Cannabis Compound Database: Showing Compound Card for Farnesyl pyrophosphate (CDB005224)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 14 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:21:47 UTC

Updated at

2020-12-07 19:11:47 UTC

CannabisDB ID

CDB005224

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Farnesyl pyrophosphate

Description

Farnesyl pyrophosphate, also known as farnesyl diphosphoric acid 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 is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E,6E)-Farnesol diphosphate	ChEBI
(2E,6E)-Farnesyl diphosphate	ChEBI
(2E,6E)-Farnesyl pyrophosphate	ChEBI
(all-e)-Farnesyl diphosphate	ChEBI
(e,e)-Farnesyl pyrophosphate	ChEBI
2-trans,6-trans-Farnesyl pyrophosphate	ChEBI
all-trans-Farnesyl pyrophosphate	ChEBI
Farnesyl diphosphate	ChEBI
trans,trans-Farnesyl diphosphate	ChEBI
trans-trans-Farnesyl diphosphate	ChEBI
2-trans,6-trans-Farnesyl diphosphate	Kegg
(2E,6E)-Farnesol diphosphoric acid	Generator
(2E,6E)-Farnesyl diphosphoric acid	Generator
(2E,6E)-Farnesyl pyrophosphoric acid	Generator
(all-e)-Farnesyl diphosphoric acid	Generator
(e,e)-Farnesyl pyrophosphoric acid	Generator
2-trans,6-trans-Farnesyl pyrophosphoric acid	Generator
all-trans-Farnesyl pyrophosphoric acid	Generator
Farnesyl diphosphoric acid	Generator
trans,trans-Farnesyl diphosphoric acid	Generator
trans-trans-Farnesyl diphosphoric acid	Generator
2-trans,6-trans-Farnesyl diphosphoric acid	Generator
Farnesyl pyrophosphoric acid	Generator
(e,e)-Farnesyl diphosphate	HMDB
Farnesyl-PP	HMDB
trans-Farnesyl pyrophosphate	HMDB
trans-trans-Farnesyl pyrophosphate	HMDB
Farnesyl pyrophosphate, (e,e)-isomer	HMDB
Farnesyl pyrophosphate, (e,Z)-isomer	HMDB
Farnesyl pyrophosphate, (Z,e)-isomer	HMDB
Farnesyl pyrophosphate, (Z,Z)-isomer	HMDB
Farnesylpyrophosphate	HMDB

Chemical Formula

C₁₅H₂₈O₇P₂

Average Molecular Weight

382.33

Monoisotopic Molecular Weight

382.131

IUPAC Name

{[hydroxy({[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]oxy})phosphoryl]oxy}phosphonic acid

Traditional Name

farnesyl diphosphate

CAS Registry Number

13058-04-3

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O

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 Key

VWFJDQUYCIWHTN-YFVJMOTDSA-N

Chemical Taxonomy

Description

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

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 Framework

Aliphatic acyclic compounds

External Descriptors

farnesyl diphosphate (CHEBI:17407 )
Acyclic farnesane sesquiterpenoids (C00448 )
Farnesenes (C00448 )
Acyclic farnesane sesquiterpenoids (LMPR0103010002 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Testicle

Cell and elements:

Extracellular

Cell:

Nerve cell

Biofluid and excreta:

Blood

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Farnesyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-7943000000-ab6d749700f510a94133	Spectrum
Predicted GC-MS	Farnesyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 26V, negative	splash10-014i-0090000000-09efa5f4e481376eae3d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-001i-2009000000-b2358e50ee86b2ebccb5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-004i-9004000000-b255d40b3beef0ddd16f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, negative	splash10-004i-9001000000-64cd48aa93040d775977	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 19V, negative	splash10-004i-9000000000-84a4e8d938e03661128e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-004i-9000000000-eb2e768f7c19af669f74	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 26V, negative	splash10-03di-0209000000-651c59dc3e732ea880d7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 26V, negative	splash10-0a4i-0900000000-ae4be9bde4ed56cfa99b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 26V, positive	splash10-0002-0294000000-7019f71a6e4f542dddae	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pc0-1469000000-e3fd27c0418d0977f84e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-6791000000-1ca128d2b96287a5b2f1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0q29-9820000000-3277fbdf16e288ab1142	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0409000000-f8bbf786ee9d33cb48d4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9501000000-8d060d3ceac94de45b8d	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a265a369e6802359a7df	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0009000000-ea5bda9906940e9694b2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2409000000-4b044bb59695723b85bd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9600000000-a090357e0efeb6192936	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0019000000-66a0a5510c1d34aea230	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-114i-0394000000-89ab3170c9695823fb2f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05rs-6900000000-7b5163a81d3cbdf1feb4	2021-09-24	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Porphyrin Metabolism
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Squalene synthase	FDFT1	8p23.1-p22	P37268	details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Farnesyl pyrophosphate synthase	FDPS	1q22	P14324	details
Protoheme IX farnesyltransferase, mitochondrial	COX10		Q12887	details
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	FNTA	8p11	P49354	details
Dehydrodolichyl diphosphate synthase	DHDDS		Q86SQ9	details
Protein farnesyltransferase subunit beta	FNTB	14q23.3	P49356	details
Decaprenyl-diphosphate synthase subunit 2	PDSS2	6q21	Q86YH6	details
Decaprenyl-diphosphate synthase subunit 1	PDSS1	10p12.1	Q5T2R2	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Farnesyl pyrophosphate synthase	FDPS	1q22	P14324	details
Protein farnesyltransferase subunit beta	FNTB	14q23.3	P49356	details
Decaprenyl-diphosphate synthase subunit 1	PDSS1	10p12.1	Q5T2R2	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	FNTA	8p11	P49354	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000961

DrugBank ID

DB07780

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Farnesyl pyrophosphate

METLIN ID

403

PubChem Compound

445713

PDB ID

Not Available

ChEBI ID

17407

References

General References

Not Available

Only showing the first 10 proteins. There are 14 proteins in total.

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Enzymes

Enzyme Details

1. Squalene synthase

General function:: Involved in transferase activity
Specific function:: Not Available
Gene Name:: FDFT1
Uniprot ID:: P37268
Molecular weight:: 48114.87

Enzyme Details

2. Geranylgeranyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
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

Enzyme Details

3. Farnesyl pyrophosphate synthase

General function:: Involved in isoprenoid biosynthetic process
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, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, dimethylallyl pyrophosphate, and then with the resultant geranylpyrophosphate to the ultimate product farnesyl pyrophosphate.
Gene Name:: FDPS
Uniprot ID:: P14324
Molecular weight:: 48275.03

Enzyme Details

4. Protoheme IX farnesyltransferase, mitochondrial

General function:: Involved in protoheme IX farnesyltransferase activity
Specific function:: Converts protoheme IX and farnesyl diphosphate to heme O (By similarity).
Gene Name:: COX10
Uniprot ID:: Q12887
Molecular weight:: Not Available

Enzyme Details

5. Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha

General function:: Involved in protein prenyltransferase activity
Specific function:: Catalyzes the transfer of a farnesyl or geranyl-geranyl moiety from farnesyl or geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. The alpha subunit is thought to participate in a stable complex with the substrate. The beta subunit binds the peptide substrate. Through RAC1 prenylation and activation may positively regulate neuromuscular junction development downstream of MUSK (By similarity).
Gene Name:: FNTA
Uniprot ID:: P49354
Molecular weight:: 44408.32

Enzyme Details

6. Dehydrodolichyl diphosphate synthase

General function:: Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:: Catalyzes cis-prenyl chain elongation to produce the polyprenyl backbone of dolichol, a glycosyl carrier-lipid required for the biosynthesis of several classes of glycoprotein.
Gene Name:: DHDDS
Uniprot ID:: Q86SQ9
Molecular weight:: Not Available

Enzyme Details

7. Protein farnesyltransferase subunit beta

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins. The beta subunit is responsible for peptide-binding.
Gene Name:: FNTB
Uniprot ID:: P49356
Molecular weight:: 48773.2

Enzyme Details

8. Decaprenyl-diphosphate synthase subunit 2

General function:: Not Available
Specific function:: Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:: PDSS2
Uniprot ID:: Q86YH6
Molecular weight:: 44128.17

Enzyme Details

9. Decaprenyl-diphosphate synthase subunit 1

General function:: Not Available
Specific function:: Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:: PDSS1
Uniprot ID:: Q5T2R2
Molecular weight:: 46260.6

Only showing the first 10 proteins. There are 14 proteins in total.

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Showing Compound Card for Farnesyl pyrophosphate (CDB005224)

Structure for CDB005224 (Farnesyl pyrophosphate)

Enzymes