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Identification
YMDB IDYMDB00181
NameMevalonic acid-5P
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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. 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 yeast, mevalonic acid-5P participates in a number of enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonic acid; which is mediated by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into (S)-5-diphosphomevalonic acid through its interaction with the enzyme phosphomevalonate kinase. In yeast, mevalonic acid-5P is involved in the metabolic pathway called terpenoid backbone biosynthesis pathway.
Structure
Thumb
Synonyms
  • (R)-5-phosphomevalonate
  • (R)-5-phosphomevalonic acid
  • (R)-5-phosphomevaloonate
  • (R)-5-phosphomevaloonic acid
  • (R)-mevalonic acid 5-phosphate
  • 5-phosphomevalonate
  • mevalonate-5-p
  • mevalonate-5-phosphate
  • mevalonate-5P
  • mevalonate-p
  • p-mevalonate
  • (R)-Mevalonate 5-phosphate
  • (R)-Mevalonic acid 5-phosphoric acid
  • 5-Phosphomevalonic acid
  • Mevalonate 5-phosphate
  • Phosphomevalonate
  • Phosphomevalonic acid
  • Phosphomevalonic acid, (+-)-isomer
CAS number73566-35-5
WeightAverage: 228.137
Monoisotopic: 228.039889282
InChI KeyOKZYCXHTTZZYSK-ZCFIWIBFSA-N
InChIInChI=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
IUPAC Name(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
Traditional IUPAC Namemevalonate-5-phosphate
Chemical FormulaC6H13O7P
SMILES[H]OC(=O)C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])OP(=O)(O[H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(10:0)PW002545 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(14:0)PW002544 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(16:0)PW002550 ThumbThumb?image type=greyscaleThumb?image type=simple
Cholesterol biosynthesis and metabolism CE(18:0)PW002551 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Steroid biosynthesisec00100 Map00100
Terpenoid backbone biosynthesisec00900 Map00900
SMPDB Reactions
(R)-Mevalonic acid + Adenosine triphosphateMevalonic acid-5P + ADP
Adenosine triphosphate + Mevalonic acid-5PADP + 5-Diphosphomevalonic acid
KEGG Reactions
Adenosine triphosphate + (R)-Mevalonic acidMevalonic acid-5P + hydron + ADP
(R)-Mevalonic acid + Cytidine triphosphateMevalonic acid-5P + CDP + hydron
GTP + (R)-Mevalonic acidMevalonic acid-5P + hydron + Guanosine diphosphate
Uridine triphosphate + (R)-Mevalonic acidMevalonic acid-5P + Uridine 5'-diphosphate + hydron
Adenosine triphosphate + Mevalonic acid-5P5-Diphosphomevalonic acid + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17436
HMDB IDHMDB01343
Pubchem Compound ID439400
Kegg IDC01107
ChemSpider ID388517
FOODB IDFDB022566
Wikipedia5-phosphomevalonate
BioCyc IDCPD-499

Enzymes

General function:
Involved in ATP binding
Specific function:
RAR (regulation of autonomous replication) is a protein whose activity increases the mitotic stability of plasmids
Gene Name:
ERG12
Uniprot ID:
P07277
Molecular weight:
48458.89844
Reactions
ATP + (R)-mevalonate → ADP + (R)-5-phosphomevalonate.
General function:
Involved in ATP binding
Specific function:
ATP + (R)-5-phosphomevalonate = ADP + (R)-5- diphosphomevalonate
Gene Name:
ERG8
Uniprot ID:
P24521
Molecular weight:
50454.39844
Reactions
ATP + (R)-5-phosphomevalonate → ADP + (R)-5-diphosphomevalonate.