You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2006-05-22 14:17:30 UTC
Update Date2017-09-27 08:24:10 UTC
HMDB IDHMDB0001981
Secondary Accession Numbers
  • HMDB01981
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
Mevalonate pyrophosphateMeSH
5-Diphosphomevalonic acidMeSH
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 KeySIGQQUBJQXSAMW-LURJTMIESA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganic oxoanionic compounds
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Organic phosphoric acid derivative
  • Fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity56.26 m³·mol⁻¹ChemAxon
Polarizability23.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1491000000-8b66d9021d8692cc58b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-5930000000-ed4d02286446a704e70dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ea-9810000000-99f0d148c2b3cc6b87e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bvi-0494000000-00b15359794ef7c74743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9410000000-5d44f0388a33861701feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-b038a323df0665a33d9cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue Location
  • Lymphocyte
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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
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. [PubMed: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. [PubMed: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