all-trans-Hexaprenyl diphosphate (BioCAD00000006121)

plant natural products microbial natural products

Metabolite Card

Formula: C30H52O7P2 (586.3188)
SMILES: CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

Synonyms [en]

all-trans-hexaprenyl diphosphate; (2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl trihydrogen diphosphate; [({[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid; 3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl phosphono hydrogen phosphate; 3,7,11,15,19,23-hexamethyltetracosa-2E,6E,10E,14E,18E,22-hexaen-1-yl trihydrogen diphosphate; all-trans-Hexaprenyl diphosphoric acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

all-trans-Hexaprenyl diphosphate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000006121). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

all-trans-Hexaprenyl diphosphate is the final product of the hexaprenyl diphosphate biosynthesis pathway. In this pathway, multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form various polyisoprenoids. There are two different pathways for the biosynthesis of IPP. Bacteria that possess ubiquinone generally use the methylerythritol phosphate pathway (MEP), while the eukaryotic microorganisms use the mevalonate pathway. However, exceptions exist. For example, some eukaryotic microbes, like the green algae and the malarial parasite Plasmodium falciparum, appear to utilize the MEP pathway, and some bacteria utilize the mevalonate pathway (Eisenreich01, Eisenreich04). In Saccharomyces cerevisiae S288C, the initial addition of two isoprenyl units to form (E, E)-farnesyl diphosphate is catalyzed by geranyltransferase / dimethylallyltransferase, encoded by FPP1. An additional unit is added by farnesyltranstransferase (encoded by BTS1), resulting in the formation of all-trans-geranyl-geranyl diphosphate. The last enzyme in this pathway is hexaprenyl diphosphate synthase (encoded by COQ1), which adds additional isoprenoid units to a maximal length unique to the organism. In the case of Saccharomyces cerevisiae S288C, it is 6 units. Polyprenyl diphosphate synthase enzymes, such as hexaprenyl diphosphate synthase, are responsible for determining the final length of the tail. When yeast COQ1 mutants are complemented with homologs from other organisms, ubiquinone biosynthesis is restored, but the tail length of the quinone depends on the source of the enzyme.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 207513-95-9
  • PubChem: 5280413
  • ChEBI: ChEBI:17528
  • HMDB: HMDB0012188
  • LipidMaps: LMPR03030005
  • KEGG: C01230
  • Metlin: METLIN_53853
  • Coconut NaturalProduct: CNP0083596.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R05612 2.5.1.- C01230 + C00129<=>C04216 + C00013
KEGG:R05613 2.5.1.- C04217 + C00129<=>C01230 + C00013
KEGG:R05616 2.5.1.39 all-trans-hexaprenyl diphosphate:4-hydroxybenzoate hexaprenyltransferase
KEGG:R09245 2.5.1.83 (2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate farnesyltranstransferase (adding 3 isopentenyl units)
KEGG:R09246 2.5.1.82 geranylgeranyl-diphosphate:isopentenyl-diphosphate transferase (adding 2 isopentenyl units)
KEGG:R11854 4.2.3.188 all-trans-hexaprenyl-diphosphate diphosphate-lyase (beta-hexaprene-forming)
KEGG:R13228 4.2.3.213 pentaprenyl-diphosphate diphosphate-lyase [cyclizing, colleterpenol-forming]
KEGG:R13292 4.2.3.220 pentaprenyl-diphosphate diphosphate-lyase [cyclizing, talaropentaene-forming]
KEGG:R13293 4.2.3.221 pentaprenyl-diphosphate diphosphate-lyase [cyclizing, macrophomene-forming]
KEGG:R13302 2.5.1.158 prenyl-diphosphate:3-methylbut-3-en-1-yl-diphosphate transferase (adding 5 units of 3-methylbut-3-en-1-yl)
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Organism Source

Taxonomy Source

  1. Citrullus lanatus [ncbi taxid: 3654]
  2. Mus musculus [ncbi taxid: 10090]
  3. Saccharomyces cerevisiae [ncbi taxid: 4932]

Pathway Synthetic

pathway id name
PathBank:SMP0000065 Ubiquinone Biosynthesis
PathBank:SMP0087310 Ubiquinone Biosynthesis
PathBank:SMP0063685 Ubiquinone Biosynthesis
PathBank:SMP0002372 Ubiquinone Biosynthesis
PathBank:SMP0087215 Ubiquinone Biosynthesis
PathBank:SMP0087388 Ubiquinone Biosynthesis
PathBank:SMP0002384 Terpenoid Backbone Biosynthesis
PathBank:SMP0087443 Ubiquinone Biosynthesis
View All Pathways