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Identification
NameDimethylallyl Diphosphate
Accession NumberDB01785  (EXPT01221)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS number358-72-5
WeightAverage: 246.0921
Monoisotopic: 246.005825762
Chemical FormulaC5H12O7P2
InChI KeyCBIDRCWHNCKSTO-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[P@](O)(=O)OP(O)(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Farnesyl pyrophosphate synthaseProteinunknownNot AvailableHumanP14324 details
Isopentenyl-diphosphate Delta-isomerase 1ProteinunknownNot AvailableHumanQ13907 details
4-hydroxy-3-methylbut-2-enyl diphosphate reductaseProteinunknownNot AvailableEscherichia coli (strain K12)P62623 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Alendronate Action PathwayDrug actionSMP00095
Zoledronate Action PathwayDrug actionSMP00107
Wolman diseaseDiseaseSMP00511
Pravastatin Action PathwayDrug actionSMP00089
Risedronate Action PathwayDrug actionSMP00112
HypercholesterolemiaDiseaseSMP00209
Rosuvastatin Action PathwayDrug actionSMP00092
Fluvastatin Action PathwayDrug actionSMP00119
CHILD SyndromeDiseaseSMP00387
Hyper-IgD syndromeDiseaseSMP00509
Cerivastatin Action PathwayDrug actionSMP00111
Pamidronate Action PathwayDrug actionSMP00117
Atorvastatin Action PathwayDrug actionSMP00131
Cholesteryl ester storage diseaseDiseaseSMP00508
Mevalonic aciduriaDiseaseSMP00510
Steroid BiosynthesisMetabolicSMP00023
Ibandronate Action PathwayDrug actionSMP00079
Simvastatin Action PathwayDrug actionSMP00082
Lovastatin Action PathwayDrug actionSMP00099
Lysosomal Acid Lipase Deficiency (Wolman Disease)DiseaseSMP00319
DesmosterolosisDiseaseSMP00386
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)DiseaseSMP00388
Smith-Lemli-Opitz Syndrome (SLOS)DiseaseSMP00389
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9660000000-6e2c34b818f993a966d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-08a00604e05fbe36065bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-01b0ee5834d30012257bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-3b55dbb5fc89be39fcb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-3521e5fb3dcbf2e3590eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-15ed4ecee7cc175e3833View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
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 phosphate
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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, and ubiquinones. FPP also serves as substrate for protein farnesylation and geranylgeranylation. Catalyzes the sequential condensation of isopentenyl pyrophosphate with the allylic pyrophosphates, d...
Gene Name:
FDPS
Uniprot ID:
P14324
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
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 stringent response. Seems to directly or indirectly interact with RelA to maintain it in an inactive form during normal growth.
Gene Name:
ispH
Uniprot ID:
P62623
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23