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Record Information
Version1.0
Creation Date2016-09-30 22:40:35 UTC
Update Date2020-05-21 16:28:28 UTC
BMDB IDBMDB0001062
Secondary Accession Numbers
  • BMDB01062
Metabolite Identification
Common NameN-Acetyl-D-Glucosamine 6-Phosphate
DescriptionN-Acetyl-D-glucosamine 6-phosphate, also known as N-acetyl-D-glucosamine-6-p or n-acetyl-d-glucosamine 6-phosphate, 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-Acetyl-D-glucosamine 6-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). N-Acetyl-D-glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. N-Acetyl-D-glucosamine 6-phosphate participates in a number of enzymatic reactions, within cattle. In particular, N-Acetyl-D-glucosamine 6-phosphate can be biosynthesized from N-acetyl-D-glucosamine through its interaction with the enzyme N-acetyl-D-glucosamine kinase. In addition, N-Acetyl-D-glucosamine 6-phosphate can be converted into glucosamine 6-phosphate and acetic acid through the action of the enzyme putative N-acetyl-d-glucosamine 6-phosphatehosphate deacetylase. In cattle, N-acetyl-D-glucosamine 6-phosphate is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
2-Acetamido-2-deoxy-6-O-phosphono-D-glucopyranoseChEBI
N-Acetyl-D-glucosamine 6-phosphoric acidGenerator
N-Acetyl-D-glucosamine-6-pHMDB
N-Acetyl-D-glucosamine-6-phosphateHMDB
N-Acetyl-glucosamine-6-pHMDB
N-Acetyl-glucosamine-6-phosphateHMDB
N-Acetylglucosamine-6-pHMDB
N-Acetylglucosamine 6-phosphateHMDB
GlcNAc6pHMDB
Chemical FormulaC8H16NO9P
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
IUPAC Name{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid
CAS Registry Number18191-20-3
SMILES
CC(=O)N[C@H]1C(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-RTRLPJTCSA-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
StatusExpected 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
Polarizability25.8 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9730000000-66d6101e8cb0c5ca3fc1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fk9-7391350000-2eb6c4c504e0841c1908View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-50926fdd7300073d5059View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9412000000-a1461b202e6744bf4f35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-e7ac8ef113fa566a7265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-364ae19f8cdb4e2d51caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-ecee6a11feb4582407b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2196000000-8aa0b82454ed7fe1de1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2a-4591000000-dca968a4092f312565acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900000000-933daf9b2c351b0a86b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v00-5931000000-4a813f2d6d4480fc5e41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8cdef6bcf81376fb24e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a998778a46bb52c7223aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001062
DrugBank IDDB03951
Phenol Explorer Compound IDNot Available
FooDB IDFDB022401
KNApSAcK IDC00019661
Chemspider ID389821
KEGG Compound IDC00357
BioCyc IDNot Available
BiGG ID34733
Wikipedia LinkNot Available
METLIN ID5975
PubChem Compound440996
PDB IDNot Available
ChEBI ID15784
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Carbohydrate transport and metabolism
Specific function:
Converts endogenous N-acetylglucosamine (GlcNAc), a major component of complex carbohydrates, from lysosomal degradation or nutritional sources into GlcNAc 6-phosphate. Involved in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway. Also has ManNAc kinase activity (By similarity).
Gene Name:
NAGK
Uniprot ID:
Q3SZM9
Molecular weight:
37268.0
Reactions
3 N-Acetyl-D-Glucosamine 6-Phosphate + 3 Adenosine diphosphate ribose →3 Chitin +3 Adenosine triphosphatedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Hydrolyzes the N-glycolyl group from N-glycolylglucosamine 6-phosphate (GlcNGc-6-P) in the N-glycolylneuraminic acid (Neu5Gc) degradation pathway.
Gene Name:
AMDHD2
Uniprot ID:
A7MBC0
Molecular weight:
43496.0
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate + Water → Glucosamine 6-phosphate + Acetic aciddetails
General function:
Not Available
Specific function:
Catalyzes the conversion of GlcNAc-6-P into GlcNAc-1-P during the synthesis of uridine diphosphate/UDP-GlcNAc, a sugar nucleotide critical to multiple glycosylation pathways including protein N- and O-glycosylation.
Gene Name:
PGM3
Uniprot ID:
F1MS56
Molecular weight:
59950.0
Reactions
N-Acetyl-D-Glucosamine 6-Phosphate → N-Acetyl-glucosamine 1-phosphatedetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
GNPNAT1
Uniprot ID:
Q08DV2
Molecular weight:
20776.0
Reactions
Acetyl-CoA + Glucosamine 6-phosphate → N-Acetyl-D-Glucosamine 6-Phosphate + Coenzyme Adetails