Record Information
Version2.0
Creation Date2012-08-15 08:51:30 -0600
Update Date2015-06-03 17:22:00 -0600
Secondary Accession Numbers
  • ECMDB21644
Identification
Name:2-Dehydro-3-deoxy-L-rhamnonate
Description2-dehydro-3-deoxy-l-rhamnonate belongs to the class of Keto Fatty Acids. These are fatty acids containing a ketone group attached to the acyl chain.
Structure
Thumb
Synonyms:
  • 2-Dehydro-3,6-dideoxy-L-mannonate
  • 2-Dehydro-3,6-dideoxy-L-mannonic acid
  • 2-Dehydro-3-deoxy-L-rhamnonate
  • 2-Dehydro-3-deoxy-L-rhamnonic acid
  • 3,6-Dideoxy-L-arabino-hex-2-ulosonate
  • 3,6-Dideoxy-L-arabino-hex-2-ulosonic acid
Chemical Formula:C6H10O5
Weight:Average: 162.1406
Monoisotopic: 162.05282343
InChI Key:FRIWJYNKZPJVRL-IUYQGCFVSA-N
InChI:InChI=1S/C6H10O5/c1-3(7)4(8)2-5(9)6(10)11/h3-4,7-8H,2H2,1H3,(H,10,11)/t3-,4+/m0/s1
CAS number:Not Available
IUPAC Name:(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid
Traditional IUPAC Name:(4R,5S)-4,5-dihydroxy-2-oxohexanoic acid
SMILES:[H][C@@](C)(O)[C@]([H])(O)CC(=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Alpha-hydroxy ketone
  • 1,2-diol
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility119 g/LALOGPS
logP-1.3ALOGPS
logP-0.73ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.77 m³·mol⁻¹ChemAxon
Polarizability14.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Fructose and mannose metabolism ec00051
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-527c02e76a89144a4ebeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002k-9700000000-058bac2bc8bc9e2a411eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9100000000-58ffe2f9b9affc7bb4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3900000000-d3497eb4995bd5913e87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9300000000-2f7eaa4710b6f7eb62aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-13f3f80adf78936c1b31View in MoNA
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18078
HMDB IDNot Available
Pubchem Compound ID49852300
Kegg IDC03979
ChemSpider ID26331139
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in carbon-carbon lyase activity
Specific function:
Catalyzes the reversible retro-aldol cleavage of 2-keto- 3-deoxy-L-rhamnonate (KDR) to pyruvate and lactaldehyde. 2-keto-3- deoxy-L-mannonate, 2-keto-3-deoxy-L-lyxonate and 4-hydroxy-2- ketoheptane-1,7-dioate (HKHD) are also reasonably good substrates, although 2-keto-3-deoxy-L-rhamnonate is likely to be the physiological substrate
Gene Name:
rhmA
Uniprot ID:
P76469
Molecular weight:
28916
Reactions
2-dehydro-3-deoxy-L-rhamnonate = pyruvate + (R)-lactaldehyde.
General function:
Involved in L-rhamnonate dehydratase activity
Specific function:
Catalyzes the dehydration of L-rhamnonate to 2-keto-3- deoxy-L-rhamnonate (KDR). Can also dehydrate L-lyxonate, L- mannonate and D-gulonate, although less efficiently, but not 2- keto-4-hydroxyheptane-1,7-dioate
Gene Name:
rhmD
Uniprot ID:
P77215
Molecular weight:
44226
Reactions
L-rhamnonate = 2-dehydro-3-deoxy-L-rhamnonate + H(2)O.