Identification
- Generic Name
- Farnesyl diphosphate
- DrugBank Accession Number
- DB07780
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Farnesyl diphosphate (DB07780)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Not Available Humans UProtein farnesyltransferase subunit beta Not Available Humans UGTPase KRas Not Available Humans U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Not Available Shewanella oneidensis (strain MR-1) UFarnesyl pyrophosphate synthase Not Available Humans UDitrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific) Not Available Escherichia coli (strain K12) ULantibiotic nisin-Z Not Available Lactococcus lactis subsp. lactis UGeranylgeranyl pyrophosphate synthase Not Available Humans U(2Z,6E)-farnesyl diphosphate synthase Not Available Mycobacterium tuberculosis UGeranylgeranyl transferase type-2 subunit alpha Not Available Humans UGeranylgeranyl transferase type-2 subunit beta Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Farnesyl diphosphate is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Ajmaline is combined with Farnesyl diphosphate. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Farnesyl diphosphate. Alimemazine The risk or severity of QTc prolongation can be increased when Alimemazine is combined with Farnesyl diphosphate. - 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
- External Links
- 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 54 more
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
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
Property Value Source Water Solubility 0.0807 mg/mL ALOGPS logP 2.4 ALOGPS logP 3.62 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 1.77 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 113.29 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 96.73 m3·mol-1 Chemaxon Polarizability 37.94 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.681 Blood Brain Barrier + 0.7921 Caco-2 permeable - 0.5967 P-glycoprotein substrate Substrate 0.5257 P-glycoprotein inhibitor I Non-inhibitor 0.8021 P-glycoprotein inhibitor II Non-inhibitor 0.6218 Renal organic cation transporter Non-inhibitor 0.9235 CYP450 2C9 substrate Non-substrate 0.8276 CYP450 2D6 substrate Non-substrate 0.828 CYP450 3A4 substrate Non-substrate 0.5088 CYP450 1A2 substrate Non-inhibitor 0.8244 CYP450 2C9 inhibitor Non-inhibitor 0.7835 CYP450 2D6 inhibitor Non-inhibitor 0.8795 CYP450 2C19 inhibitor Non-inhibitor 0.7799 CYP450 3A4 inhibitor Non-inhibitor 0.8565 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8918 Ames test Non AMES toxic 0.7621 Carcinogenicity Non-carcinogens 0.6 Biodegradation Ready biodegradable 0.6376 Rat acute toxicity 2.4092 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7452 hERG inhibition (predictor II) Non-inhibitor 0.8614
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004j-7943000000-ab6d749700f510a94133 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-e481823519be87976b00 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0119000000-81e5f96ea9e3d8da22d7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-003s-4219000000-db1c43895996a4c40669 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0r01-0192000000-ddac3328dac365760a77 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004j-9000000000-607fccefe40f8416e516 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00o1-3910000000-fae9251686616a0f2fc9 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 206.4436803 predictedDarkChem Lite v0.1.0 [M-H]- 208.2270803 predictedDarkChem Lite v0.1.0 [M-H]- 206.5937803 predictedDarkChem Lite v0.1.0 [M-H]- 176.96333 predictedDeepCCS 1.0 (2019) [M+H]+ 179.35887 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.15952 predictedDeepCCS 1.0 (2019)
Targets
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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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
- 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
- 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. [Article]
Drug created at September 15, 2010 21:25 / Updated at June 12, 2020 16:52