Showing Compound Card for (R)-mevalonate (CDB005319)

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Record Information
Version1.0
Created at2020-04-17 19:31:17 UTC
Updated at2020-11-18 16:39:43 UTC
CannabisDB IDCDB005319
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(R)-mevalonate
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. (R)-mevalonate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DL-Mevalonic acidChEBI
MVAChEBI
RS-Mevalonic acidChEBI
DL-MevalonateGenerator
RS-MevalonateGenerator
MevalonateGenerator
(3Rs)-MevalonateHMDB
(3Rs)-Mevalonic acidHMDB
2,4-Dideoxy-3-C-methylpentonateHMDB
2,4-Dideoxy-3-C-methylpentonic acidHMDB
3,5-Dihydroxy-3-methyl-valerateHMDB
3,5-Dihydroxy-3-methyl-valeric acidHMDB
3,5-Dihydroxy-3-methylpentanoateHMDB
3,5-Dihydroxy-3-methylpentanoic acidHMDB
3,5-Dihydroxy-3-methylvalerateHMDB
3,5-Dihydroxy-3-methylvaleric acidHMDB
b,D-Dihydroxy-b-methylvalerateHMDB
b,D-Dihydroxy-b-methylvaleric acidHMDB
b,D-Dihydroxy-beta-methylvalerateHMDB
b,D-Dihydroxy-beta-methylvaleric acidHMDB
Hiochic acidHMDB
MK 91HMDB
MVSHMDB
Acid, mevalonicMeSH, HMDB
(R)-MevalonateGenerator, HMDB
Mevalonic acidMeSH
Chemical FormulaC6H12O4
Average Molecular Weight148.16
Monoisotopic Molecular Weight148.0736
IUPAC Name3,5-dihydroxy-3-methylpentanoic acid
Traditional NameRS-mevalonic acid
CAS Registry Number150-97-0
SMILES
CC(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)
InChI KeyKJTLQQUUPVSXIM-UHFFFAOYSA-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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-mevalonate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-9400000000-875fe9eef6c0fc4dbd86Spectrum
Predicted GC-MS(R)-mevalonate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00bj-9372000000-2a6b263d37306947c327Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-2900000000-d1dc97020c103f2a916b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9000000000-b4dc45e964aee6759d932012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9100000000-98f7e8ee013680f4f6102012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-1900000000-0bb212794cd101490acd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q1-9800000000-95e2c177f1ee0c9cd3122017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g9-9200000000-f5d0630f14fa9249d4c92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f92-2900000000-8b015723cd087b29e9742017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9800000000-93639d7d95cd6690d44d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4s-9100000000-094b07bf98ce319b48242017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000227
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMevalonic acid
METLIN IDNot Available
PubChem Compound449
PDB IDNot Available
ChEBI ID25351
References
General ReferencesNot Available