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
ValueSource
(2S)-2-Amino-4-(methylsulfanyl)butanoic acidChEBI
(S)-2-Amino-4-(methylthio)butanoic acidChEBI
(S)-2-Amino-4-(methylthio)butyric acidChEBI
(S)-MethionineChEBI
L-(-)-MethionineChEBI
L-alpha-Amino-gamma-methylmercaptobutyric acidChEBI
L-MethioninChEBI
MChEBI
MetChEBI
METHIONINEChEBI
L-2-Amino-4methylthiobutyric acidKegg
L-Methionine ZKegg
(2S)-2-Amino-4-(methylsulfanyl)butanoateGenerator
(2S)-2-Amino-4-(methylsulphanyl)butanoateGenerator
(2S)-2-Amino-4-(methylsulphanyl)butanoic acidGenerator
(S)-2-Amino-4-(methylthio)butanoateGenerator
(S)-2-Amino-4-(methylthio)butyrateGenerator
L-a-Amino-g-methylmercaptobutyrateGenerator
L-a-Amino-g-methylmercaptobutyric acidGenerator
L-alpha-Amino-gamma-methylmercaptobutyrateGenerator
L-Α-amino-γ-methylmercaptobutyrateGenerator
L-Α-amino-γ-methylmercaptobutyric acidGenerator
L-2-Amino-4methylthiobutyrateGenerator
(L)-MethionineHMDB
(S)-(+)-MethionineHMDB
(S)-2-Amino-4-(methylthio)-butanoateHMDB
(S)-2-Amino-4-(methylthio)-butanoic acidHMDB
2-Amino-4-(methylthio)butyrateHMDB
2-Amino-4-(methylthio)butyric acidHMDB
2-Amino-4-methylthiobutanoateHMDB
2-Amino-4-methylthiobutanoic acidHMDB
a-Amino-g-methylmercaptobutyrateHMDB
a-Amino-g-methylmercaptobutyric acidHMDB
AcimethinHMDB
alpha-Amino-alpha-aminobutyric acidHMDB
alpha-Amino-gamma-methylmercaptobutyrateHMDB
alpha-Amino-gamma-methylmercaptobutyric acidHMDB
CymethionHMDB
g-Methylthio-a-aminobutyrateHMDB
g-Methylthio-a-aminobutyric acidHMDB
gamma-Methylthio-alpha-aminobutyrateHMDB
gamma-Methylthio-alpha-aminobutyric acidHMDB
H-Met-HHMDB
H-Met-OHHMDB
L(-)-Amino-alpha-amino-alpha-aminobutyric acidHMDB
L(-)-Amino-gamma-methylthiobutyric acidHMDB
L-2-Amino-4-(methylthio)butyric acidHMDB
L-2-Amino-4-methylthiobutyric acidHMDB
L-a-Amino-g-methylthiobutyrateHMDB
L-a-Amino-g-methylthiobutyric acidHMDB
L-alpha-Amino-gamma-methylthiobutyrateHMDB
L-alpha-Amino-gamma-methylthiobutyric acidHMDB
L-gamma-Methylthio-alpha-aminobutyric acidHMDB
L-MethioninumHMDB
LiquimethHMDB
MepronHMDB
MethilaninHMDB
MethioninumHMDB
MetioninaHMDB
Neo-methidinHMDB
Poly-L-methionineHMDB
PolymethionineHMDB
S-MethionineHMDB
S-Methyl-L-homocysteineHMDB
Toxin warHMDB
L-Isomer methionineHMDB
Methionine, L-isomerHMDB
PedamethHMDB
Methionine, L isomerHMDB
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-BETA,BETA-carotene-3,3'-diolChEBI
Bo-xanChEBI
e 161bChEBI
XanthophyllChEBI
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-b,b-carotene-3,3'-diolGenerator
(3R,3'r,6S)-4,5-DIDEHYDRO-5,6-dihydro-β,β-carotene-3,3'-diolGenerator
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
TypeDescriptionSplash KeyView
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-004i-0920000000-945c85aa7c9f5eb2dfbbSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-b837ee0f4413856560f1Spectrum
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-00b9-7910000000-5a1558fbb2f5e86edc9bSpectrum
GC-MSL-Methionine, 1 TMS, GC-MS Spectrumsplash10-0udi-1900000000-1a97567ce4f25c4e8263Spectrum
GC-MSL-Methionine, 2 TMS, GC-MS Spectrumsplash10-004i-0910000000-1b0477118cb20549bf4dSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0920000000-8ffae5d87508e0704903Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0920000000-945c85aa7c9f5eb2dfbbSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-b837ee0f4413856560f1Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-01bc-2692000000-c6a4af434abaeea2de87Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-00b9-7910000000-5a1558fbb2f5e86edc9bSpectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-0udi-1900000000-1a97567ce4f25c4e8263Spectrum
GC-MSL-Methionine, non-derivatized, GC-MS Spectrumsplash10-004i-0910000000-1b0477118cb20549bf4dSpectrum
Predicted GC-MSL-Methionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0mbd-9200000000-77e5cfb78936ad02d71cSpectrum
Predicted GC-MSL-Methionine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9510000000-c03dec8575710eed861eSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-1900000000-b991859b2c5bed6592a8Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-08fr-9000000000-66855ace60e59837f131Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-08fr-9000000000-56a567791c824c6a9da6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fe0-0900000000-d680295f21b2e2b40366Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-062d3540db4db22da836Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-84467513e2c9ec1a6851Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-88dc2bebb198eea550efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0920000000-b444ad79abeb16acde43Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6e24a8df417e5f3db58cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-c60ef880eb9a816a274bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a7b7d1a3481c0c691a5bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-9156f088f4cc9eafa892Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9200000000-f78ba2aab8d5a0e0b135Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-e7b819fd2d0ac3862860Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-c3557cb41fd6fe268819Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-6900000000-6bf5af2d1c561013948aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-08fr-9000000000-63c9b1c138f9a27490e5Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9000000000-e133c47b0efe4992589fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-dee78b4f34f8732fedb0Spectrum
MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0udi-0900000000-d3f03ff5e8eacc8b6c8eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-e0dd5ff44b7962f6a2d2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-305916dde72c899993b6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9800000000-47e0a34a2ec02bd762bfSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Methionine synthaseMTR1q43Q99707 details
Methylenetetrahydrofolate reductaseMTHFR1p36.3P42898 details
Tyrosine aminotransferaseTAT16q22.1P17735 details
S-adenosylmethionine synthase isoform type-2MAT2A2p11.2P31153 details
Arsenite methyltransferaseAS3MT10q24.32Q9HBK9 details
Indolethylamine N-methyltransferaseINMT7p14.3O95050 details
S-adenosylmethionine synthase isoform type-1MAT1A10q22Q00266 details
Methionine synthase reductaseMTRR5p15.31Q9UBK8 details
Kynurenine--oxoglutarate transaminase 1CCBL19q34.11Q16773 details
Mitochondrial peptide methionine sulfoxide reductaseMSRA8p23.1Q9UJ68 details
Betaine--homocysteine S-methyltransferase 1BHMT5q14.1Q93088 details
Methionine--tRNA ligase, cytoplasmicMARS12q13P56192 details
Glutamine synthetaseGLUL1q31P15104 details
Lipoyl synthase, mitochondrialLIAS4p14O43766 details
Methionine adenosyltransferase 2 subunit betaMAT2BQ9NZL9 details
S-methylmethionine--homocysteine S-methyltransferase BHMT2BHMT25q13Q9H2M3 details
Methionine aminopeptidase 2METAP212q22P50579 details
L-amino-acid oxidaseIL4I119q13.3-q13.4Q96RQ9 details
Kynurenine--oxoglutarate transaminase 3CCBL21p22.2Q6YP21 details
Methionine-R-sulfoxide reductase B2, mitochondrialMSRB210p12Q9Y3D2 details
Methionine-R-sulfoxide reductase B3MSRB312q14.3Q8IXL7 details
Methionine--tRNA ligase, mitochondrialMARS22q33.1Q96GW9 details
Methionine-R-sulfoxide reductase B1MSRB116p13.3Q9NZV6 details
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.