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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:27:36 UTC
HMDB IDHMDB0001343
Secondary Accession Numbers
  • HMDB01343
Metabolite Identification
Common NameMevalonic acid-5P
Description5-Phosphomevalonate is a metabolic intermediate in the mevalonate pathway, catalyzed by the enzyme mevalonate kinase from Mevalonate. (wikipedia).
Structure
Thumb
Synonyms
ValueSource
(R)-5-PhosphomevalonateChEBI
(R)-5-Phosphomevaloonic acidChEBI
(R)-Mevalonic acid 5-phosphateChEBI
(R)-5-Phosphomevalonic acidGenerator
Mevalonate-5PGenerator
(R)-5-PhosphomevaloonateGenerator
(R)-Mevalonate 5-phosphateGenerator
(R)-Mevalonic acid 5-phosphoric acidGenerator
5-PhosphomevalonateHMDB
Mevalonate-5-PHMDB
Mevalonate-5-phosphateHMDB
Mevalonate-PHMDB
P-MevalonateHMDB
5-Phosphomevalonic acidMeSH
Mevalonate 5-phosphateMeSH
PhosphomevalonateMeSH
Phosphomevalonic acidMeSH
Phosphomevalonic acid, (+-)-isomerMeSH
Chemical FormulaC6H13O7P
Average Molecular Weight228.137
Monoisotopic Molecular Weight228.039889282
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
DescriptionThis compound belongs to the class of chemical entities known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic phosphoric acids and derivatives
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

Biological Location:

  Subcellular:

  Organ and components:

  Tissue and substructures:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 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
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, Positivesplash10-0292-9600000000-a4f04a66624afb8d522aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9413000000-7329637530b2ddc29e0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1960000000-a02358583ea07452bacfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-4900000000-ef07c3371552f7c1c11dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-9800000000-bba2c1c56648b04a1fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-8960000000-de18bb77f2282c89d45aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-6dd83d59bdb427eeee24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9c715a4954dce4d5a856View in MoNA
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Heart
  • Kidney
  • Liver
  • Pancreas
  • Skeletal Muscle
Pathways
NameSMPDB/PathwhizKEGG
Alendronate pathwayPw000137Pw000137 greyscalePw000137 simpleNot Available
Atorvastatin PathwayPw000275Pw000275 greyscalePw000275 simpleNot Available
CHILD SyndromePw000096Pw000096 greyscalePw000096 simpleNot Available
Cerivastatin PathwayPw000271Pw000271 greyscalePw000271 simpleNot Available
Cholesteryl ester storage diseasePw000484Pw000484 greyscalePw000484 simpleNot 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 IDFDB022566
KNApSAcK IDNot Available
Chemspider ID388517
KEGG Compound IDC01107
BioCyc IDCPD-499
BiGG ID36819
Wikipedia Link5-phosphomevalonate
METLIN ID6177
PubChem Compound439400
PDB IDPMV
ChEBI ID17436
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Popjak G, Boehm G, Parker TS, Edmond J, Edwards PA, Fogelman AM: Determination of mevalonate in blood plasma in man and rat. Mevalonate "tolerance" tests in man. J Lipid Res. 1979 Aug;20(6):716-28. [PubMed:226640 ]
  2. Campos N, Rodriguez-Concepcion M, Sauret-Gueto S, Gallego F, Lois LM, Boronat A: Escherichia coli engineered to synthesize isopentenyl diphosphate and dimethylallyl diphosphate from mevalonate: a novel system for the genetic analysis of the 2-C-methyl-d-erythritol 4-phosphate pathway for isoprenoid biosynthesis. Biochem J. 2001 Jan 1;353(Pt 1):59-67. [PubMed:11115399 ]
  3. Houten SM, Waterham HR: Nonorthologous gene displacement of phosphomevalonate kinase. Mol Genet Metab. 2001 Mar;72(3):273-6. [PubMed:11243736 ]

Enzymes

General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745
Reactions
Adenosine triphosphate + Mevalonic acid-5P → ADP + (S)-5-Diphosphomevalonic aciddetails
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
Reactions
Adenosine triphosphate + (R)-mevalonate → ADP + Mevalonic acid-5Pdetails