Showing Compound Dimethylallylpyrophosphate (FDB022434)

Record Information

Version

1.0

Creation date

2011-09-21 00:13:55 UTC

Update date

2020-09-17 15:41:14 UTC

Primary ID

FDB022434

Secondary Accession Numbers

FDB030829

Chemical Information

FooDB Name

Dimethylallylpyrophosphate

Description

Dimethylallylpyrophosphate, also known as 2-isopentenyl diphosphate or delta-prenyl diphosphoric acid, 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. Dimethylallylpyrophosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

CAS Number

358-72-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Isopentenyl diphosphate	ChEBI
3,3-Dimethylallyl pyrophosphate	ChEBI
3-Methylbut-2-enyl phosphono hydrogen phosphate	ChEBI
delta-Prenyl diphosphate	ChEBI
delta2-Isopentenyl diphosphate	ChEBI
Dimethylallyl diphosphate	ChEBI
Dimethylallyl pyrophosphate	ChEBI
DMAPP	ChEBI
Monoprenyl diphosphate	ChEBI
Prenol pyrophosphate	ChEBI
Prenyl diphosphate	Kegg
2-Isopentenyl diphosphoric acid	Generator
3,3-Dimethylallyl pyrophosphoric acid	Generator
3-Methylbut-2-enyl phosphono hydrogen phosphoric acid	Generator
delta-Prenyl diphosphoric acid	Generator
Δ-prenyl diphosphate	Generator
Δ-prenyl diphosphoric acid	Generator
delta2-Isopentenyl diphosphoric acid	Generator
Δ2-isopentenyl diphosphate	Generator
Δ2-isopentenyl diphosphoric acid	Generator
Dimethylallyl diphosphoric acid	Generator
Dimethylallyl pyrophosphoric acid	Generator
Monoprenyl diphosphoric acid	Generator
Prenol pyrophosphoric acid	Generator
Prenyl diphosphoric acid	Generator
Dimethylallylpyrophosphoric acid	Generator
1,1-Dimethyl-4-phenylpiperazinium iodide	HMDB
3-Methyl-2-buten-1-ol pyrophosphate	HMDB
3-Methyl-2-buten-1-ol trihydrogen pyrophosphate	HMDB
3-Methyl-2-butenyl pyrophosphate	HMDB
3-Methylbut-2-enyl pyrophosphate	HMDB
Delta2-Isopentenyl-diphosphate	HMDB
Dimethylallyl-diphosphate	HMDB
Dimethylallyl-PP	HMDB
Dimethylallyl-ppi	HMDB
Dimethylallyl-pyrophosphate	HMDB
Diphosphoric acid mono(3-methyl-2-butenyl) ester	HMDB
DMPP	HMDB
IPE	HMDB
Prenyl-diphosphate	HMDB
3,3-Dimethylallyl pyrophosphate, (14)C-labeled	HMDB
DMADP CPD	HMDB
3-Methyl-2-butenyl trihydrogen diphosphate	HMDB
Dimethylallylpyrophosphate	HMDB
gamma,gamma-Dimethylallyl pyrophosphate	HMDB
γ,γ-Dimethylallyl pyrophosphate	HMDB
2-Isopentenyl diate	ChEBI
2-Isopentenyl diic acid	Generator
3-Methyl-2-buten-1-ol pyroate	HMDB
3-methyl-2-Buten-1-ol pyrophosphate	hmdb
3-Methyl-2-buten-1-ol trihydrogen pyroate	HMDB
3-methyl-2-Buten-1-ol trihydrogen pyrophosphate	hmdb
3-Methyl-2-butenyl pyroate	HMDB
3-Methylbut-2-enyl ONO hydrogen ate	ChEBI
3-Methylbut-2-enyl ONO hydrogen ic acid	Generator
3-Methylbut-2-enyl pyroate	HMDB
3-methylbut-2-enyl pyrophosphate	hmdb
3,3-Dimethylallyl pyroate	ChEBI
3,3-Dimethylallyl pyroic acid	Generator
delta-Prenyl diate	ChEBI
delta-Prenyl diic acid	Generator
delta2-Isopentenyl diate	ChEBI
delta2-Isopentenyl diic acid	Generator
Delta2-Isopentenyl-diate	HMDB
delta2-isopentenyl-diphosphate	hmdb
Dimethylallyl diate	ChEBI
Dimethylallyl diic acid	Generator
Dimethylallyl pyroate	ChEBI
Dimethylallyl pyroic acid	Generator
dimethylallyl pyrophosphate	hmdb
Dimethylallyl-diate	HMDB
dimethylallyl-diphosphate	hmdb
dimethylallyl-PP	hmdb
dimethylallyl-PPi	hmdb
Dimethylallyl-pyroate	HMDB
dimethylallyl-pyrophosphate	hmdb
Dimethylallylpyroate	HMDB
Dimethylallylpyrophosphic acid	hmdb
Dioric acid mono(3-methyl-2-butenyl) ester	HMDB
Monoprenyl diate	ChEBI
Monoprenyl diic acid	Generator
Prenol pyroate	ChEBI
Prenol pyroic acid	Generator
Prenyl diate	ChEBI
Prenyl diic acid	Generator
Prenyl-diate	HMDB
prenyl-diphosphate	hmdb
δ-prenyl diate	Generator
δ-prenyl diic acid	Generator
δ2-isopentenyl diate	Generator
δ2-isopentenyl diic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	6.54 g/L	ALOGPS
logP	0.3	ALOGPS
logP	0.3	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	49.13 m³·mol⁻¹	ChemAxon
Polarizability	19.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H12O7P2

IUPAC name

({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid

InChI Identifier

InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)

InChI Key

CBIDRCWHNCKSTO-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CCO[P@](O)(=O)OP(O)(O)=O

Average Molecular Weight

246.0921

Monoisotopic Molecular Weight

246.005825762

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid 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 Framework

Aliphatic acyclic compounds

External Descriptors

prenol phosphate (CHEBI:16057 )
C5 isoprenoids (hemiterpenes) (C00235 )
C5 isoprenoids (hemiterpenes) (LMPR01010001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Tissue and substructures:

Muscle

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dimethylallylpyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-9700000000-678abe159a77eee761ec	Spectrum
Predicted GC-MS	Dimethylallylpyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 17V, negative	splash10-004i-3690000000-be82b5d8f3a1d675c6de	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9660000000-6e2c34b818f993a966d7	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9200000000-08a00604e05fbe36065b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9100000000-01b0ee5834d30012257b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-3b55dbb5fc89be39fcb4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9510000000-3521e5fb3dcbf2e3590e	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-15ed4ecee7cc175e3833	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3290000000-0d2c2679aff41e5a2aa8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9100000000-1ca46da447e4b1c42222	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-a94de2be1fc80e7f3ca7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-d1cdea0da4ab0affcc51	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056s-9600000000-f42e0441eb797a5faf85	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-c8d7613f7f9dc6aa7e47	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum