Record Information
Version1.0
Creation Date2016-09-30 23:01:41 UTC
Update Date2020-05-11 20:40:10 UTC
BMDB IDBMDB0002817
Secondary Accession Numbers
  • BMDB02817
Metabolite Identification
Common NameN-Acetylglucosamine 6-phosphate
DescriptionN-Acetylglucosamine 6-phosphate, also known as GLCNAC6P, 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. N-Acetylglucosamine 6-phosphate exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on N-Acetylglucosamine 6-phosphate.
Structure
Thumb
Synonyms
ValueSource
N-Acetylglucosamine 6-phosphoric acidGenerator
GlcNAc6pMeSH
2-Acetamido-2-deoxy-D-glucose 6-phosphateHMDB
GlcNAc-6-PHMDB
N-Acetyl-D-glucosamine 6-phosphateHMDB
N-Acetylglucosamine 6-phosphateHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
IUPAC Name{[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R,6S)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number1746-32-3
SMILES
CC(=O)N[C@H]1[C@@H](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 KeyBRGMHAYQAZFZDJ-PVFLNQBWSA-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected 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-2ALOGPS
logP-3.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.23ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m³·mol⁻¹ChemAxon
Polarizability25.69 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
  • Liver
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002817
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023067
KNApSAcK IDNot Available
Chemspider ID388358
KEGG Compound IDNot Available
BioCyc IDN-ACETYL-D-GLUCOSAMINE-6-P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3429
PubChem Compound439219
PDB ID16G
ChEBI IDNot Available
References
Synthesis ReferenceMaley, Frank; Lardy, Henry A. Phosphoric esters of biological importance. VI. The synthesis of D-glucosamine 6-phosphate and N-acetyl-D-glucosamine 6-phosphate. Journal of the American Chemical Society (1956), 78 1393-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available