ISOPENTENYL PYROPHOSPHATE

Identification

Name
ISOPENTENYL PYROPHOSPHATE
Accession Number
DB04714
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 246.0921
Monoisotopic: 246.005825762
Chemical Formula
C5H12O7P2
InChI Key
NUHSROFQTUXZQQ-UHFFFAOYSA-N
InChI
InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)
IUPAC Name
({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
SMILES
CC(=C)CCO[P@](O)(=O)OP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDitrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)Not AvailableEscherichia coli (strain K12)
UFarnesyl pyrophosphate synthaseNot AvailableHuman
UGeranylgeranyl pyrophosphate synthaseNot AvailableHuman
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseNot AvailableMycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
UDecaprenyl diphosphate synthaseNot AvailableMycobacterium tuberculosis
U4-hydroxy-3-methylbut-2-enyl diphosphate reductaseNot AvailableEscherichia coli (strain K12)
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
PathwayCategory
Rosuvastatin Action PathwayDrug action
Fluvastatin Action PathwayDrug action
DesmosterolosisDisease
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2)Disease
Farnesene BiosynthesisMetabolic
Atorvastatin Action PathwayDrug action
Hyper-IgD SyndromeDisease
Secondary Metabolites: Isoprenoid Biosynthesis (Nonmevalonate Pathway)Metabolic
Cholesterol Biosynthesis and Metabolism CE(14:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(16:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(18:0)Metabolic
Epoxysqualene BiosynthesisMetabolic
Simvastatin Action PathwayDrug action
CHILD SyndromeDisease
Mevalonic AciduriaDisease
Secondary Metabolites: Methylerythritol Phosphate and Polyisoprenoid BiosynthesisMetabolic
Secondary Metabolites: Ubiquinol BiosynthesisMetabolic
Secondary Metabolites: Ubiquinol Biosynthesis 2Metabolic
Cholesterol Biosynthesis and Metabolism CE(10:0)Metabolic
Cholesterol Biosynthesis and Metabolism CE(12:0)Metabolic
Pravastatin Action PathwayDrug action
Cerivastatin Action PathwayDrug action
Risedronate Action PathwayDrug action
Pamidronate Action PathwayDrug action
HypercholesterolemiaDisease
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
Wolman DiseaseDisease
Steroid BiosynthesisMetabolic
Cholesterol Biosynthesis and MetabolismMetabolic
Steroid BiosynthesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Jay Keasling, "Biosynthesis of isopentenyl pyrophosphate." U.S. Patent US20030148479, issued August 07, 2003.

US20030148479
General References
Not Available
External Links
Human Metabolome Database
HMDB0001347
KEGG Compound
C00129
PubChem Compound
1195
PubChem Substance
46508890
ChemSpider
1158
BindingDB
25257
ChEBI
16584
ChEMBL
CHEMBL356362
HET
IPE
PDB Entries
1rqj / 1x07 / 1x08 / 1x09 / 1yhm / 1zw5 / 2e8t / 2e8u / 2e8w / 2f8z
show 41 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 Solubility6.69 mg/mLALOGPS
logP0.04ALOGPS
logP0.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.21 m3·mol-1ChemAxon
Polarizability19.01 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.917
Blood Brain Barrier+0.8933
Caco-2 permeable-0.6159
P-glycoprotein substrateNon-substrate0.5146
P-glycoprotein inhibitor INon-inhibitor0.8072
P-glycoprotein inhibitor IINon-inhibitor0.9666
Renal organic cation transporterNon-inhibitor0.8964
CYP450 2C9 substrateNon-substrate0.7909
CYP450 2D6 substrateNon-substrate0.8282
CYP450 3A4 substrateNon-substrate0.551
CYP450 1A2 substrateNon-inhibitor0.8083
CYP450 2C9 inhibitorNon-inhibitor0.807
CYP450 2D6 inhibitorNon-inhibitor0.8539
CYP450 2C19 inhibitorNon-inhibitor0.7755
CYP450 3A4 inhibitorNon-inhibitor0.8896
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8961
Ames testNon AMES toxic0.7174
CarcinogenicityNon-carcinogens0.688
BiodegradationReady biodegradable0.6571
Rat acute toxicity2.3133 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7409
hERG inhibition (predictor II)Non-inhibitor0.9111
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/MSsplash10-014j-9670000000-fa3d42a8ff93d345cea7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9200000000-78e51dcb039157700c59
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9100000000-a585b43371cb54efe2eb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0490000000-391e90cfd97e6adcbb06
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9510000000-fed3169adff6f1179e01
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-5c099085cd907446a2fb

Taxonomy

Description
This compound belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Isoprenoid phosphates
Direct Parent
Isoprenoid phosphates
Alternative Parents
Organic pyrophosphates / Monoalkyl phosphates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Organic pyrophosphate / Isoprenoid phosphate / Monoalkyl phosphate / Alkyl phosphate / Phosphoric acid ester / Organic phosphoric acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
prenol phosphate (CHEBI:16584) / C5 isoprenoids (hemiterpenes) (C00129) / C5 isoprenoids (hemiterpenes) (LMPR01010008)

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
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. [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
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidy...
Gene Name
ispF
Uniprot ID
A0R559
Uniprot Name
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
Molecular Weight
16546.59 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
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Catalyzes the sequential condensation of isopentenyl diphosphate (IPP) in the cis configuration with (2Z,6E)-farnesyl diphosphate (Z-FPP or EZ-FPP) generating the 50 carbon product trans,polycis-decaprenyl diphosphate. When (2E,6E)-farnesyl diphosphate (E-FPP or EE-FPP) is used in vitro, both primary products decaprenyl diphosphate and (2E,6E,10E)-geranylgeranyl diphosphate (EEE-GGPP) are synthesized. M.tuberculosis does not synthesize (2E,6E,10Z)-geranylgeranyl diphosphate (EEZ-GGPP) and heptaprenyl diphosphate. Can also accept many different allylic substrates, including E-geranyl diphosphate (E-GPP), neryl diphosphate (NPP), and all-trans-geranyl-geranyl diphosphate.
Specific Function
Di-trans,poly-cis-decaprenylcistransferase activity
Gene Name
uppS
Uniprot ID
P9WFF7
Uniprot Name
Decaprenyl diphosphate synthase
Molecular Weight
33790.985 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
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is also involved in penicillin tolerance and control of the stringe...
Gene Name
ispH
Uniprot ID
P62623
Uniprot Name
4-hydroxy-3-methylbut-2-enyl diphosphate reductase
Molecular Weight
34774.275 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 November 02, 2018 06:04