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Showing Compound mevalonate-5-phosphate (FDB031001)

Record Information
Version1.0
Creation date2015-05-07 20:46:34 UTC
Update date2019-11-26 03:22:03 UTC
Primary IDFDB031001
Secondary Accession Numbers
  • FDB022566
Chemical Information
FooDB Namemevalonate-5-phosphate
DescriptionMevalonic acid-5p, also known as (R)-5-phosphomevalonate or mevalonate-5p, is a member of the class of compounds known as monoalkyl phosphates. Monoalkyl phosphates are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Thus, mevalonic acid-5p is considered to be a fatty acid lipid molecule. Mevalonic acid-5p is soluble (in water) and a moderately acidic compound (based on its pKa). Mevalonic acid-5p can be found in a number of food items such as rowanberry, common oregano, caraway, and cherry tomato, which makes mevalonic acid-5p a potential biomarker for the consumption of these food products. Mevalonic acid-5p can be found primarily throughout most human tissues. Mevalonic acid-5p exists in all eukaryotes, ranging from yeast to humans. In humans, mevalonic acid-5p is involved in several metabolic pathways, some of which include pamidronate action pathway, rosuvastatin action pathway, pravastatin action pathway, and lovastatin action pathway. Mevalonic acid-5p is also involved in several metabolic disorders, some of which include hypercholesterolemia, lysosomal acid lipase deficiency (wolman disease), hyper-igd syndrome, and mevalonic aciduria.
CAS Number73566-35-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(R)-5-PhosphomevalonateChEBI
(R)-5-Phosphomevaloonic acidChEBI
(R)-Mevalonic acid 5-phosphateChEBI
(R)-5-Phosphomevalonic acidGenerator
(R)-5-PhosphomevaloonateGenerator
(R)-Mevalonate 5-phosphateGenerator
(R)-Mevalonic acid 5-phosphoric acidGenerator
Mevalonate-5PGenerator
5-PhosphomevalonateHMDB
Mevalonate-5-pHMDB
Mevalonate-5-phosphateHMDB
Mevalonate-pHMDB
p-MevalonateHMDB
5-Phosphomevalonic acidHMDB
Mevalonate 5-phosphateHMDB
PhosphomevalonateHMDB
Phosphomevalonic acidHMDB
Phosphomevalonic acid, (+-)-isomerHMDB
(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
Mevalonic acid phosphateHMDB
Mevalonic acid-5PHMDB
Predicted Properties
PropertyValueSource
Water Solubility19.9 g/LALOGPS
logP-2.2ALOGPS
logP-1.2ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.38 m³·mol⁻¹ChemAxon
Polarizability19.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13O7P
IUPAC name(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
InChI IdentifierInChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1
InChI KeyOKZYCXHTTZZYSK-ZCFIWIBFSA-N
Isomeric SMILESC[C@@](O)(CCOP(O)(O)=O)CC(O)=O
Average Molecular Weight228.137
Monoisotopic Molecular Weight228.039889282
Classification
Description Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Fatty acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
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-MSMevalonic acid-5P, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0292-9600000000-a4f04a66624afb8d522aSpectrum
Predicted GC-MSMevalonic acid-5P, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9413000000-7329637530b2ddc29e0bSpectrum
Predicted GC-MSMevalonic acid-5P, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1960000000-a02358583ea07452bacf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-4900000000-ef07c3371552f7c1c11d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-9800000000-bba2c1c56648b04a1fdd2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-8960000000-de18bb77f2282c89d45a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-6dd83d59bdb427eeee242016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9c715a4954dce4d5a8562016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-1940000000-c405e8487510c01d67be2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0229-9300000000-84bcd8640d320dd874e32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ry-9200000000-6589ef1abdd6045116392021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5090000000-98125cefd75fccd3e5642021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9020000000-74f440cb4e3ffa40388d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 Reference