Isopentenyl pyrophosphate (CHEM035184)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:33:26 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035184
Identification
Common NameIsopentenyl pyrophosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methyl-3-butenyl pyrophosphateChEBI
3-Methylbut-3-en-1-yl trihydrogen diphosphateChEBI
3-Methylbut-3-enyl phosphono hydrogen phosphateChEBI
delta-3-Isopentenyl pyrophosphateChEBI
delta3-Isopentenyl diphosphateChEBI
delta3-Methyl-3-butenyl diphosphateChEBI
Diphosphoric acid mono(3-methyl-3-butenyl) esterChEBI
IPPChEBI
IPPPChEBI
mono(3-Methyl-3-butenyl) diphosphateChEBI
3-Methyl-3-butenyl pyrophosphoric acidGenerator
3-Methylbut-3-en-1-yl trihydrogen diphosphoric acidGenerator
3-Methylbut-3-enyl phosphono hydrogen phosphoric acidGenerator
delta-3-Isopentenyl pyrophosphoric acidGenerator
Δ-3-isopentenyl pyrophosphateGenerator
Δ-3-isopentenyl pyrophosphoric acidGenerator
delta3-Isopentenyl diphosphoric acidGenerator
Δ3-isopentenyl diphosphateGenerator
Δ3-isopentenyl diphosphoric acidGenerator
delta3-Methyl-3-butenyl diphosphoric acidGenerator
Δ3-methyl-3-butenyl diphosphateGenerator
Δ3-methyl-3-butenyl diphosphoric acidGenerator
Diphosphate mono(3-methyl-3-butenyl) esterGenerator
mono(3-Methyl-3-butenyl) diphosphoric acidGenerator
Isopentenyl pyrophosphoric acidGenerator
delta(3)-Isopentenyl-PPHMDB
delta-3-Isopentenyl pyrophosphatHMDB
IPRHMDB
Isopentenyl diphosphateHMDB
Isopentenyl-PPHMDB
Isopentenyl pyrophosphate, 4-(14)C-labeledHMDB
Chemical FormulaC5H12O7P2
Average Molecular Mass246.092 g/mol
Monoisotopic Mass246.006 g/mol
CAS Registry Number358-71-4
IUPAC Name({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional Nameisopentenyl-diphosphate
SMILESCC(=C)CCO[P@](O)(=O)OP(O)(O)=O
InChI IdentifierInChI=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)
InChI KeyNUHSROFQTUXZQQ-UHFFFAOYSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9600000000-930df1e6e1c7e4eed108Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-004i-0190000000-d2895fc0c10b183f43eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-056r-3980000000-627cfd435c85e88822b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-056r-3980000000-23fe88b159964959e66fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-056r-2960000000-19354ef717c66764cd68Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-056r-9740000000-022ac5cb9631af8164eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-004i-9300000000-aee23682a2c1fa358b3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004i-9100000000-6318f24bf41c952270c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9000000000-84d7ad80acc22ebadc08Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-004i-9000000000-52e623d1c0e3c5eec628Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-9000000000-71f08ee06355626ebfd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-0a4i-0900000000-8b768e6e6fd82a9e52fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-00kr-0900000000-1e624fb025fa3835685bSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-014i-1900000000-2c64756ee3a8e3d9493cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0006-0090000000-5185751820ffb8d752a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0006-0090000000-03743901b1bb8cf365e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0006-2090000000-9e4213acb94b27ef7c83Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-004l-9080000000-43b0fb277b1db3562d57Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-004i-9010000000-863fed72efb5d1767ed2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9670000000-fa3d42a8ff93d345cea7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-78e51dcb039157700c59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-a585b43371cb54efe2ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-391e90cfd97e6adcbb06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-fed3169adff6f1179e01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c099085cd907446a2fbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04714
HMDB IDHMDB0001347
FooDB IDFDB030946
Phenol Explorer IDNot Available
KNApSAcK IDC00000848
BiGG ID33956
BioCyc IDDELTA3-ISOPENTENYL-PP
METLIN ID6181
PDB IDNot Available
Wikipedia LinkIsopentenyl pyrophosphate
Chemspider ID1158
ChEBI ID16584
PubChem Compound ID1195
Kegg Compound IDC00129
YMDB IDYMDB00200
ECMDB IDECMDB01347
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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. Org Lett. 2005 Dec 8;7(25):5677-80.
2. 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.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11278429
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15450402
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23000003
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23543734
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23747531
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23872678
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7584140
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7753173