Geranylgeranyl diphosphate

Identification

Generic Name
Geranylgeranyl diphosphate
DrugBank Accession Number
DB07841
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 450.449
Monoisotopic: 450.193627495
Chemical Formula
C20H36O7P2
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHumans
UGeranylgeranyl transferase type-1 subunit betaNot AvailableHumans
UProtein farnesyltransferase subunit betaNot AvailableHumans
UGeranylgeranyl pyrophosphate synthaseNot AvailableHumans
UFarnesyl pyrophosphate synthaseNot AvailableHumans
UGeranylgeranyl transferase type-2 subunit alphaNot AvailableHumans
UGeranylgeranyl transferase type-2 subunit betaNot AvailableHumans
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
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AcebutololThe risk or severity of QTc prolongation can be increased when Geranylgeranyl diphosphate is combined with Acebutolol.
AcrivastineThe risk or severity of QTc prolongation can be increased when Geranylgeranyl diphosphate is combined with Acrivastine.
AdenosineThe risk or severity of QTc prolongation can be increased when Geranylgeranyl diphosphate is combined with Adenosine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Geranylgeranyl diphosphate.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Geranylgeranyl diphosphate.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Geranylgeranyl diphosphate.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Geranylgeranyl diphosphate resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Geranylgeranyl diphosphate.
AmifampridineThe risk or severity of QTc prolongation can be increased when Geranylgeranyl diphosphate is combined with Amifampridine.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Geranylgeranyl diphosphate is combined with Amiodarone.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Diterpenoids
Direct Parent
Acyclic diterpenoids
Alternative Parents
Organic pyrophosphates / Isoprenoid phosphates / Monoalkyl phosphates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Acyclic diterpenoid / Aliphatic acyclic compound / Alkyl phosphate / Hydrocarbon derivative / Isoprenoid phosphate / Monoalkyl phosphate / Organic oxide / Organic oxygen compound / Organic phosphoric acid derivative / Organic pyrophosphate
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
polyprenol diphosphate (CHEBI:15831)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OINNEUNVOZHBOX-UHFFFAOYSA-N
InChI
InChI=1S/C20H36O7P2/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-26-29(24,25)27-28(21,22)23/h9,11,13,15H,6-8,10,12,14,16H2,1-5H3,(H,24,25)(H2,21,22,23)
IUPAC Name
({hydroxy[(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)oxy]phosphoryl}oxy)phosphonic acid
SMILES
CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCOP(O)(=O)OP(O)(O)=O

References

Synthesis Reference

Chikara Ohto, Chika Asada, Shinichi Ohnuma, Tokuzo Nishino, Kazutake Hirooka, Hisashi Hemmi, "Process for the production of prenyl diphosphate using mutants of geranylgeranyl diphosphate synthase." U.S. Patent US5885810, issued September, 1995.

US5885810
General References
Not Available
PubChem Compound
447277
PubChem Substance
99444312
ChemSpider
715
ChEBI
15831
PDBe Ligand
BUE
Wikipedia
Geranylgeranyl_pyrophosphate
PDB Entries
6ejj / 6ejk

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00463 mg/mLALOGPS
logP3.57ALOGPS
logP5.28ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity120.53 m3·mol-1ChemAxon
Polarizability47.24 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.681
Blood Brain Barrier+0.7921
Caco-2 permeable-0.5967
P-glycoprotein substrateSubstrate0.5257
P-glycoprotein inhibitor INon-inhibitor0.8021
P-glycoprotein inhibitor IINon-inhibitor0.6218
Renal organic cation transporterNon-inhibitor0.9235
CYP450 2C9 substrateNon-substrate0.8276
CYP450 2D6 substrateNon-substrate0.828
CYP450 3A4 substrateNon-substrate0.5088
CYP450 1A2 substrateNon-inhibitor0.8244
CYP450 2C9 inhibitorNon-inhibitor0.7835
CYP450 2D6 inhibitorNon-inhibitor0.8795
CYP450 2C19 inhibitorNon-inhibitor0.7799
CYP450 3A4 inhibitorNon-inhibitor0.8565
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8918
Ames testNon AMES toxic0.7621
CarcinogenicityNon-carcinogens0.6
BiodegradationReady biodegradable0.6376
Rat acute toxicity2.4092 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7452
hERG inhibition (predictor II)Non-inhibitor0.8614
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 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

Targets

Drugtargets
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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
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of proteins having the C-terminal sequence Cys-aliphat...
Gene Name
PGGT1B
Uniprot ID
P53609
Uniprot Name
Geranylgeranyl transferase type-1 subunit beta
Molecular Weight
42367.81 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. [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
  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. [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
  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. [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
  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. [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
  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. [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
  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. [Article]

Drug created on September 15, 2010 21:26 / Updated on June 12, 2020 16:52