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Human Metabolome Database Version 3.5

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Showing metabocard for S-Adenosylhomocysteine (HMDB00939)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:37 -0700
HMDB ID HMDB00939
Secondary Accession Numbers None
Metabolite Identification
Common Name S-Adenosylhomocysteine
Description S-Adenosylhomocysteine (AdoHcy) is the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of AdoHcy. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase, which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, AdoHcy is the product of all methylation reactions that involve S-adenosylmethionine (AdoMet) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these AdoMet-mediated processes by AdoHcy is a proven mechanism for metabolic alteration. Because the conversion of AdoHcy to homocysteine is reversible, with the equilibrium favoring the formation of AdoHcy, increases in plasma homocysteine are accompanied by an elevation of AdoHcy in most cases. Disturbances in the transmethylation pathway indicated by abnormal S-adenosylmethionine, S-adenosylhomocysteine or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression or Parkinson's disease. (PMID: 18065573 Link_out, 17892439 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine
  2. 2-S-Adenosyl-L-homocysteine
  3. 5'-Deoxy-S-adenosyl-L-homocysteine
  4. 5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-Adenosine
  5. Adenosyl-homo-CYS
  6. Adenosyl-L-homocysteine
  7. Adenosylhomo-CYS
  8. Adenosylhomocysteine
  9. Adohcy
  10. Formycinylhomocysteine
  11. L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-Adenosine
  12. L-S-Adenosyl-Homocysteine
  13. L-S-Adenosylhomocysteine
  14. S-(5'-Adenosyl)-L-homocysteine
  15. S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine
  16. S-(5'-Deoxyadenosine-5')-L-homocysteine
  17. S-Adenosyl-homocysteine
  18. S-Adenosyl-L-homocysteine
  19. SAH
Chemical Formula C14H20N6O5S
Average Molecular Weight 384.411
Monoisotopic Molecular Weight 384.12158847
IUPAC Name (2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid
Traditional IUPAC Name S-adenosyl-L-homocysteine
CAS Registry Number 979-92-0
SMILES N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12)C(O)=O
InChI Identifier InChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1
InChI Key ZJUKTBDSGOFHSH-WFMPWKQPSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Glycoamino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Purine Nucleosides and Analogues
  • amino acid zwitterion(ChEBI)
Substituents
  • 1,2 Diol
  • Alpha Amino Acid Or Derivative
  • Aminopyrimidine
  • Carboxylic Acid
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • Oxolane
  • Pentose Monosaccharide
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Thioether
Direct Parent Glycoamino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of Glycerophospholipid metabolism
  • Component of Glycine, serine and threonine metabolism
  • Component of Histidine metabolism
  • Component of Methionine metabolism
  • Component of Nicotinate and nicotinamide metabolism
  • Component of Selenoamino acid metabolism
  • Component of Tryptophan metabolism
  • Component of Tyrosine metabolism
  • Component of Ubiquinone biosynthesis
Application Not Available
Cellular locations
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 209 - 211 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.08 g/L ALOGPS
LogP -2.37 ALOGPS
LogP -4 ChemAxon
LogS -1.97 ALOGPS
pKa (strongest acidic) 1.81 ChemAxon
pKa (strongest basic) 9.5 ChemAxon
Hydrogen Acceptor Count 10 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 182.63 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 92.72 ChemAxon
Polarizability 38.41 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
  • Nucleus
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Location
  • Neuron
  • Placenta
  • Myelin
  • Prostate
  • Lymphoblast
Pathways
Name SMPDB Link KEGG Link
Betaine Metabolism SMP00123 map00260 Link_out
Methionine Metabolism SMP00033 map00270 Link_out
Carnitine Synthesis SMP00465 Not Available
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.46 +/- 0.02 uM Elderly (>65 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.01 (0.009-0.014) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0243 +/- 0.0068 uM Not Specified Not Specified Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.016 (0.009-0.025) uM Adult (>18 years old) Both Neurodegenerative diseases Not Available
Blood Detected and Quantified
Article_icon
0.49 +/- 0.05 uM Elderly (>65 years old) Both Parkinson's Disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
0.0269 +/- 0.0062 uM Adult (>18 years old) Not Specified Alzheimer's disease Not Available
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • Cheng H, Gomes-Trolin C, Aquilonius SM, Steinberg A, Lofberg C, Ekblom J, Oreland L: Levels of L-methionine S-adenosyltransferase activity in erythrocytes and concentrations of S-adenosylmethionine and S-adenosylhomocysteine in whole blood of patients with Parkinson's disease. Exp Neurol. 1997 Jun;145(2 Pt 1):580-5. Pubmed: 9217094 Link_out
    Neurodegenerative disease
    • Obeid R, Kostopoulos P, Knapp JP, Kasoha M, Becker G, Fassbender K, Herrmann W: Biomarkers of folate and vitamin B12 are related in blood and cerebrospinal fluid. Clin Chem. 2007 Feb;53(2):326-33. Epub 2007 Jan 2. Pubmed: 17200133 Link_out
      Associated OMIM IDs
      DrugBank ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022327
      KNApSAcK ID Not Available
      Chemspider ID 388301 Link_out
      KEGG Compound ID C00021 Link_out
      BioCyc ID ADENOSYL-HOMO-CYS Link_out
      BiGG ID 33543 Link_out
      Wikipedia Link SAH Link_out
      NuGOwiki Link HMDB00939 Link_out
      Metagene Link HMDB00939 Link_out
      METLIN ID 296 Link_out
      PubChem Compound 439155 Link_out
      PDB ID SAH Link_out
      ChEBI ID 16680 Link_out
      References
      Synthesis Reference Holy, Antonin; Rosenberg, Ivan. Studies on S-adenosyl-L-homocysteine hydrolase. Part XV. An improved synthesis of S-adenosyl-L-homocysteine and related compounds. Collection of Czechoslovak Chemical Communications (1985), 50(7), 1514-18.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Miller AL: The methionine-homocysteine cycle and its effects on cognitive diseases. Altern Med Rev. 2003 Feb;8(1):7-19. Pubmed: 12611557 Link_out
      2. Hershfield MS, Kredich NM, Koller CA, Mitchell BS, Kurtzberg J, Kinney TR, Falletta JM: S-adenosylhomocysteine catabolism and basis for acquired resistance during treatment of T-cell acute lymphoblastic leukemia with 2'-deoxycoformycin alone and in combination with 9-beta-D-arabinofuranosyladenine. Cancer Res. 1983 Jul;43(7):3451-8. Pubmed: 6601986 Link_out
      3. Struys EA, Jansen EE, de Meer K, Jakobs C: Determination of S-adenosylmethionine and S-adenosylhomocysteine in plasma and cerebrospinal fluid by stable-isotope dilution tandem mass spectrometry. Clin Chem. 2000 Oct;46(10):1650-6. Pubmed: 11017945 Link_out
      4. Wang J, Dudman NP, Wilcken DE: Effects of homocysteine and related compounds on prostacyclin production by cultured human vascular endothelial cells. Thromb Haemost. 1993 Dec 20;70(6):1047-52. Pubmed: 8165599 Link_out
      5. Palella TD, Schatz RA, Wilens TE, Fox IH: S-Adenosylhomocysteine accumulation and selective cytotoxicity in cultured J Lab Clin Med. 1982 Aug;100(2):269-78. Pubmed: 6980250 Link_out
      6. van Guldener C, Stehouwer CD: Homocysteine and methionine metabolism in renal failure. Semin Vasc Med. 2005 May;5(2):201-8. Pubmed: 16047272 Link_out
      7. Muskiet FA: The importance of (early) folate status to primary and secondary coronary artery disease prevention. Reprod Toxicol. 2005 Sep-Oct;20(3):403-10. Pubmed: 15964170 Link_out
      8. Augoustides-Savvopoulou P, Luka Z, Karyda S, Stabler SP, Allen RH, Patsiaoura K, Wagner C, Mudd SH: Glycine N -methyltransferase deficiency: a new patient with a novel mutation. J Inherit Metab Dis. 2003;26(8):745-59. Pubmed: 14739680 Link_out
      9. Fowler B: Homocysteine: overview of biochemistry, molecular biology, and role in disease processes. Semin Vasc Med. 2005 May;5(2):77-86. Pubmed: 16047261 Link_out
      10. Gordon RK, Ginalski K, Rudnicki WR, Rychlewski L, Pankaskie MC, Bujnicki JM, Chiang PK: Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17. Pubmed: 12919315 Link_out
      11. Metz J: Cobalamin deficiency and the pathogenesis of nervous system disease. Annu Rev Nutr. 1992;12:59-79. Pubmed: 1354465 Link_out
      12. Mulder C, Schoonenboom NS, Jansen EE, Verhoeven NM, van Kamp GJ, Jakobs C, Scheltens P: The transmethylation cycle in the brain of Alzheimer patients. Neurosci Lett. 2005 Sep 30;386(2):69-71. Pubmed: 16040194 Link_out
      13. Delabar U, Kloor D, Luippold G, Muhlbauer B: Simultaneous determination of adenosine, S-adenosylhomocysteine and S-adenosylmethionine in biological samples using solid-phase extraction and high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Mar 19;724(2):231-8. Pubmed: 10219663 Link_out
      14. Hermes M, von Hippel S, Osswald H, Kloor D: S-adenosylhomocysteine metabolism in different cell lines: effect of hypoxia and cell density. Cell Physiol Biochem. 2005;15(5):233-44. Pubmed: 15956786 Link_out
      15. Weir DG, Molloy AM, Keating JN, Young PB, Kennedy S, Kennedy DG, Scott JM: Correlation of the ratio of S-adenosyl-L-methionine to S-adenosyl-L-homocysteine in the brain and cerebrospinal fluid of the pig: implications for the determination of this methylation ratio in human brain. Clin Sci (Lond). 1992 Jan;82(1):93-7. Pubmed: 1310924 Link_out
      16. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
      Enzymes
      Name: Phosphatidylethanolamine N-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + phosphatidylethanolamine = S-adenosyl-L-homocysteine + phosphatidyl-N-methylethanolamine [RN:R02056]
      Gene Name: PEMT
      Uniprot ID: Q9UBM1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Hydroxyindole O-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + N-acetylserotonin = S-adenosyl-L-homocysteine + melatonin [RN:R03130]
      Gene Name: ASMT
      Uniprot ID: P46597 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Catechol O-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + a catechol = S-adenosyl-L-homocysteine + a guaiacol [RN:R07330]
      Gene Name: COMT
      Uniprot ID: P21964 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone-lysine N-methyltransferase, H3 lysine-79 specific
      Reactions:
      • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
      Gene Name: DOT1L
      Uniprot ID: Q8TEK3 Link_out
      Protein Sequence: FASTA
      Name: Glycine N-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + glycine = S-adenosyl-L-homocysteine + sarcosine [RN:R00367]
      Gene Name: GNMT
      Uniprot ID: Q14749 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Histone-lysine N-methyltransferase SETD7
      Reactions:
      • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
      Gene Name: SETD7
      Uniprot ID: Q8WTS6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Phenylethanolamine N-methyltransferase
      Reactions:
      • S-adenosyl-L-methionine + phenylethanolamine = S-adenosyl-L-homocysteine + N-methylphenylethanolamine [RN:R04033]
      Gene Name: PNMT
      Uniprot ID: P11086 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Arsenite methyltransferase
      Reactions:
      • (1) S-adenosyl-L-methionine + arsenite = S-adenosyl-L-homocysteine + methylarsonate [RN:R05755]
      • (2) S-adenosyl-L-methionine + methylarsonite = S-adenosyl-L-homocysteine + dimethylarsinate [RN:R05756]
      Gene Name: AS3MT
      Uniprot ID: Q9HBK9 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Mitochondrial tRNA-specific 2-thiouridylase 1
      Reactions:
        Gene Name: TRMU
        Uniprot ID: O75648 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase, H3 lysine-36 and H4 lysine-20 specific
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: NSD1
        Uniprot ID: Q96L73 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETDB1
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETDB1
        Uniprot ID: Q15047 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Protein-L-isoaspartate(D-aspartate) O-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + protein L-isoaspartate = S-adenosyl-L-homocysteine + protein L-isoaspartate alpha-methyl ester [RN:R04190]
        Gene Name: PCMT1
        Uniprot ID: P22061 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Protein-S-isoprenylcysteine O-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + protein C-terminal S-farnesyl-L-cysteine = S-adenosyl-L-homocysteine + protein C-terminal S-farnesyl-L-cysteine methyl ester [RN:R04496]
        Gene Name: ICMT
        Uniprot ID: O60725 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Indolethylamine N-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + an amine = S-adenosyl-L-homocysteine + a methylated amine [RN:R02808]
        Gene Name: INMT
        Uniprot ID: O95050 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: DNA (cytosine-5)-methyltransferase 3A
        Reactions:
        • S-adenosyl-L-methionine + DNA = S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine [RN:R00380]
        Gene Name: DNMT3A
        Uniprot ID: Q9Y6K1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial
        Reactions:
        • S-adenosyl-L-methionine + 3-hexaprenyl-4,5-dihydroxybenzoate = S-adenosyl-L-homocysteine + 3-hexaprenyl-4-hydroxy-5-methoxybenzoate [RN:R04711]
        Gene Name: COQ3
        Uniprot ID: Q9NZJ6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase, H3 lysine-9 specific 3
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: EHMT2
        Uniprot ID: Q96KQ7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Methionine synthase reductase
        Reactions:
        • 2 [methionine synthase]-methylcob(I)alamin + 2 S-adenosylhomocysteine + NADP+ = 2 [methionine synthase]-cob(II)alamin + NADPH + H+ + 2 S-adenosyl-L-methionine [RN:R05182]
        Gene Name: MTRR
        Uniprot ID: Q9UBK8 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SUV39H1
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SUV39H1
        Uniprot ID: O43463 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Nicotinamide N-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + nicotinamide = S-adenosyl-L-homocysteine + 1-methylnicotinamide [RN:R01269]
        Gene Name: NNMT
        Uniprot ID: P40261 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SUV39H2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SUV39H2
        Uniprot ID: Q9H5I1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase, H3 lysine-9 specific 5
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: EHMT1
        Uniprot ID: Q9H9B1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Guanidinoacetate N-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + guanidinoacetate = S-adenosyl-L-homocysteine + creatine [RN:R01883]
        Gene Name: GAMT
        Uniprot ID: Q14353 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histamine N-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + histamine = S-adenosyl-L-homocysteine + Ntau-methylhistamine [RN:R02155]
        Gene Name: HNMT
        Uniprot ID: P50135 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Thiopurine S-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + a thiopurine = S-adenosyl-L-homocysteine + a thiopurine S-methylether [RN:R03701]
        Gene Name: TPMT
        Uniprot ID: P51580 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: N6-adenosine-methyltransferase 70 kDa subunit
        Reactions:
        • S-adenosyl-L-methionine + m7G(5')pppAm = S-adenosyl-L-homocysteine + m7G(5')pppm6Am (mRNA containing an N6,2'-O-dimethyladenosine cap) [RN:R03788]
        Gene Name: METTL3
        Uniprot ID: Q86U44 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Putative adenosylhomocysteinase 3
        Reactions:
        • S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine [RN:R00192]
        Gene Name: AHCYL2
        Uniprot ID: Q96HN2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Adenosylhomocysteinase
        Reactions:
        • S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine [RN:R00192]
        Gene Name: AHCY
        Uniprot ID: P23526 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Putative adenosylhomocysteinase 2
        Reactions:
        • S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine [RN:R00192]
        Gene Name: AHCYL1
        Uniprot ID: O43865 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Protein arginine N-methyltransferase 5
        Reactions:
        • S-adenosyl-L-methionine + histone-arginine = S-adenosyl-L-homocysteine + histone-Nomega-methyl-arginine [RN:R04718]
        Gene Name: PRMT5
        Uniprot ID: O14744 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETD1A
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETD1A
        Uniprot ID: O15047 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: DNA (cytosine-5)-methyltransferase 3B
        Reactions:
        • S-adenosyl-L-methionine + DNA = S-adenosyl-L-homocysteine + DNA containing 5-methylcytosine [RN:R00380]
        Gene Name: DNMT3B
        Uniprot ID: Q9UBC3 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: tRNA (cytosine-5-)-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + tRNA = S-adenosyl-L-homocysteine + tRNA containing 5-methylcytosine [RN:R00595]
        Gene Name: TRDMT1
        Uniprot ID: O14717 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETD8
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETD8
        Uniprot ID: Q9NQR1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETDB2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETDB2
        Uniprot ID: Q96T68 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Probable histone-lysine N-methyltransferase ASH1L
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: ASH1L
        Uniprot ID: Q9NR48 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-arginine methyltransferase CARM1
        Reactions:
        • S-adenosyl-L-methionine + histone-arginine = S-adenosyl-L-homocysteine + histone-Nomega-methyl-arginine [RN:R04718]
        Gene Name: CARM1
        Uniprot ID: Q86X55 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase EZH2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: EZH2
        Uniprot ID: Q15910 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: mRNA cap guanine-N7 methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + G(5')pppR-RNA = S-adenosyl-L-homocysteine + m7G(5')pppR-RNA (mRNA containing an N7-methylguanine cap) [RN:R03805]
        Gene Name: RNMT
        Uniprot ID: O43148 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Probable histone-lysine N-methyltransferase NSD2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: WHSC1
        Uniprot ID: O96028 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase NSD3
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: WHSC1L1
        Uniprot ID: Q9BZ95 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETD1B
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETD1B
        Uniprot ID: Q9UPS6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETD2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETD2
        Uniprot ID: Q9BYW2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SETMAR
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SETMAR
        Uniprot ID: Q53H47 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SUV420H1
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SUV420H1
        Uniprot ID: Q4FZB7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Histone-lysine N-methyltransferase SUV420H2
        Reactions:
        • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
        Gene Name: SUV420H2
        Uniprot ID: Q86Y97 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: N(2),N(2)-dimethylguanosine tRNA methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + tRNA = S-adenosyl-L-homocysteine + tRNA containing N2-methylguanine [RN:R00598]
        Gene Name: TRMT1
        Uniprot ID: Q9NXH9 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: tRNA (adenine-N(1)-)-methyltransferase catalytic subunit TRMT61A
        Reactions:
        • S-adenosyl-L-methionine + tRNA = S-adenosyl-L-homocysteine + tRNA containing N1-methyladenine [RN:R00596]
        Gene Name: TRMT61A
        Uniprot ID: Q96FX7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: tRNA (guanine-N(7)-)-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + tRNA = S-adenosyl-L-homocysteine + tRNA containing N7-methylguanine [RN:R00600]
        Gene Name: METTL1
        Uniprot ID: Q9UBP6 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: DNA (cytosine-5)-methyltransferase 3-like
        Reactions:
          Gene Name: DNMT3L
          Uniprot ID: Q9UJW3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase EZH1
          Reactions:
          • S-adenosyl-L-methionine + histone L-lysine = S-adenosyl-L-homocysteine + histone N6-methyl-L-lysine [RN:R03938]
          Gene Name: EZH1
          Uniprot ID: Q92800 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA