FARNESYL THIOPYROPHOSPHATE

Identification

Name
FARNESYL THIOPYROPHOSPHATE
Accession Number
DB04695
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 398.392
Monoisotopic: 398.108182342
Chemical Formula
C15H28O6P2S
InChI Key
MYMLCRQRXFRQGP-YFVJMOTDSA-N
InChI
InChI=1S/C15H28O6P2S/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-24-23(19,20)21-22(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]sulfanyl})phosphoryl]oxy}phosphonic acid
SMILES
[H]\C(CC\C(C)=C(/[H])CSP(O)(=O)OP(O)(O)=O)=C(\C)CCC=C(C)C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDitrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)Not AvailableEscherichia coli (strain K12)
UGeranylgeranyl pyrophosphate synthaseNot AvailableHuman
UMevalonate kinaseNot AvailableHuman
UDehydrosqualene synthaseNot AvailableStaphylococcus aureus
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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
657041
PubChem Substance
46506151
ChemSpider
571259
HET
FPS
PDB Entries
1x06 / 1x08 / 2e8t / 2r42 / 3q78 / 3sae / 3vkb / 3vzz / 3w00 / 3w7f
show 10 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 Solubility0.138 mg/mLALOGPS
logP2.44ALOGPS
logP4.11ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity103.23 m3·mol-1ChemAxon
Polarizability40.62 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6707
Blood Brain Barrier+0.7849
Caco-2 permeable-0.5989
P-glycoprotein substrateSubstrate0.5222
P-glycoprotein inhibitor INon-inhibitor0.7409
P-glycoprotein inhibitor IINon-inhibitor0.7184
Renal organic cation transporterNon-inhibitor0.9272
CYP450 2C9 substrateNon-substrate0.7724
CYP450 2D6 substrateNon-substrate0.8188
CYP450 3A4 substrateNon-substrate0.5454
CYP450 1A2 substrateNon-inhibitor0.7732
CYP450 2C9 inhibitorNon-inhibitor0.7454
CYP450 2D6 inhibitorNon-inhibitor0.8731
CYP450 2C19 inhibitorNon-inhibitor0.7273
CYP450 3A4 inhibitorNon-inhibitor0.8392
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8597
Ames testNon AMES toxic0.7158
CarcinogenicityNon-carcinogens0.5926
BiodegradationReady biodegradable0.7134
Rat acute toxicity2.7904 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7679
hERG inhibition (predictor II)Non-inhibitor0.84
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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 phosphoric acids and derivatives / Sulfenyl compounds / Organothiophosphorus compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Farsesane sesquiterpenoid / Sesquiterpenoid / Organic phosphoric acid derivative / Sulfenyl compound / Organothiophosphorus compound / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organosulfur compound / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

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
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
Human
Pharmacological action
Unknown
General Function
Mevalonate kinase activity
Specific Function
May be a regulatory site in cholesterol biosynthetic pathway.
Gene Name
MVK
Uniprot ID
Q03426
Uniprot Name
Mevalonate kinase
Molecular Weight
42450.475 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
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific Function
Catalyzes the head-to-head condensation of two molecules of farnesyl diphosphate (FPP) into the colorless C(30) carotenoid dehydrosqualene (4,4'-diapophytoene). This is the initial step in the bios...
Gene Name
crtM
Uniprot ID
A9JQL9
Uniprot Name
Dehydrosqualene synthase
Molecular Weight
34312.78 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 11, 2007 11:49 / Updated on December 01, 2017 15:31