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MetaCyc Compound: isopentenyl diphosphate

Abbrev Name: IPP

Synonyms: isopentenyl-pp, isopentenyl pyrophosphate, IPP, δ(3)-isopentenyl-PP, Δ3-isopentenyl-PP, 3-methylbut-3-enyl diphosphate, 3-methylbut-3-enyl pyrophosphate

Chemical Formula: C5H9O7P2

Molecular Weight: 243.07 Daltons

Monoisotopic Molecular Weight: 246.0058257599 Daltons

SMILES: C=C(C)CCOP([O-])(=O)OP([O-])(=O)[O-]

InChI: InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)/p-3

InChIKey: InChIKey=NUHSROFQTUXZQQ-UHFFFAOYSA-K

Unification Links: ChEBI:128769 , ChemSpider:13115335 , HMDB:HMDB01347 , IAF1260:33956 , KEGG:C00129 , MetaboLights:MTBLC128769 , PubChem:15983957

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -350.20844 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

all-trans-decaprenyl diphosphate biosynthesis , ubiquinol-10 biosynthesis (eukaryotic) :
(2E,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate → all-trans-decaprenyl diphosphate + 7 diphosphate

bergamotene biosynthesis II :
dimethylallyl diphosphate + 2 isopentenyl diphosphate → (2Z,6Z)-farnesyl diphosphate + 2 diphosphate

brassicicene C biosynthesis , fusicoccin A biosynthesis , geranylgeranyl diphosphate biosynthesis , paspaline biosynthesis , plaunotol biosynthesis :
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → geranylgeranyl diphosphate + diphosphate

dolichol and dolichyl phosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 13 isopentenyl diphosphatedi-trans, poly-cis-polyprenyl diphosphate (C80) + 13 diphosphate

mono-trans, poly-cis decaprenyl phosphate biosynthesis :
(2Z,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate → ω, mono-trans,octa-cis-decaprenyl diphosphate + 7 diphosphate
geranyl diphosphate + isopentenyl diphosphate → (2Z,6E)-farnesyl diphosphate + diphosphate

nonaprenyl diphosphate biosynthesis I :
geranyl diphosphate + 7 isopentenyl diphosphate → all-trans-nonaprenyl diphosphate + 7 diphosphate

nonaprenyl diphosphate biosynthesis II :
geranylgeranyl diphosphate + 5 isopentenyl diphosphate → all-trans-nonaprenyl diphosphate + 5 diphosphate

octaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate → all-trans-octaprenyl diphosphate + 5 diphosphate

trichome monoterpenes biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate → neryl diphosphate + diphosphate

Reactions known to produce the compound:

isoprene biosynthesis II (engineered) , mevalonate pathway I :
(R)-mevalonate diphosphate + ATP → isopentenyl diphosphate + CO2 + ADP + phosphate

methylerythritol phosphate pathway I , methylerythritol phosphate pathway II :
isopentenyl diphosphate + NAD(P)+ + H2O ← 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + NAD(P)H + H+

Reactions known to both consume and produce the compound:

all-trans-farnesol biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate
isopentenyl diphosphate ↔ dimethylallyl diphosphate
geranyl diphosphate + isopentenyl diphosphate ↔ (2E,6E)-farnesyl diphosphate + diphosphate

bisabolene biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate
isopentenyl diphosphate ↔ dimethylallyl diphosphate
geranyl diphosphate + isopentenyl diphosphate ↔ (2E,6E)-farnesyl diphosphate + diphosphate

geranyl diphosphate biosynthesis , ipsdienol biosynthesis , linalool biosynthesis I , linalool biosynthesis II , superpathway of linalool biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate

isoprene biosynthesis II (engineered) , methylerythritol phosphate pathway I , methylerythritol phosphate pathway II , mevalonate pathway I :
isopentenyl diphosphate ↔ dimethylallyl diphosphate

mevalonate pathway II (archaea) :
isopentenyl phosphate + ATP ↔ isopentenyl diphosphate + ADP
isopentenyl diphosphate ↔ dimethylallyl diphosphate

mevalonate pathway III (archaea) :
isopentenyl phosphate + ATP ↔ isopentenyl diphosphate + ADP
isopentenyl diphosphate ↔ dimethylallyl diphosphate

mono-trans, poly-cis decaprenyl phosphate biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate
isopentenyl diphosphate ↔ dimethylallyl diphosphate

trans, trans-farnesyl diphosphate biosynthesis :
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate
isopentenyl diphosphate ↔ dimethylallyl diphosphate
geranyl diphosphate + isopentenyl diphosphate ↔ (2E,6E)-farnesyl diphosphate + diphosphate

In Reactions of unknown directionality:

all trans undecaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = all-trans-undecaprenyl diphosphate + 8 diphosphate

di-trans,poly-cis-undecaprenyl phosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + 8 diphosphate

dodecaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 9 isopentenyl diphosphate = all-trans-dodecaprenyl diphosphate + 9 diphosphate

heptaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 4 isopentenyl diphosphate = all-trans-heptaprenyl diphosphate + 4 diphosphate

hexaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 3 isopentenyl diphosphate = all-trans-hexaprenyl diphosphate + 3 diphosphate

rubber biosynthesis :
isopentenyl diphosphate + di-trans-(cis-polyprenyl)n-diphosphate = di-trans-(cis-polyprenyl)n+1-diphosphate + diphosphate

tridecaprenyl diphosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 10 isopentenyl diphosphate = all-trans-tridecaprenyl diphosphate + 10 diphosphate

Not in pathways:
(2Z,6Z)-farnesyl diphosphate + n isopentenyl diphosphate = a mono-trans, poly-cis-polyisoprenyl diphosphate + n diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate = 2-cis,6-trans,10-trans-geranylgeranyl diphosphate + diphosphate
2-cis,6-trans,10-trans-geranylgeranyl diphosphate + 7 isopentenyl diphosphate = tri-trans,hepta-cis-undecaprenyl diphosphate + 7 diphosphate
(2Z,6E)-farnesyl diphosphate + n isopentenyl diphosphate = a mono-trans, poly-cis-polyisoprenyl diphosphate + n diphosphate
(2Z,6E)-farnesyl diphosphate + 9 isopentenyl diphosphate = ω, mono-trans,deca-cis-dodecaprenyl diphosphate + 9 diphosphate
isopentenyl diphosphate + geranylgeranyl diphosphate = geranylfarnesyl diphosphate + diphosphate
(cis-polyprenyl)n-diphosphate + isopentenyl diphosphate = (cis-polyprenyl)(n+1)-diphosphate + diphosphate
neryl diphosphate + isopentenyl diphosphate = (2Z,6Z)-farnesyl diphosphate + diphosphate
(2E,6E)-farnesyl diphosphate + n isopentenyl diphosphate = a di-trans, poly-cis-polyisoprenyl diphosphate + n diphosphate
geranylgeranyl diphosphate + 2 isopentenyl diphosphate = all-trans-hexaprenyl diphosphate + 2 diphosphate
geranylgeranyl diphosphate + 3 isopentenyl diphosphate = all-trans-heptaprenyl diphosphate + 3 diphosphate
ω, mono-trans, poly-cis-heptaprenyl diphosphate + isopentenyl diphosphate = ω, mono-trans, poly-cis-octaprenyl diphosphate + diphosphate
ω, mono-trans, poly-cis-hexaprenyl diphosphate + isopentenyl diphosphate = ω, mono-trans, poly-cis-heptaprenyl diphosphate + diphosphate
ω, mono-trans, poly-cis-pentaprenyl diphosphate + isopentenyl diphosphate = ω, mono-trans, poly-cis-hexaprenyl diphosphate + diphosphate
(2Z,6Z,10E)-tetraprenyl diphosphate + isopentenyl diphosphate = ω, mono-trans, poly-cis-pentaprenyl diphosphate + diphosphate
di-trans-ply-cispolyisoprenyln-PP + isopentenyl diphosphate = di-trans-ply-cispolyisoprenyln+1-PP + diphosphate

Enzymes inhibited by isopentenyl diphosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: trihydroxypterocarpan dimethylallyltransferase [Welle91a] , trihydroxypterocarpan dimethylallyltransferase [Welle91a]

Inhibitor (Mechanism unknown) of: 4-hydroxybenzoate-polyprenyltransferase [Kawahara91]


References

Kawahara91: Kawahara, K., Koizumi, N., Kawaji, H., Oishi, K., Uchida, K. (1991). "Partial Purification and Characterization of 4-Hydroxybenzoate-polyprenyltransferase in Ubiquinone Biosynthesis of Pseudomonas putida." Agricultural and biological chemistry 55(9):2307-2311.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Welle91a: Welle R, Grisebach H, (1991) "Properties and solubiltzation of the prenyltransferase of isoflavonoid phytoalexin biosynthesis in soybean ." Phytochemistry (1991), 30(2), 479-484.


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Thu Nov 27, 2014, BIOCYC13A.