Record Information
Version1.0
Creation date2011-09-21 00:13:26 UTC
Update date2018-05-28 18:32:44 UTC
Primary IDFDB022401
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetyl-D-glucosamine 6-phosphate
DescriptionN-Acetyl-D-Glucosamine 6-Phosphate, also known as N-acetyl-D-glucosamine-6-p or GLCNAC6P, 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 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.
CAS Number18191-20-3
Structure
Thumb
Synonyms
SynonymSource
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
2-acetamido-2-Deoxy-6-O-ONO-D-glucopyranoseChEBI
N-Acetyl-D-glucosamine 6-ateChEBI
N-Acetyl-D-glucosamine 6-ic acidGenerator
N-Acetyl-D-Glucosamine 6-Phosphatehmdb
N-Acetyl-D-Glucosamine 6-Phosphic acidhmdb
N-Acetyl-D-glucosamine-6-ateHMDB
n-acetyl-d-glucosamine-6-phmdb
N-acetyl-D-glucosamine-6-phosphatehmdb
N-Acetyl-glucosamine-6-ateHMDB
n-acetyl-glucosamine-6-phmdb
n-acetyl-glucosamine-6-phosphatehmdb
n-acetylglucosamine-6-phmdb
Predicted Properties
PropertyValueSource
Water Solubility17.6 g/LALOGPS
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H16NO9P
IUPAC name{[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=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
Isomeric SMILESCC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Average Molecular Weight301.1877
Monoisotopic Molecular Weight301.056267627
Classification
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
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2943000000-e2bb568a8e9b660ec0beJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-2934000000-4140d40b85c7474418f6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9730000000-66d6101e8cb0c5ca3fc1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fk9-7391350000-2eb6c4c504e0841c1908JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0009000000-50926fdd7300073d5059JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9412000000-a1461b202e6744bf4f35JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-e7ac8ef113fa566a7265JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-364ae19f8cdb4e2d51caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9000000000-ecee6a11feb4582407b4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2196000000-8aa0b82454ed7fe1de1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2a-4591000000-dca968a4092f312565acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dm-6900000000-933daf9b2c351b0a86b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0v00-5931000000-4a813f2d6d4480fc5e41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8cdef6bcf81376fb24e2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a998778a46bb52c7223aJSpectraViewer
ChemSpider ID389821
ChEMBL IDNot Available
KEGG Compound IDC00357
Pubchem Compound ID440996
Pubchem Substance IDNot Available
ChEBI ID15784
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01062
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34733
KNApSAcK IDNot Available
HET ID1FRZ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glucosamine-6-phosphate isomerase 2GNPDA2Q8TDQ7
N-acetyl-D-glucosamine kinaseNAGKQ9UJ70
Putative N-acetylglucosamine-6-phosphate deacetylaseAMDHD2Q9Y303
Glucosamine 6-phosphate N-acetyltransferaseGNPNAT1Q96EK6
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Glutamate MetabolismSMP00072 map00250
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference