Dimethylallyl Diphosphate

Identification

Name
Dimethylallyl Diphosphate
Accession Number
DB01785  (EXPT01221)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
358-72-5
Weight
Average: 246.0921
Monoisotopic: 246.005825762
Chemical Formula
C5H12O7P2
InChI Key
CBIDRCWHNCKSTO-UHFFFAOYSA-N
InChI
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)
IUPAC Name
({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
SMILES
CC(C)=CCO[[email protected]](O)(=O)OP(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UFarnesyl pyrophosphate synthaseNot AvailableHuman
UIsopentenyl-diphosphate Delta-isomerase 1Not AvailableHuman
U4-hydroxy-3-methylbut-2-enyl diphosphate reductaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Alendronate Action PathwayDrug action
Zoledronate Action PathwayDrug action
Wolman diseaseDisease
Pravastatin Action PathwayDrug action
Risedronate Action PathwayDrug action
HypercholesterolemiaDisease
Rosuvastatin Action PathwayDrug action
Fluvastatin Action PathwayDrug action
CHILD SyndromeDisease
Hyper-IgD syndromeDisease
Cerivastatin Action PathwayDrug action
Pamidronate Action PathwayDrug action
Atorvastatin Action PathwayDrug action
Cholesteryl ester storage diseaseDisease
Mevalonic aciduriaDisease
Steroid BiosynthesisMetabolic
Ibandronate Action PathwayDrug action
Simvastatin Action PathwayDrug action
Lovastatin Action PathwayDrug action
Lysosomal Acid Lipase Deficiency (Wolman Disease)Disease
DesmosterolosisDisease
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)Disease
Smith-Lemli-Opitz Syndrome (SLOS)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB01120
KEGG Compound
C00235
PubChem Compound
647
PubChem Substance
46507688
ChemSpider
627
ChEBI
16057
ChEMBL
CHEMBL343480
HET
DMA
PDB Entries
1uby / 1yhl / 2ick / 2zrx / 2zrz / 3b06 / 3epl / 3kef / 3oyr / 3p41
show 9 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.54 mg/mLALOGPS
logP0.3ALOGPS
logP0.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.13 m3·mol-1ChemAxon
Polarizability19.19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6689
Blood Brain Barrier+0.8384
Caco-2 permeable-0.646
P-glycoprotein substrateNon-substrate0.5538
P-glycoprotein inhibitor INon-inhibitor0.8499
P-glycoprotein inhibitor IINon-inhibitor0.9464
Renal organic cation transporterNon-inhibitor0.9317
CYP450 2C9 substrateNon-substrate0.8176
CYP450 2D6 substrateNon-substrate0.838
CYP450 3A4 substrateNon-substrate0.5755
CYP450 1A2 substrateNon-inhibitor0.8712
CYP450 2C9 inhibitorNon-inhibitor0.8098
CYP450 2D6 inhibitorNon-inhibitor0.8769
CYP450 2C19 inhibitorNon-inhibitor0.791
CYP450 3A4 inhibitorNon-inhibitor0.9481
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9149
Ames testNon AMES toxic0.6544
CarcinogenicityCarcinogens 0.5
BiodegradationNot ready biodegradable0.6244
Rat acute toxicity2.7766 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9206
hERG inhibition (predictor II)Non-inhibitor0.9347
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-9660000000-6e2c34b818f993a966d7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9200000000-08a00604e05fbe36065b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-9100000000-01b0ee5834d30012257b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0490000000-3b55dbb5fc89be39fcb4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9510000000-3521e5fb3dcbf2e3590e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-15ed4ecee7cc175e3833
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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
Organic pyrophosphates / Monoalkyl phosphates / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
prenol phosphate (CHEBI:16057) / C5 isoprenoids (hemiterpenes) (C00235) / C5 isoprenoids (hemiterpenes) (LMPR01010001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Poly(a) rna binding
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...
Gene Name
FDPS
Uniprot ID
P14324
Uniprot Name
Farnesyl pyrophosphate synthase
Molecular Weight
48275.03 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
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
Uniprot Name
Isopentenyl-diphosphate Delta-isomerase 1
Molecular Weight
26318.93 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Converts 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate into isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). Is also involved in penicillin tolerance and control of the stringe...
Gene Name
ispH
Uniprot ID
P62623
Uniprot Name
4-hydroxy-3-methylbut-2-enyl diphosphate reductase
Molecular Weight
34774.275 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:04