Showing Compound Card for (R)-Mevalonic acid-5-pyrophosphate (CDB005321)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:31:29 UTC
Updated at2020-11-18 16:39:43 UTC
CannabisDB IDCDB005321
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(R)-Mevalonic acid-5-pyrophosphate
Description(R)-Mevalonic acid-5-pyrophosphate, also known as 5-diphosphomevalonic acid or pyrophosphomevalonate, 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 (R)-Mevalonic acid-5-pyrophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, (R)-mevalonic acid-5-pyrophosphate participates in a number of enzymatic reactions. In particular, (R)-mevalonic acid-5-pyrophosphate can be biosynthesized from mevalonic acid-5P; which is mediated by the enzyme phosphomevalonate kinase. In addition, (R)-mevalonic acid-5-pyrophosphate can be converted into isopentenyl pyrophosphate through the action of the enzyme diphosphomevalonate decarboxylase. In humans, (R)-mevalonic acid-5-pyrophosphate is involved in mevalonate pathway. (R)-Mevalonic acid-5-pyrophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight308.12
Monoisotopic Molecular Weight308.0062
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
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-Mevalonic acid-5-pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004m-9820000000-20a5a060549dcb7bd8d3Spectrum
Predicted GC-MS(R)-Mevalonic acid-5-pyrophosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dv-9243200000-6d8177d69adb810da37fSpectrum
Predicted GC-MS(R)-Mevalonic acid-5-pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-000i-0090000000-27d85eaaa9c4e19f0fcf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-000i-0090000000-8e9a7018cd26631895212020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-002r-3490000000-b2f4bcb965dfbe91ce8f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-004r-7690000000-533cfa9b6449fe59e31d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, negativesplash10-004i-9540000000-ba3a429bcc345a49d5ff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, negativesplash10-004i-9310000000-b552a514df86bf2034832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-004i-9200000000-73f02610e11b09ea0ae02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-004i-9100000000-e99ccf8685bbb8c58b7f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-004i-9000000000-df1600382f0903920e952020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-1900000000-0d135499da95ac5499d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-b559d4679fc0eaa79be72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-9000000000-46d4cee1b5ac630ba9b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-004i-1590000000-bd14b17224627a5d24182020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0a4i-0900000000-dc954ce23ecf1a2631892020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0kdi-0490000000-356afce14b98128806e52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-0009000000-ece59023c1177bedb2f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-0009000000-cbc9841391b1e5bea83c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0a4i-1109000000-71626d1a601d118a3d292020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, negativesplash10-0a6r-9516000000-b1e714407672ea74b65f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-004i-9300000000-79a6a45a050a4557acba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 17V, negativesplash10-004i-9100000000-53b8fc8a95948a4c97642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-004i-9100000000-0afb1187a03463994c7a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 24V, negativesplash10-004i-9000000000-92672b421a976d0722e32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 28V, negativesplash10-004i-9000000000-ad774759f01ecd0224632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 33V, negativesplash10-004i-9000000000-028cfb3af846dc9c0ee52020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Diphosphomevalonate decarboxylaseMVD16q24.3P53602 details
Phosphomevalonate kinasePMVK1q22Q15126 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001981
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Diphosphomevalonate decarboxylase
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
Enzyme Details
2. Phosphomevalonate kinase
General function:
Involved in phosphomevalonate kinase activity
Specific function:
Not Available
Gene Name:
PMVK
Uniprot ID:
Q15126
Molecular weight:
21994.745