prenyl diphosphate

Description

Dimethylallyl pyrophosphate (DMAPP) is a central C5 isoprenoid building block and a key precursor for the biosynthesis of nearly all isoprenoids [344, 346, 354]. Together with its isomer isopentenyl diphosphate (IPP), DMAPP 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 [354]. DMAPP can be generated from IPP by isopentenyl diphosphate isomerase and functions as the allylic starter unit for prenyltransferase reactions, leading to the formation of geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and longer polyprenyl diphosphates [346].

Chemical Formula:

C₅H₉O₇P₂

Molecular Weight:

243.069 Daltons

Monoisotopic Mass:

246.0058257599 Daltons

SMILES:

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

InChIKey:

CBIDRCWHNCKSTO-UHFFFAOYSA-K

Synonyms

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

Databases

MetaCyc: CPD-4211

BiGG: dmpp

MetaboLights: MTBLC57623

HMDB: HMDB01120

ChemSpider: 13115336

ChEBI: 57623 16057

PubChem (CID): 15983958

KEGG: C00235

PupChem (SID): 3534

CHEMBL: CHEMBL343480

NIKKAJI: J39.581A

3DMET: B01196

PDB-CCD: DMA

LIPID MAPS: LMPR01010001

LIPIDBANK: IIP0002

Seed: cpd00202

MetaNetX: MNXM132

KNApSAcK: C00007294

CAS: 358-71-4