-89. Pubmed: 3757018
  6. Kamakura K, Kaida K, Kusunoki S, Miyamoto N, Masaki T, Nakamura R, Motoyoshi K, Fukuda J: Harmful effects of anti-GalNAc-GD1a antibodies and TNF-alpha on rat dorsal root ganglia. J Peripher Nerv Syst. 2005 Jun;10(2):190-201. Pubmed: 15958130
  7. Petri WA Jr, Chaudhry O, Haque R, Houpt E: Adherence-blocking vaccine for amebiasis. Arch Med Res. 2006 Feb;37(2):288-91. Pubmed: 16380334
  8. Petry K, Greinix HT, Nudelman E, Eisen H, Hakomori S, Levy HL, Reichardt JK: Characterization of a novel biochemical abnormality in galactosemia: deficiency of glycolipids containing galactose or N-acetylgalactosamine and accumulation of precursors in brain and lymphocytes. Biochem Med Metab Biol. 1991 Aug;46(1):93-104. Pubmed: 1931160
  9. Kaida K, Kusunoki S, Kamakura K, Motoyoshi K, Kanazawa I: GalNAc-GD1a in human peripheral nerve: target sites of anti-ganglioside antibody. Neurology. 2003 Aug 26;61(4):465-70. Pubmed: 12939418
  10. Gupta D, Sabesan S, Brewer CF: Selective inhibition of N-acetylglucosamine and galactose-specific lectins including the 14-kDa vertebrate lectin by novel synthetic biantennary oligosaccharides. Eur J Biochem. 1993 Sep 15;216(3):789-97. Pubmed: 8404897
  11. Sutherlin ME, Nishimori I, Caffrey T, Bennett EP, Hassan H, Mandel U, Mack D, Iwamura T, Clausen H, Hollingsworth MA: Expression of three UDP-N-acetyl-alpha-D-galactosamine:polypeptide GalNAc N-acetylgalactosaminyltransferases in adenocarcinoma cell lines. Cancer Res. 1997 Nov 1;57(21):4744-8. Pubmed: 9354435
  12. Kariniemi AL, Virtanen I: Dolichos biflorus agglutinin (DBA) reveals a similar basal cell differentiation in normal and psoriatic epidermis. Histochemistry. 1989;93(2):129-32. Pubmed: 2482277
  13. Yuki N: Infectious origins of, and molecular mimicry in, Guillain-Barre and Fisher syndromes. Lancet Infect Dis. 2001 Aug;1(1):29-37. Pubmed: 11871407
  14. Tao X, Gao G, Zhang HZ, Zhu DX, Boersma A, Lamblin G, Han KK: Isolation and characterization of human urinary colony-stimulating factor. Biol Chem Hoppe Seyler. 1987 Mar;368(3):187-94. Pubmed: 3496105
  15. Hiruma T, Togayachi A, Okamura K, Sato T, Kikuchi N, Kwon YD, Nakamura A, Fujimura K, Gotoh M, Tachibana K, Ishizuka Y, Noce T, Nakanishi H, Narimatsu H: A novel human beta1,3-N-acetylgalactosaminyltransferase that synthesizes a unique carbohydrate structure, GalNAcbeta1-3GlcNAc. J Biol Chem. 2004 Apr 2;279(14):14087-95. Epub 2004 Jan 14. Pubmed: 14724282
  16. Chikakiyo H, Kunishige M, Yoshino H, Asano A, Sumitomo Y, Endo I, Matsumoto T, Mitsui T: Delayed motor and sensory neuropathy in a patient with brainstem encephalitis. J Neurol Sci. 2005 Jul 15;234(1-2):105-8. Pubmed: 15936038
  17. Roelen HC, Bijsterbosch MK, Bakkeren HF, van Berkel TJ, Kempen HJ, Buytenhek M, van der Marel GA, van Boom JH: Water-soluble cholesteryl-containing phosphorothioate monogalactosides: synthesis, properties, and use in lowering blood cholesterol by directing plasma lipoproteins to the liver. J Med Chem. 1991 Mar;34(3):1036-42. Pubmed: 2002447
  18. Smith PL, Bousfield GR, Kumar S, Fiete D, Baenziger JU: Equine lutropin and chorionic gonadotropin bear oligosaccharides terminating with SO4-4-GalNAc and Sia alpha 2,3Gal, respectively. J Biol Chem. 1993 Jan 15;268(2):795-802. Pubmed: 8419356
  19. Szkudlinski MW, Thotakura NR, Tropea JE, Grossmann M, Weintraub BD: Asparagine-linked oligosaccharide structures determine clearance and organ distribution of pituitary and recombinant thyrotropin. Endocrinology. 1995 Aug;136(8):3325-30. Pubmed: 7628367
  20. Taguchi K, Ren J, Utsunomiya I, Aoyagi H, Fujita N, Ariga T, Miyatake T, Yoshino H: Neurophysiological and immunohistochemical studies on Guillain-Barre syndrome with IgG anti-GalNAc-GD1a antibodies-effects on neuromuscular transmission. J Neurol Sci. 2004 Oct 15;225(1-2):91-8. Pubmed: 15465091
  21. Hoyte K, Kang C, Martin PT: Definition of pre- and postsynaptic forms of the CT carbohydrate antigen at the neuromuscular junction: ubiquitous expression of the CT antigens and the CT GalNAc transferase in mouse tissues. Brain Res Mol Brain Res. 2002 Dec 30;109(1-2):146-60. Pubmed: 12531524
  22. Brunngraber EG, Brown BD, Aro A: Distribution and age-dependent concentration in brain tissue of glycoproteins containing N-acetylgalactosamine. Neurobiology. 1975 Dec;5(6):339-46. Pubmed: 1207868
  23. Maury CP: Carbohydrate patterns of endoscopic mucosal biopsies in cancer of the stomach and chronic gastritis. Clin Chim Acta. 1982 Dec 9;126(2):155-9. Pubmed: 7151277
  24. Pastuszak I, Drake R, Elbein AD. Kidney N-acetylgalactosamine (GalNAc)-1-phosphate kinase, a new pathway of GalNAc activation. J Biol Chem. 1996 Aug 23;271(34):20776-82.

Enzymes

Gene Name:
GALK2
Uniprot ID:
Q01415
Gene Name:
GALNS
Uniprot ID:
P34059
Gene Name:
HYAL1
Uniprot ID:
Q12794
Gene Name:
SPAM1
Uniprot ID:
P38567
Gene Name:
HYAL2
Uniprot ID:
Q12891