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Record Information
Version1.0
Created at2017-03-23 03:12:34 UTC
Updated at2021-10-07 20:38:22 UTC
NP-MRD IDNP0000751
Secondary Accession NumbersNone
Natural Product Identification
Common NameFructose-1P
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. 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
Thumb
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
b-D-Fructofuranose 1-phosphateHMDB
b-D-Fructofuranose 1-phosphoric acidHMDB
beta-D-Fructofuranose 1-phosphoric acidHMDB
Β-D-fructofuranose 1-phosphateHMDB
Β-D-fructofuranose 1-phosphoric acidHMDB
Chemical FormulaC6H12O6
Average Mass180.1559 Da
Monoisotopic Mass180.06339 Da
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 Number57-48-7
SMILES
[H][C@@](O)(CO)[C@@]([H])(O)[C@]([H])(O)C(=O)CO
InChI Identifier
InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1
InChI KeyBJHIKXHVCXFQLS-UYFOZJQFSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Actinidia hemsleyanaLOTUS Database
Allium cepaLOTUS Database
Allium suworowiiLOTUS Database
Aloe veraLOTUS Database
Alstroemeria revolutaLOTUS Database
Anethum graveolensLOTUS Database
Annona squamosaLOTUS Database
Arabidopsis thalianaLOTUS Database
Arbutus unedoLOTUS Database
Aristolochia arcuataLOTUS Database
Aristolochia baeticaLOTUS Database
Ascoseira mirabilisLOTUS Database
Astragalus hamosusLOTUS Database
Bryum capillareLOTUS Database
Cajanus cajanLOTUS Database
Cannabis sativaLOTUS Database
Carum carviLOTUS Database
Centaurea jaceaLOTUS Database
Colchicum schimperiLOTUS Database
Coriandrum sativumLOTUS Database
Cucurbita foetidissimaLOTUS Database
Dovyalis caffraLOTUS Database
Euphorbia helioscopiaLOTUS Database
Evernia prunastriLOTUS Database
Foeniculum vulgareLOTUS Database
Fragaria x ananassaLOTUS Database
Gastrodia elataLOTUS Database
Gentiana orbicularisLOTUS Database
Glycine maxLOTUS Database
Glycyrrhiza glabraLOTUS Database
Helianthus annuusLOTUS Database
Hypericum perforatumLOTUS Database
Inga spectabilisLOTUS Database
Levisticum officinaleLOTUS Database
Ligularia intermediaLOTUS Database
Maclura pomiferaLOTUS Database
Marsdenia tomentosaLOTUS Database
Medicago sativaLOTUS Database
Momordica cochinchinensisLOTUS Database
Mus musculusLOTUS Database
Nicotiana tabacumLOTUS Database
Olea europaeaLOTUS Database
Olearia paniculataLOTUS Database
Panax ginsengLOTUS Database
Panax quinquefoliusLOTUS Database
Passiflora oerstediiLOTUS Database
Phaseolus coccineusLOTUS Database
Phyllostachys edulisLOTUS Database
Piper retrofractumLOTUS Database
Pisum sativumLOTUS Database
Planchonella vitiensisLOTUS Database
Plinia caulifloraLOTUS Database
Prunus aviumPlant
Prunus domesticaLOTUS Database
Prunus laurocerasusLOTUS Database
Psidium guajavaLOTUS Database
Pycnandra acuminataLOTUS Database
Pyrus communisLOTUS Database
Rehmannia glutinosaLOTUS Database
Salacia oblongaLOTUS Database
Salacia reticulataLOTUS Database
Salsola collinaLOTUS Database
Schleichera oleosaLOTUS Database
Streptomyces murinusLOTUS Database
Tamarix aphyllaLOTUS Database
Tecoma stansLOTUS Database
Tetrapleura tetrapteraLOTUS Database
Theobroma cacaoLOTUS Database
Theonella swinhoei-
Tillandsia usneoidesLOTUS Database
Torilis japonicaLOTUS Database
Tragopogon pratensisLOTUS Database
Tulipa turkestanicaLOTUS Database
Turnera diffusaLOTUS Database
Vitis viniferaLOTUS Database
Xylocarpus granatumLOTUS Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility399 g/lTetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)
LogP-2.23Tetko, I. V., Gasteiger, J., Todeschini, R., Mauri, A., Livingstone, D., Ertl, P., Palyulin, V.A., Radchenko, E.V., Zefirov, N.S., Makarenko, A.S., Tanchuk, V.Y. & Prokopenko, V. V. (2005). Virtual computational chemistry laboratory-design and description. Journal of computer-aided molecular design, 19(6), 453-463. (http://www.vcclab.org/lab/alogps/)
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0001076
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022410
KNApSAcK IDC00019676
Chemspider ID8575807
KEGG Compound IDC01094
BioCyc IDFRU1P
BiGG ID40936
Wikipedia LinkFructose 1-phosphate
METLIN ID378
PubChem Compound10400369
PDB IDNot Available
ChEBI ID139419
Good Scents IDNot Available
References
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  3. 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. doi: 10.1046/j.0022-3042.2001.00677.x. [PubMed:11796742 ]
  4. 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 ]
  5. 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. doi: 10.1301/002966402320289377. [PubMed:12199300 ]