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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-11 17:41:05 UTC
HMDB IDHMDB0001367
Secondary Accession Numbers
  • HMDB01367
Metabolite Identification
Common NameN-Acetyl-glucosamine 1-phosphate
DescriptionN-Acetyl-glucosamine 1-phosphate, also known as glcnac-1-phosphate, 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. N-Acetyl-glucosamine 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-glucosamine 1-phosphate exists in all eukaryotes, ranging from yeast to humans. Within humans, N-acetyl-glucosamine 1-phosphate participates in a number of enzymatic reactions. In particular, N-acetyl-glucosamine 1-phosphate can be biosynthesized from N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme phosphoacetylglucosamine mutase. In addition, N-acetyl-glucosamine 1-phosphate and uridine triphosphate can be converted into uridine diphosphate-N-acetylglucosamine; which is catalyzed by the enzyme UDP-N-acetylhexosamine pyrophosphorylase. A N-acetyl-N-Acetyl-glucosamine 1-phosphate that is 2-deoxy-D-glucopyranose 1-(dihydrogen phosphate) substituted by an acetamido group at position 2. In humans, N-acetyl-glucosamine 1-phosphate is involved in the metabolic disorder called the salla disease/infantile sialic acid storage disease pathway.
Structure
Data?1589218865
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
N-Acetyl-D-glucosamine 1-phosphoric acidGenerator
N-Acetylglucosamine-1-phosphoric acidGenerator
N-Acetyl-glucosamine 1-phosphoric acidGenerator
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
GlcNAc-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 Number6866-69-9
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 KeyFZLJPEPAYPUMMR-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.9 m³·mol⁻¹ChemAxon
Polarizability25.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007k-9230000000-37cdd3ef185356d03c19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0f6t-9211240000-817e06893a2ccced098bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1094000000-f1e04aaf05d431b8b0abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-9620000000-3e2ee2ffc3801abdb7daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9211000000-7f3631860a58ca188060Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-9614f2b717f8fb17cc08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1a4f6aa02a49053d5b95Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Saliva
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022581
KNApSAcK IDC00019581
Chemspider ID389248
KEGG Compound IDC04256
BioCyc IDN-ACETYL-D-GLUCOSAMINE-1-P
BiGG ID43457
Wikipedia LinkNot Available
METLIN ID6194
PubChem Compound440272
PDB IDNot Available
ChEBI ID7125
Food Biomarker OntologyNot Available
VMH IDACGAM1P
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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