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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:38 UTC
HMDB IDHMDB0000227
Secondary Accession Numbers
  • HMDB00227
  • HMDB0059629
  • HMDB59629
Metabolite Identification
Common NameMevalonic acid
DescriptionMevalonic acid, also known as MVA, mevalonate, or hiochic acid, 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 a key organic compound in biochemistry. It is found in most higher organisms ranging from plants to animals. Mevalonic acid is a precursor in the biosynthetic pathway known as the mevalonate pathway that produces terpenes (in plants) and steroids (in animals). Mevalonic acid is the primary precursor of isopentenyl pyrophosphate (IPP), that is in turn the basis for all terpenoids. The production of mevalonic acid by the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, is the rate-limiting step in the biosynthesis of cholesterol (PMID: 12872277 ). The cholesterol biosynthetic pathway has three major steps: (1) acetate to mevalonate, (2) mevalonate to squalene, and (3) squalene to cholesterol. In the first step, which catalyzed by thiolase, two acetyl-CoA molecules form acetoacetyl-CoA and one CoA molecule is released, then the acetoacetyl-CoA reacts with another molecule of acetyl-CoA and generates 3-hydroxy-3-methylglutaryl-CoA (HMGCoA). The enzyme responsible for this reaction is 3-hydroxy-3-methylglutaryl-CoA synthase (HMG-CoA synthase): In the pathway to synthesize cholesterol, one of the HMG-CoA carboxyl groups undergoes reduction to an alcohol, releasing CoA, leading to the formation of mevalonate, a six carbon compound. This reaction is catalyzed by hydroxy-methylglutaryl-CoA reductase, In the second step (mevalonate to squalene) mevalonate receives a phosphoryl group from ATP to form 5-phosphomevalonate. This compound accepts another phosphate to generate mevalonate-5-pyrophosphate. After a third phosphorylation, the compound is decarboxylated, loses water, and generates isopentenyl pyrophosphate (IPP). Then through successive condensations, IPP forms squalene, a terpene hydrocarbon that contains 30 carbon atoms. By cyclization and other changes, this compound will finally result in cholesterol. Mevalonic acid is found, on average, in the highest concentration within a few different foods, such as apples, corns, and wild carrots and in a lower concentration in garden tomato (var.), pepper (C. frutescens), and cucumbers. Mevalonic acid has also been detected, but not quantified in, several different foods, such as sweet oranges, potato, milk (cow), cabbages, and white cabbages. This could make mevalonic acid a potential biomarker for the consumption of these foods. Plasma concentrations and urinary excretion of MVA are decreased by HMG-CoA reductase inhibitor drugs such as pravastatin, simvastatin, and atorvastatin (PMID: 8808497 ).
Structure
Data?1676999678
Synonyms
ValueSource
(R)-3,5-Dihydroxy-3-methylvaleric acidChEBI
(R)-MevalonateChEBI
3,5-Dihydroxy-3-methylvaleric acidChEBI
(R)-3,5-Dihydroxy-3-methylvalerateGenerator
(R)-Mevalonic acidGenerator
3,5-Dihydroxy-3-methylvalerateGenerator
MevalonateGenerator
Mevalonic acidChEBI
Acid, mevalonicMeSH
(3R)-3,5-Dihydroxy-3-methylpentanoic acidHMDB
(3R)-Mevalonic acidHMDB
(R)-(-)-Mevalonic acidHMDB
(R)-3,5-Dihydroxy-3-methylpentanoic acidHMDB
2,4-Dideoxy-3-C-methylpentonic acidHMDB
3,5-Dihydroxy-3-methylpentanoic acidHMDB
Hiochic acidHMDB
MVAHMDB
R-Mevalonic acidHMDB
beta,delta-Dihydroxy-beta-methylvaleric acidHMDB
β,δ-Dihydroxy-β-methylvaleric acidHMDB
Chemical FormulaC6H12O4
Average Molecular Weight148.1571
Monoisotopic Molecular Weight148.073558872
IUPAC Name(3R)-3,5-dihydroxy-3-methylpentanoic acid
Traditional Namemevalonic acid
CAS Registry Number17817-88-8
SMILES
C[C@@](O)(CCO)CC(O)=O
InChI Identifier
InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
InChI KeyKJTLQQUUPVSXIM-ZCFIWIBFSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point24 - 27 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Astarita_neg127.030932474
[M-H]-Baker133.98330932474
[M-H]-MetCCS_test_neg125.830932474
[M-H]-Not Available129.9http://allccs.zhulab.cn/database/detail?ID=AllCCS00000280
[M-H]-Not Available129.4http://allccs.zhulab.cn/database/detail?ID=AllCCS00002149
Predicted Molecular 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
Polarizability14.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.53631661259
DarkChem[M-H]-127.99331661259
AllCCS[M+H]+133.96732859911
AllCCS[M-H]-130.34932859911
DeepCCS[M+H]+126.81430932474
DeepCCS[M-H]-122.98430932474
DeepCCS[M-2H]-159.80930932474
DeepCCS[M+Na]+135.38130932474
AllCCS[M+H]+134.032859911
AllCCS[M+H-H2O]+130.032859911
AllCCS[M+NH4]+137.732859911
AllCCS[M+Na]+138.832859911
AllCCS[M-H]-130.332859911
AllCCS[M+Na-2H]-132.732859911
AllCCS[M+HCOO]-135.332859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mevalonic acid,1TMS,isomer #1C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C1427.7Semi standard non polar33892256
Mevalonic acid,1TMS,isomer #1C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C1301.0Standard non polar33892256
Mevalonic acid,1TMS,isomer #1C[C@@](CCO)(CC(=O)O)O[Si](C)(C)C1918.3Standard polar33892256
Mevalonic acid,1TMS,isomer #2C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O1425.3Semi standard non polar33892256
Mevalonic acid,1TMS,isomer #2C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O1323.7Standard non polar33892256
Mevalonic acid,1TMS,isomer #2C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O1919.9Standard polar33892256
Mevalonic acid,1TMS,isomer #3C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C1386.5Semi standard non polar33892256
Mevalonic acid,1TMS,isomer #3C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C1324.3Standard non polar33892256
Mevalonic acid,1TMS,isomer #3C[C@@](O)(CCO)CC(=O)O[Si](C)(C)C1909.2Standard polar33892256
Mevalonic acid,2TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C1532.2Semi standard non polar33892256
Mevalonic acid,2TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C1448.1Standard non polar33892256
Mevalonic acid,2TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C1667.7Standard polar33892256
Mevalonic acid,2TMS,isomer #2C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1467.8Semi standard non polar33892256
Mevalonic acid,2TMS,isomer #2C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1460.0Standard non polar33892256
Mevalonic acid,2TMS,isomer #2C[C@@](CCO)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1658.8Standard polar33892256
Mevalonic acid,2TMS,isomer #3C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C1474.9Semi standard non polar33892256
Mevalonic acid,2TMS,isomer #3C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C1475.4Standard non polar33892256
Mevalonic acid,2TMS,isomer #3C[C@@](O)(CCO[Si](C)(C)C)CC(=O)O[Si](C)(C)C1672.1Standard polar33892256
Mevalonic acid,3TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1556.0Semi standard non polar33892256
Mevalonic acid,3TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1567.1Standard non polar33892256
Mevalonic acid,3TMS,isomer #1C[C@@](CCO[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1497.3Standard polar33892256
Mevalonic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O1662.6Semi standard non polar33892256
Mevalonic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O1502.3Standard non polar33892256
Mevalonic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@](C)(CCO)CC(=O)O1958.2Standard polar33892256
Mevalonic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O1660.2Semi standard non polar33892256
Mevalonic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O1517.5Standard non polar33892256
Mevalonic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O2021.4Standard polar33892256
Mevalonic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO1613.0Semi standard non polar33892256
Mevalonic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO1521.2Standard non polar33892256
Mevalonic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(O)CCO1985.8Standard polar33892256
Mevalonic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C1977.3Semi standard non polar33892256
Mevalonic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C1865.3Standard non polar33892256
Mevalonic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O)O[Si](C)(C)C(C)(C)C1903.4Standard polar33892256
Mevalonic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C1912.7Semi standard non polar33892256
Mevalonic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C1900.9Standard non polar33892256
Mevalonic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(CCO)O[Si](C)(C)C(C)(C)C1883.7Standard polar33892256
Mevalonic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C1911.8Semi standard non polar33892256
Mevalonic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C1889.2Standard non polar33892256
Mevalonic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCC[C@@](C)(O)CC(=O)O[Si](C)(C)C(C)(C)C1916.1Standard polar33892256
Mevalonic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2208.2Semi standard non polar33892256
Mevalonic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2159.8Standard non polar33892256
Mevalonic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC[C@](C)(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1917.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-9400000000-1432953ab200e13ed3a72016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c3272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mevalonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916b2020-04-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d932020-04-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mevalonic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f6102020-04-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 10V, Positive-QTOFsplash10-01q9-2900000000-00a30c20b0fe2afce7d82016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 20V, Positive-QTOFsplash10-03ej-9700000000-c6f9687555150d5ef1a72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 40V, Positive-QTOFsplash10-01bi-9100000000-7047d67f0ba1f8aa28ef2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 10V, Negative-QTOFsplash10-0f72-3900000000-0f765b34011b73405add2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 20V, Negative-QTOFsplash10-0002-9500000000-dd24fe04989af5af11512016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 40V, Negative-QTOFsplash10-052s-9100000000-251b958b3e4355c6f2f62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 10V, Negative-QTOFsplash10-0fbj-2900000000-fb0c642b03cb9422a9e42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 20V, Negative-QTOFsplash10-0a4r-9300000000-1b45622114c4f19f4a9a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 40V, Negative-QTOFsplash10-0006-9000000000-42ee087c307b5e92b0592021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 10V, Positive-QTOFsplash10-01qa-3900000000-2c25572adb25887608452021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 20V, Positive-QTOFsplash10-000j-9200000000-b6d834223509e1430e612021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mevalonic acid 40V, Positive-QTOFsplash10-0006-9000000000-e4b7f6f9a91f771bd4532021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2020-04-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-04-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Peroxisome
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Fibroblasts
  • Leukocyte
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.028 +/- 0.006 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.043 +/- 0.013 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.026(0.013-0.042) uMInfant (0-1 year old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.160 (0.0800-0.300) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
UrineDetected and Quantified0.14 (0.06-0.22) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0531 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.178 (0.0515-0.545) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.012 +/- 0.002 uMAdult (>18 years old)BothSmith-Lemli-Opitz syndrome details
BloodDetected and Quantified70-540 uMInfant (0-1 year old)BothMevalonic aciduria details
BloodDetected and Quantified20-140 uMChildren (1-13 years old)BothMevalonic aciduria details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleAttachment loss  details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleMissing teeth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleTooth Decay details
UrineDetected and Quantified2100-56000 umol/mmol creatinineInfant (0-1 year old)BothMevalonic aciduria details
UrineDetected and Quantified900-14500 umol/mmol creatinineChildren (1-13 years old)BothMevalonic aciduria details
Associated Disorders and Diseases
Disease References
Smith-Lemli-Opitz syndrome
  1. Honda M, Tint GS, Honda A, Salen G, Shefer S, Batta AK, Matsuzaki Y, Tanaka N: Regulation of cholesterol biosynthetic pathway in patients with the Smith-Lemli-Opitz syndrome. J Inherit Metab Dis. 2000 Jul;23(5):464-74. [PubMed:10947201 ]
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Mevalonic aciduria
  1. Hoffmann GF, Charpentier C, Mayatepek E, Mancini J, Leichsenring M, Gibson KM, Divry P, Hrebicek M, Lehnert W, Sartor K, et al.: Clinical and biochemical phenotype in 11 patients with mevalonic aciduria. Pediatrics. 1993 May;91(5):915-21. [PubMed:8386351 ]
Associated OMIM IDs
DrugBank IDDB03518
Phenol Explorer Compound IDNot Available
FooDB IDFDB005126
KNApSAcK IDC00001195
Chemspider ID388367
KEGG Compound IDC00418
BioCyc IDMEVALONATE
BiGG IDNot Available
Wikipedia LinkMevalonic_acid
METLIN IDNot Available
PubChem Compound439230
PDB IDNot Available
ChEBI ID17710
Food Biomarker OntologyNot Available
VMH IDMEV_R
MarkerDB IDMDB00000109
Good Scents IDNot Available
References
Synthesis ReferenceTakahara, Kenji; Nakamura, Yoshio; Ohashi, Takehisa; Watanabe, Kiyoshi. Fermentative production of mevalonic acid. Jpn. Kokai Tokkyo Koho (1985), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Houten SM, Kuis W, Duran M, de Koning TJ, van Royen-Kerkhof A, Romeijn GJ, Frenkel J, Dorland L, de Barse MM, Huijbers WA, Rijkers GT, Waterham HR, Wanders RJ, Poll-The BT: Mutations in MVK, encoding mevalonate kinase, cause hyperimmunoglobulinaemia D and periodic fever syndrome. Nat Genet. 1999 Jun;22(2):175-7. [PubMed:10369261 ]
  2. Hoffmann G, Gibson KM, Brandt IK, Bader PI, Wappner RS, Sweetman L: Mevalonic aciduria--an inborn error of cholesterol and nonsterol isoprene biosynthesis. N Engl J Med. 1986 Jun 19;314(25):1610-4. [PubMed:3012338 ]
  3. Dmitrieva NA, Perrun'kina AM, Khomulo PS: [Determination of mevalonic acid in the urine and its concentration in the urine of patients with atherosclerosis]. Vopr Med Khim. 1968 Jan-Feb;14(1):106-8. [PubMed:5683362 ]
  4. Larson RA, Chung J, Scanu AM, Yachnin S: Neutrophils are required for the DNA synthetic response of human lymphocytes to mevalonic acid: evidence suggesting that a nonsterol product of mevalonate is involved. Proc Natl Acad Sci U S A. 1982 May;79(9):3028-32. [PubMed:6953445 ]
  5. Siavoshian S, Simoneau C, Maugeais P, Marks L, Rodary L, Gardette J, Krempf M: Measurement of mevalonic acid in human urine by bench top gas chromatography-mass spectrometry. Clin Chim Acta. 1995 Dec 29;243(2):129-36. [PubMed:8747489 ]
  6. Mitchell ED Jr, Avigan J: Control of phosphorylation and decarboxylation of mevalonic acid and its metabolites in cultured human fibroblasts and in rat liver in vivo. J Biol Chem. 1981 Jun 25;256(12):6170-3. [PubMed:6263908 ]
  7. Abrar M, Martin PD: Validation and application of an assay for the determination of mevalonic acid in human plasma by liquid chromatography tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jun 25;773(2):103-11. [PubMed:12031835 ]
  8. Haas D, Kelley RI, Hoffmann GF: Inherited disorders of cholesterol biosynthesis. Neuropediatrics. 2001 Jun;32(3):113-22. [PubMed:11521206 ]
  9. Larson RA, Kluskens LE, Yachnin S: The DNA synthetic response of normal and abnormal human lymphocytes to mevalonic acid: the role of granulocytes as a helper population. J Allergy Clin Immunol. 1984 Sep;74(3 Pt 1):280-90. [PubMed:6236250 ]
  10. Larson RA, Yachnin S: Mevalonic acid induces DNA synthesis in chronic lymphocytic leukemia cells. Blood. 1984 Jul;64(1):257-62. [PubMed:6610447 ]
  11. Parker TS, McNamara DJ, Brown CD, Kolb R, Ahrens EH Jr, Alberts AW, Tobert J, Chen J, De Schepper PJ: Plasma mevalonate as a measure of cholesterol synthesis in man. J Clin Invest. 1984 Sep;74(3):795-804. [PubMed:6565710 ]
  12. Hoffmann GF, Sweetman L, Bremer HJ, Hunneman DH, Hyanek J, Kozich V, Lehnert W, Nyhan WL, Speidel I, Trefz FK, et al.: Facts and artefacts in mevalonic aciduria: development of a stable isotope dilution GCMS assay for mevalonic acid and its application to physiological fluids, tissue samples, prenatal diagnosis and carrier detection. Clin Chim Acta. 1991 May 15;198(3):209-27. [PubMed:1653652 ]
  13. Jemal M, Schuster A, Whigan DB: Liquid chromatography/tandem mass spectrometry methods for quantitation of mevalonic acid in human plasma and urine: method validation, demonstration of using a surrogate analyte, and demonstration of unacceptable matrix effect in spite of use of a stable isotope analog internal standard. Rapid Commun Mass Spectrom. 2003;17(15):1723-34. [PubMed:12872277 ]
  14. Lindenthal B, von Bergmann K: Urinary excretion and serum concentration of mevalonic acid during acute intake of alcohol. Metabolism. 2000 Jan;49(1):62-6. [PubMed:10647065 ]
  15. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  16. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  17. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  18. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  19. Naoumova RP, Marais AD, Mountney J, Firth JC, Rendell NB, Taylor GW, Thompson GR: Plasma mevalonic acid, an index of cholesterol synthesis in vivo, and responsiveness to HMG-CoA reductase inhibitors in familial hypercholesterolaemia. Atherosclerosis. 1996 Jan 26;119(2):203-13. doi: 10.1016/0021-9150(95)05649-1. [PubMed:8808497 ]
  20. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular weight:
97475.155
Reactions
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPHdetails
Mevalonic acid + Coenzyme A + NADP → 3-Hydroxy-3-methylglutaryl-CoA + NADPH + Hydrogen Iondetails
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 + Mevalonic acid → ADP + Mevalonic acid-5Pdetails