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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001343
Secondary Accession Numbers
  • HMDB01343
Metabolite Identification
Common NameMevalonic acid-5P
DescriptionMevalonic acid-5P (CAS: 1189-94-2), also known as 5-phosphomevalonic acid, 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. Within humans, mevalonic acid-5P participates in many enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonate; which is mediated by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into mevalonic acid-5-pyrophosphate through its interaction with the enzyme phosphomevalonate kinase. In humans, mevalonic acid-5P is involved in the mevalonate pathway. Outside of the human body, mevalonic acid-5P has been detected, but not quantified in, several different foods, such as oriental wheat, devilfish, pepper (spice), redcurrants, and star fruits. This could make mevalonic acid-5P a potential biomarker for the consumption of these foods.
Structure
Data?1593186954
Synonyms
ValueSource
(R)-5-PhosphomevalonateChEBI
(R)-5-Phosphomevaloonic acidChEBI
(R)-Mevalonic acid 5-phosphateChEBI
(R)-5-Phosphomevalonic acidGenerator
(R)-5-PhosphomevaloonateGenerator
(R)-Mevalonate 5-phosphateGenerator
(R)-Mevalonic acid 5-phosphoric acidGenerator
Mevalonate-5PGenerator
5-PhosphomevalonateHMDB
Mevalonate-5-pHMDB
Mevalonate-5-phosphateHMDB
Mevalonate-pHMDB
p-MevalonateHMDB
5-Phosphomevalonic acidHMDB
Mevalonate 5-phosphateHMDB
PhosphomevalonateHMDB
Phosphomevalonic acidHMDB
Phosphomevalonic acid, (+-)-isomerHMDB
(3R)-3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
3-Hydroxy-3-methyl-5-(phosphonooxy)pentanoic acidHMDB
Mevalonic acid phosphateHMDB
Mevalonic acid-5PHMDB
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M-H]-ExperimentalNot Available140.015http://allccs.zhulab.cn/database/detail?ID=AllCCS00001771
DarkChem[M+H]+PredictedNot Available151.3231661259
DarkChem[M-H]-PredictedNot Available144.43631661259
AllCCS[M+H]+PredictedNot Available149.71132859911
AllCCS[M-H]-PredictedNot Available144.05432859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Mevalonic acid-5P,1TMS,#11998.3623https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,1TMS,#21933.9684https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,1TMS,#31964.1869https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TMS,#11991.1501https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TMS,#22020.3032https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TMS,#31958.1321https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TMS,#41996.4867https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,1TBDMS,#12225.1257https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,1TBDMS,#22167.2466https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,1TBDMS,#32188.6174https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TBDMS,#12415.7178https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TBDMS,#22433.4722https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TBDMS,#32391.661https://arxiv.org/abs/1905.12712
Mevalonic acid-5P,2TBDMS,#42431.4878https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0292-9600000000-a4f04a66624afb8d522a2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9413000000-7329637530b2ddc29e0b2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1960000000-a02358583ea07452bacf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-4900000000-ef07c3371552f7c1c11d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ti-9800000000-bba2c1c56648b04a1fdd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-8960000000-de18bb77f2282c89d45a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-6dd83d59bdb427eeee242016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9c715a4954dce4d5a8562016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5090000000-98125cefd75fccd3e5642021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9020000000-74f440cb4e3ffa40388d2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-07View Spectrum
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Heart
  • Kidney
  • Liver
  • Pancreas
  • Skeletal Muscle
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031001
KNApSAcK IDC00007304
Chemspider ID388517
KEGG Compound IDC01107
BioCyc IDCPD-499
BiGG ID36819
Wikipedia LinkNot Available
METLIN ID6177
PubChem Compound439400
PDB IDNot Available
ChEBI ID17436
Food Biomarker OntologyNot Available
VMH ID5PMEV
MarkerDB IDNot Available
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 + (R)-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 + Mevalonic acid → ADP + Mevalonic acid-5Pdetails