isopentenyl diphosphate

Description

Isopentenyl pyrophosphate (IPP) is a central C5 precursor for the biosynthesis of nearly all isoprenoids [344,346,354]. Together with its isomer dimethylallyl pyrophosphate (DMAPP), IPP is produced through two independent metabolic routes: the methylerythritol phosphate (MEP) pathway, present in most bacteria and plant plastids, and the mevalonate (MVA) pathway, which operates in eukaryotes, archaea, and certain bacteria [346,354]. IPP is subsequently condensed with DMAPP by prenyltransferases to form longer isoprenoid chains that are essential for terpenoid biosynthesis [346].

Chemical Formula:

C₅H₉O₇P₂

Molecular Weight:

243.069 Daltons

Monoisotopic Mass:

246.0058257599 Daltons

SMILES:

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

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:

NUHSROFQTUXZQQ-UHFFFAOYSA-K

Synonyms

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

Databases

MetaCyc: DELTA3-ISOPENTENYL-PP

RefMet: Isopentenyl-diphosphate

BiGG: ipdp

MetaboLights: MTBLC128769

HMDB: HMDB01347

ChemSpider: 13115335

ChEBI: 128769

PubChem (CID): 15983957 1195

KEGG: C00129

Seed: cpd00113

MetaNetX: MNXM83