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Identification
NameL-Methionine
Accession NumberDB00134  (NUTR00038)
TypeSmall Molecule
GroupsApproved, Nutraceutical
Description

A sulfur containing essential amino acid that is important in many body functions. It is a chelating agent for heavy metals. [PubChem]

Structure
Thumb
Synonyms
(2S)-2-amino-4-(Methylsulfanyl)butanoic acid
(S)-2-amino-4-(methylthio)butanoic acid
(S)-2-amino-4-(methylthio)butyric acid
(S)-methionine
L-(-)-Methionine
L-a-Amino-g-methylthiobutyric acid
L-alpha-amino-gamma-Methylmercaptobutyric acid
L-Methionin
L-Methionine
L-α-amino-γ-methylmercaptobutyric acid
M
Met
Methionine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcimethinNot Available
Brand mixtures
NameLabellerIngredients
2.5% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection With Electrolytes In 10% Dextrose ClinimixBaxter Corporation Clintec Nutrition Division
2.5% Travasol Amino Acid Injection Without Electrolytes In 10% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.5%travasol Amino Acid InJ.W.eleC.W.25%dexClintec Nutrition Company
2.75% Travas. Amino Acid InJ.W.elecw.25%dexClintec Nutrition Company
2.75% Travasol Amino Acid Injection With Electrolytes In 25% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
2.75%travasol Amino Acid InJ.W.eleC.W.5%dex.Clintec Nutrition Company
4.25% Amino Acid Injection Without Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 20% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection With Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrlytes In 10% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
4.25% Travasol Amino Acid Without Electrolytes In 5% Dextrose QuickmixBaxter Corporation Clintec Nutrition Division
4.25%trav. Amino Acid InJ.W.O.elect.5%dext.Clintec Nutrition Company
4.25%travasol Amino Acid InJ.W.elecw.5%dex.Clintec Nutrition Company
5% Travasol Amino Acid Injection With Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 20% DextroseBaxter Corporation Clintec Nutrition Division
5% Travasol Amino Acid Injection Without Electrolytes In 25% DextroseBaxter Corporation Clintec Nutrition Division
AminosynHospira, Inc.
Aminosyn 10%Hospira Healthcare Corporation
Aminosyn 10% W ElectrolytesAbbott Laboratories, Limited
Aminosyn 3.5% MAbbott Laboratories, Limited
Aminosyn 5%Hospira Healthcare Corporation
Aminosyn 7%Hospira Healthcare Corporation
Aminosyn 8.5%Hospira Healthcare Corporation
Aminosyn 8.5% Injection With ElectrolytesHospira Healthcare Corporation
Aminosyn IIHospira, Inc.
Aminosyn II 10%Hospira Healthcare Corporation
Aminosyn II 10% With ElectrolytesHospira Healthcare Corporation
Aminosyn II 15%Hospira Healthcare Corporation
Aminosyn II 5% InjAbbott Laboratories, Limited
Aminosyn II 7% InjectionHospira Healthcare Corporation
Aminosyn II 7% M In 10% Dextrose(dual Chamber)Hospira Healthcare Corporation
Aminosyn II 7% With 10% DextroseHospira Healthcare Corporation
Aminosyn II 7% With 50% DextroseHospira Healthcare Corporation
Aminosyn II 8.5% InjectionHospira Healthcare Corporation
Aminosyn II 8.5% M In 20% Dextrose (dual Chamber)Hospira Healthcare Corporation
Aminosyn II 8.5% With 50% DextroseHospira Healthcare Corporation
Aminosyn II In Dextrose InjectionHospira Healthcare Corporation
Aminosyn II With ElectrolytesHospira, Inc.
Aminosyn RFHospira, Inc.
Aminosyn RF InjectionHospira Healthcare Corporation
Aminosyn Sulfite FreeHospira, Inc.
Aminosyn-PFHospira, Inc.
Aminosyn-PF 10%Hospira Healthcare Corporation
Aminosyn-PF 7%Hospira Healthcare Corporation
ClinimixBaxter Healthcare Corporation
Clinimix 2.5% Travasol Aa Without Electrolytes In 10% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Clinimix EBaxter Healthcare Corporation
ClinisolBaxter Healthcare Corporation
Derma-forcePrairie Naturals
Formula CmNutrivention Nutritional Products
Formula CwBody Wise International Llc
Formula Cw-capletBody Wise International Llc
Freamine HbcB. Braun Medical Inc.
Freamine IIIB. Braun Medical Inc.
HepatamineB. Braun Medical Inc.
Inhibitol - TabPep Products Inc.
NephramineB. Braun Medical Inc.
NovamineHospira, Inc.
Olimel 3.3% EBaxter Corporation
Olimel 4.4%Baxter Corporation
Olimel 4.4% EBaxter Corporation
Olimel 5.7%Baxter Corporation
Olimel 5.7% EBaxter Corporation
Periolimel 2.5% EBaxter Corporation
PlenamineB. Braun Medical Inc.
Premasol - Sulfite-free (amino Acid)Baxter Healthcare Corporation
Primene 10%Baxter Corporation
Primene 10%-liq IVClintec Nutrition Company
ProsolBaxter Healthcare Corporation
Quick Mix 2.5% Travasol Aa With Electrolytes With 25% Dextrose InjecBaxter Corporation Clintec Nutrition Division
Renamin (amino Acids) InjectionBaxter Corporation
Selenium PlusSisu Inc.
TravasolBaxter Healthcare Corporation
Travasol Amino Acid Inj 5.5%Baxter Corporation
Travasol Amino Acid Inj 8.5%Baxter Corporation
Travasol EBaxter Corporation
Travasol Inj Without Electrolytes 5.5%Baxter Corporation
TrophamineB. Braun Medical Inc.
Vamin 18 Electrolyte-freeFresenius Kabi Ab
Vamin NFresenius Kabi Ab
SaltsNot Available
Categories
UNIIAE28F7PNPL
CAS number63-68-3
WeightAverage: 149.211
Monoisotopic: 149.051049291
Chemical FormulaC5H11NO2S
InChI KeyInChIKey=FFEARJCKVFRZRR-BYPYZUCNSA-N
InChI
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1
IUPAC Name
(2S)-2-amino-4-(methylsulfanyl)butanoic acid
SMILES
CSCC[[email protected]](N)C(O)=O
Taxonomy
DescriptionThis compound 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
  • Methionine or derivatives
  • Thia fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationUsed for protein synthesis including the formation of SAMe, L-homocysteine, L-cysteine, taurine, and sulfate.
PharmacodynamicsL-Methionine is a principle supplier of sulfur which prevents disorders of the hair, skin and nails; helps lower cholesterol levels by increasing the liver's production of lecithin; reduces liver fat and protects the kidneys; a natural chelating agent for heavy metals; regulates the formation of ammonia and creates ammonia-free urine which reduces bladder irritation; influences hair follicles and promotes hair growth. L-methionine may protect against the toxic effects of hepatotoxins, such as acetaminophen. Methionine may have antioxidant activity.
Mechanism of actionThe mechanism of the possible anti-hepatotoxic activity of L-methionine is not entirely clear. It is thought that metabolism of high doses of acetaminophen in the liver lead to decreased levels of hepatic glutathione and increased oxidative stress. L-methionine is a precursor to L-cysteine. L-cysteine itself may have antioxidant activity. L-cysteine is also a precursor to the antioxidant glutathione. Antioxidant activity of L-methionine and metabolites of L-methionine appear to account for its possible anti-hepatotoxic activity. Recent research suggests that methionine itself has free-radical scavenging activity by virtue of its sulfur, as well as its chelating ability.
Related Articles
AbsorptionAbsorbed from the lumen of the small intestine into the enterocytes by an active transport process.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityDoses of L-methionine of up to 250 mg daily are generally well tolerated. Higher doses may cause nausea, vomiting and headache. Healthy adults taking 8 grams of L-methionine daily for four days were found to have reduced serum folate levels and leucocytosis. Healthy adults taking 13.9 grams of L-methionine daily for five days were found to have changes in serum pH and potassium and increased urinary calcium excretion. Schizophrenic patients given 10 to 20 grams of L-methionine daily for two weeks developed functional psychoses. Single doses of 8 grams precipitated encephalopathy in patients with cirrhosis.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Amikacin Action PathwayDrug actionSMP00253
Spectinomycin Action PathwayDrug actionSMP00258
Hyperglycinemia, non-ketoticDiseaseSMP00485
Homocystinuria-megaloblastic anemia due to defect in cobalamin metabolism, cblG complementation typeDiseaseSMP00570
Methionine MetabolismMetabolicSMP00033
Methionine Adenosyltransferase DeficiencyDiseaseSMP00221
HypermethioninemiaDiseaseSMP00341
Tobramycin Action PathwayDrug actionSMP00711
Arbekacin Action PathwayDrug actionSMP00713
Methacycline Action PathwayDrug actionSMP00727
Betaine MetabolismMetabolicSMP00123
Cystathionine Beta-Synthase DeficiencyDiseaseSMP00177
Clindamycin Action PathwayDrug actionSMP00249
Gentamicin Action PathwayDrug actionSMP00254
Netilmicin Action PathwayDrug actionSMP00257
Doxycycline Action PathwayDrug actionSMP00291
Minocycline Action PathwayDrug actionSMP00292
Lymecycline Action PathwayDrug actionSMP00295
Tigecycline Action PathwayDrug actionSMP00712
3-Phosphoglycerate dehydrogenase deficiencyDiseaseSMP00721
S-Adenosylhomocysteine (SAH) Hydrolase DeficiencyDiseaseSMP00214
Glycine N-methyltransferase DeficiencyDiseaseSMP00222
Non Ketotic HyperglycinemiaDiseaseSMP00223
Clarithromycin Action PathwayDrug actionSMP00248
Erythromycin Action PathwayDrug actionSMP00250
Roxithromycin Action PathwayDrug actionSMP00251
Kanamycin Action PathwayDrug actionSMP00255
Neomycin Action PathwayDrug actionSMP00256
Clomocycline Action PathwayDrug actionSMP00262
Dimethylglycine Dehydrogenase DeficiencyDiseaseSMP00484
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9797
Blood Brain Barrier+0.8447
Caco-2 permeable-0.6698
P-glycoprotein substrateNon-substrate0.5351
P-glycoprotein inhibitor INon-inhibitor0.9802
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.8913
CYP450 2C9 substrateNon-substrate0.7875
CYP450 2D6 substrateNon-substrate0.7323
CYP450 3A4 substrateNon-substrate0.7008
CYP450 1A2 substrateNon-inhibitor0.8295
CYP450 2C9 inhibitorNon-inhibitor0.9489
CYP450 2D6 inhibitorNon-inhibitor0.9567
CYP450 2C19 inhibitorNon-inhibitor0.951
CYP450 3A4 inhibitorNon-inhibitor0.9758
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9938
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9224
BiodegradationReady biodegradable0.5613
Rat acute toxicity0.6483 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9725
hERG inhibition (predictor II)Non-inhibitor0.9655
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injectionintravenous
Liquidintravenous
Tabletoral
Injection, solutionintravenous
Injection, solution, concentrateintravenous
Emulsionintravenous
Solutionintravenous
Capsuleoral
Prices
Unit descriptionCostUnit
Dl-methionine powder0.26USD g
Methionine powder0.03USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point283 dec °CPhysProp
water solubility5.66E+004 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.87HANSCH,C ET AL. (1995)
logS-0.42ADME Research, USCD
pKa2.28 (at 25 °C)ULLMANN VA2:63 (1985)
Predicted Properties
PropertyValueSource
Water Solubility23.9 mg/mLALOGPS
logP-1.9ALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.59 m3·mol-1ChemAxon
Polarizability15.5 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.39 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-004i-0920000000-945c85aa7c9f5eb2dfbbView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-004i-0910000000-b837ee0f4413856560f1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00b9-7910000000-5a1558fbb2f5e86edc9bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0udi-1900000000-1a97567ce4f25c4e8263View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-004i-0910000000-1b0477118cb20549bf4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0uea-1900000000-b991859b2c5bed6592a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-08fr-9000000000-66855ace60e59837f131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-08fr-9000000000-56a567791c824c6a9da6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0fe0-0900000000-d680295f21b2e2b40366View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-9000000000-062d3540db4db22da836View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-84467513e2c9ec1a6851View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-88dc2bebb198eea550efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0920000000-b444ad79abeb16acde43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6e24a8df417e5f3db58cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-c60ef880eb9a816a274bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-a7b7d1a3481c0c691a5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-9156f088f4cc9eafa892View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9200000000-f78ba2aab8d5a0e0b135View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-e7b819fd2d0ac3862860View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-b61396e720381bd5ff85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0udi-0900000000-c3557cb41fd6fe268819View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0udi-6900000000-6bf5af2d1c561013948aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-08fr-9000000000-63c9b1c138f9a27490e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-9000000000-e133c47b0efe4992589fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-dee78b4f34f8732fedb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0udi-0900000000-d3f03ff5e8eacc8b6c8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0900000000-e0dd5ff44b7962f6a2d2View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Clyde Eugene Stauffer, “Process for producing N-acyl-L-methionine.” U.S. Patent US3963573, issued June, 1950.

US3963573
General ReferencesNot Available
External Links
ATC CodesV03AB26
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (72.8 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Oxidoreductase activity, oxidizing metal ions, nad or nadp as acceptor
Specific Function:
Involved in the reductive regeneration of cob(I)alamin (vitamin B12) cofactor required for the maintenance of methionine synthase in a functional state. Necessary for utilization of methylgroups from the folate cycle, thereby affecting transgenerational epigenetic inheritance. Folate pathway donates methyl groups necessary for cellular methylation and affects different pathways such as DNA meth...
Gene Name:
MTRR
Uniprot ID:
Q9UBK8
Molecular Weight:
80409.22 Da
References
  1. Kim DJ, Park BL, Koh JM, Kim GS, Kim LH, Cheong HS, Shin HD, Hong JM, Kim TH, Shin HI, Park EK, Kim SY: Methionine synthase reductase polymorphisms are associated with serum osteocalcin levels in postmenopausal women. Exp Mol Med. 2006 Oct 31;38(5):519-24. [PubMed:17079868 ]
  2. Tvedegaard KC, Rudiger NS, Pedersen BN, Moller J: Detection of MTRR 66A-->G polymorphism using the real-time polymerase chain reaction machine LightCycler for determination of composition of allele after restriction cleavage. Scand J Clin Lab Invest. 2006;66(8):685-93. [PubMed:17101561 ]
  3. Elmore CL, Wu X, Leclerc D, Watson ED, Bottiglieri T, Krupenko NI, Krupenko SA, Cross JC, Rozen R, Gravel RA, Matthews RG: Metabolic derangement of methionine and folate metabolism in mice deficient in methionine synthase reductase. Mol Genet Metab. 2007 May;91(1):85-97. Epub 2007 Mar 21. [PubMed:17369066 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Zinc ion 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 Da
References
  1. Taurog RE, Matthews RG: Activation of methyltetrahydrofolate by cobalamin-independent methionine synthase. Biochemistry. 2006 Apr 25;45(16):5092-102. [PubMed:16618098 ]
  2. Hughes JA: In vivo hydrolysis of S-adenosyl-L-methionine in Escherichia coli increases export of 5-methylthioribose. Can J Microbiol. 2006 Jun;52(6):599-602. [PubMed:16788729 ]
  3. Reynolds E: Vitamin B12, folic acid, and the nervous system. Lancet Neurol. 2006 Nov;5(11):949-60. [PubMed:17052662 ]
  4. Banks EC, Doughty SW, Toms SM, Wheelhouse RT, Nicolaou A: Inhibition of cobalamin-dependent methionine synthase by substituted benzo-fused heterocycles. FEBS J. 2007 Jan;274(1):287-99. [PubMed:17222188 ]
  5. Yamada K, Kawata T, Wada M, Mori K, Tamai H, Tanaka N, Tadokoro T, Tobimatsu T, Toraya T, Maekawa A: Testicular injury to rats fed on soybean protein-based vitamin B12-deficient diet can be reduced by methionine supplementation. J Nutr Sci Vitaminol (Tokyo). 2007 Apr;53(2):95-101. [PubMed:17615995 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Poly(a) rna binding
Specific Function:
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala-, Cys, Gly, Pro, Ser, Thr, or Val). The catalytic activity of human METAP2 toward Met-Val peptides is consistently two orders of magnitude higher than that of METAP1, suggesting that it is responsibl...
Gene Name:
METAP2
Uniprot ID:
P50579
Molecular Weight:
52891.145 Da
References
  1. Upadhya R, Zhang HS, Weiss LM: System for expression of microsporidian methionine amino peptidase type 2 (MetAP2) in the yeast Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2006 Oct;50(10):3389-95. Epub 2006 Aug 17. [PubMed:16917013 ]
  2. Sheppard GS, Wang J, Kawai M, Fidanze SD, BaMaung NY, Erickson SA, Barnes DM, Tedrow JS, Kolaczkowski L, Vasudevan A, Park DC, Wang GT, Sanders WJ, Mantei RA, Palazzo F, Tucker-Garcia L, Lou P, Zhang Q, Park CH, Kim KH, Petros A, Olejniczak E, Nettesheim D, Hajduk P, Henkin J, Lesniewski R, Davidsen SK, Bell RL: Discovery and optimization of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2: a structural basis for the reduction of albumin binding. J Med Chem. 2006 Jun 29;49(13):3832-49. [PubMed:16789740 ]
  3. Addlagatta A, Matthews BW: Structure of the angiogenesis inhibitor ovalicin bound to its noncognate target, human Type 1 methionine aminopeptidase. Protein Sci. 2006 Aug;15(8):1842-8. Epub 2006 Jul 5. [PubMed:16823043 ]
  4. Hu X, Addlagatta A, Lu J, Matthews BW, Liu JO: Elucidation of the function of type 1 human methionine aminopeptidase during cell cycle progression. Proc Natl Acad Sci U S A. 2006 Nov 28;103(48):18148-53. Epub 2006 Nov 17. [PubMed:17114291 ]
  5. Nonato MC, Widom J, Clardy J: Human methionine aminopeptidase type 2 in complex with L- and D-methionine. Bioorg Med Chem Lett. 2006 May 15;16(10):2580-3. Epub 2006 Mar 15. [PubMed:16540317 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Zinc ion binding
Specific Function:
Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
Gene Name:
BHMT
Uniprot ID:
Q93088
Molecular Weight:
44998.205 Da
References
  1. Slow S, Garrow TA: Liver choline dehydrogenase and kidney betaine-homocysteine methyltransferase expression are not affected by methionine or choline intake in growing rats. J Nutr. 2006 Sep;136(9):2279-83. [PubMed:16920841 ]
  2. Sparks JD, Collins HL, Chirieac DV, Cianci J, Jokinen J, Sowden MP, Galloway CA, Sparks CE: Hepatic very-low-density lipoprotein and apolipoprotein B production are increased following in vivo induction of betaine-homocysteine S-methyltransferase. Biochem J. 2006 Apr 15;395(2):363-71. [PubMed:16396637 ]
  3. Uthus EO, Reeves PG, Saari JT: Copper deficiency decreases plasma homocysteine in rats. J Nutr. 2007 Jun;137(6):1370-4. [PubMed:17513393 ]
  4. Liu J, Xie Y, Cooper R, Ducharme DM, Tennant R, Diwan BA, Waalkes MP: Transplacental exposure to inorganic arsenic at a hepatocarcinogenic dose induces fetal gene expression changes in mice indicative of aberrant estrogen signaling and disrupted steroid metabolism. Toxicol Appl Pharmacol. 2007 May 1;220(3):284-91. Epub 2007 Feb 6. [PubMed:17350061 ]
  5. Hazra A, Wu K, Kraft P, Fuchs CS, Giovannucci EL, Hunter DJ: Twenty-four non-synonymous polymorphisms in the one-carbon metabolic pathway and risk of colorectal adenoma in the Nurses' Health Study. Carcinogenesis. 2007 Jul;28(7):1510-9. Epub 2007 Mar 26. [PubMed:17389618 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
product of
General Function:
Zinc ion binding
Specific Function:
Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
Gene Name:
BHMT2
Uniprot ID:
Q9H2M3
Molecular Weight:
40353.84 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Manganese ion binding
Specific Function:
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
Gene Name:
GLUL
Uniprot ID:
P15104
Molecular Weight:
42064.15 Da
References
  1. Rowe WB, Meister A: Studies on the inhibition of glutamine synthetase by methionine sulfone. Biochemistry. 1973 Apr 10;12(8):1578-82. [PubMed:4144717 ]
  2. Rowe WB, Ronzio RA, Meister A: Inhibition of glutamine synthetase by methionine sulfoximine. Studies on methionine sulfoximine phosphate. Biochemistry. 1969 Jun;8(6):2674-80. [PubMed:4308004 ]
  3. Orr J, Haselkorn R: Regulation of glutamine synthetase activity and synthesis in free-living and symbiotic Anabaena spp. J Bacteriol. 1982 Nov;152(2):626-35. [PubMed:6127334 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Protein complex binding
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 Da
References
  1. Lor KL, Cossins EA: Regulation of C metabolism by L-methionine in Saccharomyces cerevisiae. Biochem J. 1972 Dec;130(3):773-83. [PubMed:4198357 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
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 Da
References
  1. Rodriguez JL, Boukaba A, Sandoval J, Georgieva EI, Latasa MU, Garcia-Trevijano ER, Serviddio G, Nakamura T, Avila MA, Sastre J, Torres L, Mato JM, Lopez-Rodas G: Transcription of the MAT2A gene, coding for methionine adenosyltransferase, is up-regulated by E2F and Sp1 at a chromatin level during proliferation of liver cells. Int J Biochem Cell Biol. 2007;39(4):842-50. Epub 2007 Jan 20. [PubMed:17317269 ]
  2. Yang H, Magilnick N, Noureddin M, Mato JM, Lu SC: Effect of hepatocyte growth factor on methionine adenosyltransferase genes and growth is cell density-dependent in HepG2 cells. J Cell Physiol. 2007 Mar;210(3):766-73. [PubMed:17154373 ]
  3. Lin WC, Lin WL: Ameliorative effect of Ganoderma lucidum on carbon tetrachloride-induced liver fibrosis in rats. World J Gastroenterol. 2006 Jan 14;12(2):265-70. [PubMed:16482628 ]
  4. Chen H, Xia M, Lin M, Yang H, Kuhlenkamp J, Li T, Sodir NM, Chen YH, Josef-Lenz H, Laird PW, Clarke S, Mato JM, Lu SC: Role of methionine adenosyltransferase 2A and S-adenosylmethionine in mitogen-induced growth of human colon cancer cells. Gastroenterology. 2007 Jul;133(1):207-18. Epub 2007 Apr 11. [PubMed:17631143 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Methionine-sulfoxide reductase that specifically reduces methionine (R)-sulfoxide back to methionine. While in many cases, methionine oxidation is the result of random oxidation following oxidative stress, methionine oxidation is also a post-translational modification that takes place on specific residue. Upon oxidative stress, may play a role in the preservation of mitochondrial integrity by d...
Gene Name:
MSRB2
Uniprot ID:
Q9Y3D2
Molecular Weight:
19536.055 Da
References
  1. Schallreuter KU, Rubsam K, Chavan B, Zothner C, Gillbro JM, Spencer JD, Wood JM: Functioning methionine sulfoxide reductases A and B are present in human epidermal melanocytes in the cytosol and in the nucleus. Biochem Biophys Res Commun. 2006 Mar 31;342(1):145-52. Epub 2006 Feb 3. [PubMed:16480945 ]
  2. Ranaivoson FM, Kauffmann B, Neiers F, Wu J, Boschi-Muller S, Panjikar S, Aubry A, Branlant G, Favier F: The X-ray structure of the N-terminal domain of PILB from Neisseria meningitidis reveals a thioredoxin-fold. J Mol Biol. 2006 Apr 28;358(2):443-54. Epub 2006 Feb 28. [PubMed:16530221 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
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 Da
References
  1. Linnebank M, Lagler F, Muntau AC, Roschinger W, Olgemoller B, Fowler B, Koch HG: Methionine adenosyltransferase (MAT) I/III deficiency with concurrent hyperhomocysteinaemia: two novel cases. J Inherit Metab Dis. 2005;28(6):1167-8. [PubMed:16435220 ]
  2. Yang H, Magilnick N, Noureddin M, Mato JM, Lu SC: Effect of hepatocyte growth factor on methionine adenosyltransferase genes and growth is cell density-dependent in HepG2 cells. J Cell Physiol. 2007 Mar;210(3):766-73. [PubMed:17154373 ]
  3. Chen H, Xia M, Lin M, Yang H, Kuhlenkamp J, Li T, Sodir NM, Chen YH, Josef-Lenz H, Laird PW, Clarke S, Mato JM, Lu SC: Role of methionine adenosyltransferase 2A and S-adenosylmethionine in mitogen-induced growth of human colon cancer cells. Gastroenterology. 2007 Jul;133(1):207-18. Epub 2007 Apr 11. [PubMed:17631143 ]
  4. Rodriguez JL, Boukaba A, Sandoval J, Georgieva EI, Latasa MU, Garcia-Trevijano ER, Serviddio G, Nakamura T, Avila MA, Sastre J, Torres L, Mato JM, Lopez-Rodas G: Transcription of the MAT2A gene, coding for methionine adenosyltransferase, is up-regulated by E2F and Sp1 at a chromatin level during proliferation of liver cells. Int J Biochem Cell Biol. 2007;39(4):842-50. Epub 2007 Jan 20. [PubMed:17317269 ]
  5. Prudova A, Bauman Z, Braun A, Vitvitsky V, Lu SC, Banerjee R: S-adenosylmethionine stabilizes cystathionine beta-synthase and modulates redox capacity. Proc Natl Acad Sci U S A. 2006 Apr 25;103(17):6489-94. Epub 2006 Apr 13. [PubMed:16614071 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Zinc ion binding
Specific Function:
Methionine-sulfoxide reductase that specifically reduces methionine (R)-sulfoxide back to methionine. While in many cases, methionine oxidation is the result of random oxidation following oxidative stress, methionine oxidation is also a post-translational modification that takes place on specific residue. Acts as a regulator of actin assembly by reducing methionine (R)-sulfoxide mediated by MIC...
Gene Name:
MSRB1
Uniprot ID:
Q9NZV6
Molecular Weight:
12760.095 Da
References
  1. Kim HY, Gladyshev VN: Alternative first exon splicing regulates subcellular distribution of methionine sulfoxide reductases. BMC Mol Biol. 2006 Mar 16;7:11. [PubMed:16542431 ]
  2. Kim HY, Fomenko DE, Yoon YE, Gladyshev VN: Catalytic advantages provided by selenocysteine in methionine-S-sulfoxide reductases. Biochemistry. 2006 Nov 21;45(46):13697-704. [PubMed:17105189 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Peptide-methionine (s)-s-oxide reductase activity
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:
26132.42 Da
References
  1. Schallreuter KU, Rubsam K, Chavan B, Zothner C, Gillbro JM, Spencer JD, Wood JM: Functioning methionine sulfoxide reductases A and B are present in human epidermal melanocytes in the cytosol and in the nucleus. Biochem Biophys Res Commun. 2006 Mar 31;342(1):145-52. Epub 2006 Feb 3. [PubMed:16480945 ]
  2. Su Z, Limberis J, Martin RL, Xu R, Kolbe K, Heinemann SH, Hoshi T, Cox BF, Gintant GA: Functional consequences of methionine oxidation of hERG potassium channels. Biochem Pharmacol. 2007 Sep 1;74(5):702-11. Epub 2007 Jun 7. [PubMed:17624316 ]
  3. Oien DB, Moskovitz J: Ablation of the mammalian methionine sulfoxide reductase A affects the expression level of cysteine deoxygenase. Biochem Biophys Res Commun. 2007 Jan 12;352(2):556-9. Epub 2006 Nov 20. [PubMed:17126812 ]
  4. Rouhier N, Vieira Dos Santos C, Tarrago L, Rey P: Plant methionine sulfoxide reductase A and B multigenic families. Photosynth Res. 2006 Sep;89(2-3):247-62. Epub 2006 Sep 22. [PubMed:17031545 ]
  5. Gand A, Antoine M, Boschi-Muller S, Branlant G: Characterization of the amino acids involved in substrate specificity of methionine sulfoxide reductase A. J Biol Chem. 2007 Jul 13;282(28):20484-91. Epub 2007 May 11. [PubMed:17500063 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Trna binding
Specific Function:
Not Available
Gene Name:
MARS
Uniprot ID:
P56192
Molecular Weight:
101114.925 Da
References
  1. Chwatko G, Boers GH, Strauss KA, Shih DM, Jakubowski H: Mutations in methylenetetrahydrofolate reductase or cystathionine beta-synthase gene, or a high-methionine diet, increase homocysteine thiolactone levels in humans and mice. FASEB J. 2007 Jun;21(8):1707-13. Epub 2007 Feb 27. [PubMed:17327360 ]
  2. Jakubowski H: Pathophysiological consequences of homocysteine excess. J Nutr. 2006 Jun;136(6 Suppl):1741S-1749S. [PubMed:16702349 ]
  3. Vaughan MD, Sampson PB, Daub E, Honek JF: Investigation of bioisosteric effects on the interaction of substrates/ inhibitors with the methionyl-tRNA synthetase from Escherichia coli. Med Chem. 2005 May;1(3):227-37. [PubMed:16787318 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Methionine-trna ligase activity
Specific Function:
Not Available
Gene Name:
MARS2
Uniprot ID:
Q96GW9
Molecular Weight:
66590.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Spencer AC, Heck A, Takeuchi N, Watanabe K, Spremulli LL: Characterization of the human mitochondrial methionyl-tRNA synthetase. Biochemistry. 2004 Aug 3;43(30):9743-54. [PubMed:15274629 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Methionine adenosyltransferase regulator activity
Specific Function:
Non-catalytic regulatory subunit of S-adenosylmethionine synthetase 2 (MAT2A), an enzyme that catalyzes the formation of S-adenosylmethionine from methionine and ATP. Regulates the activity of S-adenosylmethionine synthetase 2 by changing its kinetic properties, rendering the enzyme more susceptible to S-adenosylmethionine inhibition.
Gene Name:
MAT2B
Uniprot ID:
Q9NZL9
Molecular Weight:
37551.535 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. LeGros L, Halim AB, Chamberlin ME, Geller A, Kotb M: Regulation of the human MAT2B gene encoding the regulatory beta subunit of methionine adenosyltransferase, MAT II. J Biol Chem. 2001 Jul 6;276(27):24918-24. Epub 2001 May 3. [PubMed:11337507 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
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 (By similarity).
Gene Name:
SLC16A10
Uniprot ID:
Q8TF71
Molecular Weight:
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23