Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:07:18 UTC
Update Date2024-04-30 20:52:36 UTC
Metabolite IDMMDBc0054332
Metabolite Identification
Common Nameall-trans-heptaprenyl diphosphate
Descriptionall-trans-Heptaprenyl diphosphate is the final product of the heptaprenyl diphosphate biosynthesis pathway. In this pathway, multiple units of isopentenyl diphosphate (IPP) undergo a series of polymerizations to form a polyisoprenoid chain. The sequential addition of isoprenyl units to all-trans-farnesyl diphosphate is performed by polyprenyl diphosphate synthase enzymes such as the E. coli enzyme octaprenyl diphosphate synthase. Additional isoprenoid units are added to a maximal length that is determined by the specific enzyme. Most organisms generate polyprenyl chains of predominantly one length. Once completed, the polyprenyl chain is incorporated into other molecules, such as quinones. The enzyme that attaches the polyprenyl chain to the quinone precursor molecule does not have a preference for any particular length. Thus, the length of the polyprenyl chain in the mature quinone molecule is determined by the predominant polyprenyl diphosphate synthase enzyme of the organism. In most organisms, there is one type of predominant quinone, with a specific polyprenyl chain length. However, most organisms also have minor amounts of quinones with a different polyprenyl chain length. Organisms whose main quinone contains a chain of 7 isoprenyl units include some Gram-negative bacteria (e.g. the gliding bacterium Flexibacter elegans and the phototroph Allochromatium vinosum strain D), but mostly Gram-positive bacteria, such as many members of the Bacillus, Staphylococcus, and Listeria genera.
Structure
Synonyms
ValueSource
all-trans-Heptaprenyl diphosphoric acidGenerator
(E)-Heptaprenyl diphosphateHMDB
Molecular FormulaC35H60O7P2
Average Mass654.7942
Monoisotopic Mass654.381427298
IUPAC Name[({[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name{[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])COP(O)(=O)OP(O)(O)=O)=C(\C)CCC=C(C)C
InChI Identifier
InChI=1S/C35H60O7P2/c1-29(2)15-9-16-30(3)17-10-18-31(4)19-11-20-32(5)21-12-22-33(6)23-13-24-34(7)25-14-26-35(8)27-28-41-44(39,40)42-43(36,37)38/h15,17,19,21,23,25,27H,9-14,16,18,20,22,24,26,28H2,1-8H3,(H,39,40)(H2,36,37,38)/b30-17+,31-19+,32-21+,33-23+,34-25+,35-27+
InChI KeyLSJLEXWXRKTZAJ-YUIIPXGZSA-N