Farnesyl diphosphate

Identification

Generic Name
Farnesyl diphosphate
DrugBank Accession Number
DB07780
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 382.33
Monoisotopic: 382.131027238
Chemical Formula
C15H28O7P2
Synonyms
  • (2E,6E)-farnesol diphosphate
  • (2E,6E)-farnesyl diphosphate
  • (2E,6E)-farnesyl pyrophosphate
  • (all-E)-farnesyl diphosphate
  • (E,E)-farnesyl pyrophosphate
  • 2-trans,6-trans-farnesyl diphosphate
  • all-trans-farnesyl pyrophosphate
  • Farnesyl pyrophosphate

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHumans
UProtein farnesyltransferase subunit betaNot AvailableHumans
UGTPase KRasNot AvailableHumans
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseNot AvailableShewanella oneidensis (strain MR-1)
UFarnesyl pyrophosphate synthaseNot AvailableHumans
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 AvailableHumans
U(2Z,6E)-farnesyl diphosphate synthaseNot AvailableMycobacterium tuberculosis
UGeranylgeranyl transferase type-2 subunit alphaNot AvailableHumans
UGeranylgeranyl transferase type-2 subunit betaNot AvailableHumans
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

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
PathwayCategory
Lovastatin Action PathwayDrug action
Cerivastatin Action PathwayDrug action
HypercholesterolemiaDisease
Hereditary Coproporphyria (HCP)Disease
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseDisease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)Disease
Smith-Lemli-Opitz Syndrome (SLOS)Disease
Mevalonic AciduriaDisease
Porphyrin MetabolismMetabolic
Simvastatin Action PathwayDrug action
Pravastatin Action PathwayDrug action
Rosuvastatin Action PathwayDrug action
Zoledronate Action PathwayDrug action
Pamidronate Action PathwayDrug action
Fluvastatin Action PathwayDrug action
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
Cholesteryl Ester Storage DiseaseDisease
Steroid BiosynthesisMetabolic
Ibandronate Action PathwayDrug action
Alendronate Action PathwayDrug action
Risedronate Action PathwayDrug action
Atorvastatin Action PathwayDrug action
Acute Intermittent PorphyriaDisease
Porphyria Variegata (PV)Disease
DesmosterolosisDisease
CHILD SyndromeDisease
Hyper-IgD SyndromeDisease
Wolman DiseaseDisease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Acebutolol.
AcrivastineThe risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Farnesyl diphosphate.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Farnesyl diphosphate.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Farnesyl diphosphate.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Farnesyl diphosphate.
AmifampridineThe risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Amiodarone.
AmisulprideThe risk or severity of QTc prolongation can be increased when Amisulpride is combined with Farnesyl diphosphate.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Alkyl phosphate / Farsesane sesquiterpenoid / Hydrocarbon derivative / Isoprenoid phosphate / Monoalkyl phosphate / Organic oxide / Organic oxygen compound / Organic phosphoric acid derivative / Organic pyrophosphate
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
farnesyl diphosphate (CHEBI:17407) / Acyclic farnesane sesquiterpenoids, Farnesenes (C00448) / Acyclic farnesane sesquiterpenoids (LMPR0103010002)
Affected organisms
Not Available

Chemical Identifiers

UNII
79W6B01D07
CAS number
13058-04-3
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\COP(O)(=O)OP(O)(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0000961
KEGG Compound
C00448
PubChem Compound
445713
PubChem Substance
99444251
ChemSpider
393270
BindingDB
50366477
ChEBI
17407
ChEMBL
CHEMBL69330
ZINC
ZINC000012494625
PDBe Ligand
FPP
Wikipedia
Farnesyl_pyrophosphate
PDB Entries
1fpp / 1ft2 / 1jcq / 1jcr / 1kzo / 1ld7 / 1ld8 / 1mzc / 1o5m / 1s63
show 41 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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
Humans
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 21:25 / Updated on June 12, 2020 16:52