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1-Deoxy-L-glycero-tetrulose 4-phosphate (M2MDB003512)

Record Information
Version2.0
Creation Date2012-10-10 12:17:32 -0600
Update Date2015-06-03 17:25:58 -0600
Secondary Accession Numbers
  • ECMDB23122
Identification
Name:1-Deoxy-L-glycero-tetrulose 4-phosphate
Description1-deoxy-L-glycero-tetrulose 4-phosphate is an intermediate in the synthesis of riboflavin. It is a substrate for the enzyme 6,7-dimethyl-8-ribityllumazine synthase (RibE) which catalyzes the formation of 6,7-dimethyl-8 ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 1-deoxy-L-glycero-tetrulose 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2-hydroxy-3-oxobutyl) dihydrogen phosphate
  • (2-Hydroxy-3-oxobutyl) dihydrogen phosphoric acid
  • 1-Deoxy-L-glycero-tetrulose 4-phosphoric acid
  • 2-Hydroxy-3-oxobutyl dihydrogen phosphate
  • 2-Hydroxy-3-oxobutyl dihydrogen phosphoric acid
  • 2-Hydroxy-3-oxobutyl phosphate
  • 2-Hydroxy-3-oxobutyl phosphoric acid
  • 3,4-Dihydroxy-2-butanone 4-phosphate
  • 3,4-Dihydroxy-2-butanone 4-phosphoric acid
  • L-3,4-Dihydroxybutan-2-one 4-phosphate
  • L-3,4-Dihydroxybutan-2-one 4-phosphoric acid
Chemical Formula:C4H9O6P
Weight:Average: 184.0844
Monoisotopic: 184.013674532
InChI Key:OKYHYXLCTGGOLM-UHFFFAOYSA-N
InChI:InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)
CAS number:Not Available
IUPAC Name:(2-hydroxy-3-oxobutoxy)phosphonic acid
Traditional IUPAC Name:2-hydroxy-3-oxobutyl phosphate
SMILES:CC(=O)C(O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Monosaccharide
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility24.9 g/LALOGPS
logP-1.6ALOGPS
logP-1.3ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)1.39ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.81 m³·mol⁻¹ChemAxon
Polarizability14.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
D-Ribulose 5-phosphate > Formic acid + 1-Deoxy-L-glycero-tetrulose 4-phosphate
D-Ribulose 5-phosphate > 1-Deoxy-L-glycero-tetrulose 4-phosphate + Formic acid + Hydrogen ion
5-Amino-6-ribitylamino uracil + 1-Deoxy-L-glycero-tetrulose 4-phosphate > Water + Phosphate + Hydrogen ion + 6,7-Dimethyl-8-(1-D-ribityl)lumazine + 6,7-Dimethyl-8-(1-D-ribityl)lumazine
SMPDB Pathways:
Flavin biosynthesisPW001971 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9400000000-971962d1d681055c1e3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-3900000000-a3d7948fc05904e06862View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014s-9500000000-31ec6e7cea40d06a6892View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9000000000-beb8708b4dc7d349cdeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-5900000000-9e4612499bf4e2f07fc5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-425643565aa835d01981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0ef89293cd43e0a1a071View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-676cc37240e7d973e2afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-a6ca687b980625713d4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-9000000000-c6888871a1308dc01b19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9000000000-e30f5f83dc1e6cb4f00fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView 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 ID50608
HMDB IDHMDB0304013
Pubchem Compound ID669
Kegg IDC15556
ChemSpider ID649
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 3,4-dihydroxy-2-butanone 4-phosphate synthase
General function:
Involved in 3,4-dihydroxy-2-butanone-4-phosphate synthase activity
Specific function:
Catalyzes the conversion of D-ribulose 5-phosphate to formate and 3,4-dihydroxy-2-butanone 4-phosphate
Gene Name:
ribB
Uniprot ID:
P0A7J0
Molecular weight:
23353
Reactions
D-ribulose 5-phosphate = formate + L-3,4-dihydroxybutan-2-one 4-phosphate.
Protein Details
2. Riboflavin synthase alpha chain
General function:
Involved in riboflavin synthase activity
Specific function:
Riboflavin synthase is a bifunctional enzyme complex catalyzing the formation of riboflavin from 5-amino-6-(1'-D)- ribityl-amino-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydrohy-2- butanone-4-phosphate via 6,7-dimethyl-8-lumazine. The alpha subunit catalyzes the dismutation of 6,7-dimethyl-8-lumazine to riboflavin and 5-amino-6-(1'-D)-ribityl-amino-2,4(1H,3H)- pyrimidinedione
Gene Name:
ribE
Uniprot ID:
P0AFU8
Molecular weight:
23445
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.
Protein Details
3. 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the formation of 4-diphosphocytidyl-2-C- methyl-D-erythritol from CTP and 2-C-methyl-D-erythritol 4- phosphate (MEP)
Gene Name:
ispD
Uniprot ID:
Q46893
Molecular weight:
25737
Reactions
CTP + 2-C-methyl-D-erythritol 4-phosphate = diphosphate + 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol.