Cannabis Compound Database: Showing Compound Card for Dimethylallylpyrophosphate (CDB005222)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 10 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:21:35 UTC

Updated at

2020-12-07 19:11:47 UTC

CannabisDB ID

CDB005222

Secondary Accession Numbers

Not Available

Cannabis Compound 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. Dimethylallylpyrophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

246.09

Monoisotopic Molecular Weight

246.0058

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Muscle

Subcellular:

Role

Biological role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available
Desmosterolosis		Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Farnesyl pyrophosphate synthase	FDPS	1q22	P14324	details
Isopentenyl-diphosphate Delta-isomerase 2	IDI2	10p15.3	Q9BXS1	details
Isopentenyl-diphosphate Delta-isomerase 1	IDI1	10p15.3	Q13907	details
tRNA dimethylallyltransferase, mitochondrial	TRIT1	1p34.2	Q9H3H1	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Geranylgeranyl pyrophosphate synthase	GGPS1	1q43	O95749	details
Farnesyl pyrophosphate synthase	FDPS	1q22	P14324	details
Isopentenyl-diphosphate Delta-isomerase 2	IDI2	10p15.3	Q9BXS1	details
Isopentenyl-diphosphate Delta-isomerase 1	IDI1	10p15.3	Q13907	details
tRNA dimethylallyltransferase, mitochondrial	TRIT1	1p34.2	Q9H3H1	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001120

DrugBank ID

DB01785

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

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. 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

4. 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

5. tRNA dimethylallyltransferase, mitochondrial

General function:: Not Available
Specific function:: Catalyzes the transfer of a dimethylallyl group onto the adenine at position 37 of both cytosolic and mitochondrial tRNAs, leading to the formation of N6-(dimethylallyl)adenosine (i(6)A).
Gene Name:: TRIT1
Uniprot ID:: Q9H3H1
Molecular weight:: 52724.84

Showing Compound Card for Dimethylallylpyrophosphate (CDB005222)

Structure for CDB005222 (Dimethylallylpyrophosphate)

Enzymes