Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- ISOPENTENYL PYROPHOSPHATE
- DrugBank Accession Number
- DB04714
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for ISOPENTENYL PYROPHOSPHATE (DB04714)
- Weight
- Average: 246.0921
Monoisotopic: 246.005825762 - Chemical Formula
- C5H12O7P2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism AFarnesyl pyrophosphate synthase inhibitorHumans UGeranylgeranyl pyrophosphate synthase Not Available Humans U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Not Available Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155) UDecaprenyl diphosphate synthase Not Available Mycobacterium tuberculosis U4-hydroxy-3-methylbut-2-enyl diphosphate reductase Not Available Escherichia coli (strain K12) UDitrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific) Not Available Escherichia 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
- Adverse Effects
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Not Available
- Pathways
Pathway Category Lovastatin Action Pathway Drug action Cerivastatin Action Pathway Drug action Hypercholesterolemia Disease Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) Disease Smith-Lemli-Opitz Syndrome (SLOS) Disease Mevalonic Aciduria Disease Simvastatin Action Pathway Drug action Pravastatin Action Pathway Drug action Rosuvastatin Action Pathway Drug action Zoledronate Action Pathway Drug action Pamidronate Action Pathway Drug action Fluvastatin Action Pathway Drug action Lysosomal Acid Lipase Deficiency (Wolman Disease) Disease Cholesteryl Ester Storage Disease Disease Steroid Biosynthesis Metabolic Ibandronate Action Pathway Drug action Alendronate Action Pathway Drug action Risedronate Action Pathway Drug action Atorvastatin Action Pathway Drug action Desmosterolosis Disease CHILD Syndrome Disease Hyper-IgD Syndrome Disease Wolman Disease Disease - 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Alkyl phosphate / Hydrocarbon derivative / Isoprenoid phosphate / Monoalkyl phosphate / Organic oxide / Organic oxygen compound / Organic phosphoric acid derivative / Organic pyrophosphate / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- prenol phosphate (CHEBI:16584) / C5 isoprenoids (hemiterpenes) (C00129) / C5 isoprenoids (hemiterpenes) (LMPR01010008)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LSC8849M7B
- CAS number
- Not Available
- 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
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
- ZINC
- ZINC000008215654
- PDBe Ligand
- IPE
- PDB Entries
- 1rqj / 1x07 / 1x08 / 1x09 / 1yhm / 1zw5 / 2e8t / 2e8u / 2e8w / 2f8z … show 60 more
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 6.69 mg/mL ALOGPS logP 0.04 ALOGPS logP 0.2 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 1.78 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 113.29 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 48.21 m3·mol-1 Chemaxon Polarizability 19.01 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.917 Blood Brain Barrier + 0.8933 Caco-2 permeable - 0.6159 P-glycoprotein substrate Non-substrate 0.5146 P-glycoprotein inhibitor I Non-inhibitor 0.8072 P-glycoprotein inhibitor II Non-inhibitor 0.9666 Renal organic cation transporter Non-inhibitor 0.8964 CYP450 2C9 substrate Non-substrate 0.7909 CYP450 2D6 substrate Non-substrate 0.8282 CYP450 3A4 substrate Non-substrate 0.551 CYP450 1A2 substrate Non-inhibitor 0.8083 CYP450 2C9 inhibitor Non-inhibitor 0.807 CYP450 2D6 inhibitor Non-inhibitor 0.8539 CYP450 2C19 inhibitor Non-inhibitor 0.7755 CYP450 3A4 inhibitor Non-inhibitor 0.8896 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8961 Ames test Non AMES toxic 0.7174 Carcinogenicity Non-carcinogens 0.688 Biodegradation Ready biodegradable 0.6571 Rat acute toxicity 2.3133 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7409 hERG inhibition (predictor II) Non-inhibitor 0.9111
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002b-9600000000-930df1e6e1c7e4eed108 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-2940000000-ae55f6d71da9085e7d29 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0490000000-d1cdea0da4ab0affcc51 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kb-9000000000-93aae924b8d934599e50 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00kb-9000000000-4a34f109f8bd4d0927ed Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-056s-9400000000-2fea7d6333a511576a6d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-9700000000-661dc82d7f8c7cad7c16 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 153.8939723 predictedDarkChem Lite v0.1.0 [M-H]- 132.21489 predictedDeepCCS 1.0 (2019) [M+H]+ 136.00296 predictedDeepCCS 1.0 (2019) [M+Na]+ 145.3897 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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
- Specific Function
- dimethylallyltranstransferase activity
- Gene Name
- FDPS
- Uniprot ID
- P14324
- Uniprot Name
- Farnesyl pyrophosphate synthase
- Molecular Weight
- 48275.03 Da
References
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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
- Specific Function
- dimethylallyltranstransferase activity
- Gene Name
- GGPS1
- Uniprot ID
- O95749
- Uniprot Name
- Geranylgeranyl pyrophosphate synthase
- Molecular Weight
- 34870.625 Da
References
- 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
- Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
- Pharmacological action
- Unknown
- General 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-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-CPP) with a corresponding release of cytidine 5-monophosphate (CMP).
- Specific Function
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity
- Gene Name
- ispF
- Uniprot ID
- A0R559
- Uniprot Name
- 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
- Molecular Weight
- 16546.59 Da
References
- 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
- 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
- all-trans-nonaprenyl-diphosphate synthase (geranyl-diphosphate specific) activity
- Gene Name
- uppS
- Uniprot ID
- P9WFF7
- Uniprot Name
- Decaprenyl diphosphate synthase
- Molecular Weight
- 33790.985 Da
References
- 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
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the conversion of 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate (HMBPP) into a mixture of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Acts in the terminal step of the DOXP/MEP pathway for isoprenoid precursor biosynthesis (PubMed:11418107, PubMed:11818558, PubMed:12706830, PubMed:19569147, PubMed:22137895). In vitro, can also hydrate acetylenes to aldehydes and ketones via anti-Markovnikov/Markovnikov addition (PubMed:22948824).
- Specific Function
- 3 iron, 4 sulfur cluster binding
- Gene Name
- ispH
- Uniprot ID
- P62623
- Uniprot Name
- 4-hydroxy-3-methylbut-2-enyl diphosphate reductase
- Molecular Weight
- 34774.275 Da
References
- 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
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General 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.
- Specific Function
- di-trans,poly-cis-undecaprenyl-diphosphate synthase activity
- Gene Name
- ispU
- Uniprot ID
- P60472
- Uniprot Name
- Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific)
- Molecular Weight
- 28443.92 Da
References
- 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 at September 11, 2007 17:49 / Updated at August 26, 2024 19:22