Human Metabolome Database Version 3.5

Showing metabocard for Fructose 1-phosphate (HMDB01076)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:50 -0700
HMDB ID HMDB01076
Secondary Accession Numbers None
Metabolite Identification
Common Name Fructose 1-phosphate
Description Fructose 1-phosphate is an intermediate metabolite in the Fructose and mannose metabolism pathway.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H13O9P
Average Molecular Weight 260.1358
Monoisotopic Molecular Weight 260.029718526
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 Number 15978-08-2
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 Key RHKKZBWRNHGJEZ-ARQDHWQXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Pentoses
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 Parent Pentoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 33.4 g/L ALOGPS
LogP -2.11 ALOGPS
LogP -2.9 ChemAxon
LogS -0.89 ALOGPS
pKa (strongest acidic) 1.16 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 156.91 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 47.23 ChemAxon
Polarizability 21.06 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Fructose and Mannose Degradation SMP00064 map00051 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022410
KNApSAcK ID Not Available
Chemspider ID 8575807 Link_out
KEGG Compound ID C01094 Link_out
BioCyc ID FRU1P Link_out
BiGG ID 40936 Link_out
Wikipedia Link Fructose 1-phosphate Link_out
NuGOwiki Link HMDB01076 Link_out
Metagene Link HMDB01076 Link_out
METLIN ID 378 Link_out
PubChem Compound 10400369 Link_out
PDB ID F1X Link_out
ChEBI ID 704854 Link_out
References
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
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 Link_out
  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 Link_out
  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 Link_out
  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. Pubmed: 19212411 Link_out

Enzymes
Name: Fructose-bisphosphate aldolase A
Reactions:
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
Gene Name: ALDOA
Uniprot ID: P04075 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase C
Reactions:
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
Gene Name: ALDOC
Uniprot ID: P09972 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fructose-bisphosphate aldolase B
Reactions:
Fructose 1-phosphate unknown Dihydroxyacetone phosphate + Glyceraldehyde details
Gene Name: ALDOB
Uniprot ID: P05062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ketohexokinase
Reactions: Not Available
Gene Name: KHK
Uniprot ID: P50053 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA