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(4S)-4,5-Dihydroxypentan-2,3-dione (M2MDB002034)

Record Information
Version2.0
Creation Date2012-08-15 08:51:29 -0600
Update Date2015-06-03 17:21:59 -0600
Secondary Accession Numbers
  • ECMDB21640
Identification
Name:(4S)-4,5-Dihydroxypentan-2,3-dione
Description(4S)-4,5-dihydroxypentan-2,3-dione is a member of the chemical class known as Beta Ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the second carbon atom.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • (4S)-4,5-dihydroxypentane-2,3-dione
  • (S)-4,5-dihydroxypentane-2,3-dione
  • 4,5-Dihydroxy-2,3-pentanedione
Chemical Formula:C5H8O4
Weight:Average: 132.1146
Monoisotopic: 132.042258744
InChI Key:UYTRITJAZOPLCZ-BYPYZUCNSA-N
InChI:InChI=1S/C5H8O4/c1-3(7)5(9)4(8)2-6/h4,6,8H,2H2,1H3/t4-/m0/s1
CAS number:Not Available
IUPAC Name:(4S)-4,5-dihydroxypentane-2,3-dione
Traditional IUPAC Name:4,5-dihydroxy-2,3-pentanedione
SMILES:CC(=O)C(=O)[C@@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Monosaccharide
  • Beta-hydroxy ketone
  • Alpha-diketone
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • 1,2-diol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility272 g/LALOGPS
logP-0.95ALOGPS
logP-0.9ChemAxon
logS0.31ALOGPS
pKa (Strongest Acidic)11.69ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.28 m³·mol⁻¹ChemAxon
Polarizability12.03 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
S-Ribosyl-L-homocysteine <> (4S)-4,5-Dihydroxypentan-2,3-dione + L-Homocysteine
S-Ribosyl-L-homocysteine > L-Homocysteine + (4S)-4,5-Dihydroxypentan-2,3-dione
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-3900000000-c3606a0de0753ee55e3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xs-9300000000-5983224a4b111e5924f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-9000000000-85c056bb028337d6565aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-9700000000-c58778f342acf421218fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-9200000000-b0bb1b99ccfc328190edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-2cd2700615652d11591bView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID29484
HMDB IDNot Available
Pubchem Compound ID11170991
Kegg IDC11838
ChemSpider ID9346083
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. S-ribosylhomocysteine lyase
General function:
Involved in catalytic activity
Specific function:
Involved in the synthesis of autoinducer 2 (AI-2) which is secreted by bacteria and is used to communicate both the cell density and the metabolic potential of the environment. The regulation of gene expression in response to changes in cell density is called quorum sensing. Catalyzes the transformation of S-ribosylhomocysteine (RHC) to homocysteine (HC) and 4,5- dihydroxy-2,3-pentadione (DPD)
Gene Name:
luxS
Uniprot ID:
P45578
Molecular weight:
19416
Reactions
S-(5-deoxy-D-ribos-5-yl)-L-homocysteine = L-homocysteine + (4S)-4,5-dihydroxypentan-2,3-dione.