Showing Compound Card for 2-C-Methyl-aldotetronolactone (CDB000284)

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Record Information
Version1.0
Created at2020-03-19 00:28:51 UTC
Updated at2020-12-07 19:07:19 UTC
CannabisDB IDCDB000284
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-C-Methyl-aldotetronolactone
Description2-C-Methyl-1,4-erythrono-D-lactone, 2-C-methyl-D-erythrono-1,4-lactone (MDEL) or 2-C-Methyl-Aldotetronolactone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-membered ring with four carbon atoms, one oxygen atom, forming part of a carboxyl functional group. 2-C-Methyl-1,4-erythrono-D-lactone is a neutral, hydrophobic molecule that is not soluble in water. 2-C-Methyl-1,4-erythrono-D-lactone is a known constituent of Trifolium incarnatum (crimson clover) and Phaseolus vulgaris (kidney bean). It has also been detected, but not quantified in several different foods, such as green beans, pulses, tea, and yellow wax beans. It has been identified as an insect pheromone that acts as an oviposition stimulant for the Swallowtail butterfly (PMID: 11055405 ). 2-C-Methyl-1,4-erythrono-D-lactone is synthesized in plants via the terpenoid precursor 1‚Äêdeoxy‚ÄêD‚Äêxylulose, which is phosphorylated to 1‚Äêdeoxy‚ÄêD‚Äêxylulose‚Äê5‚Äêphosphate, which is then transformed by the enzyme 1‚Äêdeoxy‚ÄêD‚Äêxylulose‚Äê5‚Äêphosphate reducto isomerase to 2C‚ÄêMethyl‚ÄêD‚Äêerythritol‚Äê4‚Äêphosphate. This compound is then oxidized at the alcoholic group at C‚Äê1 to 2-Methyl-2,3,4-trihydroxybutanoic acid-4-phosphate by an uncharacterized dehydrogenase. Dephosphorylation yields the free acid which spontaneously forms the lactone. 2-C-Methyl-1,4-erythrono-D-lactone is one of a small number of lactones found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC5H8O4
Average Molecular Weight132.12
Monoisotopic Molecular Weight132.0423
IUPAC Name(3R,4R)-3,4-dihydroxy-3-methyloxolan-2-one
Traditional Name(3R,4R)-3,4-dihydroxy-3-methyloxolan-2-one
CAS Registry Number18465-71-9
SMILES
C[C@@]1(O)[C@H](O)COC1=O
InChI Identifier
InChI=1S/C5H8O4/c1-5(8)3(6)2-9-4(5)7/h3,6,8H,2H2,1H3/t3-,5-/m1/s1
InChI KeyOHTGZAWPVDWARE-NQXXGFSBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Oxolane
  • Tertiary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

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-1.5ALOGPS
logP-1.1ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity27.57 m³·mol⁻¹ChemAxon
Polarizability11.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-C-Methyl-aldotetronolactone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-C-Methyl-aldotetronolactone, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS2-C-Methyl-aldotetronolactone, 2 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound11126294
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Ono H, Nishida R, Kuwahara Y: A dihydroxy-gamma-lactone as an oviposition stimulant for the swallowtail butterfly, Papilio bianor, from the rutaceous plant, Orixa japonica. Biosci Biotechnol Biochem. 2000 Sep;64(9):1970-3. doi: 10.1271/bbb.64.1970. [PubMed:11055405 ]