ChemFOnt: Showing chemical card for N4-(β-N-acetyl-D-glucosaminyl)-L-asparagine (CFc000337916)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:32:02 UTC

Chemfont ID

CFc000337916

Molecule Identification

Common Name

N4-(β-N-acetyl-D-glucosaminyl)-L-asparagine

Definition

Aspartylglycosamine, 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.

Structure

MOL SDF PDB SMILES InChI

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000489)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	39.1 g/L	ALOGPS
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	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon