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Identification
NameFARNESYL THIOPYROPHOSPHATE
Accession NumberDB04695
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 398.392
Monoisotopic: 398.108182342
Chemical FormulaC15H28O6P2S
InChI KeyInChIKey=MYMLCRQRXFRQGP-PVMFERMNSA-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({[(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl})phosphoryl]oxy}phosphonic acid
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C/CS[P@@](=O)(O)OP(O)(=O)O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Sulfenyl compound
  • Organothiophosphorus compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Polarizability39.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide.
Gene Name:
ispU
Uniprot ID:
P60472
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
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
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 biosynthesis of staphyloxanthin, an orange carotenoid present in most staphylococci strains.
Gene Name:
crtM
Uniprot ID:
A9JQL9
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 ]
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Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25