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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:26 UTC
HMDB IDHMDB01367
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-glucosamine 1-phosphate
DescriptionN-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
Thumb
Synonyms
ValueSource
2-(acetylamino)-2-Deoxy-D-glucopyranose 1-(dihydrogen phosphate)ChEBI
2-acetamido-2-Deoxy-1-O-phosphono-D-glucopyranoseChEBI
N-Acetyl-D-glucosamine 1-phosphateChEBI
N-Acetylglucosamine-1-phosphateChEBI
2-(acetylamino)-2-Deoxy-D-glucopyranose 1-(dihydrogen phosphoric acid)Generator
D-Glucosamine 1-phosphateHMDB
delta-Glucosamine 1-phosphateHMDB
N-Acetyl-alpha-D-glucosamine 1-phosphateHMDB
N-Acetyl-alpha-delta-glucosamine 1-phosphateHMDB
N-Acetyl-delta-glucosamine 1-phosphateHMDB
N-Acetyl-glucosamine-1-phosphateHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
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 Number901851-43-2
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 KeyInChIKey=FZLJPEPAYPUMMR-RTRLPJTCSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentN-acyl-alpha-hexosamines
Alternative Parents
Substituents
  • N-acyl-alpha-hexosamine
  • Glucosamine
  • Amino sugar
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Aminosugars metabolism
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
Water Solubility18.4 mg/mLALOGPS
logP-2ALOGPS
logP-3.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-0.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area165.78 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m3·mol-1ChemAxon
Polarizability25.41 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Saliva
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045map00520
G(M2)-Gangliosidosis: Variant B, Tay-sachs diseaseSMP00534Not Available
Salla Disease/Infantile Sialic Acid Storage DiseaseSMP00240Not Available
Sialuria or French Type SialuriaSMP00216Not Available
Sialuria or French Type SialuriaSMP00217Not Available
Tay-Sachs DiseaseSMP00390Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.135 +/- 0.363 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.251 +/- 0.167 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.282 +/- 0.623 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.326 +/- 0.327 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022581
KNApSAcK IDNot Available
Chemspider ID389248
KEGG Compound IDC04256
BioCyc IDN-ACETYL-D-GLUCOSAMINE-1-P
BiGG ID43457
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01367
Metagene LinkHMDB01367
METLIN ID6194
PubChem Compound440272
PDB IDNot Available
ChEBI ID7125
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in nucleotidyltransferase activity
Specific function:
Converts UDP and GlcNAc-1-P into UDP-GlcNAc, and UDP and GalNAc-1-P into UDP-GalNAc. Isoform AGX1 has 2 to 3 times higher activity towards GalNAc-1-P, while isoform AGX2 has 8 times more activity towards GlcNAc-1-P.
Gene Name:
UAP1
Uniprot ID:
Q16222
Molecular weight:
57027.91
Reactions
Uridine triphosphate + N-Acetyl-glucosamine 1-phosphate → Pyrophosphate + Uridine diphosphate-N-acetylglucosaminedetails
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P.
Gene Name:
PGM3
Uniprot ID:
O95394
Molecular weight:
62940.905
Reactions
N-Acetyl-glucosamine 1-phosphate → N-Acetyl-D-Glucosamine 6-Phosphatedetails
N-Acetyl-D-Glucosamine 6-Phosphate → N-Acetyl-glucosamine 1-phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
UAP1L1
Uniprot ID:
Q3KQV9
Molecular weight:
Not Available
Reactions
Uridine triphosphate + N-Acetyl-glucosamine 1-phosphate → Pyrophosphate + Uridine diphosphate-N-acetylglucosaminedetails