Fructose 1-phosphate (PAMDB000243)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000243
Identification
Name: Fructose 1-phosphate
Description:Fructose 1-phosphate is an intermediate metabolite in the Fructose and mannose metabolism pathway. It is generated by fructokinase and it is broken down by aldolase B into glyceraldehyde and dihydroxyacetone phosphate (DHAP).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-D-fructose-1-P
  • β-D-fructose-1-phosphate
  • β-D-fructose-1-phosphoric acid
  • b-D-Fructose-1-P
  • b-D-Fructose-1-phosphate
  • b-D-Fructose-1-phosphoric acid
  • Beta-D-Fructose-1-P
  • Beta-D-Fructose-1-phosphate
  • beta-D-Fructose-1-phosphoric acid
  • D-Fructose 1-phosphate
  • D-Fructose 1-phosphoric acid
  • D-Fructose-1-P
  • D-Fructose-1-phosphate
  • D-Fructose-1-phosphoric acid
  • Fructose 1-phosphate
  • Fructose 1-phosphoric acid
  • Fructose-1-P
  • Fructose-1-phosphate
  • Fructose-1-phosphoric acid
  • Fructose1P
  • β-D-Fructose-1-P
  • β-D-Fructose-1-phosphate
  • β-D-Fructose-1-phosphoric acid
Chemical Formula: C6H13O9P
Average Molecular Weight: 260.1358
Monoisotopic Molecular Weight: 260.029718526
InChI Key: RHKKZBWRNHGJEZ-ARQDHWQXSA-N
InChI: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
CAS number: 15978-08-2
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
SMILES:OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent C-glycosyl compounds
Alternative Parents
Substituents
  • C-glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility33.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.23 m3·mol-1ChemAxon
Polarizability21.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphoenolpyruvic acid + D-Fructose > Fructose 1-phosphate + Pyruvic acid
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate + Hydrogen ion
Adenosine triphosphate + Fructose 1-phosphate <> ADP + beta-D-Fructose 1,6-bisphosphate
Fructose 1-phosphate <> Dihydroxyacetone phosphate + D-Glyceraldehyde
Protein N(pi)-phospho-L-histidine + D-Fructose <> Protein histidine + Fructose 1-phosphate
Fructose 1-phosphate + Water > D-fructose + Phosphate
D-fructose + Phosphoenolpyruvic acid > Fructose 1-phosphate + Pyruvic acid
Adenosine triphosphate + Fructose 1-phosphate > ADP + Fructose 1,6-bisphosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-9470000000-18ac582a370338a3f5f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01oy-7390000000-1a5a72af8bb734e50eb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-009y-9100000000-4f151f373d7730140f38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-9270000000-5af91634007091008210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5cf3f457b8c6f6270b68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4e6feccf18943de8c419View in MoNA
References
References:
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Hara, 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
External Links:
ResourceLink
CHEBI ID18105
HMDB IDHMDB01076
Pubchem Compound ID439394
Kegg IDC01094
ChemSpider ID8575807
WikipediaFructose 1-phosphate
BioCyc IDFRU1P
EcoCyc IDFRU1P
Ligand ExpoF1X