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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: dimethylallyl diphosphate

Abbrev Name: DMAPP

Synonyms: dimethylallyl-diphosphate, prenyl-diphosphate, δ-prenyl diphosphate, δ2-isopentenyl-diphosphate, 2-isopentenyl diphosphate, prenyl diphosphate, DMAPP, DPP, di-CH3-allyl-PPi, dimethylallyl-PP, dimethylallyl-PPi, DMPP, dimethylallyl pyrophosphate

Chemical Formula: C5H9O7P2

Molecular Weight: 243.07 Daltons

Monoisotopic Molecular Weight: 246.0058257599 Daltons

SMILES: CC(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/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)/p-3

InChIKey: InChIKey=CBIDRCWHNCKSTO-UHFFFAOYSA-K

Unification Links: CAS:358-71-4 , ChEBI:57623 , ChemSpider:13115336 , HMDB:HMDB01120 , IAF1260:131960 , KEGG:C00235 , MetaboLights:MTBLC57623 , PubChem:15983958

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -349.54843 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

3-dimethylallyl-4-hydroxybenzoate biosynthesis :
dimethylallyl diphosphate + 4-hydroxyphenylpyruvate → 3-dimethylallyl-4-hydroxyphenylpyruvate + diphosphate

5-N-acetylardeemin biosynthesis :
ardeemin FQ + dimethylallyl diphosphate → ardeemin + diphosphate

acetylaszonalenin biosynthesis :
(R)-benzodiazepinedione + dimethylallyl diphosphate → aszonalenin + diphosphate

aflatrem biosynthesis :
paspalinine + dimethylallyl diphosphate → aflatrem + diphosphate

alizarin biosynthesis :
1,4-dihydroxy-2-naphthoate + dimethylallyl diphosphate → alizarin

α-cyclopiazonate biosynthesis :
cyclo-acetoacetyl-L-tryptophan + dimethylallyl diphosphate → β-cyclopiazonate + diphosphate

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

chanoclavine I aldehyde biosynthesis :
dimethylallyl diphosphate + L-tryptophan → 4-(3-methylbut-2-enyl)-L-tryptophan + diphosphate

cis-zeatin biosynthesis :
dimethylallyl diphosphate + an adenosine37 in tRNA → N6-dimethylallyladenosine37 in tRNA + diphosphate

cohumulone biosynthesis :
4-prenylphlorisobutyrophenone + dimethylallyl diphosphate → diprenylphlorisobutyrophenone + diphosphate
phlorisobutyrophenone + dimethylallyl diphosphate → 4-prenylphlorisobutyrophenone + diphosphate + H+

fumigaclavine biosynthesis :
fumigaclavine A + dimethylallyl diphosphate → fumigaclavine C + diphosphate

fumitremorgin A biosynthesis :
verruculogen + dimethylallyl diphosphate → fumitremorgin A + diphosphate
dimethylallyl diphosphate + 12α,13α-dihydroxyfumitremorgin C → fumitremorgin B + diphosphate

fumitremorgin C biosynthesis :
dimethylallyl diphosphate + brevianamide F → tryprostatin B + diphosphate

fusicoccin A biosynthesis :
fusicoccin P + dimethylallyl diphosphate → fusicoccin J + diphosphate

glyceollin biosynthesis II :
(-)-glycinol + dimethylallyl diphosphate → (6αS,11αS)-2-dimethylallyl-3,6α,9-trihydroxypterocarpan + diphosphate
(-)-glycinol + dimethylallyl diphosphate → (6αS,11αS)-4-dimethylallyl-3,6α,9-trihydroxypterocarpan + diphosphate

humulone biosynthesis :
phlorisovalerophenone + dimethylallyl diphosphate → 4-prenylphlorisovalerophenone + diphosphate + H+
4-prenylphlorisovalerophenone + dimethylallyl diphosphate → diprenylphlorisovalerophenone + diphosphate

hyperforin and adhyperforin biosynthesis :
diprenylphlorisobutyrophenone + dimethylallyl diphosphate + geranyl diphosphate → hyperforin + 2 diphosphate
4-prenylphlorisobutyrophenone + dimethylallyl diphosphate → diprenylphlorisobutyrophenone + diphosphate
phlorisobutyrophenone + dimethylallyl diphosphate → 4-prenylphlorisobutyrophenone + diphosphate + H+

hyperxanthone E biosynthesis :
2,4,6-trihydroxybenzophenone + dimethylallyl diphosphate → hyperxanthone E + diphosphate

isoprene biosynthesis I , isoprene biosynthesis II (engineered) :
dimethylallyl diphosphate → isoprene + diphosphate

kievitone biosynthesis :
2'-hydroxygenistein + dimethylallyl diphosphate → 2,3-dehydrokievitone + diphosphate
dalbergioidin + dimethylallyl diphosphate → kievitone + diphosphate

linear furanocoumarin biosynthesis :
umbelliferone + dimethylallyl diphosphate → demethylsuberosin + diphosphate

paxilline and diprenylpaxilline biosynthesis :
paxilline + 2 dimethylallyl diphosphate → 21,22-diprenylpaxilline + 2 diphosphate

phaseollin biosynthesis :
(6aR,11aR)-3,9-dihydroxypterocarpan + dimethylallyl diphosphate → (-)-phaseollidin + diphosphate

pyrethrin I biosynthesis :
2 dimethylallyl diphosphate → chrysanthemyl diphosphate + diphosphate

sophoraflavanone G biosynthesis :
dimethylallyl diphosphate + leachianone G + H+ → sophoraflavanone G + diphosphate
dimethylallyl diphosphate + (2S)-naringenin → sophoraflavanone B + diphosphate

terrequinone A biosynthesis :
hydrodidemethylasterriquinone D + dimethylallyl diphosphate → ochrindole D + diphosphate + H2O
ochrindole D + dimethylallyl diphosphate → terrequinone A + diphosphate
didemethylasterriquinone D + dimethylallyl diphosphate → asterriquinone C1 + diphosphate

trans-zeatin biosynthesis :
dimethylallyl diphosphate + ATP + H+N6-(Δ2-isopentenyl)-adenosine 5'-triphosphate + diphosphate
dimethylallyl diphosphate + ADP → N6-(Δ2-isopentenyl)-adenosine 5'-diphosphate + diphosphate
dimethylallyl diphosphate + AMP → N6-(Δ2-isopentenyl)-adenosine 5'-monophosphate + diphosphate

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

wighteone and luteone biosynthesis :
genistein + dimethylallyl diphosphate → lupiwighteone + diphosphate
genistein + dimethylallyl diphosphate → isowighteone + diphosphate
2'-hydroxygenistein + dimethylallyl diphosphate → phaseoluteone + diphosphate
genistein + dimethylallyl diphosphate → wighteone + diphosphate
2'-hydroxygenistein + dimethylallyl diphosphate → luteone + diphosphate

xanthohumol biosynthesis :
2',4,4',6'-tetrahydroxychalcone + dimethylallyl diphosphate → desmethylxanthohumol + diphosphate + H+

Not in pathways:
dimethylallyl diphosphate + H2O → isopentenol + diphosphate

Reactions known to produce the compound:

methylerythritol phosphate pathway I , methylerythritol phosphate pathway II :
dimethylallyl 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 :
isopentenyl diphosphate ↔ dimethylallyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate

bisabolene biosynthesis :
isopentenyl diphosphate ↔ dimethylallyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl 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 , mevalonate pathway II (archaea) , mevalonate pathway III (archaea) :
isopentenyl diphosphate ↔ dimethylallyl diphosphate

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

trans, trans-farnesyl diphosphate biosynthesis :
isopentenyl diphosphate ↔ dimethylallyl diphosphate
dimethylallyl diphosphate + isopentenyl diphosphate ↔ geranyl diphosphate + diphosphate

In Reactions of unknown directionality:

methylbutenol biosynthesis :
dimethylallyl diphosphate + H2O = methylbutenol + diphosphate

Not in pathways:
dimethylallyl diphosphate + L-tyrosine = 4-O-dimethylallyl-L-tyrosine + diphosphate
dimethylallyl diphosphate + 5,10-dihydro-phenazine-1-carboxylate = 5,10-dihydro-9-dimethylallylphenazine 1-carboxylate + diphosphate
dimethylallyl diphosphate + brevianamide F = deoxybrevianamide E + diphosphate
2 dimethylallyl diphosphate = lavandulyl diphosphate + diphosphate
dimethylallyl diphosphate + L-tryptophan = 7-(3-methylbut-2-enyl)-L-tryptophan + diphosphate
2 dimethylallyl diphosphate + aspulvinone-e = aspulvinone-h + 2 diphosphate


References

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


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 Fri Nov 28, 2014, BIOCYC13A.