Dimethylallyl pyrophosphate

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Dimethylallyl pyrophosphate
Names
Skeletal formula
Ball-and-stick model
IUPAC name (hydroxy-(3-methylbut-2-enoxy) phosphoryl) oxyphosphonic acid
Other names Dimethylallyl diphosphate; isoprenyl pyrophosphate; isoprenyl diphosphate
Identifiers
CAS Number	358-72-5
3D model (JSmol)	Interactive image Interactive image
ChemSpider	19951350
MeSH	3,3-dimethylallyl+pyrophosphate
PubChem CID	647
CompTox Dashboard (EPA)	DTXSID70189331
InChI InChI=1S/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3Key: WTLAYXVNIWTZJI-UHFFFAOYSA-N InChI=1/C20H36O7P2/c1-13-17(5,6)23-28(21,24-18(7,8)14-2)27-29(22,25-19(9,10)15-3)26-20(11,12)16-4/h13-16H,1-4H2,5-12H3Key: WTLAYXVNIWTZJI-UHFFFAOYAD
SMILES CC(=CCOP(=O)(O)OP(=O)(O)O)C O=P(OP(=O)(OC(C)(C)C=C)OC(C)(C)C=C)(OC(C)(C)C=C)OC(C)(C)C=C
Properties
Chemical formula	C₅H₁₂O₇P₂
Molar mass	246.092
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. It is an isomer of isopentenyl pyrophosphate (IPP) and exists in virtually all life forms. The enzyme isopentenyl pyrophosphate isomerase catalyzes the isomerization of DMAPP from IPP.

Precursor of DMAPP in the MVA pathway is mevalonic acid, and 2-C-methyl-D-erythritol-e-P in the MEP/DOXP pathway.

At present, it is believed that there is crossover between the two pathways in organisms that use both pathways to create terpenes and terpenoids, such as in plants, and that DMAPP is the crossover product.

External links

Cholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMB HMB-CoA HMG-CoA
Ketone bodies	Acetone Acetoacetic acid β-Hydroxybutyric acid
to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate
Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate
Carotenoid	Prephytoene diphosphate Phytoene

Non-mevalonate pathway

To Cholesterol

From Cholesterol
to Steroid hormones

Nonhuman

To Sitosterol	Cycloartenol Cycloeucalenol Obtusifoliol 4α-methylfecosterol Isofucosterol 24-Methylenelophenol Sitosterol More Phytosterols see here instead.
To Ergocalciferol	Fecosterol Episterol Ergostatrienol Ergostatetraenol Ergosterol Ergocalciferol

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