Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000216
Identification
Name: S-Adenosylmethioninamine
Description:S-Adenosylmethioninamine is a biological sulfonium compound known as the major biological methyl donor. It is also a donor of methylene groups, amino groups, ribosyl groups and aminopropyl groups (PMID 15130560). S-Adenosylmethioninamine is a prodcut of enzyme adenosylmethionine decarboxylase [EC 4.1.1.50] in methionine metabolism pathway (KEGG).
Structure
Thumb
Synonyms:
  • (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt
  • (5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt
  • 3-amino-propyl-S-adenosine
  • 3-Amino-propyl-S-adenosine
  • S-adenosylmethioninamine
  • S-methyl-S-adenosyl homocysteamine
  • DAdoMet
  • DcSAM
  • Decarboxylated AdoMet
  • Decarboxylated S-adenosylmethionine
  • Decarboxylated SAM
  • S-Adenosyl-(5')-3-methylthiopropylamine
  • S-Adenosyl-L-methioninamine
  • S-Adenosylmethioninamine
  • S-Methyl-S-adenosyl homocysteamine
Chemical Formula: C14H23N6O3S
Average Molecular Weight: 355.436
Monoisotopic Molecular Weight: 355.155234322
InChI Key: ZUNBITIXDCPNSD-LSRJEVITSA-N
InChI:InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
CAS number: 22365-13-5
IUPAC Name:{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-aminopropyl)methylsulfanium
Traditional IUPAC Name: decarboxylated sam
SMILES:C[S+](CCCN)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N
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
Substituents
  • N-glycosyl compound
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.27 mg/mLALOGPS
logP0.28ALOGPS
logP-2.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)10.09ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area145.33 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.4 m3·mol-1ChemAxon
Polarizability36.97 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
References
References:
  • Fontecave, M., Atta, M., Mulliez, E. (2004). "S-adenosylmethionine: nothing goes to waste." Trends Biochem Sci 29:243-249. Pubmed: 15130560
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Pegg, Anthony E. Assay of aminopropyltransferases. Methods in Enzymology (1983), 94(Polyamines), 260-5.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID15625
HMDB IDHMDB00988
Pubchem Compound ID1078
Kegg IDC01137
ChemSpider ID388529
Wikipedia IDNot Available
BioCyc IDS-ADENOSYLMETHIONINAMINE
EcoCyc IDS-ADENOSYLMETHIONINAMINE