ChemFOnt: Showing chemical card for N-Acetyl-glucosamine 1-phosphate (CFc000001055)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:36 UTC

Chemfont ID

CFc000001055

Molecule Identification

Common Name

N-Acetyl-glucosamine 1-phosphate

Definition

N-Acetyl-glucosamine 1-phosphate is an intermediate in aminosugar metabolism. It is a substrate for the enzymes phosphoglucomutase 3 [EC:5.4.2.2 and EC:5.4.2.3] and UDP-N-acteylglucosamine pyrophosphorylase 1 [EC:2.7.7.23] (KEGG). It is involved in UDP-N-acetyl-D-glucosamine biosynthesis and UDP-N-acetylgalactosamine biosynthesis (BioCyc).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphate)	ChEBI
2-Acetamido-2-deoxy-1-O-phosphono-D-glucopyranose	ChEBI
N-Acetyl-D-glucosamine 1-phosphate	ChEBI
N-Acetylglucosamine-1-phosphate	ChEBI
2-(Acetylamino)-2-deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-D-glucosamine 1-phosphoric acid	Generator
N-Acetylglucosamine-1-phosphoric acid	Generator
N-Acetyl-glucosamine 1-phosphoric acid	Generator
D-Glucosamine 1-phosphate	HMDB
delta-Glucosamine 1-phosphate	HMDB
N-Acetyl-alpha-D-glucosamine 1-phosphate	HMDB
N-Acetyl-alpha-delta-glucosamine 1-phosphate	HMDB
N-Acetyl-delta-glucosamine 1-phosphate	HMDB
N-Acetyl-glucosamine-1-phosphate	HMDB
GlcNAc-1-phosphate	HMDB

Chemical Formula

C₈H₁₆NO₉P

Average Molecular Weight

301.1877

Monoisotopic Molecular Weight

301.056267627

IUPAC Name

{[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

[(3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid

CAS Registry Number

6866-69-9

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O

InChI Identifier

InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8?/m1/s1

InChI Key

FZLJPEPAYPUMMR-RTRLPJTCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Carbonyl group
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetyl-D-glucosamine 1-phosphate (CHEBI:7125 )

Functional Ontology

Not Available

Placenta (HMDB: HMDB0001367)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0001367)

Cellular substructure

Cytoplasm (HMDB: HMDB0001367)

Source

Endogenous

Endogenous (HMDB: HMDB0001367)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Amino Sugar Metabolism (HMDB: HMDB0001367)
Amino Sugar Metabolism (PathBank: SMP0063580)
Peptidoglycan Biosynthesis II (PathBank: SMP0122239)
1,6-Anhydro-N-acetylmuramic Acid Recycling (PathBank: SMP0122240)
Lipopolysaccharide Biosynthesis (PathBank: SMP0121299)
Peptidoglycan Biosynthesis I (PathBank: SMP0121305)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Lipopolysaccharide Biosynthesis II (PathBank: SMP0122112)
Lipopolysaccharide Biosynthesis III (PathBank: SMP0122237)
O-Antigen Building Blocks Biosynthesis (PathBank: SMP0122253)
Amino Sugar and Nucleotide Sugar Metabolism (PathBank: SMP0002331)
Chitin Biosynthesis (PathBank: SMP0094667)

Disease pathway

Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Sialuria or French Type Sialuria (PathBank: SMP0120737)
Tay-Sachs Disease (PathBank: SMP0120545)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	18.4 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-0.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.9 m³·mol⁻¹	ChemAxon
Polarizability	25.41 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