FARNESYL DIPHOSPHATE

Identification

Name
FARNESYL DIPHOSPHATE
Accession Number
DB07780
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
79W6B01D07
CAS number
Not Available
Weight
Average: 382.3261
Monoisotopic: 382.131026274
Chemical Formula
C15H28O7P2
InChI Key
VWFJDQUYCIWHTN-YFVJMOTDSA-N
InChI
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
IUPAC Name
{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CO[P@@](=O)(O)OP(=O)(O)O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHuman
UProtein farnesyltransferase subunit betaNot AvailableHuman
UGTPase KRasNot AvailableHuman
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseNot AvailableShewanella oneidensis (strain MR-1)
UFarnesyl pyrophosphate synthaseNot AvailableHuman
UDitrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)Not AvailableEscherichia coli (strain K12)
ULantibiotic nisin-ZNot AvailableLactococcus lactis subsp. lactis
UGeranylgeranyl pyrophosphate synthaseNot AvailableHuman
U(2Z,6E)-farnesyl diphosphate synthaseNot AvailableMycobacterium tuberculosis
UGeranylgeranyl transferase type-2 subunit alphaNot AvailableHuman
UGeranylgeranyl transferase type-2 subunit betaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Atorvastatin Action PathwayDrug action
Hyper-IgD SyndromeDisease
Cholesterol Biosynthesis and Metabolism CE(14:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(16:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(18:0)Metabolic
Epoxysqualene BiosynthesisMetabolic
Rosuvastatin Action PathwayDrug action
Fluvastatin Action PathwayDrug action
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
DesmosterolosisDisease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)Disease
Porphyrin Metabolism Metabolic
Farnesene BiosynthesisMetabolic
Pravastatin Action PathwayDrug action
Cerivastatin Action PathwayDrug action
Risedronate Action PathwayDrug action
Pamidronate Action PathwayDrug action
HypercholesterolemiaDisease
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
Acute Intermittent PorphyriaDisease
Wolman DiseaseDisease
Steroid BiosynthesisMetabolic
Cholesterol Biosynthesis and MetabolismMetabolic
Simvastatin Action PathwayDrug action
CHILD SyndromeDisease
Mevalonic AciduriaDisease
Porphyrin MetabolismMetabolic
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid BiosynthesisMetabolic
Secondary Metabolites: Ubiquinol BiosynthesisMetabolic
Secondary Metabolites: Ubiquinol Biosynthesis 2Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000961
KEGG Compound
C00448
PubChem Compound
445713
PubChem Substance
99444251
ChemSpider
393270
BindingDB
50366477
ChEBI
17407
ChEMBL
CHEMBL69330
HET
FPP
PDB Entries
1fpp / 1ft2 / 1jcq / 1jcr / 1kzo / 1ld7 / 1ld8 / 1mzc / 1o5m / 1s63
show 38 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0807 mg/mLALOGPS
logP2.4ALOGPS
logP3.62ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability37.94 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.681
Blood Brain Barrier+0.7921
Caco-2 permeable-0.5967
P-glycoprotein substrateSubstrate0.5257
P-glycoprotein inhibitor INon-inhibitor0.8021
P-glycoprotein inhibitor IINon-inhibitor0.6218
Renal organic cation transporterNon-inhibitor0.9235
CYP450 2C9 substrateNon-substrate0.8276
CYP450 2D6 substrateNon-substrate0.828
CYP450 3A4 substrateNon-substrate0.5088
CYP450 1A2 substrateNon-inhibitor0.8244
CYP450 2C9 inhibitorNon-inhibitor0.7835
CYP450 2D6 inhibitorNon-inhibitor0.8795
CYP450 2C19 inhibitorNon-inhibitor0.7799
CYP450 3A4 inhibitorNon-inhibitor0.8565
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8918
Ames testNon AMES toxic0.7621
CarcinogenicityNon-carcinogens0.6
BiodegradationReady biodegradable0.6376
Rat acute toxicity2.4092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7452
hERG inhibition (predictor II)Non-inhibitor0.8614
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pc0-1469000000-e3fd27c0418d0977f84e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-6791000000-1ca128d2b96287a5b2f1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0q29-9820000000-3277fbdf16e288ab1142
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0409000000-f8bbf786ee9d33cb48d4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9501000000-8d060d3ceac94de45b8d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-a265a369e6802359a7df

Taxonomy

Description
This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Sesquiterpenoids
Direct Parent
Sesquiterpenoids
Alternative Parents
Organic pyrophosphates / Isoprenoid phosphates / Monoalkyl phosphates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Farsesane sesquiterpenoid / Sesquiterpenoid / Organic pyrophosphate / Isoprenoid phosphate / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
farnesyl diphosphate (CHEBI:17407) / Acyclic farnesane sesquiterpenoids, Farnesenes (C00448) / Acyclic farnesane sesquiterpenoids (LMPR0103010002)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rab geranylgeranyltransferase activity
Specific Function
Essential subunit of both the farnesyltransferase and the geranylgeranyltransferase complex. Contributes to the transfer of a farnesyl or geranylgeranyl moiety from farnesyl or geranylgeranyl dipho...
Gene Name
FNTA
Uniprot ID
P49354
Uniprot Name
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Molecular Weight
44408.32 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential subunit of the farnesyltransferase complex. Catalyzes the transfer of a farnesyl moiety from farnesyl diphosphate to a cysteine at the fourth position from the C-terminus of several prote...
Gene Name
FNTB
Uniprot ID
P49356
Uniprot Name
Protein farnesyltransferase subunit beta
Molecular Weight
48773.2 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein complex binding
Specific Function
Ras proteins bind GDP/GTP and possess intrinsic GTPase activity. Plays an important role in the regulation of cell proliferation (PubMed:23698361, PubMed:22711838).
Gene Name
KRAS
Uniprot ID
P01116
Uniprot Name
GTPase KRas
Molecular Weight
21655.67 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Shewanella oneidensis (strain MR-1)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidy...
Gene Name
ispF
Uniprot ID
Q8EBR3
Uniprot Name
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
Molecular Weight
16995.47 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Key enzyme in isoprenoid biosynthesis which catalyzes the formation of farnesyl diphosphate (FPP), a precursor for several classes of essential metabolites including sterols, dolichols, carotenoids...
Gene Name
FDPS
Uniprot ID
P14324
Uniprot Name
Farnesyl pyrophosphate synthase
Molecular Weight
48275.03 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Generates ditrans,octacis-undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP) and farnesyl diphosphate (FPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of...
Gene Name
ispU
Uniprot ID
P60472
Uniprot Name
Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)
Molecular Weight
28443.92 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Lactococcus lactis subsp. lactis
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Lanthionine-containing peptide antibiotic (lantibiotic) active on Gram-positive bacteria. The bactericidal activity of lantibiotics is based on depolarization of energized bacterial cytoplasmic mem...
Gene Name
nisZ
Uniprot ID
P29559
Uniprot Name
Lantibiotic nisin-Z
Molecular Weight
5939.87 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the trans-addition of the three molecules of IPP onto DMAPP to form geranylgeranyl pyrophosphate, an important precursor of carotenoids and geranylated proteins.
Gene Name
GGPS1
Uniprot ID
O95749
Uniprot Name
Geranylgeranyl pyrophosphate synthase
Molecular Weight
34870.625 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the condensation of only one isopentenyl pyrophosphate (IPP) unit in the cis configuration to E-geranyl diphosphate (E-GPP) generating the 15 carbon product (2Z,6E)-farnesyl diphosphate (Z-FPP or EZ-FPP). Z-FPP is the precursor of decaprenyl diphosphate, which has a central role in the biosynthesis of the mycobacterial cell wall.
Specific Function
Magnesium ion binding
Gene Name
Not Available
Uniprot ID
P9WFF5
Uniprot Name
(2Z,6E)-farnesyl diphosphate synthase
Molecular Weight
29409.955 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a geranylgeranyl moiety from geranylgeranyl diphosphate to both cysteines of Rab proteins with the C-terminal sequence -XXCC, -XCXC and -CCXX, such as RAB1A, RAB3A, RAB5A ...
Gene Name
RABGGTA
Uniprot ID
Q92696
Uniprot Name
Geranylgeranyl transferase type-2 subunit alpha
Molecular Weight
65071.06 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a geranylgeranyl moiety from geranylgeranyl diphosphate to both cysteines of Rab proteins with the C-terminal sequence -XXCC, -XCXC and -CCXX, such as RAB1A, RAB3A, RAB5A ...
Gene Name
RABGGTB
Uniprot ID
P53611
Uniprot Name
Geranylgeranyl transferase type-2 subunit beta
Molecular Weight
36924.04 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:25 / Updated on October 01, 2018 14:27