Showing metabocard for Aspartylglycosamine (BMDB0000489)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:31:29 UTC
Update Date2020-05-11 20:52:45 UTC
BMDB IDBMDB0000489
Secondary Accession Numbers
  • BMDB00489
Metabolite Identification
Common NameAspartylglycosamine
DescriptionAspartylglycosamine, also known as AADG or N-adgp-asn, 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). Aspartylglycosamine, with regard to humans, has been linked to the inborn metabolic disorder aspartylglucosaminuria. Based on a literature review a significant number of articles have been published on Aspartylglycosamine.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Placenta
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000489
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
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 ReferencesNot Available