Showing Compound Card for Methionine (CDB000060)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:18 UTC
Updated at2022-12-13 23:36:24 UTC
CannabisDB IDCDB000060
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethionine
DescriptionMethionine, l-methionine abbreviated Met or M, is one of 9 essential amino acids (meaning the body cannot synthesize it; it must be obtained from the diet) required for protein synthesis and for normal growth and development of humans, other mammals, and avian species. It is a white crystalline powder with a mild acidic and sulfurous taste. It is an intermediate in transmethylation reactions, serving as the major methyl group donor for DNA and RNA intermediates. Methionine is a methyl acceptor for 5-methyltetrahydrofolate-homocysteine methyltransferase (methionine synthase), the only reaction that allows for the recycling of this form of folate and is also a methyl acceptor for the catabolism of betaine. Methionine is the metabolic precursor for cysteine where the sulfur atom from methionine is transferred to cysteine (PMID: 16702340 ). Methionine is an amino acid found in cannabis plants (PMID: 6991645 ). Methionine is one of 4 sulfur amino acids (SAA) that also include cysteine, taurine and homocysteine (with the latter two not incorporated into proteins). The WHO recommends that healthy adults consume 13 mg/kg per 24 h of normal SAA and roughly double this amount in artificial nutrition regimens. However, in disease or after trauma, SAA requirements may vary. SAA supplementation exceeding 2-3 times the minimum recommended daily intake can be considered safe except in specific cases of congenital enzyme deficiency, prematurity, or diminished liver function where hypermethioninemia or hyperhomocysteinemia may occur. Apart from acetaminophen poisoning, the usefulness of SAA supplementation is not yet established (PMID: 16702341 ). When present in high levels, methionine can act as an atherogen which is a compound that causes atherosclerosis and cardiovascular disease. Methionine is a precursor of homocysteine. Acute doses of methionine can lead to acute increases in plasma homocysteine, which has been used as an indicator of susceptibility to cardiovascular disease. Longer-term studies in adults have indicated that methionine intakes higher than 5 times the normal amount resulted in elevated homocysteine levels. Rodents fed high levels of methionine developed atherosclerotic plaques independently of homocysteine levels (PMID: 26647293 ). A similar study in Finnish men showed that high dietary methionine increased the risk of acute coronary events in middle-aged men (PMID: 16487911 ). These effects of methionine on homocysteine and vascular function are moderated by supplements of vitamins B-6, B-12, C, and folic acid (PMID: 16702346 ). Methionine is also a metabotoxin, which is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of methionine are associated with at least ten inborn errors of metabolism, including cystathionine beta-synthase deficiency, glycine N-methyltransferase deficiency, homocystinuria, tyrosinemia, galactosemia, homocystinuria-megaloblastic anemia due to defects in cobalamin metabolism, methionine adenosyltransferase deficiency, methylenetetrahydrofolate reductase deficiency, and S-adenosylhomocysteine (SAH) hydrolase deficiency (PMID: 16702350 ). Chronically elevated levels of methionine in infants can lead to intellectual disability and other neurological problems, delays in motor skills, sluggishness, muscle weakness, and liver problems. Many individuals with these metabolic disorders tend to develop cardiovascular disease later in life. Methionine is known to exacerbate psychopathological symptoms in schizophrenic patients, with no effects on healthy subjects.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-2-Amino-4-(methylsulfanyl)butanoic acidChEBI
(R)-2-Amino-4-(methylthio)butanoic acidChEBI
(R)-MethionineChEBI
D-2-Amino-4-(methylthio)butyric acidChEBI
D-MethioninChEBI
MEDChEBI
(2R)-2-Amino-4-(methylsulfanyl)butanoateGenerator
(2R)-2-Amino-4-(methylsulphanyl)butanoateGenerator
(2R)-2-Amino-4-(methylsulphanyl)butanoic acidGenerator
(R)-2-Amino-4-(methylthio)butanoateGenerator
D-2-Amino-4-(methylthio)butyrateGenerator
L-Isomer methionineMeSH
L-MethionineMeSH
PedamethMeSH
LiquimethMeSH
Methionine, L isomerMeSH
Methionine, L-isomerMeSH
MethionineMeSH
Chemical FormulaC5H11NO2S
Average Molecular Weight149.21
Monoisotopic Molecular Weight149.051
IUPAC Name(2R)-2-amino-4-(methylsulfanyl)butanoic acid
Traditional NameD-methionine
CAS Registry Number348-67-4
SMILES
CSCC[C@@H](N)C(O)=O
InChI Identifier
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m1/s1
InChI KeyFFEARJCKVFRZRR-SCSAIBSYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methionine and derivatives. Methionine and derivatives are compounds containing methionine or a derivative thereof resulting from reaction of methionine 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 ParentMethionine and derivatives
Alternative Parents
Substituents
  • Methionine or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Thia fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Thioether
  • Sulfenyl compound
  • Dialkylthioether
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point281 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.8ALOGPS
logP-2.2ChemAxon
logS-0.8ALOGPS
pKa (Strongest Acidic)2.53ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.59 m³·mol⁻¹ChemAxon
Polarizability15.46 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-MSMethionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0mbd-9200000000-77e5cfb78936ad02d71cSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-67e023372cdbac09cb362015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-1e589df1b14865d84d742015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-9000000000-efb0cddabddaf5231dbd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-9ef89c92bce71adb0b812015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-8507980760c8afb7f4542015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9000000000-544c2c943904dcca737e2015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Methionine synthaseMTR1q43Q99707 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Methionine synthaseMTR1q43Q99707 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00744 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00958 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.0124 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.0117 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00798 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.0138 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDDB02893
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00855
BioCyc IDCPD-218
BiGG IDNot Available
Wikipedia LinkMethionine
METLIN IDNot Available
PubChem Compound84815
PDB IDNot Available
ChEBI ID16867
References
General References
  1. Ball RO, Courtney-Martin G, Pencharz PB: The in vivo sparing of methionine by cysteine in sulfur amino acid requirements in animal models and adult humans. J Nutr. 2006 Jun;136(6 Suppl):1682S-1693S. doi: 10.1093/jn/136.6.1682S. [PubMed:16702340 ]
  2. 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 ]
  3. van de Poll MC, Dejong CH, Soeters PB: Adequate range for sulfur-containing amino acids and biomarkers for their excess: lessons from enteral and parenteral nutrition. J Nutr. 2006 Jun;136(6 Suppl):1694S-1700S. doi: 10.1093/jn/136.6.1694S. [PubMed:16702341 ]
  4. Selhub J, Troen AM: Sulfur amino acids and atherosclerosis: a role for excess dietary methionine. Ann N Y Acad Sci. 2016 Jan;1363:18-25. doi: 10.1111/nyas.12962. Epub 2015 Dec 8. [PubMed:26647293 ]
  5. Virtanen JK, Voutilainen S, Rissanen TH, Happonen P, Mursu J, Laukkanen JA, Poulsen H, Lakka TA, Salonen JT: High dietary methionine intake increases the risk of acute coronary events in middle-aged men. Nutr Metab Cardiovasc Dis. 2006 Mar;16(2):113-20. doi: 10.1016/j.numecd.2005.05.005. Epub 2005 Nov 2. [PubMed:16487911 ]
  6. Garlick PJ: Toxicity of methionine in humans. J Nutr. 2006 Jun;136(6 Suppl):1722S-1725S. doi: 10.1093/jn/136.6.1722S. [PubMed:16702346 ]
  7. Finkelstein JD: Inborn errors of sulfur-containing amino acid metabolism. J Nutr. 2006 Jun;136(6 Suppl):1750S-1754S. doi: 10.1093/jn/136.6.1750S. [PubMed:16702350 ]

Enzymes

Enzyme Details
1. Methionine synthase
General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91