Human Metabolome Database Version 3.5

Showing metabocard for S-Adenosylhomocysteine (HMDB00939)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:29:45 -0600
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 | PDB | 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
  • Drug metabolite
  • 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
  • Waste products
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)
  • Urine
Tissue Location
  • Neuron
  • Placenta
  • Kidney
  • Liver
  • 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 Reference
Blood Detected and Quantified
0.46 +/- 0.02 uM Elderly (>65 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.01 (0.009-0.014) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0243 +/- 0.0068 uM Not Specified Not Specified Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Normal
  • Not Applicable
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.016 (0.009-0.025) uM Adult (>18 years old) Both Neurodegenerative diseases
Blood Detected and Quantified 0.49 +/- 0.05 uM Elderly (>65 years old) Both Parkinson's Disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0269 +/- 0.0062 uM Adult (>18 years old) Not Specified Alzheimer's disease
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
          DrugBank Metabolite ID DBMET00514 Link_out
          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
          17. Wagner C, Koury MJ: S-Adenosylhomocysteine: a better indicator of vascular disease than homocysteine? Am J Clin Nutr. 2007 Dec;86(6):1581-5. Pubmed: 18065573 Link_out
          18. Herrmann W, Obeid R: Biomarkers of folate and vitamin B(12) status in cerebrospinal fluid. Clin Chem Lab Med. 2007;45(12):1614-20. Pubmed: 17892439 Link_out

          Enzymes

          Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 94 enzymes in total.

          Name: Phosphatidylethanolamine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + phosphatidyl-N-methylethanolamine unknown S-Adenosylhomocysteine + phosphatidyl-N-dimethylethanolamine details
          S-Adenosylmethionine + phosphatidyl-N-dimethylethanolamine unknown S-Adenosylhomocysteine + phosphatidylcholine details
          S-Adenosylmethionine + Phosphatidylethanolamine unknown S-Adenosylhomocysteine + phosphatidyl-N-methylethanolamine details
          S-Adenosylmethionine + Phosphatidyl-N-dimethylethanolamine unknown S-Adenosylhomocysteine + Phosphatidylcholine details
          S-Adenosylmethionine + Phosphatidylethanolamine unknown S-Adenosylhomocysteine + Phosphatidyl-N-methylethanolamine details
          Gene Name: PEMT
          Uniprot ID: Q9UBM1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Acetylserotonin O-methyltransferase
          Reactions:
          S-Adenosylmethionine + N-Acetylserotonin unknown S-Adenosylhomocysteine + Melatonin details
          S-Adenosylmethionine + 5-Hydroxyindoleacetic acid unknown S-Adenosylhomocysteine + 5-Methoxyindoleacetate details
          Gene Name: ASMT
          Uniprot ID: P46597 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Catechol O-methyltransferase
          Reactions:
          S-Adenosylmethionine + a catechol unknown S-Adenosylhomocysteine + a guaiacol details
          S-Adenosylmethionine + Norepinephrine unknown S-Adenosylhomocysteine + Normetanephrine details
          S-Adenosylmethionine + Epinephrine unknown S-Adenosylhomocysteine + Metanephrine details
          S-Adenosylmethionine + 3,4-Dihydroxybenzeneacetic acid unknown S-Adenosylhomocysteine + Homovanillic acid details
          S-Adenosylmethionine + Dopamine unknown S-Adenosylhomocysteine + 3-Methoxytyramine details
          2-Hydroxyestrone + S-Adenosylmethionine unknown 2-Methoxyestrone + S-Adenosylhomocysteine details
          2-Hydroxyestradiol + S-Adenosylmethionine unknown 2-Methoxyestradiol + S-Adenosylhomocysteine details
          S-Adenosylmethionine + 3,4-Dihydroxyphenylglycol unknown S-Adenosylhomocysteine + Vanylglycol details
          S-Adenosylmethionine + 3,4-Dihydroxymandelic acid unknown S-Adenosylhomocysteine + Vanillylmandelic acid details
          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-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: DOT1L
          Uniprot ID: Q8TEK3 Link_out
          Protein Sequence: FASTA
          Name: Glycine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + Glycine unknown S-Adenosylhomocysteine + Sarcosine details
          Gene Name: GNMT
          Uniprot ID: Q14749 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SETD7
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SETD7
          Uniprot ID: Q8WTS6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Phenylethanolamine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + 2-Hydroxyphenethylamine unknown S-Adenosylhomocysteine + N-Methylphenylethanolamine details
          S-Adenosylmethionine + Norepinephrine unknown S-Adenosylhomocysteine + Epinephrine details
          Gene Name: PNMT
          Uniprot ID: P11086 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Diphthine synthase
          Reactions:
          S-Adenosylmethionine + 2-(3-Carboxy-3-aminopropyl)-L-histidine unknown S-Adenosylhomocysteine + 2-(3-carboxy-3-(trimethylammonio)propyl)-L-histidine details
          Gene Name: DPH5
          Uniprot ID: Q9H2P9 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Arsenite methyltransferase
          Reactions:
          S-Adenosylmethionine + Arsenite unknown S-Adenosylhomocysteine + Methylarsonate details
          S-Adenosylmethionine + Methylarsonite unknown S-Adenosylhomocysteine + Dimethylarsinate details
          Gene Name: AS3MT
          Uniprot ID: Q9HBK9 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Mitochondrial tRNA-specific 2-thiouridylase 1
          Reactions: Not Available
          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-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: NSD1
          Uniprot ID: Q96L73 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SETDB1
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SETDB1
          Uniprot ID: Q15047 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Protein-L-isoaspartate(D-aspartate) O-methyltransferase
          Reactions:
          S-Adenosylmethionine + protein L-isoaspartate unknown S-Adenosylhomocysteine + protein L-isoaspartate alpha-methyl ester details
          Gene Name: PCMT1
          Uniprot ID: P22061 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Protein-S-isoprenylcysteine O-methyltransferase
          Reactions:
          S-Adenosylmethionine + protein C-terminal S-farnesyl-L-cysteine unknown S-Adenosylhomocysteine + protein C-terminal S-farnesyl-L-cysteine methyl ester details
          Gene Name: ICMT
          Uniprot ID: O60725 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Indolethylamine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + an amine unknown S-Adenosylhomocysteine + a methylated amine details
          S-Adenosylmethionine + Dimethylsulfide unknown S-Adenosylhomocysteine + Trimethyl sulfonium details
          S-Adenosylmethionine + Tryptamine unknown S-Adenosylhomocysteine + N-Methyltryptamine details
          S-Adenosylmethionine + Serotonin unknown S-Adenosylhomocysteine + N-Methylserotonin details
          S-Adenosylmethionine + Dimethyl selenide unknown S-Adenosylhomocysteine + Trimethylselenonium details
          Gene Name: INMT
          Uniprot ID: O95050 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: DNA (cytosine-5)-methyltransferase 3A
          Reactions:
          S-Adenosylmethionine + DNA unknown S-Adenosylhomocysteine + DNA containing 5-methylcytosine details
          S-Adenosylmethionine + DNA cytosine unknown S-Adenosylhomocysteine + DNA 5-methylcytosine details
          Gene Name: DNMT3A
          Uniprot ID: Q9Y6K1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial
          Reactions:
          S-Adenosylmethionine + 3,4-dihydroxy-5-all-trans-polyprenylbenzoate unknown S-Adenosylhomocysteine + 3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate details
          S-Adenosylmethionine + 3-demethylubiquinone-n unknown S-Adenosylhomocysteine + ubiquinone-n details
          S-Adenosylmethionine + 3-(all-trans-polyprenyl)benzene-1,2-diol unknown S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol details
          2-Hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine unknown Ubiquinone 6 + S-Adenosylhomocysteine details
          S-Adenosylmethionine + 3-Hexaprenyl-4,5-Dihydroxybenzoic acid unknown S-Adenosylhomocysteine + 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid + Hydrogen Ion details
          S-Adenosylmethionine + 3-Demethylubiquinone-9 unknown S-Adenosylhomocysteine + Coenzyme Q9 details
          3-Polyprenyl-4,5-dihydroxybenzoate + S-Adenosylmethionine unknown 3-Polyprenyl-4-hydroxy-5-methoxybenzoate + S-Adenosylhomocysteine details
          2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine unknown Ubiquinone-2 + S-Adenosylhomocysteine details
          Gene Name: COQ3
          Uniprot ID: Q9NZJ6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase EHMT2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: EHMT2
          Uniprot ID: Q96KQ7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Methionine synthase reductase
          Reactions:
          [methionine synthase]-methylcob(I)alamin + S-Adenosylhomocysteine + NADP unknown [methionine synthase]-cob(II)alamin + NADPH + S-Adenosylmethionine details
          Gene Name: MTRR
          Uniprot ID: Q9UBK8 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SUV39H1
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SUV39H1
          Uniprot ID: O43463 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Nicotinamide N-methyltransferase
          Reactions:
          S-Adenosylmethionine + Niacinamide unknown S-Adenosylhomocysteine + 1-Methylnicotinamide details
          S-Adenosylmethionine + Niacinamide + Hydrogen Ion unknown S-Adenosylhomocysteine + 1-Methylnicotinamide details
          Gene Name: NNMT
          Uniprot ID: P40261 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SUV39H2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SUV39H2
          Uniprot ID: Q9H5I1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase EHMT1
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: EHMT1
          Uniprot ID: Q9H9B1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Guanidinoacetate N-methyltransferase
          Reactions:
          S-Adenosylmethionine + Guanidoacetic acid unknown S-Adenosylhomocysteine + Creatine details
          Gene Name: GAMT
          Uniprot ID: Q14353 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histamine N-methyltransferase
          Reactions:
          S-Adenosylmethionine + Histamine unknown S-Adenosylhomocysteine + 1-Methylhistamine details
          Gene Name: HNMT
          Uniprot ID: P50135 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Thiopurine S-methyltransferase
          Reactions:
          S-Adenosylmethionine + a thiopurine unknown S-Adenosylhomocysteine + a thiopurine S-methylether details
          Mercaptopurine + S-Adenosylmethionine unknown 6-Methylmercaptopurine + S-Adenosylhomocysteine details
          6-Thioinosine-5'-monophosphate + S-Adenosylmethionine unknown 6-Methylthiopurine 5'-monophosphate ribonucleotide + S-Adenosylhomocysteine details
          6-Thioguanosine monophosphate + S-Adenosylmethionine unknown 6-Methylthioguanosine monophosphate + S-Adenosylhomocysteine details
          Gene Name: TPMT
          Uniprot ID: P51580 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: N6-adenosine-methyltransferase 70 kDa subunit
          Reactions:
          S-Adenosylmethionine + m(7)G(5')pppAm unknown S-Adenosylhomocysteine + m(7)G(5')pppm(6)Am details
          Gene Name: METTL3
          Uniprot ID: Q86U44 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Putative adenosylhomocysteinase 3
          Reactions:
          S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
          Gene Name: AHCYL2
          Uniprot ID: Q96HN2 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Adenosylhomocysteinase
          Reactions:
          S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
          Gene Name: AHCY
          Uniprot ID: P23526 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Putative adenosylhomocysteinase 2
          Reactions:
          S-Adenosylhomocysteine + Water unknown Homocysteine + Adenosine details
          Gene Name: AHCYL1
          Uniprot ID: O43865 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Protein arginine N-methyltransferase 5
          Reactions:
          S-Adenosylmethionine + arginine-[histone] unknown S-Adenosylhomocysteine + N(omega)-methyl-arginine-[histone] details
          Gene Name: PRMT5
          Uniprot ID: O14744 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SETD1A
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SETD1A
          Uniprot ID: O15047 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: PR domain zinc finger protein 2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Gene Name: PRDM2
          Uniprot ID: Q13029 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase MLL
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: MLL
          Uniprot ID: Q03164 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: DNA (cytosine-5)-methyltransferase 3B
          Reactions:
          S-Adenosylmethionine + DNA unknown S-Adenosylhomocysteine + DNA containing 5-methylcytosine details
          S-Adenosylmethionine + DNA cytosine unknown S-Adenosylhomocysteine + DNA 5-methylcytosine details
          Gene Name: DNMT3B
          Uniprot ID: Q9UBC3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: tRNA (cytosine(38)-C(5))-methyltransferase
          Reactions:
          S-Adenosylmethionine + cytosine(38) in tRNA unknown S-Adenosylhomocysteine + 5-methylcytosine(38) in tRNA details
          Gene Name: TRDMT1
          Uniprot ID: O14717 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: N-lysine methyltransferase SETD8
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SETD8
          Uniprot ID: Q9NQR1 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase MLL3
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: MLL3
          Uniprot ID: Q8NEZ4 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: DNA (cytosine-5)-methyltransferase 1
          Reactions:
          S-Adenosylmethionine + DNA unknown S-Adenosylhomocysteine + DNA containing 5-methylcytosine details
          S-Adenosylmethionine + DNA cytosine unknown S-Adenosylhomocysteine + DNA 5-methylcytosine details
          Gene Name: DNMT1
          Uniprot ID: P26358 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase SETDB2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: SETDB2
          Uniprot ID: Q96T68 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: tRNA (cytosine(34)-C(5))-methyltransferase
          Reactions:
          S-Adenosylmethionine + cytosine(34) in tRNA precursor unknown S-Adenosylhomocysteine + 5-methylcytosine(34) in tRNA precursor details
          Gene Name: NSUN2
          Uniprot ID: Q08J23 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: 2-methoxy-6-polyprenyl-1,4-benzoquinol methylase, mitochondrial
          Reactions:
          S-Adenosylmethionine + 2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol unknown S-Adenosylhomocysteine + 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol details
          2-Hexaprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine unknown 2-Hexaprenyl-3-methyl-6-methoxy-1,4 benzoquinone + S-Adenosylhomocysteine details
          2-Polyprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine unknown 2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + S-Adenosylhomocysteine details
          Gene Name: COQ5
          Uniprot ID: Q5HYK3 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase ASH1L
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: ASH1L
          Uniprot ID: Q9NR48 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-arginine methyltransferase CARM1
          Reactions:
          S-Adenosylmethionine + arginine-[histone] unknown S-Adenosylhomocysteine + N(omega)-methyl-arginine-[histone] details
          Gene Name: CARM1
          Uniprot ID: Q86X55 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase EZH2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Gene Name: EZH2
          Uniprot ID: Q15910 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: mRNA cap guanine-N7 methyltransferase
          Reactions:
          S-Adenosylmethionine + G(5')pppR-RNA unknown S-Adenosylhomocysteine + m(7)G(5')pppR-RNA details
          Gene Name: RNMT
          Uniprot ID: O43148 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase MLL2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: MLL2
          Uniprot ID: O14686 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase MLL4
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: WBP7
          Uniprot ID: Q9UMN6 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase MLL5
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: MLL5
          Uniprot ID: Q8IZD2 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Histone-lysine N-methyltransferase NSD2
          Reactions:
          S-Adenosylmethionine + L-lysine-[histone] unknown S-Adenosylhomocysteine + N(6)-methyl-L-lysine-[histone] details
          Protein lysine + S-Adenosylmethionine unknown Protein N6-methyl-L-lysine + S-Adenosylhomocysteine details
          S-Adenosylmethionine + Protein N6-methyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6-dimethyl-L-lysine details
          S-Adenosylmethionine + Protein N6,N6-dimethyl-L-lysine unknown S-Adenosylhomocysteine + Protein N6,N6,N6-trimethyl-L-lysine details
          Gene Name: WHSC1
          Uniprot ID: O96028 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA