2.0
2012-05-31 14:23:15 -0600
2015-09-17 16:24:16 -0600
ECMDB20020
M2MDB000869
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
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.
(<i>E</i>)-4-hydroxy-3-methylbut 2-en-1-yl diphosphate
(<i>E</i>)-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
C5H12O8P2
262.0915
262.000740384
{[hydroxy({[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid
{hydroxy[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxyphosphoryl}oxyphosphonic acid
CC(CO)=CCOP(O)(=O)OP(O)(O)=O
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)
MDSIZRKJVDMQOQ-UHFFFAOYSA-N
Cytosol
logp
-0.31
ALOGPS
logs
-1.56
ALOGPS
solubility
7.16e+00 g/l
ALOGPS
logp
-0.98
ChemAxon
pka_strongest_acidic
1.77
ChemAxon
pka_strongest_basic
-2.7
ChemAxon
iupac
{[hydroxy({[(2E)-4-hydroxy-3-methylbut-2-en-1-yl]oxy})phosphoryl]oxy}phosphonic acid
ChemAxon
average_mass
262.0915
ChemAxon
mono_mass
262.000740384
ChemAxon
smiles
CC(CO)=CCOP(O)(=O)OP(O)(O)=O
ChemAxon
formula
C5H12O8P2
ChemAxon
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)
ChemAxon
inchikey
MDSIZRKJVDMQOQ-UHFFFAOYSA-N
ChemAxon
polar_surface_area
133.52
ChemAxon
refractivity
50.9
ChemAxon
polarizability
20.3
ChemAxon
rotatable_bond_count
6
ChemAxon
acceptor_count
6
ChemAxon
donor_count
4
ChemAxon
physiological_charge
-2
ChemAxon
formal_charge
0
ChemAxon
Terpenoid backbone biosynthesis
ec00900
Metabolic pathways
eco01100
methylerythritol phosphate pathway
NONMEVIPP-PWY
Specdb::MsMs
1243438
Specdb::MsMs
1243439
Specdb::MsMs
1243440
Specdb::MsMs
1358803
Specdb::MsMs
1358804
Specdb::MsMs
1358805
786
4445244
C11811
15664
HYDROXY-METHYL-BUTENYL-DIP
H6P
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.
21097882
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.
22080510
4-hydroxy-3-methylbut-2-en-1-yl diphosphate synthase
P62620
ISPG_ECOLI
ispG
http://ecmdb.ca/proteins/P62620.xml
4-hydroxy-3-methylbut-2-enyl diphosphate reductase
P62623
ISPH_ECOLI
ispH
http://ecmdb.ca/proteins/P62623.xml
Flavodoxin-2
P0ABY4
FLAW_ECOLI
fldB
http://ecmdb.ca/proteins/P0ABY4.xml
Flavodoxin-1
P61949
FLAV_ECOLI
fldA
http://ecmdb.ca/proteins/P61949.xml
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
R08209
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Dimethylallylpyrophosphate + Water + NAD
R08210
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water
R05884
Dimethylallylpyrophosphate + NADP + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion
R07219
Isopentenyl pyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion
R08209
Dimethylallylpyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion
R08210
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
R08689
Isopentenyl pyrophosphate + NAD(P)<sup>+</sup> + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ion
ISPH2-RXN
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water + Oxidized-ferredoxins < 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + Hydrogen ion + Reduced-ferredoxins
RXN0-882
NAD(P)<sup>+</sup> + Dimethylallylpyrophosphate + Water < NAD(P)H + Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate
RXN0-884
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
R05884 R08209
2 2-C-Methyl-D-erythritol-2,4-cyclodiphosphate + 2 Reduced ferredoxin + Oxidized ferredoxin <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + Water
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD