Ademetionine

Identification

Generic Name
Ademetionine
DrugBank Accession Number
DB00118
Background

Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 398.44
Monoisotopic: 398.137239006
Chemical Formula
C15H22N6O5S
Synonyms
  • Ademetionine
  • AdoMet
  • L-S-Adenosylmethionine
  • S-Adenosylmethionine
  • SAM
  • SAM-e
  • SAMe

Pharmacology

Indication

S-Adenosylmethionine (SAMe) is used as a drug in Europe for the treatment of depression, liver disorders, fibromyalgia, and osteoarthritis. It has also been introduced into the United States market as a dietary supplement for the support of bone and joint health, as well as mood and emotional well being.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofFatigue••••••••••••••••••• ••••••
Treatment ofIntrahepatic cholestasis••••••••••••••••••••••••••••••••• ••••••• •••••••
Treatment ofIntrahepatic cholestasis•••••••••••••••••••••••• ••••••• •••••••
Treatment ofIntrahepatic cholestasis•••••••••••••••••••••••••••••• •••••••••••• ••••••• •••••••
Treatment ofIntrahepatic cholestasis••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

S-adenosylmethionine is an intermediate metabolite of methionine. Its involvement in methylation assists in cellular growth and repair, maintains the phospho-bilipid layer in cell membranes. It also helps in the maintenance of the action of several hormones and neurotransmitters that affect mood. Highest concentration are found in the brain and the liver.

Mechanism of action

S-Adenosylmethionine (SAMe) is a natural substance present in the cells of the body. It is a direct metabolite of the essential amino acid L-methionine. SAMe plays a crucial biochemical role in the body by donating a one-carbon methyl group in a process called transmethylation. SAMe, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine and other molecules.

TargetActionsOrganism
UCatechol O-methyltransferase
cofactor
Humans
UCap-specific mRNA (nucleoside-2'-O-)-methyltransferase 1Not AvailableHumans
UArsenite methyltransferaseNot AvailableHumans
UGlycine N-methyltransferase
cofactor
Humans
US-adenosylmethionine decarboxylase proenzyme
cofactor
Humans
US-adenosylmethionine synthase isoform type-2
cofactor
Humans
UCystathionine beta-synthase
activator
Humans
US-adenosylmethionine synthase isoform type-1
cofactor
Humans
Absorption

S-Adenosylmethionine is absorbed from the small intestine following oral intake. As absorption is affected by food, it is best to take on an empty stomach. Bioavailability is low following oral intake.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Significant first-pass metabolism in the liver. Approximately 50% of S-Adenosylmethionine (SAMe) is metabolized in the liver. SAMe is metabolized to S-adenosylhomocysteine, which is then metabolized to homocysteine. Homocysteine can either be metabolized to cystathionine and then cysteine or to methionine. The cofactor in the metabolism of homocysteine to cysteine is vitamin B6. Cofactors for the metabolism of homocysteine to methionine are folic acid, vitamin B12 and betaine.

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Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Irritating to mucus membranes and upper respiratory tract. Can cause CNS depression.

Pathways
PathwayCategory
Glycine and Serine MetabolismMetabolic
Tyrosine MetabolismMetabolic
Catecholamine BiosynthesisMetabolic
Arginine and Proline MetabolismMetabolic
Histidine MetabolismMetabolic
Betaine MetabolismMetabolic
Cystathionine beta-Synthase DeficiencyDisease
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
HistidinemiaDisease
Tyrosinemia Type IDisease
Phenytoin (Antiarrhythmic) Action PathwayDrug action
Hyperprolinemia Type IIDisease
Hyperprolinemia Type IDisease
Mercaptopurine Action PathwayDrug action
Disulfiram Action PathwayDrug action
Carnitine SynthesisMetabolic
L-Arginine:Glycine Amidinotransferase DeficiencyDisease
Methylhistidine MetabolismMetabolic
Sarcosine Oncometabolite PathwayDisease
Phosphatidylcholine Biosynthesis PC(14:0/14:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/15:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/16:1(9Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/18:2(9Z,12Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:0)Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:1(11Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:2(11Z,14Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:4(5Z,8Z,11Z,14Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/20:5(5Z,8Z,11Z,14Z,17Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/22:5(4Z,7Z,10Z,13Z,16Z))Metabolic
Phosphatidylcholine Biosynthesis PC(14:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z))Metabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetaminophenAdemetionine may increase the hepatotoxic activities of Acetaminophen.
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Ademetionine.
BenzocaineThe metabolism of Benzocaine can be decreased when combined with Ademetionine.
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Ademetionine.
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Ademetionine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Ademetionine butanedisulfonateC5BTS0548U200393-05-1TYXBLACMHQBEEW-XKGORWRGSA-N
Ademetionine disulfate ditosylateNot AvailableNot AvailableNot applicable
Ademetionine disulfate monotosylateNot AvailableNot AvailableNot applicable
Ademetionine disulfate tosylate564ROC9U0997540-22-2XDCFCHNAIMYBAZ-XQVUROGGSA-N
Ademetionine tosylateNot AvailableNot AvailableNot applicable
International/Other Brands
Donamet / Sam-Sulfate (Natrol) / SAMe / SAMe Rx-Mood (Nature's Plus)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Heptral 500mg Gastroresistant TabletsTabletOralABBOTT LABORATORIES (M) SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETLİ ŞİŞEAdemetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETSİZ ŞİŞEAdemetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPATAMINE %8 500 ML(SETLI)Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag
HEPATAMINE %8 500 ML(SETSIZ)Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Aspartame (0.9 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag

Categories

ATC Codes
A16AA02 — Ademetionine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 5'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
5'-deoxy-5'-thionucleosides
Direct Parent
5'-deoxy-5'-thionucleosides
Alternative Parents
Methionine and derivatives / Glycosylamines / Pentoses / 6-aminopurines / L-alpha-amino acids / Thia fatty acids / Aminopyrimidines and derivatives / Hydroxy fatty acids / N-substituted imidazoles / Imidolactams
show 18 more
Substituents
1,2-diol / 5'-deoxy-5'-thionucleoside / 6-aminopurine / Alcohol / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonium betaine (CHEBI:67040) / Coenzymes (C00019)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7LP2MPO46S
CAS number
29908-03-0
InChI Key
MEFKEPWMEQBLKI-AIRLBKTGSA-N
InChI
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27?/m0/s1
IUPAC Name
(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(methyl)sulfaniumyl)butanoate
SMILES
C[S+](CC[C@H](N)C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N

References

Synthesis Reference

Takayasu Tsuchida, Fumihiro Yoshinaga, Shinji Okumura, "Method for producing S-adenosylmethionine or methylthioadenosine by yeast." U.S. Patent US3962034, issued November, 1971.

US3962034
General References
  1. Finkelstein JD, Martin JJ: Homocysteine. Int J Biochem Cell Biol. 2000 Apr;32(4):385-9. [Article]
  2. Fodinger M, Horl WH, Sunder-Plassmann G: Molecular biology of 5,10-methylenetetrahydrofolate reductase. J Nephrol. 2000 Jan-Feb;13(1):20-33. [Article]
  3. Roje S: S-Adenosyl-L-methionine: beyond the universal methyl group donor. Phytochemistry. 2006 Aug;67(15):1686-98. [Article]
  4. Loenen WA: S-adenosylmethionine: jack of all trades and master of everything? Biochem Soc Trans. 2006 Apr;34(Pt 2):330-3. [Article]
  5. Chiang PK, Gordon RK, Tal J, Zeng GC, Doctor BP, Pardhasaradhi K, McCann PP: S-Adenosylmethionine and methylation. FASEB J. 1996 Mar;10(4):471-80. [Article]
Human Metabolome Database
HMDB0062709
KEGG Compound
C00019
PubChem Compound
34755
PubChem Substance
46505280
ChemSpider
31982
BindingDB
28422
RxNav
9504
ChEBI
67040
ChEMBL
CHEMBL1088977
PharmGKB
PA164754994
PDBe Ligand
SAM
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
S-Adenosyl_methionine
MSDS
Download (35.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentDecompensated Cirrhosis / Hepatic Failure / Thrombocytopenia1
4Unknown StatusTreatmentCholestasis / Viral Hepatitis B1
3CompletedTreatmentHepatitis1
3CompletedTreatmentIntrahepatic Cholestasis Associated With Alcoholic Liver Disease1
3CompletedTreatmentSevere alcoholic liver disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • CVS Pharmacy
  • Pharmavite
Dosage Forms
FormRouteStrength
Tablet, delayed releaseOral300 MG
Tablet, delayed releaseOral500 MG
TabletOral
SolutionIntravenous
Injection, powder, for solutionIntramuscular; Intravenous100 MG/5ML
Injection, powder, for solutionIntramuscular; Intravenous200 MG/5ML
Injection, powder, for solutionIntramuscular; Intravenous400 MG/5ML
Tablet, delayed releaseOral200 MG
Tablet, delayed releaseOral400 MG
Injection, powder, for solutionIntramuscular; Intravenous300 MG/5ML
Injection, powder, for solutionIntramuscular; Intravenous500 MG/5ML
TabletOral300 MG
TabletOral500 MG
Prices
Unit descriptionCostUnit
Sam-e 400 mg tablet0.86USD tablet
CVS Pharmacy sam-e 400 mg tablet0.79USD tablet
Sam-e 200 mg tablet0.59USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)78 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.62 mg/mLALOGPS
logP0.05ALOGPS
logP-5.3Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.7Chemaxon
pKa (Strongest Basic)9.41Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area185.46 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.07 m3·mol-1Chemaxon
Polarizability39.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8102
Blood Brain Barrier-0.8894
Caco-2 permeable-0.7307
P-glycoprotein substrateSubstrate0.7584
P-glycoprotein inhibitor INon-inhibitor0.9664
P-glycoprotein inhibitor IINon-inhibitor0.993
Renal organic cation transporterNon-inhibitor0.9295
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.8224
CYP450 3A4 substrateSubstrate0.5753
CYP450 1A2 substrateNon-inhibitor0.8308
CYP450 2C9 inhibitorNon-inhibitor0.8396
CYP450 2D6 inhibitorNon-inhibitor0.9192
CYP450 2C19 inhibitorNon-inhibitor0.8457
CYP450 3A4 inhibitorNon-inhibitor0.9731
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.6899
CarcinogenicityNon-carcinogens0.9417
BiodegradationNot ready biodegradable0.9486
Rat acute toxicity2.5758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9755
hERG inhibition (predictor II)Non-inhibitor0.7962
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a6r-5945000000-faee11753c0aa9b74806
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.3486255
predicted
DarkChem Lite v0.1.0
[M-H]-203.0333255
predicted
DarkChem Lite v0.1.0
[M-H]-181.81721
predicted
DeepCCS 1.0 (2019)
[M+H]+204.3834255
predicted
DarkChem Lite v0.1.0
[M+H]+200.4574255
predicted
DarkChem Lite v0.1.0
[M+H]+183.88329
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.3789255
predicted
DarkChem Lite v0.1.0
[M+Na]+202.2660255
predicted
DarkChem Lite v0.1.0
[M+Na]+189.84372
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Lee BW, Sun HG, Zang T, Kim BJ, Alfaro JF, Zhou ZS: Enzyme-catalyzed transfer of a ketone group from an S-adenosylmethionine analogue: a tool for the functional analysis of methyltransferases. J Am Chem Soc. 2010 Mar 24;132(11):3642-3. doi: 10.1021/ja908995p. [Article]
  2. Rutherford K, Le Trong I, Stenkamp RE, Parson WW: Crystal structures of human 108V and 108M catechol O-methyltransferase. J Mol Biol. 2008 Jun 27;380(1):120-30. doi: 10.1016/j.jmb.2008.04.040. Epub 2008 Apr 23. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
S-adenosyl-L-methionine-dependent methyltransferase that mediates mRNA cap1 2'-O-ribose methylation to the 5'-cap structure of mRNAs. Methylates the ribose of the first nucleotide of a m(7)GpppG-capped mRNA and small nuclear RNA (snRNA) to produce m(7)GpppRm (cap1). Displays a preference for cap0 transcripts. Cap1 modification is linked to higher levels of translation. May be involved in the interferon response pathway.
Specific Function
Mrna (nucleoside-2'-o-)-methyltransferase activity
Gene Name
CMTR1
Uniprot ID
Q8N1G2
Uniprot Name
Cap-specific mRNA (nucleoside-2'-O-)-methyltransferase 1
Molecular Weight
95319.96 Da
References
  1. Haline-Vaz T, Silva TC, Zanchin NI: The human interferon-regulated ISG95 protein interacts with RNA polymerase II and shows methyltransferase activity. Biochem Biophys Res Commun. 2008 Aug 8;372(4):719-24. doi: 10.1016/j.bbrc.2008.05.137. Epub 2008 Jun 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
S-Adenosylmethionine is a substrate to the enzyme
General Function
S-adenosylmethionine-dependent 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...
Gene Name
AS3MT
Uniprot ID
Q9HBK9
Uniprot Name
Arsenite methyltransferase
Molecular Weight
41747.49 Da
References
  1. Wang S, Li X, Song X, Geng Z, Hu X, Wang Z: Rapid equilibrium kinetic analysis of arsenite methylation catalyzed by recombinant human arsenic (+3 oxidation state) methyltransferase (hAS3MT). J Biol Chem. 2012 Nov 9;287(46):38790-9. doi: 10.1074/jbc.M112.368050. Epub 2012 Sep 6. [Article]
  2. Wang S, Geng Z, Shi N, Li X, Wang Z: The functions of crucial cysteine residues in the arsenite methylation catalyzed by recombinant human arsenic (III) methyltransferase. PLoS One. 2014 Oct 28;9(10):e110924. doi: 10.1371/journal.pone.0110924. eCollection 2014. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Glycine n-methyltransferase activity
Specific Function
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial ...
Gene Name
GNMT
Uniprot ID
Q14749
Uniprot Name
Glycine N-methyltransferase
Molecular Weight
32742.0 Da
References
  1. Rowling MJ, Schalinske KL: Retinoid compounds activate and induce hepatic glycine N-methyltransferase in rats. J Nutr. 2001 Jul;131(7):1914-7. [Article]
  2. Luka Z, Cerone R, Phillips JA 3rd, Mudd HS, Wagner C: Mutations in human glycine N-methyltransferase give insights into its role in methionine metabolism. Hum Genet. 2002 Jan;110(1):68-74. Epub 2001 Dec 7. [Article]
  3. Rowling MJ, McMullen MH, Chipman DC, Schalinske KL: Hepatic glycine N-methyltransferase is up-regulated by excess dietary methionine in rats. J Nutr. 2002 Sep;132(9):2545-50. [Article]
  4. Moller MT, Samari HR, Fengsrud M, Stromhaug PE, oStvold AC, Seglen PO: Okadaic acid-induced, naringin-sensitive phosphorylation of glycine N-methyltransferase in isolated rat hepatocytes. Biochem J. 2003 Jul 15;373(Pt 2):505-13. [Article]
  5. Uthus EO, Brown-Borg HM: Altered methionine metabolism in long living Ames dwarf mice. Exp Gerontol. 2003 May;38(5):491-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Putrescine binding
Specific Function
Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
Gene Name
AMD1
Uniprot ID
P17707
Uniprot Name
S-adenosylmethionine decarboxylase proenzyme
Molecular Weight
38339.335 Da
References
  1. Dudkowska M, Stachurska A, Grzelakowska-Sztabert B, Manteuffel-Cymborowska M: Up-regulation of spermidine/spermine N1-acetyltransferase (SSAT) expression is a part of proliferative but not anabolic response of mouse kidney. Acta Biochim Pol. 2002;49(4):969-77. [Article]
  2. Ndjonka D, Zou Y, Bi X, Woster P, Walter RD, Luersen K: The activator-binding site of Onchocerca volvulus S-adenosylmethionine decarboxylase, a potential drug target. Biol Chem. 2003 Aug;384(8):1195-201. [Article]
  3. Notari S, Lucchi R, Traversa U, Fabbri E, Poli A: Reversible changes in goldfish brain polyamine concentrations and synthetic enzymes after cold exposure. Brain Res. 2004 May 1;1006(2):241-7. [Article]
  4. Yerlikaya A, Stanley BA: Structural basis for the inactivation of AdoMetDC K12R mutant. Protein Pept Lett. 2006;13(3):313-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Methionine adenosyltransferase activity
Specific Function
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name
MAT2A
Uniprot ID
P31153
Uniprot Name
S-adenosylmethionine synthase isoform type-2
Molecular Weight
43660.37 Da
References
  1. Mudd SH, Cerone R, Schiaffino MC, Fantasia AR, Minniti G, Caruso U, Lorini R, Watkins D, Matiaszuk N, Rosenblatt DS, Schwahn B, Rozen R, LeGros L, Kotb M, Capdevila A, Luka Z, Finkelstein JD, Tangerman A, Stabler SP, Allen RH, Wagner C: Glycine N-methyltransferase deficiency: a novel inborn error causing persistent isolated hypermethioninaemia. J Inherit Metab Dis. 2001 Aug;24(4):448-64. [Article]
  2. Farrar C, Clarke S: Altered levels of S-adenosylmethionine and S-adenosylhomocysteine in the brains of L-isoaspartyl (D-Aspartyl) O-methyltransferase-deficient mice. J Biol Chem. 2002 Aug 2;277(31):27856-63. Epub 2002 May 22. [Article]
  3. Martinez-Chantar ML, Latasa MU, Varela-Rey M, Lu SC, Garcia-Trevijano ER, Mato JM, Avila MA: L-methionine availability regulates expression of the methionine adenosyltransferase 2A gene in human hepatocarcinoma cells: role of S-adenosylmethionine. J Biol Chem. 2003 May 30;278(22):19885-90. Epub 2003 Mar 26. [Article]
  4. Martinez-Chantar ML, Garcia-Trevijano ER, Latasa MU, Martin-Duce A, Fortes P, Caballeria J, Avila MA, Mato JM: Methionine adenosyltransferase II beta subunit gene expression provides a proliferative advantage in human hepatoma. Gastroenterology. 2003 Apr;124(4):940-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Activator
General Function
Ubiquitin protein ligase binding
Specific Function
Hydro-lyase catalyzing the first step of the transsulfuration pathway, where the hydroxyl group of L-serine is displaced by L-homocysteine in a beta-replacement reaction to form L-cystathionine, th...
Gene Name
CBS
Uniprot ID
P35520
Uniprot Name
Cystathionine beta-synthase
Molecular Weight
60586.05 Da
References
  1. Janosik M, Kery V, Gaustadnes M, Maclean KN, Kraus JP: Regulation of human cystathionine beta-synthase by S-adenosyl-L-methionine: evidence for two catalytically active conformations involving an autoinhibitory domain in the C-terminal region. Biochemistry. 2001 Sep 4;40(35):10625-33. [Article]
  2. Jacobs RL, Stead LM, Brosnan ME, Brosnan JT: Hyperglucagonemia in rats results in decreased plasma homocysteine and increased flux through the transsulfuration pathway in liver. J Biol Chem. 2001 Nov 23;276(47):43740-7. Epub 2001 Sep 14. [Article]
  3. Choumenkovitch SF, Selhub J, Bagley PJ, Maeda N, Nadeau MR, Smith DE, Choi SW: In the cystathionine beta-synthase knockout mouse, elevations in total plasma homocysteine increase tissue S-adenosylhomocysteine, but responses of S-adenosylmethionine and DNA methylation are tissue specific. J Nutr. 2002 Aug;132(8):2157-60. [Article]
  4. Evande R, Blom H, Boers GH, Banerjee R: Alleviation of intrasteric inhibition by the pathogenic activation domain mutation, D444N, in human cystathionine beta-synthase. Biochemistry. 2002 Oct 1;41(39):11832-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Cofactor
General Function
Methionine adenosyltransferase activity
Specific Function
Catalyzes the formation of S-adenosylmethionine from methionine and ATP.
Gene Name
MAT1A
Uniprot ID
Q00266
Uniprot Name
S-adenosylmethionine synthase isoform type-1
Molecular Weight
43647.6 Da
References
  1. Carretero MV, Latasa MU, Garcia-Trevijano ER, Corrales FJ, Wagner C, Mato JM, Avila MA: Inhibition of liver methionine adenosyltransferase gene expression by 3-methylcolanthrene: protective effect of S-adenosylmethionine. Biochem Pharmacol. 2001 May 1;61(9):1119-28. [Article]
  2. Martinez-Chantar ML, Corrales FJ, Martinez-Cruz LA, Garcia-Trevijano ER, Huang ZZ, Chen L, Kanel G, Avila MA, Mato JM, Lu SC: Spontaneous oxidative stress and liver tumors in mice lacking methionine adenosyltransferase 1A. FASEB J. 2002 Aug;16(10):1292-4. Epub 2002 Jun 7. [Article]
  3. Santamaria E, Avila MA, Latasa MU, Rubio A, Martin-Duce A, Lu SC, Mato JM, Corrales FJ: Functional proteomics of nonalcoholic steatohepatitis: mitochondrial proteins as targets of S-adenosylmethionine. Proc Natl Acad Sci U S A. 2003 Mar 18;100(6):3065-70. Epub 2003 Mar 11. [Article]
  4. Martinez-Chantar ML, Latasa MU, Varela-Rey M, Lu SC, Garcia-Trevijano ER, Mato JM, Avila MA: L-methionine availability regulates expression of the methionine adenosyltransferase 2A gene in human hepatocarcinoma cells: role of S-adenosylmethionine. J Biol Chem. 2003 May 30;278(22):19885-90. Epub 2003 Mar 26. [Article]
  5. Martinez-Chantar ML, Garcia-Trevijano ER, Latasa MU, Martin-Duce A, Fortes P, Caballeria J, Avila MA, Mato JM: Methionine adenosyltransferase II beta subunit gene expression provides a proliferative advantage in human hepatoma. Gastroenterology. 2003 Apr;124(4):940-8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Spermidine synthase activity
Specific Function
Catalyzes the production of spermidine from putrescine and decarboxylated S-adenosylmethionine (dcSAM). Has a strong preference for putrescine as substrate, and has very low activity towards 1,3-di...
Gene Name
SRM
Uniprot ID
P19623
Uniprot Name
Spermidine synthase
Molecular Weight
33824.455 Da
References
  1. Cyriac J, Haleem R, Cai X, Wang Z: Androgen regulation of spermidine synthase expression in the rat prostate. Prostate. 2002 Mar 1;50(4):252-61. [Article]
  2. Dejima H, Kobayashi M, Takasaki H, Takeda N, Shirahata A, Samejima K: Synthetic decarboxylated S-adenosyl-L-methionine as a substrate for aminopropyl transferases. Biol Pharm Bull. 2003 Jul;26(7):1005-8. [Article]
  3. Franceschetti M, Fornale S, Tassonia A, Zuccherelli K, Mayer MJ, Bagni N: Effects of spermidine synthase overexpression on polyamine biosynthetic pathway in tobacco plants. J Plant Physiol. 2004 Sep;161(9):989-1001. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Caro AA, Cederbaum AI: Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Biochem Pharmacol. 2005 Apr 1;69(7):1081-93. [Article]
  2. Cederbaum AI: Hepatoprotective effects of S-adenosyl-L-methionine against alcohol- and cytochrome P450 2E1-induced liver injury. World J Gastroenterol. 2010 Mar 21;16(11):1366-76. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42