Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:09:50 UTC
HMDB IDHMDB01076
Secondary Accession NumbersNone
Metabolite Identification
Common NameFructose 1-phosphate
DescriptionFructose 1-phosphate is an intermediate metabolite in the Fructose and mannose metabolism pathway.
Structure
Thumb
Synonyms
  1. D-Fructose 1-phosphate
  2. D-Fructose-1-P
  3. D-Fructose-1-phosphate
  4. Fructose 1-phosphate
  5. Fructose-1-P
  6. Fructose-1-phosphate
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 IUPAC 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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Monosaccharide Phosphates
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 area156.91ChemAxon
rotatable bond count4ChemAxon
refractivity47.23ChemAxon
polarizability21.06ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Fructose and Mannose DegradationSMP00064map00051
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022410
KNApSAcK IDNot Available
Chemspider ID8575807
KEGG Compound IDC01094
BioCyc IDFRU1P
BiGG ID40936
Wikipedia LinkFructose 1-phosphate
NuGOwiki LinkHMDB01076
Metagene LinkHMDB01076
METLIN ID378
PubChem Compound10400369
PDB IDF1X
ChEBI ID704854
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. 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. Pubmed: 19212411
  2. 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
  3. 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
  4. 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

Enzymes

Gene Name:
ALDOA
Uniprot ID:
P04075
Reactions
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehydedetails
Gene Name:
ALDOC
Uniprot ID:
P09972
Reactions
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehydedetails
Gene Name:
ALDOB
Uniprot ID:
P05062
Reactions
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehydedetails
Gene Name:
KHK
Uniprot ID:
P50053