ChemFOnt: Showing chemical card for N-Acetyl-D-Glucosamine 6-Phosphate (CFc000000837)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:20 UTC

Chemfont ID

CFc000000837

Molecule Identification

Common Name

N-Acetyl-D-Glucosamine 6-Phosphate

Definition

N-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Acetamido-2-deoxy-6-O-phosphono-D-glucopyranose	ChEBI
N-Acetyl-D-glucosamine 6-phosphoric acid	Generator
N-Acetyl-D-glucosamine-6-p	HMDB
N-Acetyl-D-glucosamine-6-phosphate	HMDB
N-Acetyl-glucosamine-6-p	HMDB
N-Acetyl-glucosamine-6-phosphate	HMDB
N-Acetylglucosamine-6-p	HMDB
N-Acetylglucosamine 6-phosphate	HMDB
GlcNAc6p	HMDB

Chemical Formula

C₈H₁₆NO₉P

Average Molecular Weight

301.1877

Monoisotopic Molecular Weight

301.056267627

IUPAC Name

{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid

CAS Registry Number

18191-20-3

SMILES

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

InChI Identifier

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

InChI Key

BRGMHAYQAZFZDJ-RTRLPJTCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
Hexose phosphate
N-acyl-alpha-hexosamine
Monosaccharide phosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Alkyl phosphate
Oxane
Phosphoric acid ester
Acetamide
1,2-diol
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acyl-D-glucosamine 6-phosphate (CHEBI:15784 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0001062)

Cellular substructure

Cytoplasm (HMDB: HMDB0001062)

Source

Endogenous

Endogenous (HMDB: HMDB0001062)

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: HMDB0001062)
Amino Sugar Metabolism (PathBank: SMP0063580)
Glutamate Metabolism (PathBank: SMP0087278)
Amino Sugar and Nucleotide Sugar Metabolism III (PathBank: SMP0121303)
1,6-Anhydro-N-acetylmuramic Acid Recycling (PathBank: SMP0122240)
Inner Membrane Transport (PathBank: SMP0121270)
Amino Sugar and Nucleotide Sugar Metabolism I (PathBank: SMP0121302)
Amino Sugar and Nucleotide Sugar Metabolism II (PathBank: SMP0000906)
N-Acetylneuraminate, N-Acetylmannosamine, and N-Acetylglucosamine Degradation (PathBank: SMP0002044)
Chitobiose Degradation (PathBank: SMP0002056)
Amino Sugar and Nucleotide Sugar Metabolism (PathBank: SMP0002331)
Chitin Biosynthesis (PathBank: SMP0094667)

Disease pathway

4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120445)
Salla Disease/Infantile Sialic Acid Storage Disease (PathBank: SMP0120524)
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease (PathBank: SMP0120599)
Succinic Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120631)
Homocarnosinosis (HMDB: HMDB0001062)
Sialuria or French Type Sialuria (PathBank: SMP0000216)
Tay-Sachs Disease (PathBank: SMP0120545)
Homocarnosinosis (PathBank: SMP0120494)
2-Hydroxyglutric Aciduria (D and L Form) (PathBank: SMP0120659)
Hyperinsulinism-Hyperammonemia Syndrome (PathBank: SMP0120496)

Protein pathway

Operon: Mannose Uptake Inactivation (PathBank: SMP0002194)

Signaling pathway

Operon: Sugar Uptake (PathBank: SMP0002207)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001062)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	17.6 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	1.23	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	25.8 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