Record Information
Version2.0
Creation Date2012-05-31 13:50:27 -0600
Update Date2015-06-03 15:53:57 -0600
Secondary Accession Numbers
  • ECMDB01347
Identification
Name:Isopentenyl pyrophosphate
DescriptionIsopentenyl pyrophosphate, IPP or isopentenyl diphosphate, is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids. IPP is formed from Mevalonate-5-pyrophosphate, in a reaction catalyzed by the enzyme mevalonate-5-pyrophosphate decarboxylase. (wikipedia)
Structure
Thumb
Synonyms:
  • δ(3)-isopentenyl-PP
  • Δ3-isopentenyl-PP
  • Δ3-isopentenyl-PP
  • 3-Methyl-3-butenyl pyrophosphate
  • 3-Methyl-3-butenyl pyrophosphoric acid
  • Delta(3)-Isopentenyl-PP
  • Delta-3-Isopentenyl pyrophosphat
  • Delta3-isopentenyl diphosphate
  • delta3-Isopentenyl diphosphoric acid
  • Delta3-isopentenyl-PP
  • Delta3-methyl-3-butenyl diphosphate
  • delta3-Methyl-3-butenyl diphosphoric acid
  • Diphosphate mono(3-methyl-3-butenyl) ester
  • Diphosphorate mono(3-methyl-3-butenyl) ester
  • Diphosphoric acid mono(3-methyl-3-butenyl) ester
  • IPP
  • IPR
  • Isopentenyl diphosphate
  • Isopentenyl diphosphoric acid
  • Isopentenyl pyrophosphate
  • Isopentenyl pyrophosphoric acid
  • Isopentenyl-pp
  • Mono(3-methyl-3-butenyl) diphosphate
  • mono(3-Methyl-3-butenyl) diphosphoric acid
  • δ(3)-Isopentenyl-PP
  • δ-3-Isopentenyl pyrophosphat
  • δ3-Isopentenyl diphosphate
  • δ3-Isopentenyl diphosphoric acid
  • δ3-Isopentenyl-PP
  • δ3-Methyl-3-butenyl diphosphate
  • δ3-Methyl-3-butenyl diphosphoric acid
Chemical Formula:C5H12O7P2
Weight:Average: 246.0921
Monoisotopic: 246.005825762
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)
CAS number:358-71-4
IUPAC Name:({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name:isopentenyl-diphosphate
SMILES:CC(=C)CCO[P@](O)(=O)OP(O)(O)=O
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassIsoprenoid phosphates
Direct ParentIsoprenoid phosphates
Alternative Parents
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
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.69 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.21 m³·mol⁻¹ChemAxon
Polarizability19.01 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Hydrogen ion + 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH > Water + Isopentenyl pyrophosphate + NAD
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Geranyl-PP + Pyrophosphate
Geranyl-PP + Isopentenyl pyrophosphate + Geranyl diphosphate <> Farnesyl pyrophosphate + Pyrophosphate
Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate <> Octaprenyl diphosphate +5 Pyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate <> Pyrophosphate + Geranyl-PP
Geranyl-PP + Isopentenyl pyrophosphate <> Pyrophosphate + Farnesyl pyrophosphate
1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADPH + Hydrogen ion <> Isopentenyl pyrophosphate + NADP + Water
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate
Isopentenyl pyrophosphate + NAD + Water <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + Hydrogen ion
Geranyl-PP + Isopentenyl pyrophosphate > Farnesyl pyrophosphate + Pyrophosphate
Isopentenyl pyrophosphate + NAD(P)<sup>+</sup> + Water < 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H + Hydrogen ion
Farnesyl pyrophosphate + Isopentenyl pyrophosphate > all-<i>trans</i>-octaprenyl diphosphate + Pyrophosphate
Farnesyl pyrophosphate + Isopentenyl pyrophosphate > Undecaprenyl diphosphate + Pyrophosphate
Isopentenyl pyrophosphate > Dimethylallylpyrophosphate
Farnesyl pyrophosphate + 5 Isopentenyl pyrophosphate >5 Pyrophosphate + Octaprenyl diphosphate
Isopentenyl pyrophosphate + NAD(P)(+) + Water > 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NAD(P)H
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate
Isopentenyl pyrophosphate + NAD + NADP + Water + Dimethylallylpyrophosphate <> 1-Hydroxy-2-methyl-2-butenyl 4-diphosphate + NADH + NADPH + Hydrogen ion
1-Hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate + Hydrogen ion + NADPH + NADPH > Water + NADPH + Isopentenyl pyrophosphate + Isopentenyl pyrophosphate
Isopentenyl pyrophosphate + Isopentenyl pyrophosphate <> Dimethylallylpyrophosphate + Dimethylallylpyrophosphate
Dimethylallylpyrophosphate + Isopentenyl pyrophosphate + Dimethylallylpyrophosphate + Isopentenyl pyrophosphate > Pyrophosphate + Geranyl-PP + Geranyl-PP
Geranyl-PP + Isopentenyl pyrophosphate + Geranyl-PP + Isopentenyl pyrophosphate > Pyrophosphate + Farnesyl pyrophosphate + Farnesyl pyrophosphate
Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate + Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + di-trans,octa-cis-undecaprenyl diphosphate

SMPDB Pathways:
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: isoprenoid biosynthesis (nonmevalonate pathway)PW000975 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: methylerythritol phosphate and polyisoprenoid biosynthesisPW000958 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • trans, trans-farnesyl diphosphate biosynthesis PWY-5123
  • di-trans,poly-cis-undecaprenyl phosphate biosynthesis PWY-5785
  • methylerythritol phosphate pathway NONMEVIPP-PWY
  • octaprenyl diphosphate biosynthesis PWY-5783
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9600000000-930df1e6e1c7e4eed108View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9670000000-fa3d42a8ff93d345cea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-78e51dcb039157700c59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-a585b43371cb54efe2ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-391e90cfd97e6adcbb06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-fed3169adff6f1179e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c099085cd907446a2fbView in MoNA
References
References:
  • Daubenberger CA, Salomon M, Vecino W, Hubner B, Troll H, Rodriques R, Patarroyo ME, Pluschke G: Functional and structural similarity of V gamma 9V delta 2 T cells in humans and Aotus monkeys, a primate infection model for Plasmodium falciparum malaria. J Immunol. 2001 Dec 1;167(11):6421-30. Pubmed: 11714808
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Kao, Chai-Lin; Kittleman, William; Zhang, Hua; Seto, Haruo; Liu, Hung-Wen. Stereochemical Analysis of Isopentenyl Diphosphate Isomerase Type II from Staphylococcus aureus Using Chemically Synthesized (S)- and (R)-[2-2H]Isopentenyl Diphosphates.Organic Let
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16584
HMDB IDHMDB01347
Pubchem Compound ID1195
Kegg IDC00129
ChemSpider ID1158
WikipediaIsopentenyl pyrophosphate
BioCyc IDDELTA3-ISOPENTENYL-PP
EcoCyc IDDELTA3-ISOPENTENYL-PP
Ligand ExpoIPE

Enzymes

General function:
Involved in isoprenoid biosynthetic process
Specific function:
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + trans,trans-farnesyl diphosphate
Gene Name:
ispA
Uniprot ID:
P22939
Molecular weight:
32159
Reactions
Geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2E,6E)-farnesyl diphosphate.
General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide
Gene Name:
uppS
Uniprot ID:
P60472
Molecular weight:
28444
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + di-trans,octa-cis-undecaprenyl diphosphate.
General function:
Involved in isopentenyl diphosphate biosynthetic process, mevalonate-independent pathway
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 stringent response. Seems to directly or indirectly interact with relA to maintain it in an inactive form during normal growth
Gene Name:
ispH
Uniprot ID:
P62623
Molecular weight:
34774
Reactions
Isopentenyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
Dimethylallyl diphosphate + NAD(P)(+) + H(2)O = (E)-4-hydroxy-3-methylbut-2-en-1-yl diphosphate + NAD(P)H.
General function:
Involved in isopentenyl-diphosphate delta-isomerase activity
Specific function:
Catalyzes the 1,3-allylic rearrangement of the homoallylic substrate isopentenyl (IPP) to its highly electrophilic allylic isomer, dimethylallyl diphosphate (DMAPP)
Gene Name:
idi
Uniprot ID:
Q46822
Molecular weight:
20508
Reactions
Isopentenyl diphosphate = dimethylallyl diphosphate.
General function:
Involved in isoprenoid biosynthetic process
Specific function:
Supplies octaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone and menaquinone
Gene Name:
ispB
Uniprot ID:
P0AD57
Molecular weight:
35217
Reactions
(2E,6E)-farnesyl diphosphate + 5 isopentenyl diphosphate = 5 diphosphate + all-trans-octaprenyl diphosphate.