1-Hydroxy-2-methyl-2-butenyl 4-diphosphate (PAMDB000869)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000869
Identification
Name: 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
Description:1-hydroxy-2-methyl-2-butenyl 4-diphosphate is a member of the chemical class known as Organic Pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate
  • (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate
  • (E)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate
  • (e)-4-Hydroxy-3-methylbut 2-en-1-yl diphosphoric acid
  • (E)-4-Hydroxy-3-methylbut-2-en-1-yl diphosphate
  • (e)-4-Hydroxy-3-methylbut-2-en-1-yl diphosphoric acid
  • 1-Hydroxy-2-methyl-2-butenyl 4-diphosphoric acid
  • Hmbdp
  • HMeBuPP
Chemical Formula: C5H12O8P2
Average Molecular Weight: 262.0915
Monoisotopic Molecular Weight: 262.000740384
InChI Key: MDSIZRKJVDMQOQ-UHFFFAOYSA-N
InChI:InChI=1S/C5H12O8P2/c1-5(4-6)2-3-12-15(10,11)13-14(7,8)9/h2,6H,3-4H2,1H3,(H,10,11)(H2,7,8,9)
CAS number: Not Available
IUPAC Name:{[hydroxy({[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional IUPAC Name: {hydroxy[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxyphosphoryl}oxyphosphonic acid
SMILES:CC(CO)=CCOP(O)(=O)OP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility7.16 mg/mLALOGPS
logP-0.31ALOGPS
logP-0.98ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity50.9 m3·mol-1ChemAxon
Polarizability20.3 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Flavodoxin reduced + Hydrogen ion >2 flavodoxin semi oxidized + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Dimethylallylpyrophosphate + Water + NAD
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water
Dimethylallylpyrophosphate + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion
2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Reduced ferredoxin + Oxidized ferredoxin <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water +2 Oxidized ferredoxin + Reduced ferredoxin
Isopentenyl pyrophosphate + NAD(P)<sup>+</sup> + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ion
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + Oxidized-ferredoxins < 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Hydrogen ion + Reduced-ferredoxins
NAD(P)<sup>+</sup> + Dimethylallylpyrophosphate + Water < NAD(P)H + Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + 2 oxidized ferredoxin > 2-C-Methyl-D-erythritol 2,4-cyclodiphosphate +2 reduced ferredoxin
Isopentenyl pyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H
Dimethylallylpyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H
Isopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ion
Pathways:
Spectra
Spectra:
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15664
HMDB IDNot Available
Pubchem Compound ID786
Kegg IDC11811
ChemSpider ID4445244
Wikipedia IDNot Available
BioCyc IDHYDROXY-METHYL-BUTENYL-DIP
EcoCyc IDHYDROXY-METHYL-BUTENYL-DIP
Ligand ExpoH6P

Enzymes

Protein Details
• 4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase
General function:
Involved in catalytic activity
Specific function:
Converts 2C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-2,4cPP) into 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate
Gene Name:
ispG
Locus Tag:
PA3803
Molecular weight:
40.1 kDa
Reactions
(E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + H(2)O + 2 oxidized ferredoxin = 2-C-methyl-D-erythritol 2,4-cyclodiphosphate + 2 reduced ferredoxin.
Protein Details
• 4-hydroxy-3-methylbut-2-enyl diphosphate reductase
General function:
Involved in isopentenyl diphosphate biosynthetic process, mevalonate-independent pathway
Specific function:
Converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is also involved in penicillin tolerance and control of the stringent response. Seems to directly or indirectly interact with relA to maintain it in an inactive form during normal growth
Gene Name:
ispH
Locus Tag:
PA4557
Molecular weight:
34.8 kDa
Reactions
Isopentenyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
Dimethylallyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.