N-Acetyl-glucosamine 1-phosphate (PAMDB000357)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000357
Identification
Name: N-Acetyl-glucosamine 1-phosphate
Description:N-acetyl-glucosamine 1-phosphate is a member of the chemical class known as N-acetyl-alpha-hexosamine-1-phosphates. These are carbohydrates derivative which is structurally characterized by the presence of an hexosamine bearing a phosphate group attached to the C1 carbon atom, and another moeity N-linked through the amine group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-D-glucosamine 1-phosphate
  • α-D-glucosamine 1-phosphoric acid
  • α-D-glucosamine 1P
  • a-D-Glucosamine 1-phosphate
  • a-D-Glucosamine 1-phosphoric acid
  • a-D-Glucosamine 1P
  • Alpha-D-Glucosamine 1-phosphate
  • alpha-D-Glucosamine 1-phosphoric acid
  • Alpha-D-Glucosamine 1P
  • D-Glucosamine 1-phosphate
  • D-Glucosamine 1-phosphoric acid
  • Delta-glucosamine 1-phosphate
  • delta-Glucosamine 1-phosphoric acid
  • GlcNAc-P
  • Glucosamine-1P
  • N-Acetyl-a-D-glucosamine 1-phosphate
  • N-Acetyl-a-D-glucosamine 1-phosphoric acid
  • N-Acetyl-a-delta-glucosamine 1-phosphate
  • N-Acetyl-a-delta-glucosamine 1-phosphoric acid
  • N-Acetyl-a-δ-glucosamine 1-phosphate
  • N-Acetyl-a-δ-glucosamine 1-phosphoric acid
  • N-Acetyl-alpha-D-glucosamine 1-phosphate
  • N-Acetyl-alpha-D-glucosamine 1-phosphoric acid
  • N-acetyl-alpha-delta-glucosamine 1-phosphate
  • N-Acetyl-alpha-delta-glucosamine 1-phosphoric acid
  • N-Acetyl-D-glucosamine 1-phosphate
  • N-Acetyl-D-glucosamine 1-phosphoric acid
  • N-acetyl-delta-glucosamine 1-phosphate
  • N-Acetyl-delta-glucosamine 1-phosphoric acid
  • N-Acetyl-glucosamine 1-phosphoric acid
  • N-Acetyl-glucosamine-1-phosphate
  • N-Acetyl-glucosamine-1-phosphoric acid
  • N-Acetyl-α-D-glucosamine 1-phosphate
  • N-Acetyl-α-D-glucosamine 1-phosphoric acid
  • N-Acetyl-α-δ-glucosamine 1-phosphate
  • N-Acetyl-α-δ-glucosamine 1-phosphoric acid
  • N-Acetyl-δ-glucosamine 1-phosphate
  • N-Acetyl-δ-glucosamine 1-phosphoric acid
  • α-D-Glucosamine 1-phosphate
  • α-D-Glucosamine 1-phosphoric acid
  • α-D-Glucosamine 1P
  • δ-Glucosamine 1-phosphate
  • δ-Glucosamine 1-phosphoric acid
Chemical Formula: C8H16NO9P
Average Molecular Weight: 301.1877
Monoisotopic Molecular Weight: 301.056267627
InChI Key: FZLJPEPAYPUMMR-RTRLPJTCSA-N
InChI: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
CAS number: Not Available
IUPAC Name:{[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name: [3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid
SMILES:CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OP(O)(O)=O
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct Parent N-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
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability25.23 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Water + Uridine diphosphate-N-acetylglucosamine > N-Acetyl-glucosamine 1-phosphate +2 Hydrogen ion + Uridine 5'-monophosphate
N-Acetyl-glucosamine 1-phosphate <> Glucosamine 6-phosphate
Acetyl-CoA + N-Acetyl-glucosamine 1-phosphate > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion
Acetyl-CoA + N-Acetyl-glucosamine 1-phosphate > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion
N-Acetyl-glucosamine 1-phosphate + Hydrogen ion + Uridine triphosphate > Pyrophosphate + Uridine diphosphate-N-acetylglucosamine
Glucosamine-1P + Acetyl-CoA + Glucosamine-1P > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate > Uridine diphosphate-N-acetylglucosamine + Pyrophosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2095000000-3f794f17ca517402d93bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7n-7291000000-35c02a8944d0b1eb51e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9320000000-6572e916ffe2a660c8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002s-9301000000-d39360985ac352fbb64fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-2467555f88246808df5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a0ddb9f9bfa14714ebfbView in MoNA
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16446
HMDB IDHMDB01367
Pubchem Compound ID900
Kegg IDC04256
ChemSpider ID876
Wikipedia IDNot Available
BioCyc IDGLUCOSAMINE-1P
EcoCyc IDGLUCOSAMINE-1P

Enzymes

Protein Details
• Bifunctional protein glmU
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the last two sequential reactions in the de novo biosynthetic pathway for UDP-GlcNAc. Responsible for the acetylation of Glc-N-1-P to give GlcNAc-1-P and for the uridyl transfer from UTP to GlcNAc-1-P which produces UDP-GlcNAc
Gene Name:
glmU
Locus Tag:
PA5552
Molecular weight:
48.9 kDa
Reactions
Acetyl-CoA + alpha-D-glucosamine 1-phosphate = CoA + N-acetyl-alpha-D-glucosamine 1-phosphate.
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine.
Protein Details
• Phosphoglucosamine mutase
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Catalyzes the conversion of glucosamine-6-phosphate to glucosamine-1-phosphate. Can also catalyze the formation of glucose-6-P from glucose-1-P, although at a 1400-fold lower rate
Gene Name:
glmM
Locus Tag:
PA4749
Molecular weight:
47.8 kDa
Reactions
Alpha-D-glucosamine 1-phosphate = D-glucosamine 6-phosphate.

Transporters