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Record Information
Version1.0
Creation Date2016-07-13 19:41:16 UTC
Update Date2016-07-20 20:55:03 UTC
LmdbLMDB00050
Secondary Accession NumbersNone
Metabolite Identification
Common NameFructose 6-phosphate
DescriptionFructose 6-phosphate, also known as neuberg ester or D-fructose-6-p, 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. The open chain form of D-fructose 6-phosphate. Fructose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Fructose 6-phosphate exists in all living species, ranging from bacteria to humans. fructose 6-phosphate and L-glutamine can be converted into glucosamine 6-phosphate and L-glutamic acid through the action of the enzyme glutamine--fructose-6-phosphate aminotransferase. In humans, fructose 6-phosphate is involved in homocarnosinosis. Outside of the human body, Fructose 6-phosphate has been detected, but not quantified in, carrots and milk (cow). This could make fructose 6-phosphate a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
D-Fructose 6-phosphateChEBI
D-Fructose 6-phosphoric acidChEBI
Fructose-6-phosphateChEBI
Neuberg esterChEBI
Fructose-6-phosphoric acidGenerator
Fructose 6-phosphoric acidGenerator
D-Fructose 6-phosphorateHMDB
D-Fructose-6-pHMDB
D-Fructose-6-phosphateHMDB
FPCHMDB
Fru-6-pHMDB
Fructose-6-pHMDB
Fructose-6PHMDB
Fructose-6-phosphate, (alpha-D)-isomerHMDB
Fructose-6-phosphate, (beta-D)-isomerHMDB
Fructose-6-phosphate, disodium salt, (D)-isomerHMDB
Fructose-6-phosphate, (D)-isomerHMDB
Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomerHMDB
Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomerHMDB
Fructose-6-phosphate, barium (1:1) salt, (D)-isomerHMDB
Fructose-6-phosphate, barium salt, (D)-isomerHMDB
Fructose-6-phosphate, sodium salt, (D)-isomerHMDB
Fructose-6-phosphate, calcium salt, (D)-isomerHMDB
Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomerHMDB
Fructose-6-phosphate, sodium saltHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid
Traditional NameD-fructose 6-phosphate
CAS Registry Number643-13-0
SMILES
OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1
InChI KeyGSXOAOHZAIYLCY-HSUXUTPPSA-N
Chemical Taxonomy
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
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.9ALOGPS
logP-3.4ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity48.43 m³·mol⁻¹ChemAxon
Polarizability20.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-0gba-1943000000-9b9bb3f9964b519fa26bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1943000000-0be5d726668730e99be0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-014j-1954000000-9fa83268db2925e9478dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000b-0934000000-eb61ccae8d0b23564bc7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000b-0934000000-c2a49f4f2d11d3e60a9eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-000j-0925000000-a6b6a121cb447c890019Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0f7a-1934000000-b28e738e5093324060d9Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-3966000000-fee84a4ec7828d92e8b6Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-014i-1955000000-32da70382eccbcbbb574Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-1943000000-9b9bb3f9964b519fa26bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1943000000-0be5d726668730e99be0Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-1954000000-9fa83268db2925e9478dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-0934000000-eb61ccae8d0b23564bc7Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-0934000000-c2a49f4f2d11d3e60a9eSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000j-0925000000-a6b6a121cb447c890019Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7a-1934000000-b28e738e5093324060d9Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3966000000-fee84a4ec7828d92e8b6Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1955000000-32da70382eccbcbbb574Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-1933000000-1c8febd80da1382bec31Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k97-9840000000-4f9f16f21249d9870dfaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00o9-7934540000-e23e661c1babf5e063a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00kb-9710000000-5d6429381cefb6a2bdc7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9100000000-51c3f5ca7ef3f190f1dfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-054k-9000000000-75c50b162633f723546dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-07895e6c6f3e4a816391Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0aor-0690000000-b640c7fba12f06d6bfa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-f31b175fc6a9941a2451Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-9220000000-962294aed3032864dc90Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-c2dc78595233b4d4df78Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0229-5090000000-281699f4bce06db0b1b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-006x-9730000000-b72576e6bb1ae73e6881Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kbf-9740000000-130bb715a91e870b5480Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ar9-9720000000-7ca18e5a32ef069ff21aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-00032f32c05509571a9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5e859d2084880df68725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-9620000000-1a2150ea2d68dcce9b24Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9000000000-f2969657deda9ac99077Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d5aaca13a836cb9f1725Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-3590000000-3fc4dac2f46082421870Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c04-9610000000-77e7a6ced5ab4dda6f86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9200000000-e4500e644878a4632447Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-2980000000-ccecfa1c0258f9267846Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-550809f9719b91a7807aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-501178ab2f5d5affab48Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB04493
HMDB IDHMDB0000124
FooDB IDFDB021896
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID33795
BioCyc IDCPD-15709
METLIN ID5159
PDB IDNot Available
Wikipedia LinkFructose 6-phosphate
Chemspider ID62713
ChEBI ID15946
PubChem Compound ID69507
Kegg Compound IDC00085
YMDB IDYMDB00078
ECMDB IDECMDB04068
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available