Showing metabocard for Farnesyl pyrophosphate (BMDB0000961)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:39:12 UTC
Update Date2020-05-21 16:28:57 UTC
BMDB IDBMDB0000961
Secondary Accession Numbers
  • BMDB00961
Metabolite Identification
Common NameFarnesyl pyrophosphate
DescriptionFarnesyl pyrophosphate, also known as farnesyl pyrophosphate or farnesyl-PP, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Farnesyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Farnesyl pyrophosphate exists in all living species, ranging from bacteria to humans. In cattle, farnesyl pyrophosphate is involved in the metabolic pathway called the porphyrin metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,6E)-Farnesol diphosphateChEBI
(2E,6E)-Farnesyl diphosphateChEBI
(2E,6E)-Farnesyl pyrophosphateChEBI
(all-e)-Farnesyl diphosphateChEBI
(e,e)-Farnesyl pyrophosphateChEBI
2-trans,6-trans-Farnesyl pyrophosphateChEBI
all-trans-Farnesyl pyrophosphateChEBI
Farnesyl diphosphateChEBI
trans,trans-Farnesyl diphosphateChEBI
trans-trans-Farnesyl diphosphateChEBI
2-trans,6-trans-Farnesyl diphosphateKegg
(2E,6E)-Farnesol diphosphoric acidGenerator
(2E,6E)-Farnesyl diphosphoric acidGenerator
(2E,6E)-Farnesyl pyrophosphoric acidGenerator
(all-e)-Farnesyl diphosphoric acidGenerator
(e,e)-Farnesyl pyrophosphoric acidGenerator
2-trans,6-trans-Farnesyl pyrophosphoric acidGenerator
all-trans-Farnesyl pyrophosphoric acidGenerator
Farnesyl diphosphoric acidGenerator
trans,trans-Farnesyl diphosphoric acidGenerator
trans-trans-Farnesyl diphosphoric acidGenerator
2-trans,6-trans-Farnesyl diphosphoric acidGenerator
Farnesyl pyrophosphoric acidGenerator
(e,e)-Farnesyl diphosphateHMDB
Farnesyl-PPHMDB
trans-Farnesyl pyrophosphateHMDB
trans-trans-Farnesyl pyrophosphateHMDB
Farnesyl pyrophosphate, (e,e)-isomerHMDB
Farnesyl pyrophosphate, (e,Z)-isomerHMDB
Farnesyl pyrophosphate, (Z,e)-isomerHMDB
Farnesyl pyrophosphate, (Z,Z)-isomerHMDB
FarnesylpyrophosphateHMDB
Chemical FormulaC15H28O7P2
Average Molecular Weight382.33
Monoisotopic Molecular Weight382.131027238
IUPAC Name{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Namefarnesyl diphosphate
CAS Registry Number13058-04-3
SMILES
[H]OP(=O)(O[H])OP(=O)(O[H])OC\C=C(/C)CC\C=C(/C)CCC=C(C)C
InChI Identifier
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+
InChI KeyVWFJDQUYCIWHTN-YFVJMOTDSA-N
Chemical Taxonomy
Description 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 pyrophosphate
  • Isoprenoid phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity96.73 m³·mol⁻¹ChemAxon
Polarizability37.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen Locations
  • Neuron
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000961
DrugBank IDDB07780
Phenol Explorer Compound IDNot Available
FooDB IDFDB022339
KNApSAcK IDC00007268
Chemspider ID393270
KEGG Compound IDC00448
BioCyc IDFARNESYL-PP
BiGG ID35006
Wikipedia LinkFarnesyl pyrophosphate
METLIN ID403
PubChem Compound445713
PDB IDNot Available
ChEBI ID17407
References
Synthesis ReferenceCastillo-Bocanegra, Rafael. Synthesis and biological activity of farnesyl pyrophosphate analogs. University of California, San Francisco., 1977 - Farnesol  p.364
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Squalene synthase
General function:
Lipid transport and metabolism
Specific function:
Critical branch point enzyme of isoprenoid biosynthesis that is thought to regulate the flux of isoprene intermediates through the sterol pathway.
Gene Name:
FDFT1
Uniprot ID:
Q32KR6
Molecular weight:
48304.0
Reactions
2 Farnesyl pyrophosphate + NADPH → Squalene + NADP +2 Pyrophosphatedetails
Enzyme Details
2. Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
General function:
Translation, ribosomal structure and biogenesis
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 diphosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. May positively regulate neuromuscular junction development downstream of MUSK via its function in RAC1 prenylation and activation (By similarity).
Gene Name:
FNTA
Uniprot ID:
P29702
Molecular weight:
43845.0
Enzyme Details
3. Protein farnesyltransferase subunit beta
General function:
Involved in farnesyltranstransferase activity
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 proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X (By similarity).
Gene Name:
FNTB
Uniprot ID:
P49355
Molecular weight:
48768.0
Enzyme Details
4. Protoheme IX farnesyltransferase, mitochondrial
General function:
Not Available
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O.
Gene Name:
COX10
Uniprot ID:
A5D7D6
Molecular weight:
49191.0
Reactions
Heme + Farnesyl pyrophosphate → Heme Odetails