Bovine Metabolome Database: Showing metabocard for Dimethylallylpyrophosphate (BMDB0001120)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:19 UTC

Update Date

2020-05-19 22:01:18 UTC

BMDB ID

BMDB0001120

Secondary Accession Numbers

BMDB01120

Metabolite Identification

Common 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₅H₁₂O₇P₂

Average Molecular Weight

246.0921

Monoisotopic Molecular Weight

246.005825762

IUPAC Name

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

Traditional Name

dimethylallyl diphosphate

CAS Registry Number

358-72-5

SMILES

CC(C)=CCO[P@](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/h3H,4H2,1-2H3,(H,9,10)(H2,6,7,8)

InChI Key

CBIDRCWHNCKSTO-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.

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

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Mitochondria
Peroxisome

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	234 - 238 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-9700000000-678abe159a77eee761ec	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 17V, negative	splash10-004i-3690000000-be82b5d8f3a1d675c6de	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9660000000-6e2c34b818f993a966d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-9200000000-08a00604e05fbe36065b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9100000000-01b0ee5834d30012257b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-3b55dbb5fc89be39fcb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9510000000-3521e5fb3dcbf2e3590e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-15ed4ecee7cc175e3833	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-3290000000-0d2c2679aff41e5a2aa8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9100000000-1ca46da447e4b1c42222	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-9000000000-a94de2be1fc80e7f3ca7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0490000000-d1cdea0da4ab0affcc51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056s-9600000000-f42e0441eb797a5faf85	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-c8d7613f7f9dc6aa7e47	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Mitochondria
Peroxisome

Biospecimen Locations

Skeletal Muscle

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001120

DrugBank ID

DB01785

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Dimethylallyl pyrophosphate

METLIN ID

6016

PubChem Compound

647

PDB ID

Not Available

ChEBI ID

16057

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Isopentenyl-diphosphate Delta-isomerase 1

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:: IDI1
Uniprot ID:: Q1LZ95
Molecular weight:: 26467.0

Reactions

Isopentenyl pyrophosphate → Dimethylallylpyrophosphate	details

Enzyme Details

2. Farnesyl pyrophosphate synthase

General function:: Coenzyme transport and metabolism
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 (By similarity).
Gene Name:: FDPS
Uniprot ID:: Q8WMY2
Molecular weight:: 40510.0

Enzyme Details

3. Geranylgeranyl pyrophosphate synthase

General function:: Coenzyme transport and metabolism
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:: P56966
Molecular weight:: 34900.0

Showing metabocard for Dimethylallylpyrophosphate (BMDB0001120)

Structure for BMDB0001120 (Dimethylallylpyrophosphate)

Enzymes

Reactions