Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2021-09-14 15:20:03 UTC
HMDB IDHMDB0001981
Secondary Accession Numbers
  • HMDB01981
Metabolite Identification
Common Name(R)-Mevalonic acid-5-pyrophosphate
Description(R)-Mevalonic acid-5-pyrophosphate (mevalonate 5-diphosphate) is a directly synthesized product of mevalonate phosphate that is essential for cell proliferation. (PMID 2211719 ). It is a substrate for mevalonate-5-diphosphate decarboxylase, the third enzyme involved in the biosynthesis of cholesterol from mevalonic acid. This enzyme catalyzes the reaction of mevalonate 5-diphosphate (MVADP) with ATP to produce isopentenyl diphosphate, ADP, CO2, and inorganic phosphate. The overall reaction involves an anti elimination of the tertiary hydroxyl and carboxyl groups. This metabolite participates both in the biosynthesis of cholesterol and fatty acid mechanism, through which interpathway regulation could take place between the cholesterol and FA cascades. (PMID 8769113 ).
Structure
Data?1582752221
Synonyms
ValueSource
(R)-Mevalonate-5-pyrophosphateGenerator
(R)-Mevalonic acid-5-pyrophosphoric acidGenerator
(R)-5-Diphosphomevalonic acidHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-OateHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acidHMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid 1,3-dioxideHMDB
5-PyrophosphomevalonateHMDB
5-Pyrophosphomevalonic acidHMDB
Mevalonate 5-diphosphateHMDB
Mevalonic 5-pyrophosphateHMDB
Mevalonic acid 5-diphosphateHMDB
Mevalonic acid 5-pyrophosphateHMDB
Mevalonic acid pyrophosphateHMDB
MVADPHMDB
PyrophosphomevalonateHMDB
Pyrophosphomevalonic acidHMDB
R-Mevalonic acid-5-pyrophosphateHMDB
Mevalonate pyrophosphateMeSH, HMDB
5-Diphosphomevalonic acidMeSH, HMDB
(3S)-3-Hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoateGenerator, HMDB
Chemical FormulaC6H14O10P2
Average Molecular Weight308.1169
Monoisotopic Molecular Weight308.006219692
IUPAC Name(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid
Traditional Namepyrophosphomevalonate
CAS Registry Number1492-08-6
SMILES
C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O
InChI Identifier
InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m0/s1
InChI KeySIGQQUBJQXSAMW-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxoanionic compounds
Sub ClassOrganic pyrophosphates
Direct ParentOrganic pyrophosphates
Alternative Parents
Substituents
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Short-chain hydroxy acid
  • Organic phosphoric acid derivative
  • Fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Tertiary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot 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]-Not Available153.219http://allccs.zhulab.cn/database/detail?ID=AllCCS00001842
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.26 g/LALOGPS
logP-1.2ALOGPS
logP-1.6ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity56.26 m³·mol⁻¹ChemAxon
Polarizability23.59 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]+170.13331661259
DarkChem[M-H]-160.01831661259
AllCCS[M+H]+164.52832859911
AllCCS[M-H]-156.98232859911
DeepCCS[M+H]+148.44730932474
DeepCCS[M-H]-146.45930932474
DeepCCS[M-2H]-179.69730932474
DeepCCS[M+Na]+154.3630932474
AllCCS[M+H]+164.532859911
AllCCS[M+H-H2O]+161.532859911
AllCCS[M+NH4]+167.332859911
AllCCS[M+Na]+168.132859911
AllCCS[M-H]-157.032859911
AllCCS[M+Na-2H]-157.732859911
AllCCS[M+HCOO]-158.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-Mevalonic acid-5-pyrophosphateC[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O3795.9Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphateC[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O1913.2Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphateC[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O2474.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #1C[C@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C2475.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #2C[C@](O)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O[Si](C)(C)C2412.1Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #3C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O2431.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TMS,isomer #4C[C@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O2447.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #1C[C@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2422.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #2C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O)O[Si](C)(C)C2440.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #3C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2464.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #4C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)CC(=O)O[Si](C)(C)C2366.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #5C[C@](O)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2376.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #6C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O2408.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TMS,isomer #7C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O2408.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2388.4Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2350.0Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C3183.8Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2397.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2331.0Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C3269.3Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2449.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2286.6Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C3048.5Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2443.9Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2276.7Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #4C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C3063.4Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2372.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2347.0Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #5C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C3055.7Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2384.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2334.3Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #6C[C@](O)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C3063.0Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O2417.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O2283.1Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TMS,isomer #7C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O2863.7Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2436.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2384.1Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2902.6Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2442.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2375.8Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #2C[C@](CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2895.9Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2479.3Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2325.2Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #3C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O)O[Si](C)(C)C2725.7Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2399.5Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2375.3Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TMS,isomer #4C[C@](O)(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)CC(=O)O[Si](C)(C)C2730.6Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2479.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2410.1Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TMS,isomer #1C[C@](CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2610.0Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O)O)CC(=O)O2692.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O)O2633.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O)O2661.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(O)OCC[C@](C)(O)CC(=O)O2674.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C2839.5Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)CC(=O)O2857.4Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O2871.1Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O2818.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C2816.1Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OP(=O)(O)OP(=O)(OCC[C@](C)(O)CC(=O)O)O[Si](C)(C)C(C)(C)C2844.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[C@](C)(O)CC(=O)O2848.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C3035.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C2829.4Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)O[Si](C)(C)C(C)(C)C3384.9Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3036.5Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2827.0Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3459.6Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O3063.9Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O2774.6Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)CC(=O)O3264.1Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O3066.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O2733.7Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O3283.7Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3010.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C2840.1Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3268.6Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3020.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2792.7Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3279.8Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3025.6Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2738.4Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)OP(=O)(OCC[C@](C)(O)CC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3099.1Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3220.0Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2964.6Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3175.1Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3225.8Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2930.6Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3184.8Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O3263.7Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O2869.6Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC(=O)O3027.3Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3199.2Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2926.5Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,4TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@](C)(O)CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3032.4Standard polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3381.5Semi standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3069.3Standard non polar33892256
(R)-Mevalonic acid-5-pyrophosphate,5TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@](C)(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3015.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-9820000000-20a5a060549dcb7bd8d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate GC-MS (2 TMS) - 70eV, Positivesplash10-00dv-9243200000-6d8177d69adb810da37f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 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 - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 5V, negative-QTOFsplash10-000i-0090000000-27d85eaaa9c4e19f0fcf2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 6V, negative-QTOFsplash10-000i-0090000000-8e9a7018cd26631895212020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 9V, negative-QTOFsplash10-002r-3490000000-b2f4bcb965dfbe91ce8f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 11V, negative-QTOFsplash10-004r-7690000000-533cfa9b6449fe59e31d2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 12V, negative-QTOFsplash10-004i-9540000000-ba3a429bcc345a49d5ff2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 15V, negative-QTOFsplash10-004i-9310000000-b552a514df86bf2034832020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 18V, negative-QTOFsplash10-004i-9200000000-73f02610e11b09ea0ae02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 20V, negative-QTOFsplash10-004i-9100000000-e99ccf8685bbb8c58b7f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 25V, negative-QTOFsplash10-004i-9000000000-df1600382f0903920e952020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-004i-1900000000-0d135499da95ac5499d52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-0a4i-0900000000-b559d4679fc0eaa79be72020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-004i-1590000000-bd14b17224627a5d24182020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-0a4i-0900000000-dc954ce23ecf1a2631892020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate n/a 21V, negative-QTOFsplash10-0kdi-0490000000-356afce14b98128806e52020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 5V, negative-QTOFsplash10-0a4i-0009000000-ece59023c1177bedb2f32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 7V, negative-QTOFsplash10-0a4i-0009000000-cbc9841391b1e5bea83c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 9V, negative-QTOFsplash10-0a4i-1109000000-71626d1a601d118a3d292020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate Orbitrap 11V, negative-QTOFsplash10-0a6r-9516000000-b1e714407672ea74b65f2020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 10V, Positive-QTOFsplash10-0006-1491000000-8b66d9021d8692cc58b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 20V, Positive-QTOFsplash10-03ea-5930000000-ed4d02286446a704e70d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 40V, Positive-QTOFsplash10-03ea-9810000000-99f0d148c2b3cc6b87e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 10V, Negative-QTOFsplash10-0bvi-0494000000-00b15359794ef7c747432017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 20V, Negative-QTOFsplash10-004i-9410000000-5d44f0388a33861701fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mevalonic acid-5-pyrophosphate 40V, Negative-QTOFsplash10-004i-9000000000-b038a323df0665a33d9c2017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Leukocyte
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 IDFDB022779
KNApSAcK IDNot Available
Chemspider ID17216150
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6415
PubChem Compound22833574
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBloch, Konrad; Chaykin, S.; Phillips, A. H.; De Waard, A. Mevalonic acid pyrophosphate and isopentylpyrophosphate. Journal of Biological Chemistry (1959), 234 2595-2604.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cuthbert JA, Lipsky PE: Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. J Biol Chem. 1990 Oct 25;265(30):18568-75. [PubMed:2211719 ]
  2. Ku EC: Regulation of fatty acid biosynthesis by intermediates of the cholesterol biosynthetic pathway. Biochem Biophys Res Commun. 1996 Aug 5;225(1):173-9. [PubMed:8769113 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Performs the first committed step in the biosynthesis of isoprenes.
Gene Name:
MVD
Uniprot ID:
P53602
Molecular weight:
43404.125
General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745