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[Biochemistry](https://durgical.com/en/biochemistry/) · Molecule

# Isopentenyl pyrophosphate (IPP)

Isopentenyl pyrophosphate is the five-carbon building block (active isoprene) used to build cholesterol and many other isoprenoids.

Updated 2026-11-01

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## Key facts

- A five-carbon isoprene unit activated by a pyrophosphate.
- The isomerase turns it into dimethylallyl pyrophosphate (DMAPP); the two join head-to-tail.
- Six units make squalene (C30), which leads to cholesterol.
- It also gives rise to dolichol, ubiquinone (coenzyme Q), haem A and farnesyl and geranylgeranyl groups.

**Also called**
Isopentenyl diphosphate

**Formula**
C₅H₁₂O₇P₂

**PubChem**
[CID 1195](https://pubchem.ncbi.nlm.nih.gov/compound/1195)

## Structure

- A five-carbon chain with a terminal double bond and a diphosphate at the other end.
- The pyrophosphate is a good leaving group: when it leaves, a carbocation forms that joins the next isoprene.

## Clinical notes

- γδ T cells (Vγ9Vδ2) sense accumulated IPP; nitrogen-containing bisphosphonates raise it, which explains the acute-phase fever after the first infusion.
- Statins lower IPP and its products; reduced ubiquinone has been proposed to contribute to myopathy.

## Pathways

- [Cholesterol synthesis (mevalonate pathway)](https://durgical.com/en/biochemistry/pathways/cholesterol-synthesis/)

## Related

- [Mevalonate](https://durgical.com/en/biochemistry/molecules/mevalonate/)
- [Squalene](https://durgical.com/en/biochemistry/molecules/squalene/)

## Test yourself

Think of the answer, then tap the question to see it.

## How many carbons does isopentenyl pyrophosphate have, and how many units make squalene?

Five carbons; six units make 30-carbon squalene.

## Which molecules besides cholesterol come from IPP?

Dolichol, ubiquinone, haem A and the prenyl groups (farnesyl, geranylgeranyl) on some proteins.

## Why does the pyrophosphate make IPP reactive?

It is a good leaving group: its release creates a carbocation that joins another isoprene.

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Molecules are shown in their neutral form, as the databases deposit them; in the cell the acids and phosphates are ionised.

Educational information, not medical advice. For any symptom, see a health professional.

Sources: [Isopentenyl diphosphate (CID 1195)](https://pubchem.ncbi.nlm.nih.gov/compound/1195) (PubChem, NCBI, 2026) · Public domain; [Cholesterol biosynthesis (R-HSA-191273)](https://reactome.org/PathwayBrowser/#/R-HSA-191273) (Reactome, 2026).

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License: CC BY 4.0 (https://creativecommons.org/licenses/by/4.0/). Cite as: DurgiPedia (durgical.com), https://durgical.com/en/biochemistry/molecules/isopentenyl-pyrophosphate/