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N-Acetyl-glucosamine 1-phosphate (M2MDB000357)

Record Information
Version2.0
Creation Date2012-05-31 13:50:57 -0600
Update Date2015-09-17 15:41:10 -0600
Secondary Accession Numbers
  • ECMDB01367
Identification
Name:N-Acetyl-glucosamine 1-phosphate
DescriptionN-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 301.1877
Monoisotopic: 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
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
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organopnictogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Polarizability25.23 ųChemAxon
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
SMPDB Pathways:
1,6-anhydro-<i>N</i>-acetylmuramic acid recyclingPW002064 ThumbThumb?image type=greyscaleThumb?image type=simple
Amino sugar and nucleotide sugar metabolism IPW000886 ThumbThumb?image type=greyscaleThumb?image type=simple
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIPW001905 ThumbThumb?image type=greyscaleThumb?image type=simple
lipopolysaccharide biosynthesis IIIPW002059 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis IPW000906 ThumbThumb?image type=greyscaleThumb?image type=simple
peptidoglycan biosynthesis I 2PW002062 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
82± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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
1. Protein ushA
General function:
Involved in hydrolase activity
Specific function:
Degradation of external UDP-glucose to uridine monophosphate and glucose-1-phosphate, which can then be used by the cell
Gene Name:
ushA
Uniprot ID:
P07024
Molecular weight:
60824
Reactions
UDP-sugar + H(2)O = UMP + alpha-D-aldose 1-phosphate.
A 5'-ribonucleotide + H(2)O = a ribonucleoside + phosphate.
Protein Details
2. 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
Uniprot ID:
P0ACC7
Molecular weight:
49190
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
3. 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
Uniprot ID:
P31120
Molecular weight:
47543
Reactions
Alpha-D-glucosamine 1-phosphate = D-glucosamine 6-phosphate.

Transporters

Protein Details
1. Outer membrane protein N
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
Protein Details
2. Outer membrane pore protein E
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
Protein Details
3. Outer membrane protein F
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
Protein Details
4. Outer membrane protein C
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368