Record Information
Version1.0
Created at2020-03-18 23:25:31 UTC
Updated at2020-12-07 19:07:07 UTC
CannabisDB IDCDB000120
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameLysine
DescriptionLysine and its bioactive form L-lysine, abbreviated Lys or L, is an essential amino acid. Normal requirements for adults are between 8 g per day or 12 mg/kg. Children and infants need more: 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize these levels and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture and has helped to reduce the number and occurrence of cold sores in clinical studies. Beneficial clinical effects occurred with lysine doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes as excess arginine antagonizes lysine. Lysine also may be a useful adjunct in the treatment of osteoporosis because it reduces calcium losses in urine. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine is high in foods such as wheat germ, cottage cheese, chicken, wild game and pork. Less lysine is found in apple, apricot, bananas, avocados, guava, lime, brazil nuts, cashews, mung bean, fava bean and black bean as well as other seeds, nuts and fruits. Lysine is also found in cannabis plants (PMID: 6991645 ). Lysin is also a constituent of cannabis smok and is volatilized during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
Synonyms
ValueSource
(R)-2,6-Diaminohexanoic acidChEBI
D-2,6-Diaminohexanoic acidChEBI
D-LysinChEBI
DLYChEBI
(R)-2,6-DiaminohexanoateGenerator
D-2,6-DiaminohexanoateGenerator
Chemical FormulaC6H14N2O2
Average Molecular Weight146.19
Monoisotopic Molecular Weight146.1055
IUPAC Name(2R)-2,6-diaminohexanoic acid
Traditional NameD-lysine
CAS Registry Number923-27-3
SMILES
NCCCC[C@@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1
InChI KeyKDXKERNSBIXSRK-RXMQYKEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.5Wikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.8ALOGPS
logP-3.2ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.81 m³·mol⁻¹ChemAxon
Polarizability15.91 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, Positivesplash10-0f8a-2900000000-d5972dfce0860da55a0aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9700000000-d8e3259076e214ba9a3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-0b901a2eb0a82d41fc3dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-603377bb44b83d433b77Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-e5d6ccb8cd7879780fafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-e7f9a18ab48141069feeSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified2.82 mg/g dry wt
    • Jiamin Zheng, Yil...
details
GabriolaDetected and Quantified1.69 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Island HoneyDetected and Quantified2.08 mg/g dry wt
    • Jiamin Zheng, Yil...
details
QuadraDetected and Quantified1.08 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Sensi StarDetected and Quantified0.679 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Tangerine DreamDetected and Quantified1.39 mg/g dry wt
    • Jiamin Zheng, Yil...
details
HMDB IDHMDB0003405
DrugBank IDDB03252
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023163
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00739
BioCyc IDCPD-219
BiGG IDNot Available
Wikipedia LinkLysine
METLIN IDNot Available
PubChem Compound57449
PDB IDNot Available
ChEBI ID16855
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 ]