Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000205
Name: S-Adenosylhomocysteine
Description:S-Adenosylhomocysteine (AdoHcy) is the immediate precursor of homocysteine. 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.
  • (S)-5'-(S)-(3-Amino-3-carboxypropyl)-5'-thioadenosine
  • 2-S-adenosyl-L-homocysteine
  • 2-S-Adenosyl-L-homocysteine
  • 5'-Deoxy-S-adenosyl-L-homocysteine
  • 5'-S-(3-Amino-3-carboxypropyl)-5'-thio-L-Adenosine
  • S-adenosyl-homocysteine
  • S-adenosylhomocysteine
  • Adenosyl-homo-CYS
  • Adenosyl-L-homocysteine
  • Adenosylhomo-CYS
  • Adenosylhomocysteine
  • Adohcy
  • Formycinylhomocysteine
  • L-5'-S-(3-Amino-3-carboxypropyl)-5'-thior-Adenosine
  • L-S-Adenosyl-Homocysteine
  • L-S-Adenosylhomocysteine
  • S-(5'-Adenosyl)-L-homocysteine
  • S-(5'-Deoxyadenosin-5'-yl)-L-homocysteine
  • S-(5'-Deoxyadenosine-5')-L-homocysteine
  • S-Adenosyl-homocysteine
  • S-Adenosyl-L-homocysteine
  • S-adenosylhomocysteine
  • SAH
  • SAHC
Chemical Formula: C14H20N6O5S
Average Molecular Weight: 384.411
Monoisotopic Molecular Weight: 384.12158847
CAS number: 979-92-0
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
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an?amine?with a?beta-N-glycosidic bond?to a carbohydrate, thus forming a cyclic?hemiaminal ether?bond (alpha-amino ether).
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent Glycosylamines
Alternative Parents
  • N-glycosyl compound
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Thia fatty acid
  • Aminopyrimidine
  • Amino fatty acid
  • Fatty acyl
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 209-211 °C
Experimental Properties:
Predicted Properties
Water Solubility4.08 mg/mLALOGPS
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)9.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.63 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity92.72 m3·mol-1ChemAxon
Polarizability38.41 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion
S-Adenosylhomocysteine + Water <> Adenine + S-Ribosyl-L-homocysteine
S-Adenosylmethionine + L-Homocysteine + S-Methylmethionine <> S-Adenosylhomocysteine + Hydrogen ion + L-Methionine
S-Adenosylmethionine + Malonyl-CoA > S-Adenosylhomocysteine + malonyl-CoA methyl ester
trans-Aconitic acid + S-Adenosylmethionine > E-3-Carboxy-2-pentenedioate 6-methyl ester + S-Adenosylhomocysteine
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PE(14:0/14:0) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylethanolamine (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PG(16:1(9Z)/16:1(9Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dihexadec-9,10-cyclo-anoyl, N-C16:0 cyclo) +2 Hydrogen ion
2 S-Adenosylmethionine + PG(18:1(11Z)/18:1(11Z)) >2 S-Adenosylhomocysteine + Cyclopropane phosphatidylglycerol (dioctadec-11,12-cyclo-anoyl, N-C18:0 cyclo) +2 Hydrogen ion
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine > 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine + Hydrogen ion
2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Ubiquinol-8
2-Demethylmenaquinol 8 + S-Adenosylmethionine > S-Adenosylhomocysteine + Hydrogen ion + Menaquinol 8
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion
S-Adenosylmethionine + L-Homocysteine <> S-Adenosylhomocysteine + L-Methionine
2 S-Adenosylmethionine + Uroporphyrinogen III <>2 S-Adenosylhomocysteine + Precorrin 2
S-Adenosylmethionine + DNA cytosine <> S-Adenosylhomocysteine + DNA 5-methylcytosine
2-Octaprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Octaprenyl-6-methoxyphenol + S-Adenosylhomocysteine
2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine
2-Phytyl-1,4-naphthoquinone + S-Adenosylmethionine <> Phylloquinone + S-Adenosylhomocysteine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N6-methyladenine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N1-methylguanine
S-Adenosylmethionine + rRNA <> S-Adenosylhomocysteine + rRNA containing N2-methylguanine
2-Polyprenyl-6-hydroxyphenol + S-Adenosylmethionine <> 2-Polyprenyl-6-methoxyphenol + S-Adenosylhomocysteine
2-Polyprenyl-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> 2-Polyprenyl-3-methyl-6-methoxy-1,4-benzoquinone + S-Adenosylhomocysteine
2-Polyprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + S-Adenosylmethionine <> Ubiquinone-1 + S-Adenosylhomocysteine
Demethylmenaquinol + S-Adenosylmethionine + Demethylmenaquinol <> Menaquinol 6 + S-Adenosylhomocysteine
S-Adenosylmethionine + precorrin-1 > S-Adenosylhomocysteine + Precorrin 2
S-Adenosylmethionine + a [protein]-L-glutamine > Hydrogen ion + S-Adenosylhomocysteine + a [protein]-N<sup>5</sup>-methyl-L-glutamine
tellurite + S-Adenosylmethionine methylated tellurite + S-Adenosylhomocysteine
S-Adenosylmethionine + Uroporphyrinogen III <> S-Adenosylhomocysteine + precorrin-1 + Hydrogen ion
S-Adenosylmethionine + a [protein]-L-&beta;-isoaspartate > S-Adenosylhomocysteine + a protein L-&beta;-isoaspartate &alpha;-methyl ester + Hydrogen ion
a phospholipid olefinic fatty acid + S-Adenosylmethionine > a phospholipid cyclopropane fatty acid + S-Adenosylhomocysteine + Hydrogen ion
L-Homocysteine + S-Adenosylmethionine Hydrogen ion + L-Methionine + S-Adenosylhomocysteine
S-Adenosylmethionine + a demethylated methyl acceptor > S-Adenosylhomocysteine + a methylated methyl acceptor
N-6-isopentyl adenosine-37 tRNA + S-Adenosylmethionine + <i>S</i>-sulfanyl-[acceptor] 2-methylthio-N-6-isopentyl adenosine-37 tRNA + S-Adenosylhomocysteine + L-Methionine + 5'-Deoxyadenosine + an unsulfurated sulfur acceptor + Hydrogen ion
a guanine<sup>1516</sup> in 16S rRNA + S-Adenosylmethionine > an <i>N</i><sup>2</sup>-methylguanine<sup>1516</sup> in 16S rRNA + S-Adenosylhomocysteine + Hydrogen ion
guanine<sup>2069</sup> in 23S rRNA + S-Adenosylmethionine > N<sup>7</sup>-methylguanine<sup>2069</sup> in 23S rRNA + S-Adenosylhomocysteine
S-Adenosylmethionine <> S-Adenosylhomocysteine
S-Adenosylmethionine + Phospholipid olefinic fatty acid <> S-Adenosylhomocysteine + Phospholipid cyclopropane fatty acid
S-Adenosylmethionine + tRNA containing 5-aminomethyl-2-thiouridine <> S-Adenosylhomocysteine + tRNA containing 5-methylaminomethyl-2-thiouridylate
S-Adenosylmethionine + DNA adenine <> S-Adenosylhomocysteine + DNA 6-methylaminopurine
2 S-Adenosylmethionine + Uroporphyrinogen III + Precorrin-1 <>2 S-Adenosylhomocysteine + Precorrin 2
2 S-Adenosylmethionine <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
2 S-Adenosylmethionine + Reduced acceptor <> S-Adenosylhomocysteine +2 L-Methionine + 5'-Deoxyadenosine
S-Adenosylmethionine + Protein glutamate <> S-Adenosylhomocysteine + Protein glutamate methyl ester
S-Adenosylmethionine <> S-Adenosylhomocysteine + DNA 5-methylcytosine
S-Adenosylmethionine + Protein L-isoaspartate <> S-Adenosylhomocysteine + Protein L-isoaspartate methyl ester
S-Adenosylmethionine + tRNA <> S-Adenosylhomocysteine + tRNA containing N6-methyladenine
S-Adenosylhomocysteine + Water > Adenine + S-ribosyl-L-homocysteine + S-ribosyl-L-homocysteine
a malonyl-[acp] + S-adenosyl-L-methionine > S-Adenosylhomocysteine + a malonyl-[acp] methyl ester
Uroporphyrinogen III + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Precorrin-1
Precorrin-1 + S-adenosyl-L-methionine > Precorrin-2 + S-Adenosylhomocysteine
2-Octaprenyl-6-hydroxyphenol + S-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenol
3-demethylubiquinol-8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Ubiquinol 8 + Ubiquinol-8
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Hydrogen ion + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
2-Demethylmenaquinol 8 + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Menaquinol 8

Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0006-0943000000-80fa5c7d919e1085bc5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-3f143852503952daa0a8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0900000000-23694a4b657a3478ad91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udr-0980000000-a8f61dcdc8693e2725f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00kf-0974000000-b3f3632635b2847bf4d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-188a77c79aaefae8a184View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-b848c20d743785117445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udr-0980000000-64b7b303fc07300e0782View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0319020200-859d659a39a790a582f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-53acf4e10681047da062View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-5896502e31d66786e12aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0009000000-01ea51599f8d30dec7feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0409000100-2de58945ab0dfa81f099View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-1900000000-a640f1a0bafd33afdd2dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-5f685035af9b243ccff2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0009000000-8d01fd0969e47d3bcc5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-2901000000-6c40a4a43a8c3e142eceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0902000000-c6c0d5529cf011d89f7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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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)
External Links:
Pubchem Compound ID439155
Kegg IDC00021
ChemSpider ID388301
Ligand ExpoSAH