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Record Information
Version1.0
Created at2020-04-17 18:44:03 UTC
Updated at2020-12-07 19:11:07 UTC
CannabisDB IDCDB004858
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Methionine
DescriptionL-Methionine, also known as acimethin or H-met-H, 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. The L-enantiomer of methionine. L-Methionine is a drug which is used for protein synthesis including the formation of same, l-homocysteine, l-cysteine, taurine, and sulfate. L-Methionine is a very strong basic compound (based on its pKa). L-Methionine exists in all living species, ranging from bacteria to humans. Outside of the human body, L-Methionine is found, on average, in the highest concentration within a few different foods, such as milk (cow), beluga whales, and smelts and in a lower concentration in white cabbages, wax gourds, and coconuts. L-Methionine has also been detected, but not quantified in, several different foods, such as pepper (c. chinense), acerola, grass pea, oxheart cabbages, and sherries. This could make L-methionine a potential biomarker for the consumption of these foods. L-Methionine is a potentially toxic compound. L-Methionine, with regard to humans, has been found to be associated with several diseases such as autism, leukemia, obesity, and heart failure; L-methionine has also been linked to the inborn metabolic disorder celiac disease. L-Methionine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
Chemical FormulaC5H11NO2S
Average Molecular Weight149.21
Monoisotopic Molecular Weight149.051
IUPAC Name(2S)-2-amino-4-(methylsulfanyl)butanoic acid
Traditional NameL-methionine
CAS Registry Number63-68-3
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-/m0/s1
InChI KeyFFEARJCKVFRZRR-BYPYZUCNSA-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
  • L-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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point284 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility56.6 mg/mLYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.87HANSCH,C ET AL. (1995)
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
Polarizability15.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
MS/MS
NMR
Pathways
Pathways
Protein Targets
Enzymes
Transporters
Protein NameGene NameLocusUniprot IDDetails
Monocarboxylate transporter 10SLC16A106q21-q22Q8TF71 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Methionine synthaseMTR1q43Q99707 details
S-adenosylmethionine synthase isoform type-2MAT2A2p11.2P31153 details
S-adenosylmethionine synthase isoform type-1MAT1A10q22Q00266 details
Methionine synthase reductaseMTRR5p15.31Q9UBK8 details
Betaine--homocysteine S-methyltransferase 1BHMT5q14.1Q93088 details
Lipoyl synthase, mitochondrialLIAS4p14O43766 details
S-methylmethionine--homocysteine S-methyltransferase BHMT2BHMT25q13Q9H2M3 details
Methionine-R-sulfoxide reductase B2, mitochondrialMSRB210p12Q9Y3D2 details
Methionine-R-sulfoxide reductase B3MSRB312q14.3Q8IXL7 details
Methionine-R-sulfoxide reductase B1MSRB116p13.3Q9NZV6 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Methionine-R-sulfoxide reductase B2, mitochondrialMSRB210p12Q9Y3D2 details
Concentrations Data
Not Available
HMDB IDHMDB0000696
DrugBank IDDB00134
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012683
KNApSAcK IDC00001379
Chemspider ID5907
KEGG Compound IDC00073
BioCyc IDMET
BiGG ID33753
Wikipedia LinkMethionine
METLIN ID5664
PubChem Compound6137
PDB IDNot Available
ChEBI ID16643
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 35 proteins in total.

Enzymes

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
General function:
Involved in methylenetetrahydrofolate reductase (NADPH) activity
Specific function:
Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
Gene Name:
MTHFR
Uniprot ID:
P42898
Molecular weight:
74595.895
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:
TAT
Uniprot ID:
P17735
Molecular weight:
50398.895
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT2A
Uniprot ID:
P31153
Molecular weight:
43660.37
General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the transfer of a methyl group from AdoMet to trivalent arsenicals producing methylated and dimethylated arsenicals. It methylates arsenite to form methylarsonate, Me-AsO(3)H(2), which is reduced by methylarsonate reductase to methylarsonite, Me-As(OH)2. Methylarsonite is also a substrate and it is converted into the much less toxic compound dimethylarsinate (cacodylate), Me(2)As(O)-OH (By similarity).
Gene Name:
AS3MT
Uniprot ID:
Q9HBK9
Molecular weight:
41747.49
General function:
Involved in methyltransferase activity
Specific function:
Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:
INMT
Uniprot ID:
O95050
Molecular weight:
28833.695
General function:
Involved in methionine adenosyltransferase activity
Specific function:
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name:
MAT1A
Uniprot ID:
Q00266
Molecular weight:
43647.6
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the reductive regeneration of cob(I)alamin cofactor required for the maintenance of methionine synthase in a functional state.
Gene Name:
MTRR
Uniprot ID:
Q9UBK8
Molecular weight:
77672.995
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
General function:
Involved in oxidoreductase activity, acting on a sulfur group of donors, disulfide as acceptor
Specific function:
Has an important function as a repair enzyme for proteins that have been inactivated by oxidation. Catalyzes the reversible oxidation-reduction of methionine sulfoxide in proteins to methionine.
Gene Name:
MSRA
Uniprot ID:
Q9UJ68
Molecular weight:
21737.41

Transporters

General function:
Involved in transmembrane transport
Specific function:
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular weight:
55492.1

Only showing the first 10 proteins. There are 35 proteins in total.