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Showing Compound isopentenyl diphosphate (FDB030946)

Record Information
Version1.0
Creation date2015-05-07 20:34:59 UTC
Update date2019-11-26 03:21:58 UTC
Primary IDFDB030946
Secondary Accession Numbers
  • FDB022569
Chemical Information
FooDB Nameisopentenyl diphosphate
DescriptionIsopentenyl pyrophosphate, also known as delta3-isopentenyl diphosphate or ipp, is a member of the class of compounds known as isoprenoid phosphates. Isoprenoid phosphates are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit. Thus, isopentenyl pyrophosphate is considered to be an isoprenoid lipid molecule. Isopentenyl pyrophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Isopentenyl pyrophosphate can be found in a number of food items such as american butterfish, conch, tea leaf willow, and butternut, which makes isopentenyl pyrophosphate a potential biomarker for the consumption of these food products. Isopentenyl pyrophosphate can be found primarily in human spleen tissue. Isopentenyl pyrophosphate exists in all living species, ranging from bacteria to humans. In humans, isopentenyl pyrophosphate is involved in several metabolic pathways, some of which include ibandronate action pathway, lovastatin action pathway, fluvastatin action pathway, and pravastatin action pathway. Isopentenyl pyrophosphate is also involved in several metabolic disorders, some of which include hypercholesterolemia, hyper-igd syndrome, lysosomal acid lipase deficiency (wolman disease), and wolman disease. Isopentenyl pyrophosphate (IPP, isopentenyl diphosphate, or IDP) is an isoprenoid precursor. IPP is an intermediate in the classical, HMG-CoA reductase pathway (commonly called the mevalonate pathway) and in the non-mevalonate MEP pathway of isoprenoid precursor biosynthesis. Isoprenoid precursors such as IPP, and its isomer DMAPP, are used by organisms in the biosynthesis of terpenes and terpenoids .
CAS Number358-71-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H12O7P2
IUPAC name({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
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
Isomeric SMILESCC(=C)CCO[P@](O)(=O)OP(O)(O)=O
Average Molecular Weight246.0921
Monoisotopic Molecular Weight246.005825762
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsopentenyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-9600000000-930df1e6e1c7e4eed108Spectrum
Predicted GC-MSIsopentenyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsopentenyl pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-004i-0190000000-d2895fc0c10b183f43ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-056r-3980000000-627cfd435c85e88822b52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-056r-3980000000-23fe88b159964959e66f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-056r-2960000000-19354ef717c66764cd682020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-056r-9740000000-022ac5cb9631af8164ee2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-004i-9300000000-aee23682a2c1fa358b3b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004i-9100000000-6318f24bf41c952270c72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9000000000-84d7ad80acc22ebadc082020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 16V, negativesplash10-004i-9000000000-52e623d1c0e3c5eec6282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, negativesplash10-004i-9000000000-71f08ee06355626ebfd62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-0a4i-0900000000-8b768e6e6fd82a9e52fc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-004i-9000000000-5ef060d5ec4b80c35c1a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-00kr-0900000000-1e624fb025fa3835685b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, negativesplash10-014i-1900000000-2c64756ee3a8e3d9493c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0006-0090000000-5185751820ffb8d752a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0006-0090000000-03743901b1bb8cf365e92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0006-2090000000-9e4213acb94b27ef7c832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-004l-9080000000-43b0fb277b1db3562d572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-004i-9010000000-863fed72efb5d1767ed22020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9670000000-fa3d42a8ff93d345cea72015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-78e51dcb039157700c592015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-a585b43371cb54efe2eb2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-391e90cfd97e6adcbb062015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-fed3169adff6f1179e012015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c099085cd907446a2fb2015-09-15View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference