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(R)-Mevalonic acid (YMDB00707)

Identification
YMDB IDYMDB00707
Name(R)-Mevalonic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionMevalonic acid, also known as DL-mevalonate or MVA, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Mevalonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Mevalonic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (3RS)-Mevalonate
  • (3RS)-Mevalonic acid
  • (R)-3,5-dihydroxy-3-methylvaleric acid
  • (R)-5-Phosphomevalonate
  • (r)-5-phosphomevaloonic acid
  • (R)-Mevalonate
  • (R)-mevalonic acid
  • (r)-mevalonic acid 5-phosphate
  • 2,4-Dideoxy-3-C-methylpentonate
  • 2,4-Dideoxy-3-C-methylpentonic acid
  • 3,5-dihydroxy-3-methyl-Valerate
  • 3,5-dihydroxy-3-methyl-Valeric acid
  • 3,5-Dihydroxy-3-methylpentanoate
  • 3,5-Dihydroxy-3-methylpentanoic acid
  • 3,5-Dihydroxy-3-methylvalerate
  • 3,5-Dihydroxy-3-methylvaleric acid
  • b,d-Dihydroxy-b-methylvalerate
  • b,d-Dihydroxy-b-methylvaleric acid
  • b,d-Dihydroxy-beta-methylvalerate
  • b,d-Dihydroxy-beta-methylvaleric acid
  • DL-Mevalonate
  • DL-Mevalonic acid
  • Hiochic acid
  • Mevalonate
  • Mevalonic acid
  • MVA
  • MVS
  • RS-Mevalonate
  • RS-Mevalonic acid
  • MK 91
  • Acid, mevalonic
CAS number150-97-0
WeightAverage: 148.1571
Monoisotopic: 148.073558872
InChI KeyKJTLQQUUPVSXIM-ZCFIWIBFSA-N
InChIInChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
IUPAC Name3,5-dihydroxy-3-methylpentanoic acid
Traditional IUPAC NameRS-mevalonic acid
Chemical FormulaC6H12O4
SMILESC[C@@](O)(CCO)CC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Methyl-branched fatty acid
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point24-27 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility414 g/LALOGPS
logP-0.9ALOGPS
logP-1.1ChemAxon
logS0.45ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.51 m³·mol⁻¹ChemAxon
Polarizability14.54 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 triphosphate → Mevalonic acid-5P + ADP
3-Hydroxy-3-methylglutaryl-CoA + NADPH → (R)-Mevalonic acid + NADP + Coenzyme A
KEGG Reactions
NADP + (R)-Mevalonic acid + Coenzyme A ↔ 3-Hydroxy-3-methylglutaryl-CoA + hydron + NADPH
Adenosine triphosphate + (R)-Mevalonic acid → Mevalonic acid-5P + hydron + ADP
(R)-Mevalonic acid + Cytidine triphosphate → Mevalonic acid-5P + CDP + hydron
GTP + (R)-Mevalonic acid → Mevalonic acid-5P + hydron + Guanosine diphosphate
Uridine triphosphate + (R)-Mevalonic acid → Mevalonic acid-5P + Uridine 5'-diphosphate + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-9400000000-875fe9eef6c0fc4dbd86JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c327JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d93JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f610JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-0bb212794cd101490acdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q1-9800000000-95e2c177f1ee0c9cd312JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g9-9200000000-f5d0630f14fa9249d4c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f92-2900000000-8b015723cd087b29e974JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9800000000-93639d7d95cd6690d44dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-9100000000-094b07bf98ce319b4824JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
  • Chen, F., Zhou, J., Shi, Z., Liu, L., Du, G., Chen, J. (2010). "[Effect of acetyl-CoA synthase gene overexpression on physiological function of Saccharomyces cerevisiae]." Wei Sheng Wu Xue Bao 50:1172-1179.21090257
  • Asadollahi, M. A., Maury, J., Schalk, M., Clark, A., Nielsen, J. (2010). "Enhancement of farnesyl diphosphate pool as direct precursor of sesquiterpenes through metabolic engineering of the mevalonate pathway in Saccharomyces cerevisiae." Biotechnol Bioeng 106:86-96.20091767
  • Goldstein, J. L., Brown, M. S. (1990). "Regulation of the mevalonate pathway." Nature 343:425-430.1967820
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Takahara, Kenji; Nakamura, Yoshio; Ohashi, Takehisa; Watanabe, Kiyoshi. Fermentative production of mevalonic acid. Jpn. Kokai Tokkyo Koho (1985), 4 pp.
External Links:
ResourceLink
CHEBI ID17710
HMDB IDHMDB00227
Pubchem Compound ID439230
Kegg IDC01107
ChemSpider ID388367
FOODB IDNot Available
WikipediaMevalonic_acid
BioCyc IDMEVALONATE

Enzymes

Protein Details
1. 3-hydroxy-3-methylglutaryl-coenzyme A reductase 1
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
This transmembrane glycoprotein is involved in the control of cholesterol biosynthesis. It is the rate-limiting enzyme of the sterol biosynthesis
Gene Name:
HMG1
Uniprot ID:
P12683
Molecular weight:
115624.0
Reactions
(R)-mevalonate + CoA + 2 NADP(+) → (S)-3-hydroxy-3-methylglutaryl-CoA + 2 NADPH.
Protein Details
2. 3-hydroxy-3-methylglutaryl-coenzyme A reductase 2
General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
This transmembrane glycoprotein is involved in the control of cholesterol biosynthesis. It is the rate-limiting enzyme of the sterol biosynthesis
Gene Name:
HMG2
Uniprot ID:
P12684
Molecular weight:
115691.0
Reactions
(R)-mevalonate + CoA + 2 NADP(+) → (S)-3-hydroxy-3-methylglutaryl-CoA + 2 NADPH.
Protein Details
3. Mevalonate kinase
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.