Showing Metabocard for dimethylallyl diphosphate (BASm0002835)

Common NameDimethylallyl diphosphate
DescriptionDimethylallylpyrophosphate, 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
Molecular FormulaC5H12O7P2
Average Mass246.09210
Monoisotopic Mass246.00583
IUPAC Name({hydroxy[(3-methylbut-2-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
Traditional Name[hydroxy(3-methylbut-2-en-1-yl)oxyphosphoryl]oxyphosphonic acid
CAS Registry Number358-72-5
SMILESCC(C)=CCOP(=O)([O-])OP(=O)([O-])[O-]
InChI IdentifierInChI=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 KeyCBIDRCWHNCKSTO-UHFFFAOYSA-N
CHEBI IDCHEBI:57623
HMDB IDHMDB0001120
Pathways
NameSMPDB/PathBank
Steroid Biosynthesis
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Atorvastatin Action Pathway
Hypercholesterolemia
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
StateSolid
Water Solubility6.54e+00 g/l
logP0.30
logS-1.58
pKa (Strongest Acidic)1.77
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count5
Hydrogen Donor Count3
Polar Surface Area113.29 Ų
Rotatable Bond Count5
Physiological Charge-2
Formal Charge0
Refractivity49.13 m³·mol⁻¹
Polarizability19.33

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