Bovine Metabolome Database: Showing metabocard for Aspartylglycosamine (BMDB0000489)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:29 UTC

Update Date

2020-05-11 20:52:45 UTC

BMDB ID

BMDB0000489

Secondary Accession Numbers

BMDB00489

Metabolite Identification

Common Name

Aspartylglycosamine

Description

Aspartylglycosamine, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-beta-Aspartyl-N-acetyl-D-glucosaminylamine	ChEBI
2-Acetamido-1-(beta-L-aspartamido)-1,2-dideoxy-beta-D-glucose	ChEBI
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-D-glucopyranosylamine	ChEBI
2-Acetamido-N-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine	ChEBI
2-Acetamido-N(1)-L-beta-aspartyl-2-deoxy-beta-D-glucopyranosylamine	ChEBI
AADG	ChEBI
beta-N-Acetylglucosaminyl-L-asparagine	ChEBI
N-Acetylglucosaminylasparagine	ChEBI
N4-(Acetyl-beta-D-glucosaminyl)asparagine	ChEBI
N4-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine	ChEBI
1-b-Aspartyl-N-acetyl-D-glucosaminylamine	Generator
1-Β-aspartyl-N-acetyl-D-glucosaminylamine	Generator
2-Acetamido-1-(b-L-aspartamido)-1,2-dideoxy-b-D-glucose	Generator
2-Acetamido-1-(β-L-aspartamido)-1,2-dideoxy-β-D-glucose	Generator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine	Generator
2-Acetamido-N-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-N-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine	Generator
2-Acetamido-N(1)-L-b-aspartyl-2-deoxy-b-D-glucopyranosylamine	Generator
2-Acetamido-N(1)-L-β-aspartyl-2-deoxy-β-D-glucopyranosylamine	Generator
b-N-Acetylglucosaminyl-L-asparagine	Generator
Β-N-acetylglucosaminyl-L-asparagine	Generator
N4-(Acetyl-b-D-glucosaminyl)asparagine	Generator
N4-(Acetyl-β-D-glucosaminyl)asparagine	Generator
N4-(b-N-Acetyl-D-glucosaminyl)-L-asparagine	Generator
N4-(Β-N-acetyl-D-glucosaminyl)-L-asparagine	Generator
(N-g-(2-Acetamido-2-deoxy-b-D-gluco-pyranosyl)-L-asparagine	HMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-D-gluco-pyranosyl)-L-asparagine	HMDB
(N-gamma-(2-Acetamido-2-deoxy-beta-delta-gluco-pyranosyl)-L-asparagine	HMDB
2-Acetamido-1-b-(L-aspartamido)-1,2-dideoxy-D-glucose	HMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-D-glucose	HMDB
2-Acetamido-1-beta-(L-aspartamido)-1,2-dideoxy-delta-glucose	HMDB
2-Acetamido-1-N-(4'-L-aspartyl)-2-deoxy-beta-delta-glucopyranosylamine	HMDB
4-N-2-Acetamido-2-deoxy-beta-D-glucopyranosyl-L-asparagine	HMDB
4-N-2-Acetamido-2-deoxy-beta-delta-glucopyranosyl-L-asparagine	HMDB
Acetylglucosaminylasparagine	HMDB
Asparaginylglucosamine	HMDB
Aspartylglucosamine	HMDB
Aspartylglucosylamine	HMDB
b-D-GlcNAc-1->n-asn	HMDB
beta-D-GlcNAc-1->n-asn	HMDB
beta-delta-GlcNAc-1->n-asn	HMDB
H-Asn(glcnac-b-D)-OH	HMDB
H-Asn(glcnac-beta-D)-OH	HMDB
N(4)-(Acetyl-beta-D-glucosaminyl)asparagine	HMDB
N(4)-(beta-N-Acetyl-D-glucosaminyl)-L-asparagine	HMDB
N-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)L-asparagine	HMDB
N-(2-(Acetylamino)-2-deoxy-beta-delta-glucopyranosyl)L-asparagine	HMDB
N-(2-Acetylamino)-2-deoxy-beta-D-glucopyranosyl-L-asparagine	HMDB
N-(2-Acetylamino)-2-deoxy-beta-delta-glucopyranosyl-L-asparagine	HMDB
N(4)-(2-Acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine	HMDB
N(4)-(2-Acetamido-2-deoxyglucopyranosyl)asparagine	HMDB
N-ADGP-asn	HMDB
N(4)-(b-N-Acetyl-D-glucosaminyl)-L-asparagine	HMDB
N(4)-(Β-N-acetyl-D-glucosaminyl)-L-asparagine	HMDB
Aspartylglycosamine	MeSH

Chemical Formula

C₁₂H₂₁N₃O₈

Average Molecular Weight

335.3104

Monoisotopic Molecular Weight

335.132864663

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 Name

acetylglucosaminylasparagine

CAS Registry Number

2776-93-4

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 Key

YTTRPBWEMMPYSW-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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N(4)-glycosyl-L-asparagine (CHEBI:17261 )
glucosaminylamine (CHEBI:17261 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ALOGPS
logP	-6.8	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	8.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	191.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4i-9353000000-786f34e9af0ed644bf2d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0ab9-7921338000-f4887b8c9c177fb6c177	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014l-0293000000-0e6afb70f83fecf33f5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-7690000000-d891eff61408c60fc0f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mx-5930000000-b5b03176088e9e4c1abc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3589000000-878cfc8351ca28034926	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0229-4970000000-144a7c9cf2b6b1c0d0c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9500000000-d184dbc6f7857ff2cf4c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0149000000-eefcb4b7d49cc9736455	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2692000000-35c3172ea336db4c9e96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9320000000-1c2091e6c22b83332897	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0019000000-7900e8ac31b6a1fd733a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01bi-4439000000-75f483b5d93e062a4614	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-3910000000-7e17eb196465686b849e	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Placenta
Spleen

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Spleen	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000489

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022071

KNApSAcK ID

Not Available

Chemspider ID

110370

KEGG Compound ID

C04540

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5476

PubChem Compound

123826

PDB ID

Not Available

ChEBI ID

17261

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Aspartylglycosamine (BMDB0000489)

Structure for BMDB0000489 (Aspartylglycosamine)