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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:23 UTC
HMDB IDHMDB01343
Secondary Accession NumbersNone
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-PhosphomevaloonateGenerator
(R)-Mevalonate 5-phosphateGenerator
(R)-Mevalonic acid 5-phosphoric acidGenerator
5-PhosphomevalonateHMDB
Mevalonate-5-PHMDB
Mevalonate-5-phosphateHMDB
Mevalonate-5PHMDB
Mevalonate-PHMDB
P-MevalonateHMDB
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 KeyInChIKey=OKZYCXHTTZZYSK-ZCFIWIBFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Peroxisome
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.38 m3·mol-1ChemAxon
Polarizability19.23 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Peroxisome
Biofluid LocationsNot Available
Tissue Location
  • Heart
  • Kidney
  • Liver
  • Pancreas
  • Skeletal Muscle
Pathways
NameSMPDB LinkKEGG Link
Alendronate pathwaySMP00095Not Available
Atorvastatin PathwaySMP00131Not Available
Cerivastatin PathwaySMP00111Not Available
CHILD SyndromeSMP00387Not Available
Cholesteryl ester storage diseaseSMP00508Not Available
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)SMP00388Not Available
DesmosterolosisSMP00386Not Available
Fluvastatin PathwaySMP00119Not Available
Hyper-IgD syndromeSMP00509Not Available
HypercholesterolemiaSMP00209Not Available
Ibandronate PathwaySMP00079Not Available
Lovastatin PathwaySMP00099Not Available
Lysosomal Acid Lipase Deficiency (Wolman Disease)SMP00319Not Available
Mevalonic aciduriaSMP00510Not Available
Pamidronate PathwaySMP00117Not Available
Pravastatin PathwaySMP00089Not Available
Risedronate PathwaySMP00112Not Available
Rosuvastatin PathwaySMP00092Not Available
Simvastatin Action PathwaySMP00082Not Available
Smith-Lemli-Opitz Syndrome (SLOS)SMP00389Not Available
Steroid BiosynthesisSMP00023map00100
Wolman diseaseSMP00511Not Available
Zoledronate PathwaySMP00107Not 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
NuGOwiki LinkHMDB01343
Metagene LinkHMDB01343
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. [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. [11115399 ]
  3. Houten SM, Waterham HR: Nonorthologous gene displacement of phosphomevalonate kinase. Mol Genet Metab. 2001 Mar;72(3):273-6. [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