Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


L-Rhamnonate (M2MDB003465)

Record Information
Version2.0
Creation Date2012-10-10 12:15:02 -0600
Update Date2015-06-03 17:25:52 -0600
Secondary Accession Numbers
  • ECMDB23075
Identification
Name:L-Rhamnonate
DescriptionL-Rhamnoate (6-deoxy-L-mannonate) is a mono-acid sugar. It is the preferred substrate for the E. coli enzyme called L-Rhamnoate dehydratase (YfaW). L-Rhamnonate, L-mannonate, and L-lyxonate share the same configurations at carbons-2, -3, and -4; D-gulonate differs from L-rhamnonate and L-mannonate by the configuration of carbon-5.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 6-Deoxy-L-mannonate
  • 6-Deoxy-L-mannonic acid
  • L-Rhamnonic acid
Chemical Formula:C6H12O6
Weight:Average: 180.1559
Monoisotopic: 180.063388116
InChI Key:NBFWIISVIFCMDK-QMKXCQHVSA-N
InChI:InChI=1S/C6H12O6/c1-2(7)3(8)4(9)5(10)6(11)12/h2-5,7-10H,1H3,(H,11,12)/t2-,3-,4+,5+/m0/s1
CAS number:Not Available
IUPAC Name:(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanoic acid
Traditional IUPAC Name:L-rhamnonic acid
SMILES:[H][C@@](C)(O)[C@]([H])(O)[C@@]([H])(O)[C@@]([H])(O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • 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 Solubility169 g/LALOGPS
logP-2.1ALOGPS
logP-2.4ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.73 m³·mol⁻¹ChemAxon
Polarizability16.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Rhamnonate + L-Rhamnonate <> 2-Dehydro-3-deoxy-L-rhamnonate + Water
L-Rhamnonate > 2-Dehydro-3-deoxy-L-rhamnonate + Water
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_3_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-2900000000-9044f12679ca05d4a3b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-9500000000-b6b42ceebf4868143af1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9100000000-a4eebfc103952104e418View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-9700000000-39bbdaba9e867f404bb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i9-9400000000-c325f8306fafd678aa0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-0f819a95990bc10662e2View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17357
HMDB IDNot Available
Pubchem Compound ID6602429
Kegg IDC01934
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. L-rhamnonate dehydratase
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.