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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
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for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: geranylgeranyl diphosphate

Abbrev Name: GGPP

Synonyms: all-trans-geranyl-geranyl-pp, geranylgeranyl-PP, GGPP, geranylgeranyl diphosphate, (2E,6E,10E)-geranylgeranyl diphosphate, ω,E,E,E-geranylgeranyl diphosphate, (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl diphosphate, all-trans-geranylgeranyl diphosphate, 2-trans,6-trans,10-trans-geranylgeranyl diphosphate

Superclasses: a lipid an isoprenoid an isoprenoid phosphate an isoprenoid diphosphate an all-trans-polyisoprenyl diphosphate

Summary:
For polyisoprenols and polyisoprenyl phosphates nomenclature, see an isoprenoid.

Chemical Formula: C20H33O7P2

Molecular Weight: 447.42 Daltons

Monoisotopic Molecular Weight: 450.1936265303 Daltons

SMILES: CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-]

InChI: InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)/p-3/b18-11+,19-13+,20-15+

InChIKey: InChIKey=OINNEUNVOZHBOX-QIRCYJPOSA-K

Unification Links: ChEBI:58756 , ChemSpider:4593687 , DrugBank:DB07841 , HMDB:HMDB04486 , KEGG:C00353 , MetaboLights:MTBLC58756 , PubChem:5497105

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -18.771564 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene biosynthesis :
geranylgeranyl diphosphate + H2O → (E,E)-geranyllinalool + diphosphate

abietic acid biosynthesis , dehydroabietic acid biosynthesis , isopimaric acid biosynthesis , levopimaric acid biosynthesis , neoabietic acid biosynthesis , palustric acid biosynthesis :
geranylgeranyl diphosphate → (+)-copalyl diphosphate

bacteriochlorophyll a biosynthesis :
bacteriochlorophyllide a + geranylgeranyl diphosphate + H+ → geranylgeranyl-bacteriochlorophyll a + diphosphate

brassicicene C biosynthesis , fusicoccin A biosynthesis :
geranylgeranyl diphosphate → fusicocca-2,10(14)-diene + diphosphate

CDP-archaeol biosynthesis :
sn-glycerol 1-phosphate + geranylgeranyl diphosphate → 3-(O-geranylgeranyl)-sn-glycerol 1-phosphate + diphosphate
3-(O-geranylgeranyl)-sn-glycerol 1-phosphate + geranylgeranyl diphosphate → 2,3-bis-O-(geranylgeranyl)glycerol 1-phosphate + diphosphate

chlorophyll a biosynthesis II :
chlorophyllide a + geranylgeranyl diphosphate + H+ → geranylgeranyl-chlorophyll a + diphosphate

cyclooctatin biosynthesis :
geranylgeranyl diphosphate + H2O → cyclooctat-9-en-7-ol + diphosphate

diterpene phytoalexins precursors biosynthesis :
geranylgeranyl diphosphate → 9α-copalyl diphosphate
geranylgeranyl diphosphate → (-)-ent-copalyl diphosphate

ent -kaurene biosynthesis II :
geranylgeranyl diphosphate + H2O → ent-16-a-hydroxy-kaurene + diphosphate
geranylgeranyl diphosphateent-kaurene + diphosphate

ent-kaurene biosynthesis I , kauralexin biosynthesis :
geranylgeranyl diphosphate → (-)-ent-copalyl diphosphate

labdane-type diterpenes biosynthesis :
copal-8-ol-diphosphate ← geranylgeranyl diphosphate + H2O

neurosporene biosynthesis , trans-lycopene biosynthesis II (plants) :
2 geranylgeranyl diphosphate → prephytoene diphosphate + diphosphate

nonaprenyl diphosphate biosynthesis II :
geranylgeranyl diphosphate + 5 isopentenyl diphosphate → all-trans-nonaprenyl diphosphate + 5 diphosphate

paspaline biosynthesis :
geranylgeranyl diphosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate → 3-geranylgeranylindole + D-glyceraldehyde 3-phosphate + diphosphate

phytyl diphosphate biosynthesis :
geranylgeranyl diphosphate + NADPH + H+ → dihydrogeranylgeranyl-PP + NADP+

plaunotol biosynthesis :
geranylgeranyl diphosphate + H2O → geranylgeraniol + diphosphate

terpentecin biosynthesis :
geranylgeranyl diphosphate → terpentedienyl diphosphate

tuberculosinol biosynthesis :
geranylgeranyl diphosphate → tuberculosinyl diphosphate

vitamin E biosynthesis (tocotrienols) :
geranylgeranyl diphosphate + homogentisate + H+ → 2-methyl-6-geranylgeranyl-1,4-benzoquinol + CO2 + diphosphate

linoleate biosynthesis I (plants) :
oleoyl-CoA + a lipid + H+ → a lipid oleoyl-group + coenzyme A

Reactions known to produce the compound:

brassicicene C biosynthesis , fusicoccin A biosynthesis , geranylgeranyl diphosphate biosynthesis , paspaline biosynthesis , plaunotol biosynthesis :
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate → geranylgeranyl diphosphate + diphosphate

glutathione redox reactions I :
a lipid hydroperoxide + 2 glutathione + H+a lipid + glutathione disulfide + 2 H2O

Reactions known to both consume and produce the compound:

taxadiene biosynthesis (engineered) , taxol biosynthesis :
geranylgeranyl diphosphate ↔ taxa-4,11-diene + diphosphate

In Reactions of unknown directionality:

casbene biosynthesis :
geranylgeranyl diphosphate = casbene + diphosphate

Not in pathways:
phytyl diphosphate + 3 NADP+ = geranylgeranyl diphosphate + 3 NADPH + 3 H+
all-trans-geranyl-geranyl monophosphate + CTP = geranylgeranyl diphosphate + CDP
geranylgeranyl diphosphate + H2O = (1S,4E,8E,12E)-2,2,5,9,13-pentamethylcyclopentadeca-4,8,12-trien-1-ol + diphosphate
geranylgeranyl diphosphate = (R)-cembrene A + diphosphate
geranylgeranyl diphosphate + H2O = (R)-nephthenol + diphosphate
geranylgeranyl diphosphate = cembrene C + diphosphate
geranylgeranyl diphosphate + a [protein]-L-cysteine = a [protein]-S-geranylgeranyl-L-cysteine + diphosphate
geranylgeranyl diphosphate + H2O = aphidicolan-16β-ol + diphosphate
isopentenyl diphosphate + geranylgeranyl diphosphate = geranylfarnesyl diphosphate + diphosphate
2 geranylgeranyl diphosphate = all-trans-phytoene + 2 diphosphate
geranylgeranyl diphosphate + 2 isopentenyl diphosphate = all-trans-hexaprenyl diphosphate + 2 diphosphate
geranylgeranyl diphosphate + 3 isopentenyl diphosphate = all-trans-heptaprenyl diphosphate + 3 diphosphate
geranylgeranyl diphosphate = elisabethatriene + diphosphate
chlorophyllide b + geranylgeranyl diphosphate + H+ = geranylgeranyl-chlorophyll b + diphosphate


an all-trans-polyisoprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H+ = CO2 + a demethylmenaquinol + diphosphate


an isoprenoid diphosphate + 4-hydroxybenzoate = a 4-hydroxy-3-polyprenylbenzoate + diphosphate


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sat Dec 20, 2014, BIOCYC14A.