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Identification
NameISOPENTENYL PYROPHOSPHATE
Accession NumberDB04714
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
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 246.0921
Monoisotopic: 246.005825762
Chemical FormulaC5H12O7P2
InChI KeyInChIKey=NUHSROFQTUXZQQ-UHFFFAOYSA-N
InChI
InChI=1S/C5H12O7P2/c1-5(2)3-4-11-14(9,10)12-13(6,7)8/h1,3-4H2,2H3,(H,9,10)(H2,6,7,8)
IUPAC Name
({hydroxy[(3-methylbut-3-en-1-yl)oxy]phosphoryl}oxy)phosphonic acid
SMILES
CC(=C)CCO[P@](O)(=O)OP(O)(O)=O
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
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.917
Blood Brain Barrier+0.8933
Caco-2 permeable-0.6159
P-glycoprotein substrateNon-substrate0.5146
P-glycoprotein inhibitor INon-inhibitor0.8072
P-glycoprotein inhibitor IINon-inhibitor0.9666
Renal organic cation transporterNon-inhibitor0.8964
CYP450 2C9 substrateNon-substrate0.7909
CYP450 2D6 substrateNon-substrate0.8282
CYP450 3A4 substrateNon-substrate0.551
CYP450 1A2 substrateNon-inhibitor0.8083
CYP450 2C9 inhibitorNon-inhibitor0.807
CYP450 2D6 inhibitorNon-inhibitor0.8539
CYP450 2C19 inhibitorNon-inhibitor0.7755
CYP450 3A4 inhibitorNon-inhibitor0.8896
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8961
Ames testNon AMES toxic0.7174
CarcinogenicityNon-carcinogens0.688
BiodegradationReady biodegradable0.6571
Rat acute toxicity2.3133 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7409
hERG inhibition (predictor II)Non-inhibitor0.9111
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 Solubility6.69 mg/mLALOGPS
logP0.04ALOGPS
logP0.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.21 m3·mol-1ChemAxon
Polarizability19.01 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
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9670000000-fa3d42a8ff93d345cea7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9200000000-78e51dcb039157700c59View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-a585b43371cb54efe2ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0490000000-391e90cfd97e6adcbb06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9510000000-fed3169adff6f1179e01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5c099085cd907446a2fbView in MoNA
References
Synthesis Reference

Jay Keasling, “Biosynthesis of isopentenyl pyrophosphate.” U.S. Patent US20030148479, issued August 07, 2003.

US20030148479
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Magnesium ion binding
Specific Function:
Generates ditrans,octacis-undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP) and farnesyl diphosphate (FPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide.
Gene Name:
ispU
Uniprot ID:
P60472
Molecular Weight:
28443.92 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:
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 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 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
Mycobacterium smegmatis (strain ATCC 700084 / mc(2)155)
Pharmacological action
unknown
General Function:
Nucleotide binding
Specific Function:
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidyl-2-C-methyl-D-erythritol 2-phosphate (CDP-ME2P) to 2-C-methyl-D-erythritol 2,4-cyclodiphosphate (ME-CPP) with a corresponding release of cytidine 5-monophosphate (CMP) (By similarity).
Gene Name:
ispF
Uniprot ID:
A0R559
Molecular Weight:
16546.59 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
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
uppS
Uniprot ID:
P60479
Molecular Weight:
Not Available
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 September 11, 2007 11:49 / Updated on August 17, 2016 12:24