Record Information
Version2.0
Creation Date2012-05-31 14:31:00 -0600
Update Date2015-09-17 15:42:01 -0600
Secondary Accession Numbers
  • ECMDB20166
Identification
Name:L-Rhamnulose 1-phosphate
DescriptionL-rhamnulose 1-phosphate is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose.
Structure
Thumb
Synonyms:
  • 6-Deoxy-1-O-phosphono-L-sorbose
  • 6-Deoxy-L-sorbose 1-(dihydrogen phosphate)
  • 6-Deoxy-L-sorbose 1-(dihydrogen phosphoric acid)
  • 6-Deoxy-L-sorbose 1-phosphate
  • 6-Deoxy-L-sorbose 1-phosphoric acid
  • L-Rhamnulose 1-phosphoric acid
  • L-Rhamnulose-1P
  • Rhamnulose 1-phosphate
  • Rhamnulose 1-phosphoric acid
  • Rhamnulose-1-P
  • Rhamnulose-1-phosphate
  • Rhamnulose-1-phosphoric acid
Chemical Formula:C9H19O5P
Weight:Average: 238.22
Monoisotopic: 238.09701071
InChI Key:QRXAIBTYLQNPRQ-UHFFFAOYSA-N
InChI:InChI=1S/C9H19O5P/c1-6(5-14-15(3,4)13)8(11)9(12)7(2)10/h7-13H,1,3,5H2,2,4H3
CAS number:444-09-7
IUPAC Name:{[(3S,4R,5S)-3,4,5-trihydroxy-2-oxohexyl]oxy}phosphonic acid
Traditional IUPAC Name:L-rhamnulose 1-phosphate
SMILES:CC(O)C(O)C(O)C(=C)COP(C)(O)=C
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
Substituents
  • Octose monosaccharide
  • Monosaccharide phosphate
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Sugar acid
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP-1.9ALOGPS
logP-2.3ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity46.89 m³·mol⁻¹ChemAxon
Polarizability20.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
fucose and rhamnose degradationPW000826 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Microbial metabolism in diverse environments ec01120
  • Pentose and glucuronate interconversions ec00040
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-4690000000-17d50e11374f92e3400bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0570-4920000000-9ae486510db3f7669f8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9400000000-f5b1483aaa2a22aee511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fvi-9820000000-96d11cb52700915d345fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-748c93e00b37e4e87981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-17db9f9872cd5d9166e0View in MoNA
References
References:
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17892
HMDB IDNot Available
Pubchem Compound ID439413
Kegg IDC01131
ChemSpider ID388527
Wikipedia IDNot Available
BioCyc IDRHAMNULOSE-1P
EcoCyc IDRHAMNULOSE-1P

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the reversible cleavage of L-rhamnulose-1- phosphate to dihydroxyacetone phosphate (DHAP) and L-lactaldehyde
Gene Name:
rhaD
Uniprot ID:
P32169
Molecular weight:
30145
Reactions
L-rhamnulose 1-phosphate = glycerone phosphate + (S)-lactaldehyde.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
ATP + L-rhamnulose = ADP + L-rhamnulose 1- phosphate
Gene Name:
rhaB
Uniprot ID:
P32171
Molecular weight:
54069
Reactions
ATP + L-rhamnulose = ADP + L-rhamnulose 1-phosphate.