Aspartylglycosamine (CHEM021831)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:34 UTC
Update Date2026-04-03 00:01:40 UTC
Accession NumberCHEM021831
Identification
Common NameAspartylglycosamine
ClassSmall Molecule
DescriptionAn N(4)-glycosyl-L-asparagine having (beta-N-acetyl-D-glucosaminyl as the glycosyl component.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass335.310 g/mol
Monoisotopic Mass335.133 g/mol
CAS Registry Number2776-93-4
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
SMILESCC(=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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-0149000000-eefcb4b7d49cc9736455Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2692000000-35c3172ea336db4c9e96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9320000000-1c2091e6c22b83332897Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-7900e8ac31b6a1fd733aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bi-4439000000-75f483b5d93e062a4614Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-3910000000-7e17eb196465686b849eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000489
FooDB IDFDB022071
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5476
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID110370
ChEBI ID17261
PubChem Compound ID123826
Kegg Compound IDC04540
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yamamoto, 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.
2. 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.
3. 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.
4. Mononen I, Kaartinen V, Mononen T: Amniotic fluid glycoasparagines in fetal aspartylglycosaminuria. J Inherit Metab Dis. 1988;11(2):194-8.
5. Haltia M, Palo J, Autio S: Aspartylglycosaminuria: a generalized storage disease. Morphological and histochemical studies. Acta Neuropathol. 1975;31(3):243-55.
6. Mononen I, Kaartinen V, Mononen T: Laboratory detection of aspartylglycosaminuria. Scand J Clin Lab Invest Suppl. 1988;191:7-11.
7. 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.
8. 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.
9. 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.