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Farnesylfarnesylgeranyl-PP (M2MDB001924)

Record Information
Version2.0
Creation Date2012-08-09 09:25:18 -0600
Update Date2015-06-03 17:21:43 -0600
Secondary Accession Numbers
  • ECMDB21529
Identification
Name:Farnesylfarnesylgeranyl-PP
DescriptionFarnesylfarnesylgeranyl-PP is a member of the chemical class known as Tetraterpenes. These are terpene molecules containing 8 consecutively linked isoprene units. It is an intermediate in ubiquinone biosysnthesis in the reaction farnesylfarnesylgeranyl-PP + p-hydroxybenzoate = 3-octaprenyl-4-hydroxybenzoate + pyrophosphate
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • All-trans-octaprenyl diphosphate
  • all-trans-Octaprenyl diphosphoric acid
Chemical Formula:C40H65O7P2
Weight:Average: 719.8874
Monoisotopic: 719.420552458
InChI Key:IKKLDISSULFFQO-DJMILUHSSA-K
InChI:InChI=1S/C40H68O7P2/c1-33(2)17-10-18-34(3)19-11-20-35(4)21-12-22-36(5)23-13-24-37(6)25-14-26-38(7)27-15-28-39(8)29-16-30-40(9)31-32-46-49(44,45)47-48(41,42)43/h17,19,21,23,25,27,29,31H,10-16,18,20,22,24,26,28,30,32H2,1-9H3,(H,44,45)(H2,41,42,43)/p-3/b34-19+,35-21+,36-23+,37-25+,38-27+,39-29+,40-31+
CAS number:Not Available
IUPAC Name:{[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl phosphonato]oxy}phosphonate
Traditional IUPAC Name:[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl phosphonato]oxyphosphonate
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])CC\C(C)=C(/[H])COP([O-])(=O)OP([O-])([O-])=O)=C(\C)CCC=C(C)C
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTetraterpenoids
Direct ParentTetraterpenoids
Alternative Parents
Substituents
  • Tetraterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl diphosphate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00044 g/LALOGPS
logP7.92ALOGPS
logP11.92ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area121.78 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity212.38 m³·mol⁻¹ChemAxon
Polarizability84.1 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
1,4-dihydroxy-2-naphthoate + Hydrogen ion + Farnesylfarnesylgeranyl-PP + 1,4-Dihydroxy-2-naphthoyl-CoA > Carbon dioxide + Pyrophosphate + 2-Demethylmenaquinol 8
SMPDB Pathways:
Menaquinol biosythesisPW001897 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000900-2bf48d5f96b478289f70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08i0-1000039600-66d8e4759bbfa5a2eae5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6211190100-12377b8c01b34d0a47fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000900-21a4b23c55395dc9d1ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3100000900-59521e1c4c934a538571View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003s-9100000000-c9b9543f7652822b9b13View in MoNA
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID57711
HMDB IDNot Available
Pubchem Compound ID25245331
Kegg IDNot Available
ChemSpider ID26330884
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 1,4-dihydroxy-2-naphthoate octaprenyltransferase
General function:
Involved in transferase activity
Specific function:
Conversion of 1,4-dihydroxy-2-naphthoate (DHNA) to dimethylmenaquinone (DMK). Attaches octaprenylpyrophosphate, a membrane-bound 40-carbon side chain to DHNA. The conversion of DHNA to DMK proceeds in three stages:the removal of the carboxyl group of DHNA as CO(2), the attachment of the isoprenoid side chain, and a quinol-to-quinone oxidation, which is thought to be spontaneous
Gene Name:
menA
Uniprot ID:
P32166
Molecular weight:
33594
Reactions
An all-trans-polyprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO(2).
Protein Details
2. 4-hydroxybenzoate octaprenyltransferase
General function:
Involved in prenyltransferase activity
Specific function:
Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:
ubiA
Uniprot ID:
P0AGK1
Molecular weight:
32511
Reactions
4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.