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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-10-09 20:59:29 UTC
HMDB IDHMDB0000489
Secondary Accession Numbers
  • HMDB0001515
  • HMDB00489
  • HMDB01515
Metabolite Identification
Common NameAspartylglycosamine
DescriptionAspartylglycosamine, also known as n4-(beta-N-acetyl-D-glucosaminyl)-L-asparagine or 1-beta-aspartyl-N-acetyl-D-glucosaminylamine, is a member of the class of compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Aspartylglycosamine is soluble (in water) and a moderately acidic compound (based on its pKa). Aspartylglycosamine can be found primarily in urine, as well as in human spleen tissue. Within the cell, aspartylglycosamine is primarily located in the cytoplasm. Moreover, aspartylglycosamine is found to be associated with aspartylglucosaminuria, which is an inborn error of metabolism. Large amount of aspartylglycosamine appears in patients with aspartylglycosaminuria corresponding to decreased activity of aspartylglycosamine amido hydrolase.
Structure
Data?1582752134
Synonyms
ValueSource
1-beta-Aspartyl-N-acetyl-D-glucosaminylamineChEBI
2-Acetamido-1-(beta-L-aspartamido)-1,2-dideoxy-beta-D-glucoseChEBI
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamineChEBI
2-Acetamido-N-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamineChEBI
2-Acetamido-N(1)-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamineChEBI
AADGChEBI
beta-N-Acetylglucosaminyl-L-asparagineChEBI
N-AcetylglucosaminylasparagineChEBI
N4-(Acetyl-beta-D-glucosaminyl)asparagineChEBI
N4-(beta-N-Acetyl-D-glucosaminyl)-L-asparagineChEBI
1-b-Aspartyl-N-acetyl-D-glucosaminylamineGenerator
1-Β-aspartyl-N-acetyl-D-glucosaminylamineGenerator
2-Acetamido-1-(b-L-aspartamido)-1,2-dideoxy-b-D-glucoseGenerator
2-Acetamido-1-(β-L-aspartamido)-1,2-dideoxy-β-D-glucoseGenerator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-b-D-glucopyranosylamineGenerator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-β-D-glucopyranosylamineGenerator
2-Acetamido-N-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamineGenerator
2-Acetamido-N-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamineGenerator
2-Acetamido-N(1)-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamineGenerator
2-Acetamido-N(1)-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamineGenerator
b-N-Acetylglucosaminyl-L-asparagineGenerator
Β-N-acetylglucosaminyl-L-asparagineGenerator
N4-(Acetyl-b-D-glucosaminyl)asparagineGenerator
N4-(Acetyl-β-D-glucosaminyl)asparagineGenerator
N4-(b-N-Acetyl-D-glucosaminyl)-L-asparagineGenerator
N4-(Β-N-acetyl-D-glucosaminyl)-L-asparagineGenerator
(N-g-(2-Acetamido-2-deoxy-b-D-gluco-pyranosyl)-L-asparagineHMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-D-gluco-pyranosyl)-L-asparagineHMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-delta-gluco-pyranosyl)-L-asparagineHMDB
2-Acetamido-1-b-(L-aspartamido)-1,2-dideoxy-D-glucoseHMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-D-glucoseHMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-delta-glucoseHMDB
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-delta-glucopyranosylamineHMDB
4-N-2-Acetamido-2-deoxy-beta-D-glucopyranosyl-L-asparagineHMDB
4-N-2-Acetamido-2-deoxy-beta-delta-glucopyranosyl-L-asparagineHMDB
AcetylglucosaminylasparagineHMDB
AsparaginylglucosamineHMDB
AspartylglucosamineHMDB
AspartylglucosylamineHMDB
b-D-GlcNAc-1->n-asnHMDB
beta-D-GlcNAc-1->n-asnHMDB
beta-delta-GlcNAc-1->n-asnHMDB
H-Asn(glcnac-b-D)-OHHMDB
H-Asn(glcnac-beta-D)-OHHMDB
N(4)-(Acetyl-beta-D-glucosaminyl)asparagineHMDB
N(4)-(beta-N-Acetyl-D-glucosaminyl)-L-asparagineHMDB
N-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)L-asparagineHMDB
N-(2-(Acetylamino)-2-deoxy-beta-delta-glucopyranosyl)L-asparagineHMDB
N-(2-Acetylamino)-2-deoxy-beta-D-glucopyranosyl-L-asparagineHMDB
N-(2-Acetylamino)-2-deoxy-beta-delta-glucopyranosyl-L-asparagineHMDB
N(4)-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagineHMDB
N(4)-(2-Acetamido-2-deoxyglucopyranosyl)asparagineHMDB
N-ADGP-asnHMDB
N(4)-(b-N-Acetyl-D-glucosaminyl)-L-asparagineHMDB
N(4)-(Β-N-acetyl-D-glucosaminyl)-L-asparagineHMDB
AspartylglycosamineMeSH
Chemical FormulaC12H21N3O8
Average Molecular Weight335.3104
Monoisotopic Molecular Weight335.132864663
IUPAC Name(2S)-2-amino-3-{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}propanoic acid
Traditional Nameacetylglucosaminylasparagine
CAS Registry Number2776-93-4
SMILES
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1NC(=O)C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C12H21N3O8/c1-4(17)14-8-10(20)9(19)6(3-16)23-11(8)15-7(18)2-5(13)12(21)22/h5-6,8-11,16,19-20H,2-3,13H2,1H3,(H,14,17)(H,15,18)(H,21,22)/t5-,6+,8+,9+,10+,11+/m0/s1
InChI KeyYTTRPBWEMMPYSW-HRRFRDKFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlycosylamines
Alternative Parents
Substituents
  • Hexose monosaccharide
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Monosaccharide
  • Oxane
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Monocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Carbonyl group
  • Primary aliphatic amine
  • Alcohol
  • Organonitrogen compound
  • Primary amine
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility39.1 g/LALOGPS
logP-3.1ALOGPS
logP-6.8ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.58ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area191.44 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity72.02 m³·mol⁻¹ChemAxon
Polarizability31.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4i-9353000000-786f34e9af0ed644bf2dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ab9-7921338000-f4887b8c9c177fb6c177Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-0293000000-0e6afb70f83fecf33f5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-7690000000-d891eff61408c60fc0f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mx-5930000000-b5b03176088e9e4c1abcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-3589000000-878cfc8351ca28034926Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-4970000000-144a7c9cf2b6b1c0d0c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9500000000-d184dbc6f7857ff2cf4cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified87.680 (39.963-166.0153) umol/mmol creatinineAdult (>18 years old)BothAspartylglucosaminuria details
UrineDetected and Quantified70.383 (30.420-97.621) umol/mmol creatinineChildren (1-13 years old)BothAspartylglucosaminuria details
UrineDetected and Quantified0.6 (0.20-1.00) umol/mmol creatinineAdult (>18 years old)BothAspartylglucosaminuria
    • MetaGene: Metabol...
details
UrineDetected and Quantified175.0 (100.0-250.0) umol/mmol creatinineChildren (1-13 years old)BothAspartylglucosaminuria
    • MetaGene: Metabol...
details
Associated Disorders and Diseases
Disease References
Aspartylglucosaminuria
  1. Aula P, Raivio KO, Maury P: Variation of urinary excretion of aspartylglucosamine and associated clinical findings in aspartyglucosaminuria. J Inherit Metab Dis. 1980;3(4):159-62. [PubMed:6787338 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022071
KNApSAcK IDNot Available
Chemspider ID110370
KEGG Compound IDC04540
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5476
PubChem Compound123826
PDB IDNot Available
ChEBI ID17261
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000173
References
Synthesis ReferenceYamamoto, Akira; Miyashita, Chieko; Tsukamoto, Hisao. Amino sugars. II. Preparation of 2-acetamido-1-N-[L-a(and b)-aspartyl]-2-deoxy-b-D-glucosylamine and 2-acetamido-2-deoxy-N-(L-g-glutamyl)-b-D-glucosylamine. Chemical & Pharmaceutical Bulletin (1965), 13(9), 1041-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jalanko A, Tenhunen K, McKinney CE, LaMarca ME, Rapola J, Autti T, Joensuu R, Manninen T, Sipila I, Ikonen S, Riekkinen P Jr, Ginns EI, Peltonen L: Mice with an aspartylglucosaminuria mutation similar to humans replicate the pathophysiology in patients. Hum Mol Genet. 1998 Feb;7(2):265-72. [PubMed:9425233 ]
  2. Dunder U, Kaartinen V, Valtonen P, Vaananen E, Kosma VM, Heisterkamp N, Groffen J, Mononen I: Enzyme replacement therapy in a mouse model of aspartylglycosaminuria. FASEB J. 2000 Feb;14(2):361-7. [PubMed:10657992 ]
  3. Mononen I, Kaartinen V, Mononen T: Amniotic fluid glycoasparagines in fetal aspartylglycosaminuria. J Inherit Metab Dis. 1988;11(2):194-8. [PubMed:3139932 ]
  4. Haltia M, Palo J, Autio S: Aspartylglycosaminuria: a generalized storage disease. Morphological and histochemical studies. Acta Neuropathol. 1975;31(3):243-55. [PubMed:1138532 ]
  5. Mononen I, Kaartinen V, Mononen T: Laboratory detection of aspartylglycosaminuria. Scand J Clin Lab Invest Suppl. 1988;191:7-11. [PubMed:3247584 ]
  6. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [PubMed:8376520 ]
  7. Mononen T, Mononen I, Matilainen R, Airaksinen E: High prevalence of aspartylglycosaminuria among school-age children in eastern Finland. Hum Genet. 1991 Jul;87(3):266-8. [PubMed:1864600 ]
  8. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]