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Showing Compound Glucosamine 6-phosphate (FDB022515)

Record Information
Version1.0
Creation date2011-09-21 00:15:11 UTC
Update date2019-11-26 03:21:04 UTC
Primary IDFDB022515
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucosamine 6-phosphate
DescriptionGlucosamine 6-phosphate is normally produced in endothelial cells via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus. (PMID 11270676, 11842094) [HMDB]
CAS Number3616-42-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranoseChEBI
alpha-D-Glucosamine 6-(dihydrogen phosphate)ChEBI
2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranoseGenerator
2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranoseGenerator
Glucosamine 6-phosphoric acidGenerator
a-D-Glucosamine 6-(dihydrogen phosphate)Generator
a-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
α-D-Glucosamine 6-(dihydrogen phosphate)Generator
α-D-Glucosamine 6-(dihydrogen phosphoric acid)Generator
2-Amino-2-deoxy-D-glucose 6-phosphateHMDB
2-Amino-2-deoxyglucose 6-phosphateHMDB
2-Amino-D-glucose-6-phosphateHMDB
D-Glucosamine 6-phosphateHMDB
D-Glucosamine phosphateHMDB
D-Glucosamine-6-phosphateHMDB
Glucosamine 6 -phosphateHMDB
Glucosamine-6-PHMDB
Glucosamine-6-phosphateHMDB
Glucose-6-phosphorateHMDB
Glucose-6-phosphoric acidHMDB
Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) esterHMDB
GLCN-6-PMeSH, HMDB
2-amino-2-Deoxy-6-O-ONO-a-D-glucopyranoseGenerator
2-amino-2-Deoxy-6-O-ONO-alpha-D-glucopyranoseChEBI
2-amino-2-Deoxy-6-O-ONO-α-D-glucopyranoseGenerator
2-amino-2-Deoxy-D-glucose 6-ateHMDB
2-amino-2-Deoxyglucose 6-ateHMDB
2-amino-D-Glucose-6-ateHMDB
a-D-Glucosamine 6-(dihydrogen ate)Generator
a-D-Glucosamine 6-(dihydrogen ic acid)Generator
alpha-D-Glucosamine 6-(dihydrogen ate)ChEBI
alpha-D-Glucosamine 6-(dihydrogen ic acid)Generator
D-Glucosamine 6-ateHMDB
D-Glucosamine ateHMDB
D-Glucosamine-6-ateHMDB
Glucosamine 6 -ateHMDB
GLUCOSAMINE 6-ATEChEBI
GLUCOSAMINE 6-ic acidGenerator
Glucosamine 6-Phosphatehmdb
Glucosamine 6-phosphic acidhmdb
Glucosamine-6-ateHMDB
glucosamine-6-Phmdb
glucosamine-6-phosphatehmdb
Glucose-6-orateHMDB
Glucose-6-oric acidHMDB
Oric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) esterHMDB
α-D-glucosamine 6-(dihydrogen ate)Generator
α-D-glucosamine 6-(dihydrogen ic acid)Generator
Predicted Properties
PropertyValueSource
Water Solubility34.8 g/LALOGPS
logP-2.6ALOGPS
logP-4.2ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability21.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H14NO8P
IUPAC name{[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid
InChI IdentifierInChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1
InChI KeyXHMJOUIAFHJHBW-UKFBFLRUSA-N
Isomeric SMILESN[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Average Molecular Weight259.151
Monoisotopic Molecular Weight259.045702941
Classification
Description Belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Amino saccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Alkyl phosphate
  • Hemiacetal
  • 1,2-diol
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGlucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-9320000000-54466a568e39d51598c7Spectrum
Predicted GC-MSGlucosamine 6-phosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ik9-3912400000-c198d10e982d681785edSpectrum
Predicted GC-MSGlucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0970000000-095ba413dfd29c80b4452012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-9500000000-e4e82ba86236d6046d0d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-bd232a0933f76298e9432012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-03di-0190000000-778d1a36aaf5c9b3c8462012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-08i0-1690000000-f08f9e49e698f1aa134d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9010000000-8a6a96ec67621a842ce82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-9010000000-8a6a96ec67621a842ce82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0190000000-280711606909adbb88142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-08i0-1690000000-f08f9e49e698f1aa134d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-3190000000-0f9d6942fba86f12422e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03fr-2790000000-7fe42a3d5900a5984d042021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-818ec0fe39e531f561a42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-9850000000-40bb2cfef099c426fcbf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-9500000000-9bb59bf1855e5fa763052016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0699-8950000000-68f380f4fab22160c7282016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-4f7a2c18e5b29f9e60762016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-6fc65d9a14f58d847a4f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0790000000-d98731443453807103762021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9810000000-32a2cffa4a376910fdb32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-9000000000-7be390edddedcba28a232021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-054k-9040000000-fd7b28df2dbc578cfc0b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9010000000-f0f082b70bb688bd4b382021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID388356
ChEMBL IDNot Available
KEGG Compound IDC00352
Pubchem Compound ID439217
Pubchem Substance IDNot Available
ChEBI ID15873
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01254
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34709
KNApSAcK IDNot Available
HET IDGLP
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
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
Glucosamine-6-phosphate isomerase 2GNPDA2Q8TDQ7
Putative N-acetylglucosamine-6-phosphate deacetylaseAMDHD2Q9Y303
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2GFPT2O94808
Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1GFPT1Q06210
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference