Back to Compounds

Showing Compound mevalonate-diphosphate (FDB031002)

Record Information
Version1.0
Creation date2015-05-07 20:46:39 UTC
Update date2025-11-19 03:02:45 UTC
Primary IDFDB031002
Secondary Accession Numbers
  • FDB022420
Chemical Information
FooDB Namemevalonate-diphosphate
DescriptionMevalonate-diphosphate, also known as 5-diphosphomevalonic acid or mevelonic acid-5-diphosphoric acid, is a member of the class of compounds known as organic pyrophosphates. Organic pyrophosphates are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O. Thus, mevalonate-diphosphate is considered to be a fatty acid lipid molecule. Mevalonate-diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Mevalonate-diphosphate can be found in a number of food items such as kohlrabi, enokitake, avocado, and redcurrant, which makes mevalonate-diphosphate a potential biomarker for the consumption of these food products. Mevalonate-diphosphate exists in all eukaryotes, ranging from yeast to humans. In humans, mevalonate-diphosphate is involved in several metabolic pathways, some of which include zoledronate action pathway, lovastatin action pathway, pamidronate action pathway, and desmosterolosis. Mevalonate-diphosphate is also involved in several metabolic disorders, some of which include wolman disease, lysosomal acid lipase deficiency (wolman disease), cholesteryl ester storage disease, and CHILD syndrome.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(R)-5-DiphosphomevalonateChEBI
5-DiphosphomevalonateHMDB
5-Diphosphomevalonic acidHMDB
Mevalonate 5-diphosphateHMDB
Mevalonate pyrophosphateHMDB
Mevalonate-diphosphateHMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoic acidHMDB
(R)-Diphosphomevalonic acidHMDB
5-Pyrophosphomevalonic acidHMDB
Mevalonic 5-pyrophosphateHMDB
Mevalonic acid 5-diphosphateHMDB
Mevalonic acid 5-pyrophosphateHMDB
Mevalonic acid pyrophosphateHMDB
Pyrophosphomevalonic acidHMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoateHMDB
(R)-DiphosphomevalonateHMDB
5-PyrophosphomevalonateHMDB
Mevalonate 5-pyrophosphateHMDB
Mevalonic 5-pyrophosphic acidHMDB
Mevalonic acid 5-diphosphic acidHMDB
Mevalonic acid 5-pyrophosphic acidHMDB
Mevalonic acid pyrophosphic acidHMDB
PyrophosphomevalonateHMDB
(R)-5-Diphosphomevalonic acidGenerator
R-DiphosphomevalonateHMDB
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
Polarizability23.46 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H14O10P2
IUPAC name(3R)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid
InChI IdentifierInChI=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-/m1/s1
InChI KeySIGQQUBJQXSAMW-ZCFIWIBFSA-N
Isomeric SMILESC[C@@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O
Average Molecular Weight308.1169
Monoisotopic Molecular Weight308.006219692
Classification
Description 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 ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
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 Descriptors
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Diphosphomevalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004m-9820000000-7d8dd5ca92f4eb0538fdSpectrum
Predicted GC-MS5-Diphosphomevalonic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dv-9243200000-6d8177d69adb810da37fSpectrum
Predicted GC-MS5-Diphosphomevalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01wf-1391000000-a8414ad19cb44452295f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-4940000000-c856f917d05bbc77ac8a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01sr-9840000000-db467c852b0f7d795ece2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1494000000-7e72bc5c055d7b3e4f372016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-7920000000-5c36505c154e9a3abebd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-cbcfedc91b4fe71d58492016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-a7e7073b139ac0acc8552021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-9466000000-5ab0d4ae0def99221d8f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056s-9500000000-38a7f595bafdd824dd362021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0938000000-9afa28886c9f8ff753e02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3940000000-53f4c41d4cec2fbfc65d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08n9-6910000000-e20806c8945d9a51ddb12021-09-22View Spectrum
NMRNot Available
ChemSpider ID388531
ChEMBL IDCHEMBL235881
KEGG Compound IDC01143
Pubchem Compound ID439418
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0001090
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007615
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content ReferenceNot Available