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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:55 UTC
HMDB IDHMDB0001076
Secondary Accession Numbers
  • HMDB01076
Metabolite Identification
Common NameFructose 1-phosphate
DescriptionFructose 1-phosphate, also known as D-fructose-1-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. Fructose 1-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Metabolism of fructose thus essentially results in intermediates of glycolysis. The final product of glycolysis (pyruvate) may then undergo gluconeogenesis, enter the TCA cycle or be stored as fatty acids. Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, fructose 1-phosphate participates in a number of enzymatic reactions. In particular, fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. Because fructokinase has a high Vmax fructose entering cells is quickly phosphorylated to fructose 1-phosphate. In humans, fructose 1-phosphate is involved in fructose intolerance, hereditary. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It is generated mainly by hepatic fructokinase but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule. Aldolase B converts it into glyceraldehyde and dihydroxyacetone phosphate (DHAP). Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness.
Structure
Data?1582752175
Synonyms
ValueSource
beta-D-Fructose 1-phosphateChEBI
b-D-Fructose 1-phosphateGenerator
b-D-Fructose 1-phosphoric acidGenerator
beta-D-Fructose 1-phosphoric acidGenerator
Β-D-fructose 1-phosphateGenerator
Β-D-fructose 1-phosphoric acidGenerator
Fructose 1-phosphoric acidGenerator
D-Fructose 1-phosphateHMDB
D-Fructose-1-pHMDB
D-Fructose-1-phosphateHMDB
Fructose-1-pHMDB
Fructose-1-phosphateHMDB
Chemical FormulaC6H13O9P
Average Molecular Weight260.1358
Monoisotopic Molecular Weight260.029718526
IUPAC Name{[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid
Traditional Name[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid
CAS Registry Number15978-08-2
SMILES
OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1
InChI KeyRHKKZBWRNHGJEZ-ARQDHWQXSA-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
  • Pentose phosphate
  • Pentose-5-phosphate
  • C-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP-2.1ALOGPS
logP-2.9ChemAxon
logS-0.89ALOGPS
pKa (Strongest Acidic)1.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.23 m³·mol⁻¹ChemAxon
Polarizability21.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9510000000-71d828159b61f8342118Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-2912320000-08ffe3d23f5fa5d6162cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-9470000000-18ac582a370338a3f5f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-7390000000-1a5a72af8bb734e50eb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009y-9100000000-4f151f373d7730140f38Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9270000000-5af91634007091008210Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5cf3f457b8c6f6270b68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4e6feccf18943de8c419Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022410
KNApSAcK IDNot Available
Chemspider ID8575807
KEGG Compound IDC01094
BioCyc IDFRU1P
BiGG ID40936
Wikipedia LinkFructose 1-phosphate
METLIN ID378
PubChem Compound10400369
PDB IDNot Available
ChEBI ID139419
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceHara, Yoshito. Ion exchange separation of fructose 1-phosphate by using borate as the eluant. Journal of Biochemistry (Tokyo, Japan) (1959), 46 571-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Alvarez E, Roncero I, Chowen JA, Vazquez P, Blazquez E: Evidence that glucokinase regulatory protein is expressed and interacts with glucokinase in rat brain. J Neurochem. 2002 Jan;80(1):45-53. [PubMed:11796742 ]
  2. Malaisse WJ: [Metabolic interactions between glucose and fructose]. Bull Mem Acad R Med Belg. 2002;157(7-9):349-52; discussion 352-3. [PubMed:12647375 ]
  3. Watford M: Small amounts of dietary fructose dramatically increase hepatic glucose uptake through a novel mechanism of glucokinase activation. Nutr Rev. 2002 Aug;60(8):253-7. [PubMed:12199300 ]
  4. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]

Enzymes

General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:
ALDOA
Uniprot ID:
P04075
Molecular weight:
39419.675
Reactions
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOC
Uniprot ID:
P09972
Molecular weight:
39455.505
Reactions
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
General function:
Involved in fructose-bisphosphate aldolase activity
Specific function:
Not Available
Gene Name:
ALDOB
Uniprot ID:
P05062
Molecular weight:
39472.715
Reactions
Fructose 1-phosphate → Dihydroxyacetone phosphate + Glyceraldehydedetails
General function:
Carbohydrate transport and metabolism
Specific function:
Not Available
Gene Name:
KHK
Uniprot ID:
P50053
Molecular weight:
32730.055