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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2016-02-11 01:05:11 UTC
HMDB IDHMDB01981
Secondary Accession NumbersNone
Metabolite Identification
Common Name(R)-Mevalonic acid-5-pyrophosphate
Description(R)-Mevalonic acid-5-pyrophosphate (mevalonate 5-diphosphate) is a directly synthesized product of mevalonate phosphate that is essential for cell proliferation. (PMID 2211719 ). It is a substrate for mevalonate-5-diphosphate decarboxylase, the third enzyme involved in the biosynthesis of cholesterol from mevalonic acid. This enzyme catalyzes the reaction of mevalonate 5-diphosphate (MVADP) with ATP to produce isopentenyl diphosphate, ADP, CO2, and inorganic phosphate. The overall reaction involves an anti elimination of the tertiary hydroxyl and carboxyl groups. This metabolite participates both in the biosynthesis of cholesterol and fatty acid mechanism, through which interpathway regulation could take place between the cholesterol and FA cascades. (PMID 8769113 ).
Structure
Thumb
Synonyms
ValueSource
(R)-5-Diphosphomevalonic acidHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-OateHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acidHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid 1,3-dioxideHMDB
5-PyrophosphomevalonateHMDB
5-Pyrophosphomevalonic acidHMDB
Mevalonate 5-diphosphateHMDB
Mevalonic 5-pyrophosphateHMDB
Mevalonic acid 5-diphosphateHMDB
Mevalonic acid 5-pyrophosphateHMDB
Mevalonic acid pyrophosphateHMDB
MVADPHMDB
PyrophosphomevalonateHMDB
Pyrophosphomevalonic acidHMDB
R-Mevalonic acid-5-pyrophosphateHMDB
Chemical FormulaC6H14O10P2
Average Molecular Weight308.1169
Monoisotopic Molecular Weight308.006219692
IUPAC Name(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid
Traditional Namepyrophosphomevalonate
CAS Registry Number1492-08-6
SMILES
C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m0/s1
InChI KeyInChIKey=SIGQQUBJQXSAMW-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydroxy acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.26 mg/mLALOGPS
logP-1.2ALOGPS
logP-1.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity56.26 m3·mol-1ChemAxon
Polarizability23.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Lymphocyte
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022779
KNApSAcK IDNot Available
Chemspider ID17216150
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Pyrophosphomevalonate
NuGOwiki LinkHMDB01981
Metagene LinkHMDB01981
METLIN ID6415
PubChem Compound22833574
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceBloch, Konrad; Chaykin, S.; Phillips, A. H.; De Waard, A. Mevalonic acid pyrophosphate and isopentylpyrophosphate. Journal of Biological Chemistry (1959), 234 2595-2604.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cuthbert JA, Lipsky PE: Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. J Biol Chem. 1990 Oct 25;265(30):18568-75. [2211719 ]
  2. Ku EC: Regulation of fatty acid biosynthesis by intermediates of the cholesterol biosynthetic pathway. Biochem Biophys Res Commun. 1996 Aug 5;225(1):173-9. [8769113 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:
MVD
Uniprot ID:
P53602
Molecular weight:
43404.125
General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745