Showing Compound Card for Isopentenyl pyrophosphate (CDB005221)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (8) Show 13 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:21:28 UTC
Updated at2020-12-07 19:11:47 UTC
CannabisDB IDCDB005221
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameIsopentenyl pyrophosphate
DescriptionIsopentenyl pyrophosphate, also known as IPP or delta(3)-isopentenyl-PP, 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. Isopentenyl pyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Isopentenyl pyrophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight246.09
Monoisotopic Molecular Weight246.0058
IUPAC Name({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional Nameisopentenyl-diphosphate
CAS Registry Number358-71-4
SMILES
CC(=C)CCOP(O)(=O)OP(O)(O)=O
InChI Identifier
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)
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Geranylgeranyl pyrophosphate synthaseGGPS11q43O95749 details
Farnesyl pyrophosphate synthaseFDPS1q22P14324 details
Diphosphomevalonate decarboxylaseMVD16q24.3P53602 details
Isopentenyl-diphosphate Delta-isomerase 2IDI210p15.3Q9BXS1 details
Isopentenyl-diphosphate Delta-isomerase 1IDI110p15.3Q13907 details
tRNA isopentenyltransferase 1 variantTRIT11p34.2Q53F11 details
Decaprenyl-diphosphate synthase subunit 2PDSS26q21Q86YH6 details
Decaprenyl-diphosphate synthase subunit 1PDSS110p12.1Q5T2R2 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Geranylgeranyl pyrophosphate synthaseGGPS11q43O95749 details
Farnesyl pyrophosphate synthaseFDPS1q22P14324 details
Isopentenyl-diphosphate Delta-isomerase 2IDI210p15.3Q9BXS1 details
Isopentenyl-diphosphate Delta-isomerase 1IDI110p15.3Q13907 details
Decaprenyl-diphosphate synthase subunit 1PDSS110p12.1Q5T2R2 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001347
DrugBank IDDB04714
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030946
KNApSAcK IDC00000848
Chemspider ID1158
KEGG Compound IDC00129
BioCyc IDDELTA3-ISOPENTENYL-PP
BiGG ID33956
Wikipedia LinkIsopentenyl pyrophosphate
METLIN ID6181
PubChem Compound1195
PDB IDNot Available
ChEBI ID16584
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details
1. Geranylgeranyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
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
Molecular weight:
34870.625
Enzyme Details
2. Farnesyl pyrophosphate synthase
General function:
Involved in isoprenoid biosynthetic process
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, 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.
Gene Name:
FDPS
Uniprot ID:
P14324
Molecular weight:
48275.03
Enzyme Details
3. Diphosphomevalonate decarboxylase
General function:
Involved in ATP binding
Specific function:
Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:
MVD
Uniprot ID:
P53602
Molecular weight:
43404.125
Enzyme Details
4. Isopentenyl-diphosphate Delta-isomerase 2
General function:
Lipid transport and metabolism
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:
IDI2
Uniprot ID:
Q9BXS1
Molecular weight:
26752.33
Enzyme Details
5. Isopentenyl-diphosphate Delta-isomerase 1
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:
IDI1
Uniprot ID:
Q13907
Molecular weight:
32485.165
Enzyme Details
6. tRNA isopentenyltransferase 1 variant
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
TRIT1
Uniprot ID:
Q53F11
Molecular weight:
52727.9
Enzyme Details
7. Decaprenyl-diphosphate synthase subunit 2
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS2
Uniprot ID:
Q86YH6
Molecular weight:
44128.17
Enzyme Details
8. Decaprenyl-diphosphate synthase subunit 1
General function:
Not Available
Specific function:
Supplies decaprenyl diphosphate, the precursor for the side chain of the isoprenoid quinones ubiquinone-10.
Gene Name:
PDSS1
Uniprot ID:
Q5T2R2
Molecular weight:
46260.6

Only showing the first 10 proteins. There are 13 proteins in total.

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