Showing Compound Card for l-(+)-Isoleucine betaine (CDB000227)

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Record Information
Version1.0
Created at2020-03-19 00:25:36 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000227
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namel-(+)-Isoleucine betaine
DescriptionL-(+)-isoleucine betaine, also known as Isoleucine betaine, belongs to the class of compounds known as betaines. A betaine is any neutral chemical compound with a positively charged cationic functional group such as a quaternary ammonium cation that bears no hydrogen atom and with a negatively charged functional group such as a carboxylate group that may not be adjacent to the cationic site. Isoleucine betaine can also be classified as a quaternary ammonium salt with three methyl groups and one carboxyl group attached to the nitrogen atom via C-2. Isoleucine betaine is a naturally occurring organic compound first isolated from Cannabis seeds in 1973. The structure of isoleucine betaine was determined by spectroscopic methods and confirmed by synthesis ( Ref:DOI ). Isoleucine betaine was first isolated and identified as a cannabis constituent in 1973 (PMID:6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3S)-3-Methyl-2-(trimethylazaniumyl)pentanoic acidGenerator
Chemical FormulaC9H19NO2
Average Molecular Weight173.26
Monoisotopic Molecular Weight173.1416
IUPAC Name(2R,3S)-3-methyl-2-(trimethylazaniumyl)pentanoate
Traditional Name(2R,3S)-3-methyl-2-(trimethylammonio)pentanoate
CAS Registry NumberNot Available
SMILES
CC[C@H](C)[C@H](C([O-])=O)[N+](C)(C)C
InChI Identifier
InChI=1S/C9H19NO2/c1-6-7(2)8(9(11)12)10(3,4)5/h7-8H,6H2,1-5H3/t7-,8+/m0/s1
InChI KeyWEFWRGFGKPRQQC-JGVFFNPUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentIsoleucine and derivatives
Alternative Parents
Substituents
  • Isoleucine or derivatives
  • D-alpha-amino acid
  • Alpha-amino acid
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid salt
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not Available
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-2ALOGPS
logP-2.6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.91 m³·mol⁻¹ChemAxon
Polarizability19.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
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 CompoundNot Available
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 ]