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L-3,4-Dihydroxybutan-2-one 4-phosphate (M2MDB003511)

Record Information
Version2.0
Creation Date2012-10-10 12:17:30 -0600
Update Date2015-06-03 17:25:58 -0600
Secondary Accession Numbers
  • ECMDB23121
Identification
Name:L-3,4-Dihydroxybutan-2-one 4-phosphate
DescriptionL-3,4-Dihydroxybutan-2-one 4-phosphate is an intermediate involved in riboflavin metabolism. It is a substrate for the enzyme 6,7-dimethyl-8-ribityllumazine synthase which atalyzes the formation of 6,7-dimethyl-8-ribityllumazine by condensation of 5-amino-6-(D-ribitylamino)uracil with 3,4-dihydroxy-2-butanone 4-phosphate. This is the penultimate step in the biosynthesis of riboflavin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-2-hydroxy-3-oxobutyl dihydrogen phosphate
  • (2S)-2-Hydroxy-3-oxobutyl dihydrogen phosphoric acid
  • (3S)-3-hydroxy-4-(phosphonooxy)butan-2-one
  • (S)-3-hydroxy-4-(phosphonooxy)-2-butanone
  • 1-deoxy-L-glycero-tetrulose 4-phosphate
  • 1-Deoxy-L-glycero-tetrulose 4-phosphoric acid
  • 2-Butanone, 3-hydroxy-4-(phosphonooxy)-, (S)-
  • 3,4-Dhbp
  • 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-BYPYZUCNSA-N
InChI:InChI=1S/C4H9O6P/c1-3(5)4(6)2-10-11(7,8)9/h4,6H,2H2,1H3,(H2,7,8,9)/t4-/m0/s1
CAS number:Not Available
IUPAC Name:[(2S)-2-hydroxy-3-oxobutoxy]phosphonic acid
Traditional IUPAC Name:(2S)-2-hydroxy-3-oxobutoxyphosphonic acid
SMILES:CC(=O)[C@@H](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:
L-3,4-Dihydroxybutan-2-one 4-phosphate + 5-amino-6-ribitylamino-2,4(1h,3h)-pyrimidinedione > 6,7-dimethyl-8-(D-ribityl)lumazine +2 Water + Inorganic phosphate
SMPDB Pathways:Not Available
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
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID50608
HMDB IDNot Available
Pubchem Compound ID14056322
Kegg IDC15556
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 6,7-dimethyl-8-ribityllumazine synthase
General function:
Involved in riboflavin biosynthetic process
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 beta subunit catalyzes the condensation of 5-amino-6-(1'-D)-ribityl-amino- 2,4(1H,3H)-pyrimidinedione with L-3,4-dihydrohy-2-butanone-4- phosphate yielding 6,7-dimethyl-8-lumazine
Gene Name:
ribH
Uniprot ID:
P61714
Molecular weight:
16156
Reactions
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = riboflavin + 4-(1-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine.