Canmetcon
Record Information
Version1.0
Creation date2015-05-07 21:10:02 UTC
Update date2018-05-29 01:54:58 UTC
Primary IDFDB031152
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameS-adenosyl-L-methionine
DescriptionS-adenosylmethionine, also known as sam or adomet, is a member of the class of compounds known as 5'-deoxy-5'-thionucleosides. 5'-deoxy-5'-thionucleosides are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group. S-adenosylmethionine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). S-adenosylmethionine can be found in a number of food items such as common grape, half-highbush blueberry, jerusalem artichoke, and thistle, which makes S-adenosylmethionine a potential biomarker for the consumption of these food products. S-adenosylmethionine can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout most human tissues. S-adenosylmethionine exists in all eukaryotes, ranging from yeast to humans. In humans, S-adenosylmethionine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(22:1(13Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), phosphatidylcholine biosynthesis PC(22:0/18:3(9Z,12Z,15Z)), phosphatidylcholine biosynthesis PC(24:0/24:0), and phosphatidylcholine biosynthesis PC(20:5(5Z,8Z,11Z,14Z,17Z)/20:0). S-adenosylmethionine is also involved in several metabolic disorders, some of which include methylenetetrahydrofolate reductase deficiency (MTHFRD), 3-phosphoglycerate dehydrogenase deficiency, monoamine oxidase-a deficiency (MAO-A), and aromatic l-aminoacid decarboxylase deficiency. Moreover, S-adenosylmethionine is found to be associated with diabetes mellitus type 2 and neurodegenerative disease. S-adenosylmethionine is a non-carcinogenic (not listed by IARC) potentially toxic compound. S-Adenosyl methionine is a common cosubstrate involved in methyl group transfers, transsulfuration, and aminopropylation. Although these anabolic reactions occur throughout the body, most SAM-e is produced and consumed in the liver. More than 40 methyl transfers from SAM-e are known, to various substrates such as nucleic acids, proteins, lipids and secondary metabolites. It is made from adenosine triphosphate (ATP) and methionine by methionine adenosyltransferase (EC 2.5.1.6). SAM was first discovered by Giulio Cantoni in 1952 . 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 (T3DB).
CAS Number29908-03-0
Structure
Thumb
Synonyms
SynonymSource
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner saltChEBI
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfoniumChEBI
AcylcarnitineChEBI
AdoMetChEBI
S-(5'-Deoxyadenosin-5'-yl)-L-methionineChEBI
SAMChEBI
SAMeChEBI
(3S)-5'-[(3-Amino-3-carboxypropyl)methylsulphonio]-5'-deoxyadenosine, inner saltGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-b-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-beta-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulfoniumGenerator
[1-(Adenin-9-yl)-1,5-dideoxy-β-D-ribofuranos-5-yl][(3S)-3-amino-3-carboxypropyl](methyl)sulphoniumGenerator
(3S)-5'-[(3-amino-3-Carboxypropyl)methylsulfonio]-5'-deoxyadenosineHMDB
2-S-Adenosyl-L-methionineHMDB
5'-Deoxyadenosine-5'-L-methionine disulfate ditosylateHMDB
5'-Deoxyadenosine-5'-L-methionine disulphate ditosylateHMDB
Active methionineHMDB
AdemetionineHMDB, MeSH
AdenosylmethionineHMDB
DonametHMDB
L-S-AdenosylmethionineHMDB
S-(5'-Adenosyl)-L-methionineHMDB
S-Adenosyl methionineHMDB
S-Adenosyl-L-methionineHMDB, MeSH
S-Adenosyl-L-methionine disulfate tosylateHMDB
S-Adenosyl-L-methionine disulphate tosylateHMDB
S-Adenosyl-methionineHMDB
ASTA medica brand OF ademetionine tosilate disulfateMeSH, HMDB
S Adenosylmethionine sulfate tosylateMeSH, HMDB
S-Adenosylmethionine sulfate tosylateMeSH, HMDB
Sulfate tosylate, S-adenosylmethionineMeSH, HMDB
Ademetionine europharma brandMeSH, HMDB
Amet, SMeSH, HMDB
Europharma brand OF ademetionineMeSH, HMDB
GumbaralMeSH, HMDB
Knoll brand OF brand OF ademetionine tosilate disulfateMeSH, HMDB
S AdenosylmethionineMeSH, HMDB
S AmetMeSH, HMDB
SamyrMeSH, HMDB
Tosylate, S-adenosylmethionine sulfateMeSH, HMDB
S Adenosyl L methionineMeSH
SAM-eMeSH
Predicted Properties
PropertyValueSource
Water Solubility1.19 g/LALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.7ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.63 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity96.23 m³·mol⁻¹ChemAxon
Polarizability40.37 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H23N6O5S
IUPAC name[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium
InChI IdentifierInChI=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)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1
InChI KeyMEFKEPWMEQBLKI-AIRLBKTGSA-O
Isomeric SMILESC[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N)N=CN=C12
Average Molecular Weight399.445
Monoisotopic Molecular Weight399.145063566
Classification
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class5'-deoxyribonucleosides
Sub Class5'-deoxy-5'-thionucleosides
Direct Parent5'-deoxy-5'-thionucleosides
Alternative Parents
Substituents
  • 5'-deoxy-5'-thionucleoside
  • Methionine or derivatives
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • 6-aminopurine
  • Alpha-amino acid
  • L-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Thia fatty acid
  • N-substituted imidazole
  • Fatty acyl
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Amino acid or derivatives
  • 1,2-diol
  • Amino acid
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Amine
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a5c-5965000000-324e4a3cbf936132bcf1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00ea-7958582000-3dd40cf273f182ee53ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0019000000-6dfa0dc65a9863755c2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udj-0293000000-57cc9d4430592060d41dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udr-1940000000-ed4985bea80649d27efeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-8920000000-8f05e9898f0d26ddf3f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000e-9400000000-e5c5617045d9915e8e46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0090000000-93017671648813ece8a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0914000000-95030ceaf1c187dcf656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c3fae8b7a68475b614a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-44078fd7eaeafcc5bba8View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference