Showing Compound Card for Mevalonic acid-5P (CDB005320)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:31:23 UTC
Updated at2020-11-18 16:39:43 UTC
CannabisDB IDCDB005320
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMevalonic acid-5P
DescriptionMevalonic acid-5P, also known as mevalonate-5P or 5-phosphomevalonate, 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. A carboxyalkyl phosphate that is mevalonic acid phosphorylated at position 5. Mevalonic acid-5P is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Mevalonic acid-5P exists in all living species, ranging from bacteria to humans. Within humans, mevalonic acid-5P participates in a number of enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from (R)-mevalonate through its interaction with the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into (R)-mevalonic acid-5-pyrophosphate; which is mediated by the enzyme phosphomevalonate kinase. In humans, mevalonic acid-5P is involved in mevalonate pathway. Outside of the human body, Mevalonic acid-5P has been detected, but not quantified in, several different foods, such as prickly pears, safflowers, walnuts, sorrels, and italian oregano. This could make mevalonic acid-5P a potential biomarker for the consumption of these foods. Mevalonic acid-5P is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC6H13O7P
Average Molecular Weight228.14
Monoisotopic Molecular Weight228.0399
IUPAC Name(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
Traditional Namemevalonate-5-phosphate
CAS Registry Number73566-35-5
SMILES
C[C@@](O)(CCOP(O)(O)=O)CC(O)=O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phosphomevalonate kinasePMVK1q22Q15126 details
Mevalonate kinaseMVK12q24Q03426 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001343
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031001
KNApSAcK IDC00007304
Chemspider ID388517
KEGG Compound IDC01107
BioCyc IDCPD-499
BiGG ID36819
Wikipedia LinkNot Available
METLIN ID6177
PubChem Compound439400
PDB IDNot Available
ChEBI ID17436
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Phosphomevalonate kinase
General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745
Enzyme Details
2. Mevalonate kinase
General function:
Involved in ATP binding
Specific function:
May be a regulatory site in cholesterol biosynthetic pathway.
Gene Name:
MVK
Uniprot ID:
Q03426
Molecular weight:
42450.475